Phenylmethanol (BnOH) to Benzaldehyde

Page 1

Query Query OH

1. Query

O

Results

Date

435 reactions in Reaxys

2018-03-11 22h:04m:25s (EST)

Search as: As drawn, No salts, No mixtures

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

1/438

2018-03-11 22:07:32


H HO

O

Rx-ID: 817412 View in Reaxys 1/435 Yield 100 %

Conditions & References With bis(pyridine) silver permanganate in benzene, Time= 0.5h Firouzabadi, H.; Vessal, B.; Naderi, M.; Tetrahedron Letters; vol. 23; nb. 17; (1982); p. 1847 - 1850 View in Reaxys

100 %

With pyridine chromium peroxide in dichloromethane, Time= 0.5h, Ambient temperature Firouzabadi, H.; Iranpoor, N.; Kiaeezadeh, F.; Toofan, J.; Tetrahedron; vol. 42; nb. 2; (1986); p. 719 - 726 View in Reaxys

100 %

With manganese(IV) oxide, Pyridine-2,6-dicarboxylic acid in water, acetonitrile, Time= 20h, T= 20 °C Achremowicz, Lucjan; Mlochowski, Jacek; Mora, Czeslaw; Skarzewski, Jacek; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 735 - 742 View in Reaxys

100 %

With dinitratocerium (IV) chromate in benzene, Time= 1h, Heating Firouzabadi, H.; Iranpoor, N.; Kiaeezadeh, F.; Toofan, J.; Synthetic Communications; vol. 14; nb. 10; (1984); p. 973 - 982 View in Reaxys

100 %

With barium ferrate(VI) in benzene, Time= 0.8h, Heating Firouzabadi, H.; Mohajer, D.; Entezari-Moghaddam, M.; Synthetic Communications; vol. 16; nb. 6; (1986); p. 723 - 732 View in Reaxys

100 %

With pyridine, 1,4-diaza-bicyclo[2.2.2]octane, tetraethylammonium trichloride in dichloromethane, Ambient temperature Schlama, Thierry; Gabriel, Kiroubagaranne; Gouverneur, Veronique; Mioskowski, Charles; Angewandte Chemie (International Edition in English); vol. 36; nb. 21; (1997); p. 2342 - 2344 View in Reaxys

100 %

With tert.-butylhydroperoxide, diphenyl diselenide in tetrachloromethane, Time= 1h, Heating, other diaryl diselenide; var. promary and secondary alcohols, also alcohols bearing phenylthio or phenylseleno group, Product distribution Kuwajima, Isao; Shimizu, Makoto; Urabe, Hirokazu; Journal of Organic Chemistry; vol. 47; nb. 5; (1982); p. 837 842 View in Reaxys

100 %

With pyridine chromium peroxide in dichloromethane, Time= 0.5h, Ambient temperature, effect of various chromium(VI) based oxidants, Product distribution Firouzabadi, H.; Iranpoor, N.; Kiaeezadeh, F.; Toofan, J.; Tetrahedron; vol. 42; nb. 2; (1986); p. 719 - 726 View in Reaxys

100 %

With trans-lt;Ru4L1(O)2gt;ClO4 in acetonitrile, Time= 7h, T= 25 °C , stoicheiometric oxidation ( electrochemical oxidation in a non-aqueous medium (acetonitrile), an Ag-AgNO3 reference electrode Che, Chi-Ming; Tang, Wai-Tong; Lee, Wai-On; Wong, Wing-Tak; Lai, Ting-Fong; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1989); p. 2011 - 2016 View in Reaxys

100 %

With benzyltriphenylphosphonium peroxodisulfate in acetonitrile, Time= 0.5h, Heating, Oxidation Mohammadpoor-Baltork, Iraj; Hajipour, Abdol Reza; Mohammadi, Hasan; Bulletin of the Chemical Society of Japan; vol. 71; nb. 7; (1998); p. 1649 - 1653 View in Reaxys

100 %

With butyltriphenylphosphonium dichromate in chloroform, Time= 0.75h, Heating, Oxidation

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

2/438

2018-03-11 22:07:32


Baltork, I. Mohammadpoor; Sadeghi, M. M.; Mahmoodi, N.; Kharamesh, B.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 36; nb. 5; (1997); p. 438 - 441 View in Reaxys 100 %

With benzyltriphenylphosphonium dichromate in acetonitrile, Time= 0.133333h, Heating, Oxidation Hajipour, Abdol Reza; Mohammadpoor-Baltork, Iraj; Niknam, Kurosh; Organic Preparations and Procedures International; vol. 31; nb. 3; (1999); p. 335 - 341 View in Reaxys

100 %

With oxygen, perruthenate modified mesoporous silicate MCM-41 in toluene, Time= 0.5h, T= 80 °C , Oxidation Bleloch, Andrew; Johnson, Brian F. G.; Ley, Steven V.; Price, Adam J.; Shephard, Douglas S.; Thomas, Andrew W.; Chemical Communications; nb. 18; (1999); p. 1907 - 1908 View in Reaxys

100 %

With benzyltriphenylphosphonium chlorochromate in dichloromethane, Time= 0.05h, microwave irradiation, Oxidation Hajipour; Mallakpour; Backnejad; Synthetic Communications; vol. 30; nb. 21; (2000); p. 3855 - 3864 View in Reaxys

100 %

With carbon dioxide, oxygen, tetrapropylammonium perruthennate, T= 75 °C , p= 165013Torr , Kinetics Campestrini, Sandro; Carraro, Massimo; Ciriminna, Rosaria; Pagliaro, Mario; Tonellato, Umberto; Advanced Synthesis and Catalysis; vol. 347; nb. 6; (2005); p. 825 - 832 View in Reaxys

100 %

With benzyltriphenylphosphonium dichromate, silica gel, Time= 0.05h, T= 20 °C Hajipour; Mallakpour; Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals; vol. 356; (2001); p. 371 - 387 View in Reaxys

100 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, 4,4'-Dimethoxy-2,2'-bipyridin, potassium tert-butylate, copper(ll) bromide in water, acetonitrile, Time= 1h, T= 20 °C , Product distribution, Further Variations: Reagents, Solvents, Catalysts Gamez, Patrick; Arends, Isabel W. C. E.; Sheldon, Roger A.; Reedijk, Jan; Advanced Synthesis and Catalysis; vol. 346; nb. 7; (2004); p. 805 - 811 View in Reaxys

100.0 %

XV : Example XV 7.9 g of benzyl alcohol 99percent purity (72.3 mmol), toluene (10 cc) and 0.047 g MeO-TEMPO (0. 252MMOL) are charged in a jacketed glass reaction flask as in Example I. Sodium borate (0.129 g, 0.338 mmol), NAHCO3 (0. 43 g) are dissolved in water (15 cc) and the aqueous solution is added to the stirred organic fraction at 1000RPM in the reaction flask. The stirred suspension is cooled to 0°C and the emulsion is re-adjusted to pH 8.6 using 50percent solution OF CH3COOH. When the temperature of the reactants reached 0°C, 47.7 g (84.0 mmol) of 13.1percent aqueous NAOCI solution are pumped in via a gas-tight syringe over 20 minutes. The reaction mixture is stirred for an additional 15 min at 0°C and the organic layer is sampled for GC assay. The yield of benzaldehyde is 100.0percent at 2 min of post bleach-addition time. Stage 1: With sodium hydrogencarbonate, Sodium borate, 4-methoxy-2,2,6,6-tetramethyl-1-piperidinyloxy free radical in water, toluene Stage 2: With sodium hypochlorite, acetic acid, Time= 0.366667 - 0.583333h, T= 0 °C , pH= 8.6, Product distribution / selectivity Patent; THE NUTRASWEET COMPANY; WO2004/67484; (2004); (A2) English View in Reaxys

100 %

XV : EXAMPLE XV [00082] 7.9 g of benzyl alcohol 99percent purity (72.3 mmol), toluene (10 cc) and 0.047 g MeO-TEMPO (0.252 mmol) are charged in a jacketed glass reaction flask as in Example I. Sodium borate (0.129 g, 0.338 mmol), NaHCO3 (0.43 g) are dissolved in water (15 cc) and the aqueous solution is added to the stirred organic fraction at 1000 RPM in the reaction flask. The stirred suspension is cooled to 0° C. and the emulsion is re-adjusted to pH 8.6 using 50percent solution of CH3COOH. When the temperature of the reactants reached 0° C., 47.7 g (84.0 mmol) of 13.1percent aqueous NaOCl solution are pumped in via a gas-tight syringe over 20 minutes. The reaction mixture is

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

3/438

2018-03-11 22:07:32


stirred for an additional 15 min at 0° C. and the organic layer is sampled for GC assay. The yield of benzaldehyde is 100.0percent at 2 min of post bleach-addition time With sodium hypochlorite, 4-methoxy-2,2,6,6-tetramethyl-1-piperidinyloxy free radical, Na2 tetraborate in water, toluene, Time= 0.366667h, T= 0 °C , pH= 8.6, Aqueous hydrocarbonate buffer Patent; The NutraSweet Company; US6825384; (2004); (B1) English View in Reaxys 100 %

With acetic acid in acetonitrile, T= -20 °C , Kinetics, Further Variations: Reagents Zhou, Yuming; Shan, Xiaopeng; Mas-Balleste, Ruben; Bukowski, Michael R.; Stubna, Audria; Chakrabarti, Mrinmoy; Slominski, Luke; Halfen, Jason A.; Muenck, Eckard; Lawrence Jr., Que; Angewandte Chemie - International Edition; vol. 47; nb. 10; (2008); p. 1896 - 1899 View in Reaxys

100 %

With tert.-butylhydroperoxide in acetonitrile, Time= 8h, Reflux Zendehdel; Khanmohamadi; Mokhtari; Journal of the Chinese Chemical Society; vol. 57; nb. 2; (2010); p. 205 212 View in Reaxys

100 %

With potassium permanganate, boron trifluoride acetonitrile complex in acetonitrile, Time= 0.25h, T= 23 °C , Inert atmosphere, Kinetics, Temperature, Concentration, Time Du, Hongxia; Lo, Po-Kam; Hu, Zongmin; Liang, Haojun; Lau, Kai-Chung; Wang, Yi-Ning; Lam, William W. Y.; Lau, Tai-Chu; Chemical Communications; vol. 47; nb. 25; (2011); p. 7143 - 7145 View in Reaxys

100 %

With dihydrogen peroxide in acetonitrile, Time= 10h, T= 80 °C Kumar, R. Thinesh; Selvam, N. Clament Sagaya; Vijaya, J. Judith; Kennedy, L. John; Asian Journal of Chemistry; vol. 24; nb. 3; (2012); p. 1125 - 1129 View in Reaxys

100 %

With {[(VIVO)(2,2'-bipyridine)(H2O)]2(μ-P2O7)}∙3H2O, triethylamine in neat (no solvent), Time= 72h, T= 100 °C , Catalytic behavior, Concentration, Reagent/catalyst View in Reaxys

100 %

With oxygen, Time= 5h, T= 45 °C , Irradiation Sarina, Sarina; Zhu, Huaiyong; Jaatinen, Esa; Xiao, Qi; Liu, Hongwei; Jia, Jianfeng; Chen, Chao; Zhao, Jian; Journal of the American Chemical Society; vol. 135; nb. 15; (2013); p. 5793 - 5801 View in Reaxys

100 %

2.5.1 General procedure in oxidation of alcohol General procedure: In a typical experiment, a solution of Oxone (0.2 mmol) in H2O (5 ml) at room temperature was added to a solution of alcohol (0.2 mmol), tetra-n-butylammonium bromide, (0.1 mmol), and catalyst (0.01 mmol), in CH2Cl2 (1 mL), and the biphasic mixture stirred vigorously. Formation of products and consumption of substrates were monitored by gas chromatography. The identity of products was determined by comparison with authentic samples using gas–liquid chromatography. Oxidation products yields based on the oxidant, were quantified by comparison with chlorobenzene. With Oxone, [Mn(NO3)2(2,3,5,6-tetra(2-pyridyl)pyrazine)(H2O)], tetrabutylammomium bromide in dichloromethane, T= 20 °C , Catalytic behavior, Reagent/catalyst MacHura; Palion; Mrozinski; Kalinska; Amini; Najafpour; Kruszynski; Polyhedron; vol. 53; (2013); p. 132 - 143 View in Reaxys

100 %

With Cu nanoparticles dispersed on La2O2CO3 in 1,3,5-trimethyl-benzene, Time= 1h, T= 149.84 °C , Inert atmosphere, Temperature, Time Wang, Fei; Shi, Ruijuan; Liu, Zhi-Quan; Shang, Pan-Ju; Pang, Xueyong; Shen, Shuai; Feng, Zhaochi; Li, Can; Shen, Wenjie; ACS Catalysis; vol. 3; nb. 5; (2013); p. 890 - 894

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

4/438

2018-03-11 22:07:32


View in Reaxys 100 %

2 :The micro-reactor used is identical to the one of example 1B.[0107] Benzyl alcohol (c=1 mol/l) and 0.2 percent (molar) of TEMPO are dissolved in dichloromethane, thus constituting a solution for a first feed (feed 1 = the organic solution shown on figure 2B).[0108] A second feed (feed 2) is stock solution of bleach (c=11.2 percent) at a pH about 12.5. A third feed (feed 3) is a 0.7 M phosphate buffer (pH 8). This solution is brought to pH 6.2 by slow and controlled addition of H3PO4 85 percent wt. Feeds 2 and 3 (in a ratio buffer/bleach of 1.1) are mixed in one fluidic module (the first one M1 of the used microreactor) before passing a control of pH (= 8) and the mixture is then injected in the second module M2 of the micro-reactor. Feed 1 is directly pumped to the module M2 where it is mixed with aqueous phase.[0109] The total ratio (aqueous/organic phase) is 1.33.[0110] The temperature is 20°C.[0111] The results obtained (conversion (percent) and yield (percent)) are indicated in the Table 6 below related to different experiments carried out at different residence time (Rt(s)). Table 6 Rt Conversion* Yield** (s) (percent) (percent) 73 100 100 57 100 100 49 100 100 * The conversion (percent) is the ratio: difference between the starting benzyl alcohol and the remaining benzyl alcohol/the starting benzyl alcohol. ** The yield (percent) is the ratio: obtained aldhehyde /theoretically obtainable aldhehyde. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in dichloromethane, water, Time= 0.0202778h, T= 20 °C , Quantum yield, Time Patent; Corning Incorporated; Horn, Clemens; Gaurat, Olivier; Jean, Patrick; EP2617703; (2013); (A1) English View in Reaxys

100 %

2 : Example 2 (FIG. 2B) [0107] The micro-reactor used is identical to the one of example IB. [0108] Benzyl alcohol (c = 1 mo 1/1) and 0.2 percent (molar) of TEMPO are dissolved in dichloromethane, thus constituting a solution for a first feed (feed 1 = the organic solution (A-T) shown on FIG. 2B). [0109] A second feed (feed 2) (B in the figure) is stock solution of bleach (c=l 1.2 percent) at a pH about 12.5. A third feed (feed 3) (BF in the figure) is a 0.7 M phosphate buffer (pH 8), which is brought to pH 6.2 by slow and controlled addition of H3PO4 85 percent wt. Feeds 2 and 3 (in a ratio buffer/bleach of 1.1) are mixed in one fluidic module (the first one Ml of the used microreactor) before passing a control sensor S of set point pH (= 8) and the mixture is then injected in the second module M2 of the micro -reactor. Feed 1 is directly pumped to the module M2 where it is mixed with aqueous phase. [0110] The total ratio (aqueous/organic phase) is 1.33. [0112] The temperature is 20°C. [0113] The results obtained (conversion (percent) and yield (percent)) are indicated in the Table 6 below related to different experiments carried out at different residence time (Rt(s)). With sodium hypochlorite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, phosphoric acid in aq. phosphate buffer, dichloromethane, water, Time= 0.0202778h, T= 20 °C , pH= 8, Flow reactor, Catalytic behavior, Time Patent; CORNING INCORPORATED; HORN, Clemens Rudolf; WO2013/109670; (2013); (A1) English View in Reaxys

100 %

With Au–Pd alloy nanoparticle suppoted on ZrO2, Time= 5h, T= 45 °C , p= 760.051Torr , UV-irradiation, Inert atmosphere, Catalytic behavior, Kinetics, Temperature, Time, Reagent/catalyst Sarina, Sarina; Bai, Sagala; Huang, Yiming; Chen, Chao; Jia, Jianfeng; Jaatinen, Esa; Ayoko, Godwin A.; Bao, Zhaorigetu; Zhu, Huaiyong; Green Chemistry; vol. 16; nb. 1; (2014); p. 331 - 341 View in Reaxys

100 %

With TGSE, sodium hydrogencarbonate, sodium carbonate in water, Time= 1.66667h, Electrochemical reaction Karimi, Babak; Rafiee, Mohammad; Alizadeh, Saber; Vali, Hojatollah; Green Chemistry; vol. 17; nb. 2; (2015); p. 991 - 1000 View in Reaxys

100 %

Oxidation process of alcohols General procedure: In a typical process, benzyl alcohol (10 mmol), [PEO-didodecylimidazolium]3[PW12O40]2 (0.05 mol percent), 30 percent aq H2O2 (20 mmol) were then added. The mixture was stirred and under room temperature. The progress of the reaction was monitored by TLC with samples taken periodically. After completion of reaction, the mixture was extracted with ether for three times. The organic layer was dried over anhydrous MgSO4 and evaporated under reduced pressure.The product was analyzed by HPLC and purified by column chromatograph to give benzaldehyde (98 percent yield). The next run was performed under identical reaction conditions. With dihydrogen peroxide in water, Time= 6h, T= 20 °C , Green chemistry, Reagent/catalyst, Temperature

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

5/438

2018-03-11 22:07:32


Wang, Zhao-Gang; Yang, Yao; Cao, Xiao-Hua; Lu, Ming; Journal of the Iranian Chemical Society; vol. 12; nb. 10; (2015); p. 1765 - 1770 View in Reaxys 100 %

With C17H19FeN5O4 (18)O(1-) in acetonitrile, T= 26.84 °C , Kinetics, Reagent/catalyst, Temperature Ghosh, Munmun; Nikhil; Dhar, Basab B.; Sen Gupta, Sayam; Inorganic Chemistry; vol. 54; nb. 24; (2015); p. 11792 - 11798 View in Reaxys

100 %

With Iron(III) nitrate nonahydrate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, potassium hydoxide in toluene, Time= 1h, T= 100 °C Hu, Yongke; Chen, Lei; Li, Bindong; RSC Advances; vol. 6; nb. 69; (2016); p. 65196 - 65204 View in Reaxys

100 %

2.2.3. Catalytic activity of [CuLBAPP] General procedure: In a typical experiment, alcohol (1.0 mmol), [CuLBAPP] (4 mmolpercent), Cs2CO3 (0.650 g, 2 mmol) and 5mL THF (oxygen saturated) were inserted in a 25mL two-necked round-bottom flask, equipped with an oxygen balloon. The solution was stirred at room temperature, after which the mixture was filtered through a plug of silica, and then diluted with THF (2 mL). The progress of the reaction was monitored by gas chromatography. For a comparison, blank tests were performed, with the identical flask and amounts of Cs2CO3,THF (oxygen saturated) and oxygen balloon. Instead of CuLBAPP, only copper(II) acetate, or precursor ligand HLBAP were used. With C28H31CuN3O, oxygen, caesium carbonate in tetrahydrofuran, Time= 4h, T= 20 °C , Catalytic behavior, Solvent, Reagent/catalyst Safaei, Elham; Bahrami, Hadiseh; Pevec, Andrej; Kozlevčar, Bojan; Jagličić, Zvonko; Journal of Molecular Structure; vol. 1133; (2017); p. 526 - 533 View in Reaxys

100 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in acetonitrile, Time= 6h, T= 70 °C , Reagent/catalyst Taher, Abu; Kim, Dong Wook; Lee, Ik-Mo; RSC Advances; vol. 7; nb. 29; (2017); p. 17806 - 17812 View in Reaxys

99 %

With Balt;RuO3(OH)2gt; in dichloromethane, Time= 48h Green, Graham; Griffith, William P.; Hollinshead, David M.; Ley, Steven V.; Schroeder, Martin; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1984); p. 681 686 View in Reaxys

99 %

With boron trifluoride diethyl etherate, pyCo(TPP)NO2, Time= 0.75h, further reagents, further catalysts Tovrog,Benjamin S.; Diamond, Steven E.; Mares, Frank; Szalkiewicz, Andrew; Journal of the American Chemical Society; vol. 103; nb. 12; (1981); p. 3522 - 3526 View in Reaxys

99 %

With molecular sieve, lt;PPh4gt;lt;RuO2(OCOMe)Cl2gt; in dichloromethane, Time= 1h, Ambient temperature Griffith, William P.; Jolliffe, Jennifer M.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 24; (1992); p. 3483 - 3488 View in Reaxys

99 %

With bis(trimethylsilyl) chromate on montmorillonite K-10 in dichloromethane, Time= 0.166667h, T= 25 °C Heravi, Majid M.; Ajami, Dariush; Tabar-Heydar, Kourosh; Monatshefte fur Chemie; vol. 129; nb. 12; (1998); p. 1305 - 1308 View in Reaxys

99 %

With aluminium trichloride, PQQTME in acetonitrile, Time= 9h, T= 52 °C , other aluminum salt, other alcohols, other substrate, Product distribution, Mechanism Itoh, Shinobu; Mure, Minae; Ohshiro, Yoshiki; Agawa, Toshio; Tetrahedron Letters; vol. 26; nb. 35; (1985); p. 4225 - 4228

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

6/438

2018-03-11 22:07:32


View in Reaxys 99 %

With boron trifluoride diethyl etherate, pyCo(TPP)NO2, Time= 0.75h, further oxidating agents, Product distribution Tovrog,Benjamin S.; Diamond, Steven E.; Mares, Frank; Szalkiewicz, Andrew; Journal of the American Chemical Society; vol. 103; nb. 12; (1981); p. 3522 - 3526 View in Reaxys

99 %

With potassium ferrate(VI), K10 clay in cyclohexane, Time= 24h, Ambient temperature, comparision between solid catalyst; influence catalyst activation and relative amounts of reaction partners; other solvents, temperature. Oxidation of other alcohols, nitrogen derivatives, hydrocarbons, copling of thiols. Delaude, Lionel; Laszlo, Pierre; Journal of Organic Chemistry; vol. 61; nb. 18; (1996); p. 6360 - 6370 View in Reaxys

99 %

With ammonium peroxydisulfate, Montmorillonite, silver nitrate in hexane, Time= 2.5h, T= 60 °C Hirano; Kojima; Yakabe; Morimoto; Journal of Chemical Research - Part S; nb. 7; (2001); p. 274 - 276 View in Reaxys

99 %

With iodosylbenzene, tetraphenylphosphonium bromide in dichloromethane, Time= 24h, T= 24.85 °C , p= 760Torr , Product distribution, Further Variations: Reagents, Solvents, anaerobically Paraskevopoulou, Patrina; Petalidou, Eleftheria; Psaroudakis, Nikos; Stavropoulos, Pericles; Mertis, Konstantinos; Monatshefte fur Chemie; vol. 136; nb. 12; (2005); p. 2035 - 2039 View in Reaxys

99 %

With hydrotalcite, RuMn2, oxygen in toluene, Time= 1h, T= 60 °C , atmospheric pressure, Kinetics Ebitani, Kohki; Motokura, Ken; Mizugaki, Tomoo; Kaneda, Kiyotomi; Angewandte Chemie - International Edition; vol. 44; nb. 22; (2005); p. 3423 - 3426 View in Reaxys

99 %

With bismuth(III) nitrate, KP10 aluminosilicate in benzene, Time= 2.5h, T= 60 °C , Product distribution, Further Variations: Reagents, Catalysts, reaction times Farkas, Janos; Bekassy, Sandor; Madarasz, Janos; Figueras, Francois; New Journal of Chemistry; vol. 26; nb. 6; (2002); p. 750 - 754 View in Reaxys

99 %

With triethylammonium chlorochromate(VI), silica gel in dichloromethane, Time= 1.58333h Ghammamy, Shahriare; Dastpeyman, Samaneh; Journal of the Chinese Chemical Society; vol. 55; nb. 1; (2008); p. 229 - 232 View in Reaxys

99 %

With [WO(O2)2(C6H5CO2)](1-)*P(C6H5)4(1+)=[WO(O2)2(C6H5CO2)]P(C6H5)4, dihydrogen peroxide in water, acetonitrile, Time= 15h, Reflux Maiti, Swarup K.; Dinda, Subhajit; Banerjee, Surajit; Mukherjee, Alok K.; Bhattacharyya, Ramgopal; European Journal of Inorganic Chemistry; nb. 12; (2008); p. 2038 - 2051 View in Reaxys

> 99 %

With mesityltriphenylbismuthonium tetrafluoroborate, N,N,N',N'-tetramethylguanidine in chloroform-d1, Time= 1.5h, T= 20 °C Matano, Yoshihiro; Suzuki, Takeshi; Iwata, Takaharu; Shinokura, Tomonori; Imahori, Hiroshi; Bulletin of the Chemical Society of Japan; vol. 81; nb. 12; (2008); p. 1621 - 1628 View in Reaxys

99 %

With oxygen in toluene, Time= 1h, T= 80 °C Kantam, M. Lakshmi; Pal, Ujjwal; Sreedhar; Bhargava, Suresh; Iwasawa, Yasuhiro; Tada, Mizuki; Choudary; Advanced Synthesis and Catalysis; vol. 350; nb. 9; (2008); p. 1225 - 1229 View in Reaxys

99 %

With Oxone, sodium ortho-iodobenzenesulfonate in acetonitrile, Time= 2h, T= 70 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

7/438

2018-03-11 22:07:32


Uyanik, Muhammet; Akakura, Matsujiro; Ishihara, Kazuaki; Journal of the American Chemical Society; vol. 131; (2009); p. 251 - 262 View in Reaxys > 99 %

With 1-methyl-3-(2-oxo-2-(2,2,6,6-tetramethyl-1-ylooxy-4-piperidoxyl)ethyl)imidazolium chloride, 1-(carboxymethyl)-3-methylimidazolium chloride, oxygen, sodium nitrite in water, Time= 0.5h, T= 59.84 °C , p= 7500.75Torr , Inert atmosphere Miao, Cheng-Xia; He, Liang-Nian; Wang, Jin-Quan; Wang, Jing-Lun; Advanced Synthesis and Catalysis; vol. 351; nb. 13; (2009); p. 2209 - 2216 View in Reaxys

99 %

With air, potassium carbonate, Time= 10h, T= 20 °C Lakshmi Kantam; Arundhathi; Likhar, Pravin R.; Damodara; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2633 - 2637 View in Reaxys

99 %

With sodium hypochlorite, sodium hydrogencarbonate, potassium bromide in dichloromethane, water, T= 0 °C Lindner, Jean-Pierre; Roben, Caren; Studer, Armido; Stasiak, Michael; Ronge, Ramona; Greiner, Andreas; Wendorff, Hans-Joachim; Angewandte Chemie - International Edition; vol. 48; nb. 47; (2009); p. 8874 - 8877 View in Reaxys

> 99 %

With copper doped titania, oxygen, T= 200 °C Fan, Jie; Dai, Yihu; Li, Yunlong; Zheng, Nanfeng; Guo, Junfang; Yan, Xiaoqing; Stucky, Galen D.; Journal of the American Chemical Society; vol. 131; nb. 43; (2009); p. 15568 - 15569 View in Reaxys

99 %

With [bis(acetoxy)iodo]benzene, BF4 (1-)*C19H32N6O2 (1+) in dichloromethane, Time= 0.0833333h, T= 20 °C Fall, Alioune; Sene, Massene; Gaye, Mohamed; Gomez, Generosa; Fall, Yagamare; Tetrahedron Letters; vol. 51; nb. 34; (2010); p. 4501 - 4504 View in Reaxys

> 99 %

With γ-MnO2 hollow nanospheres, air in toluene, T= 110 °C , p= 750.075Torr Fu, Xiaobo; Feng, Jiyun; Wang, Huang; Ng, Ka Ming; Materials Research Bulletin; vol. 45; nb. 9; (2010); p. 1218 - 1223 View in Reaxys

99 %

With 5 ruthenium on carbon, oxygen in water, Time= 24h, T= 75 °C Akkilagunta, Vijay Kumar; Reddy, Vutukuri Prakash; Kakulapati, Rama Rao; Synlett; nb. 17; (2010); p. 2571 2574 View in Reaxys

99 %

With potassium carbonate, Time= 7h, T= 20 °C , Neat (no solvent) Layek, Keya; Maheswaran; Arundhathi; Kantam, M. Lakshmi; Bhargava, Suresh K.; Advanced Synthesis and Catalysis; vol. 353; nb. 4; (2011); p. 606 - 616 View in Reaxys

99 %

With [bis(acetoxy)iodo]benzene, Ru2(bbpmp)(OAc)2 acetate in tetrahydrofuran, acetonitrile, Time= 1h, T= 40 °C , Inert atmosphere Lee, Bao-Lin; Kaerkaes, Markus D.; Johnston, Eric V.; Inge, Andrew K.; Tran, Lien-Hoa; Xu, Yunhua; Hansson, Oerjan; Zou, Xiaodong; Akermark, Bjoern; European Journal of Inorganic Chemistry; nb. 34; (2010); p. 5462 - 5470 View in Reaxys

99 %

With dihydrogen peroxide in N,N-dimethyl-formamide, Time= 5h, T= 60 °C Najafi, Gholam Reza; Chinese Chemical Letters; vol. 21; nb. 10; (2010); p. 1162 - 1164 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

8/438

2018-03-11 22:07:32


99 %

2.5. Catalytic oxidation General procedure: Catalytic oxidation of primary alcohols to corresponding aldehydes and secondary alcohols to ketones by ruthenium(II) hydrazone Schiff base complexes were studied in the presence of NMO as co-oxidant. In a typical reaction, ruthenium(II) complexes as a catalyst and primary or secondary alcohol, as substrates at 1:100 molar ratio was described as follows. A solution of ruthenium complexes (0.01 mmol) in CH2Cl2 (20 cm3) was added to the mixture containing substrate (1 mmol), NMO (3 mmol) and molecular sieves. The solution mixture was refluxed for 3 h and the solvent was then evaporated from the mother liquor under reduced pressure. The solid residue was extracted with petroleum ether (60-80 °C) (20 ml) concentrated to ~1 ml and was analyzed by GC. The oxidation products were identified by GC co-injection with authentic samples. With RuCl(CO)(P(C6H5)3)(C5H4NCONHNCHC6H3OOCH3), 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Manikandan; Viswanathamurthi; Muthukumar; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 83; nb. 1; (2011); p. 297 - 303 View in Reaxys

> 99 %

With oxygen in toluene, Time= 7h, T= 79.84 °C Yoshida, Akihiro; Takahashi, Youichi; Ikeda, Tsuyoshi; Azemoto, Kazuki; Naito, Shuichi; Catalysis Today; vol. 164; nb. 1; (2011); p. 332 - 335 View in Reaxys

> 99 %

With oxygen, potassium hydoxide in chloroform, water, Time= 6h, T= 35 °C , p= 750.075Torr , Kinetics Buonerba, Antonio; Cuomo, Cinzia; Ortega Sanchez, Sheila; Canton, Patrizia; Grassi, Alfonso; Chemistry - A European Journal; vol. 18; nb. 2; (2012); p. 709 - 715 View in Reaxys

99 %

With 1-n-butyl-2,3-dimethylimidazolium acetate in water, Time= 24h, Reflux, Inert atmosphere Feng, Bo; Chen, Chen; Yang, Hanmin; Zhao, Xiuge; Hua, Li; Yu, Yinyin; Cao, Ting; Shi, Yu; Hou, Zhenshan; Advanced Synthesis and Catalysis; vol. 354; nb. 8; (2012); p. 1559 - 1565 View in Reaxys

> 99 %

With methyl tert-butyl peroxide in acetonitrile, Time= 3h, T= 25 °C Rahimi, Rahmatollah; Ghoreishi, Seyyedeh Zahra; Dekamin, Mohammad G.; Monatshefte fur Chemie; vol. 143; nb. 7; (2012); p. 1031 - 1038 View in Reaxys

99 %

With Pd(0) nanoparticle supported on aminopropyl grafted silica-based mesocellular foam, air in para-xylene, Time= 1h, T= 110 °C , p= 760.051Torr Johnston, Eric V.; Verho, Oscar; Kaerkaes, Markus D.; Shakeri, Mozaffar; Tai, Cheuk-Wai; Palmgren, Pal; Eriksson, Kristofer; Oscarsson, Sven; Baeckvall, Jan-E.; Chemistry - A European Journal; vol. 18; nb. 39; (2012); p. 12202 - 12206 View in Reaxys

99 %

With (tetrabutylammonium)4[Al4(H2O)10(β-SbW9O33H)2]*4H2O, dihydrogen peroxide in water, acetonitrile, Time= 1h, T= 70 °C , Catalytic behavior, Reagent/catalyst Carraro, Mauro; Bassil, Bassem S.; Soraru, Antonio; Berardi, Serena; Suchopar, Andreas; Kortz, Ulrich; Bonchio, Marcella; Chemical Communications; vol. 49; nb. 72; (2013); p. 7914 - 7916 View in Reaxys

99 %

Photocatalyti cactivity The photocatalyticselectiveoxidationofbenzylalcoholwasperformed asfollows.Amixtureofbenzylalcohol(BA, 0.1mmol)and 8mgofcatalystwasdissolvedinthesolventofbenzotri-fluoride (BTF,1.5mL),whichwassaturatedwithpuremolecularoxygen.Theabovemixturewastransferredintoa10mLPyrexglass bottle filled withmolecularoxygenatapressureof0.1MPaand stirredforhalfanhourtomakethecatalystblendevenlyinthe solution.Thesuspensionswereirradiatedbya300WXearclamp (PLS-SXE300,BeijingTrusttechCo.Ltd.)withaUV-CUT filtertocutofflightofwavelength o420 nm.Afterthereaction,themixture wascentrifugedat12,000rmpfor20mintocompletelyremovethecatalystparticles.Theremainingsolutionwasana-lyzed withanAglientGasChromatograph(GC-7820).Thecatalyticactivitywithhigherconcentrationof-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

9/438

2018-03-11 22:07:32


benzylalcohol(0.2mmoland0.3 mmol)overZIS-EtOHwaslabeledasZIS-EtOH-2BAandZIS-EtOH-3BA,respectively.Conversionofbenzylalcohol,yieldofbenzaldehyde,andselectivityforbenzaldehydeweredefined asfollows With zinc indium sulphide, oxygen, Time= 2h, p= 750.075Torr , UV-irradiation, Reagent/catalyst Chen, Zhixin; Xu, Jingjing; Ren, Zhuyun; He, Yunhui; Xiao, Guangcan; Journal of Solid State Chemistry; vol. 205; (2013); p. 134 - 141 View in Reaxys 99 %

With manganese(II) nitrate, C70H128N16O4, oxygen, cobalt(II) nitrate in acetic acid, Time= 2h, T= 20 °C , Mechanism, Reagent/catalyst, Time, Temperature Minisci, Francesco; Recupero, Francesco; Rodino, Marianna; Sala, Massimiliano; Schneider, Armin; Organic Process Research and Development; vol. 7; nb. 6; (2003); p. 794 - 798 View in Reaxys

99 %

With oxygen in water, Time= 1h, T= 25 °C , p= 760.051Torr , Solvent, Concentration, Reagent/catalyst Mahyari, Mojtaba; Shaabani, Ahmad; Bide, Yasamin; RSC Advances; vol. 3; nb. 44; (2013); p. 22509 - 22517 View in Reaxys

99 %

With aluminum oxide in N,N-dimethyl-formamide, Time= 4h, T= 120 °C , Inert atmosphere Damodara, Dandu; Arundhathi, Racha; Likhar, Pravin R.; Advanced Synthesis and Catalysis; vol. 356; nb. 1; (2014); p. 189 - 198 View in Reaxys

99 %

IBS-catalysed alcohol oxidation in CTAB micelle; general procedure General procedure: The alcohol (2 mmol) was added to a solution of IBS (0.02 mmol, 0.01 eq), oxone (2.2 mmol, 1.1 equiv.) and 3 wtpercent CTAB solution (5 mL). The mixture was stirred at room temperature. The reaction was monitored by TLC. After completion, the solution was extracted with CH2Cl2 (3 × 10 mL). The combined organic phase was then filtered through a pad of silica gel and evaporated under vacuum to afford the desired product. With 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide, Oxone, cetyltrimethylammonim bromide in water, Time= 2h, T= 20 °C , Green chemistry, chemoselective reaction Liu, Yangyang; Wang, Boliang; Journal of Chemical Research; vol. 38; nb. 7; (2014); p. 427 - 431 View in Reaxys

> 99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper 1,3,5-benzenetricarboxylate, oxygen, sodium carbonate in acetonitrile, Time= 16h, T= 75 °C , p= 760.051Torr Qi, Yue; Luan, Yi; Yu, Jie; Peng, Xiong; Wang, Ge; Chemistry - A European Journal; vol. 21; nb. 4; (2015); p. 1589 - 1597 View in Reaxys

> 99 %

With oxygen in toluene, Time= 20h, T= 80 °C , p= 760.051Torr Liu, Hongli; Chang, Lina; Chen, Liyu; Li, Yingwei; Journal of Materials Chemistry A; vol. 3; nb. 15; (2015); p. 8028 - 8033 View in Reaxys

> 99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 8h, T= 75 °C , p= 760.051Torr , Reagent/catalyst Zhang, Xiaowei; Dong, Wenjun; Luan, Yi; Yang, Mu; Tan, Li; Guo, Yangguang; Gao, Hongyi; Tang, Yinhai; Dang, Rui; Li, Jie; Wang, Ge; Journal of Materials Chemistry A; vol. 3; nb. 8; (2015); p. 4266 - 4273 View in Reaxys

99 %

Typical Procedure for the Oxidation of Alcohols General procedure: Alcohol (0.5 mmol), salophen copper (II) complex (2 molpercent), NaOH (0.6 equiv), and 70percent TBHP in water (1.1 equiv) were dissolved in acetonitrile (5 mL), and the homogeneous solution was stirred at room temperature in air overnight. After completion of the reaction, the solvent was evaporated under reduced pressure. The residue was purified over silica gel by column chromatography (10–25percent EtOAc in hexane).

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

10/438

2018-03-11 22:07:32


With tert.-butylhydroperoxide, N,N'‐disalicylidene‐1,2‐phenylenediamine copper(II), sodium hydroxide in water, acetonitrile, T= 20 °C , Catalytic behavior, Reagent/catalyst, Solvent Chen, Tingting; Cai, Chun; Synthetic Communications; vol. 45; nb. 11; (2015); p. 1334 - 1341 View in Reaxys 99 %

With dihydrogen peroxide in water, Time= 6h, T= 100 °C , Reagent/catalyst, Solvent, chemoselective reaction Wu, Suntao; Chen, Liyu; Yin, Biaolin; Li, Yingwei; Chemical Communications; vol. 51; nb. 48; (2015); p. 9884 9887 View in Reaxys

> 99 %

Stage 1: With tert.-butylhydroperoxide in diethylene glycol dimethyl ether, Time= 6h, T= 65 °C Stage 2:Time= 2h, T= 200 °C , Calcination, Activation energy Hinde, Christopher S.; Gill, Arran M.; Wells, Peter P.; Hor, T. S. Andy; Raja, Robert; ChemPlusChem; vol. 80; nb. 8; (2015); p. 1226 - 1230 View in Reaxys

99%

2.3. Typical procedure for oxidation of alcohols General procedure: The copper salt and the ligand (each 0.025 mmol) were added to CH3CN (1 mL) in an Ar atmosphere and stirred for 30min. Then 4‐OH‐TEMPO (0.025 mmol) and substrate (0.5mmol) were added successively, and the mixture was stirred at room temperature. The reaction progress was checked using thin‐layer chromatography. The reaction conversion and yield were obtained from GC measurements using nitrobenzene or nonane as an internal standard, or by column chromatography. With copper(l) iodide, TEMPOL, N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine in acetonitrile, Time= 1h, T= 20 °C , Inert atmosphere, Reagent/catalyst, Solvent, Time Zhang, Shufang; Miao, Chengxia; Xu, Daqian; Sun, Wei; Xia, Chungu; Chinese Journal of Catalysis; vol. 35; nb. 11; (2014); p. 1864 - 1873 View in Reaxys

99.2 %

With tert.-butylhydroperoxide, C38H32Cu2N4O10S2 in water, Time= 2.5h, T= 100 °C , Microwave irradiation, Catalytic behavior, Reagent/catalyst Hazra, Susanta; Martins, Luísa M. D. R. S.; Guedes Da Silva, M. Fátima C.; Pombeiro, Armando J. L.; RSC Advances; vol. 5; nb. 109; (2015); p. 90079 - 90088 View in Reaxys

> 99 %

2.6 General procedure for catalytic aerobic oxidation in water Under typical conditions, the reactions were performed in flasks at room temperature open to the air. 1.0mmol of alcohol substrate, complexes 6–9 (2molpercent based on Cu) and TEMPO or ABNO (0.050mmol, 5molpercent) were placed in the flask, to which 5cm3 of deionized water was sequentially added. The reaction was allowed to stir rigorously upon exposure to the air at room temperature for indicated times, after which ethyl acetate (8cm3) was added to extract the organic components. The products were diluted with dichloromethane and analysed by GC–MS to give the indicated conversions. With dmap, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper dichloride in water, Time= 10h, T= 20 °C , p= 760.051Torr , Reagent/catalyst Zhang, Guoqi; Zhang, Yuan Zhuo; Lo, Wen-Feng; Jiang, Jianfeng; Golen, James A.; Rheingold, Arnold L.; Polyhedron; vol. 103; (2016); p. 227 - 234 View in Reaxys

99 %

With (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride, oxygen, potassium hydoxide in dichloromethane, Time= 12h, T= 20 °C , Molecular sieve, Reagent/catalyst, Solvent Zhan, Le-Wu; Han, Lei; Xing, Ping; Jiang, Biao; Organic Letters; vol. 17; nb. 24; (2015); p. 5990 - 5993 View in Reaxys

99 %

With sodium bromate, 1,1,3,3-tetramethylguanidine sulfonic acid hydrochloride in water, acetonitrile, Time= 3h, T= 20 °C , Catalytic behavior, Solvent Shaabani, Ahmad; Laeini, Mohammad Sadegh; Shaabani, Shabnam; Seyyedhamzeh, Mozhdeh; New Journal of Chemistry; vol. 40; nb. 3; (2016); p. 2079 - 2082

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

11/438

2018-03-11 22:07:32


View in Reaxys > 99 %

With tert.-butylnitrite, oxygen, acetic acid in toluene, Time= 1h, T= 50 °C , Reagent/catalyst, Solvent Karimi, Babak; Vahdati, Saleh; Vali, Hojatollah; RSC Advances; vol. 6; nb. 68; (2016); p. 63717 - 63723 View in Reaxys

> 99 %

With titanium(IV) oxide, oxygen, Time= 6h, T= 29.84 °C , p= 760.051Torr , Sealed tube, Irradiation, Catalytic behavior, Kinetics, Reagent/catalyst Vadakkekara, Raji; Biswas, Abul Kalam; Sahoo, Tapan; Pal, Provas; Ganguly, Bishwajit; Ghosh, Subhash Chandra; Panda, Asit Baran; Chemistry - An Asian Journal; vol. 11; nb. 21; (2016); p. 3084 - 3089 View in Reaxys

> 99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, sodium carbonate in acetonitrile, Time= 6h, T= 75 °C , Reagent/catalyst Li, Jie; Gao, Hongyi; Tan, Li; Luan, Yi; Yang, Mu; European Journal of Inorganic Chemistry; vol. 2016; nb. 30; (2016); p. 4906 - 4912 View in Reaxys

99.5 %

With oxygen in toluene, T= 80 °C , p= 760.051Torr , Catalytic behavior Wang, Shuai; Yin, Shuangtao; Chen, Gaowen; Li, Lun; Zhang, Hui; Catalysis Science and Technology; vol. 6; nb. 12; (2016); p. 4090 - 4104 View in Reaxys

99 %

With oxygen in ethanol, Time= 30h, T= 80 °C , p= 750.075Torr Mao, Fei; Qi, Zhengliang; Fan, Haipeng; Sui, Dejun; Chen, Rizhi; Huang, Jun; RSC Advances; vol. 7; nb. 3; (2017); p. 1498 - 1503 View in Reaxys

99 %

2.4.1. General procedure for catalytic oxidation of alcohol General procedure: Alcohol (0.5 mmol), the catalyst (0.5 molpercent) and internal standard(0.5 mmol) were dissolved in a 1:1 mixture of water andtert-butanol (6 ml). NaIO4 (3 equivalents) was then added in oneportion and the solutions were vigorously stirred in an oil bathwith the temperature maintained at 80 C. The resultant solutionwas sampled at intervals, whereby an aliquot was removed and1 lL was injected and analyzed by GC. Control experiments inthe absence of either the catalyst or NaIO4 were performed underidentical conditions. With sodium periodate, [(η6-p-cymene)RuCl(C5H4N-2-CHN-2,4-trimethylphenyl)]PF6 in water, tert-butyl alcohol, Time= 0.5h, T= 80 °C , Schlenk technique, Catalytic behavior, Reagent/catalyst Gichumbi, Joel M.; Friedrich, Holger B.; Omondi, Bernard; Inorganica Chimica Acta; vol. 456; (2017); p. 55 - 63 View in Reaxys

99 %

With 1-methyl-1H-imidazole, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C12H20CuN6 (2+)*2ClO4 (1-) in toluene, acetonitrile, Time= 4h, T= 24.84 °C , Catalytic behavior, Concentration, Reagent/catalyst, Solvent Jain, Rahul; Gibson, Tony J.; Mashuta, Mark S.; Buchanan, Robert M.; Grapperhaus, Craig A.; Dalton Transactions; vol. 45; nb. 45; (2016); p. 18356 - 18364 View in Reaxys

99 %

With 2C36H60N9 (3+)*3O4W(2-), dihydrogen peroxide in water, Time= 0.0833333h, T= 20 °C , Green chemistry, Solvent Hosseini Eshbala, Fereshteh; Mohanazadeh, Farajollah; Sedrpoushan, Alireza; Applied Organometallic Chemistry; vol. 31; nb. 5; (2017); Art.No: E3597 View in Reaxys

> 99 %

With 1-methyl-1H-imidazole, 2,2,6,6-tetramethyl-piperidine-N-oxyl, 6C12H6Cu3N6O6 (3-)*6H O Zn*20Zn(2+)*5O(2-)*6C H N O (2-), 6 4 4 2 2 2

oxygen in acetonitrile, Time= 24h, T= 70 °C , Catalytic behavior, Re-

agent/catalyst, Time Tu, Binbin; Pang, Qingqing; Xu, Huoshu; Li, Xiaomin; Wang, Yulin; Ma, Zhen; Weng, Linhong; Li, Qiaowei; Journal of the American Chemical Society; vol. 139; nb. 23; (2017); p. 7998 - 8007

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

12/438

2018-03-11 22:07:32


View in Reaxys 99 %

With sodium carbonate in neat (no solvent), Time= 24h, T= 120 °C , Catalytic behavior, Reagent/catalyst, Temperature Akbari, Sara; Mokhtari, Javad; Mirjafari, Zohreh; RSC Advances; vol. 7; nb. 65; (2017); p. 40881 - 40886 View in Reaxys

99%

With potassium carbonate in water, Time= 2h, T= 90 °C , Reagent/catalyst, Solvent, Temperature Pourjavadi, Ali; Habibi, Zahra; Applied Organometallic Chemistry; vol. 31; nb. 11; (2017); Art.No: E3783 View in Reaxys

99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 12h, T= 60 °C , p= 760.051Torr , Catalytic behavior, Solvent, Reagent/catalyst Li, Ruilian; Zhao, Jian; Yang, Fengxia; Zhang, Yingchao; Ramella, Daniele; Peng, Yu; Luan, Yi; RSC Advances; vol. 7; nb. 81; (2017); p. 51142 - 51150 View in Reaxys

99 %

With tert.-butylhydroperoxide in toluene, Time= 4h, T= 120 °C Saha, Arijit; Payra, Soumen; Banerjee, Subhash; New Journal of Chemistry; vol. 41; nb. 22; (2017); p. 13377 13381 View in Reaxys

99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, potassium hydoxide in water, acetonitrile, Time= 10h, T= 20 °C , p= 760.051Torr , Reagent/catalyst Xu, Yang; Wang, Tianqi; He, Zidong; Zhou, Minghong; Yu, Wei; Shi, Buying; Huang, Kun; Applied Catalysis A: General; vol. 541; (2017); p. 112 - 119 View in Reaxys

99 %

With lithium perchlorate in methanol, T= 0 °C , Inert atmosphere, Sealed tube, Electrochemical reaction, Cooling with ice Barone, Mateus R.; Jones, Alan M.; Organic and Biomolecular Chemistry; vol. 15; nb. 47; (2017); p. 10010 10015 View in Reaxys

> 99 %

With 1-methyl-1H-imidazole, copper(l) iodide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in acetonitrile, Time= 1h, T= 20 °C Liu, Hui; Ramella, Daniele; Yu, Peng; Luan, Yi; RSC Advances; vol. 7; nb. 36; (2017); p. 22353 - 22359 View in Reaxys

99 %

With tert.-butylhydroperoxide, oxygen in decane, toluene, T= 80 °C , p= 1500.15Torr , Flow reactor, Catalytic behavior, Reagent/catalyst, Pressure, Temperature Giorgi, Pascal D.; Elizarov, Nelli; Antoniotti, Sylvain; ChemCatChem; vol. 9; nb. 10; (2017); p. 1830 - 1836 View in Reaxys

98 %

With tert.-butylhydroperoxide, Cr(OAc)3 impregnated NafionR 511 in chlorobenzene, benzene, Time= 6h, T= 85 °C Kanemoto, Sigekazu; Saimoto, Hiroyuki; Oshima, Koichiro; Nozaki, Hitosi; Tetrahedron Letters; vol. 25; nb. 31; (1984); p. 3317 - 3320 View in Reaxys

98 %

With calcium hypochlorite in water, acetic acid, acetonitrile, Time= 1h, T= 0 °C Nwaukwa, Stephen O.; Keehn, Philip M.; Tetrahedron Letters; vol. 23; (1982); p. 35 - 38 View in Reaxys

98 %

With silver ferrate in benzene, Time= 0.8h, Heating, further reagent K2FeO4 Firouzabadi, H.; Mohajer, D.; Moghaddam, M. Entezari; Synthetic Communications; vol. 16; nb. 2; (1986); p. 211 224

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

13/438

2018-03-11 22:07:32


View in Reaxys 98 %

With N-chloro-succinimide, diisopropylsulfide in dichloromethane, T= -78 °C Kim, Kwan Soo; Cho, In Haeng; Yoo, Byung Ki; Song, Yang Heon; Hahn, Chi Sun; Journal of the Chemical Society, Chemical Communications; nb. 12; (1984); p. 762 - 763 View in Reaxys

98 %

With oxygen, tetrapropylammonium perruthennate in dichloromethane, Time= 0.5h, Ambient temperature Lenz, Roman; Ley, Steven V.; Journal of the Chemical Society - Perkin Transactions 1; nb. 22; (1997); p. 3291 3292 View in Reaxys

98 %

With 1-benzyl-1-aza-4-azoniabicyclolt;2.2.2gt;octane periodate in acetonitrile, Time= 0.166667h, Heating Hajipour, A. R.; Mahboobkhah, N.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 37; nb. 3; (1998); p. 285 - 287 View in Reaxys

98 %

With silica gel, bis(trimethylsilyl)chromate, Time= 0.00277778h, Irradiation Heravi; Ajami; Tabar-Heydar; Synthetic Communications; vol. 29; nb. 2; (1999); p. 163 - 166 View in Reaxys

98 %

With chromium(VI) oxide, HY zeolite, Time= 0.00555556h, microwave irradiation Mirza-Aghayan, Maryam; Heravi, Majid M.; Synthetic Communications; vol. 29; nb. 5; (1999); p. 785 - 789 View in Reaxys

98 %

With bis(1-CH2Ph-3,5,7-3N-1-N(1+)tricyclo[3.3.1.13,7]decaneS2O8 in acetonitrile, Time= 0.583333h, Heating, Oxidation Minghu, Wu; Guichun, Yang; Zuxing, Chen; Synthetic Communications; vol. 30; nb. 17; (2000); p. 3127 - 3131 View in Reaxys

98 %

With KNa4[Ag(HIO6)2]*12H2O in water, T= 20 °C Bugarcic, Zorica; Novokmet, Slobodan; Senic, Zeljko; Bugarcic, Zivadin; Monatshefte fur Chemie; vol. 131; nb. 7; (2000); p. 799 - 802 View in Reaxys

98 %

With N-(tert-butyl)benzenesulfinimidoyl chloride, 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane, Time= 0.5h, T= -78 °C Matsuo, Jun-Ichi; Kitagawa, Hideo; Iida, Daisuke; Mukaiyama, Teruaki; Chemistry Letters; nb. 2; (2001); p. 150 151 View in Reaxys

98 %

With calcium hypochlorite, aluminum oxide, Time= 0.0166667h, microwave irradiation Mojtahedi, Mohammad M.; Saidi, Mohammad R.; Bolourtchian, Mohammad; Shirzi, Jafar S.; Monatshefte fur Chemie; vol. 132; nb. 5; (2001); p. 655 - 658 View in Reaxys

98 %

With prolinium chlorochromate in hexane, Time= 1.33h, Heating Mamaghani; Shirini; Parsa; Russian Journal of Organic Chemistry; vol. 38; nb. 8; (2002); p. 1113 - 1115 View in Reaxys

98 %

With N-chloro-succinimide, N-(phenylthio)-N-(tert-butyl)amine, potassium carbonate, 4 A molecular sieve in dichloromethane, Time= 1h, T= 0 °C , Product distribution, Further Variations: Reagents, Solvents, Temperatures Matsuo, Jun-Ichi; Iida, Daisuke; Yamanaka, Hiroyuki; Mukaiyama, Teruaki; Tetrahedron; vol. 59; nb. 35; (2003); p. 6739 - 6750 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

14/438

2018-03-11 22:07:32


98 %

With air, manganese(II) nitrate, macrocyclic polipiperidine-N-oxyl radical, toluene-4-sulfonic acid, cobalt(II) nitrate in acetic acid, Time= 3h, T= 20 °C Minisci, Francesco; Recupero, Francesco; Cecchetto, Andrea; Gambarotti, Cristian; Punta, Carlo; Faletti, Roberta; Paganelli, Roberto; Pedulli, Gian Franco; European Journal of Organic Chemistry; nb. 1; (2004); p. 109 - 119 View in Reaxys

98.38 %

With dithiobis[N-(2-OH-naphth-3-yl)benzamide]Cl2(H2O)2(Py)2Ru2, Heating, Product distribution, Further Variations: Reagents Jhaumeer-Laulloo, Sabina; Bhowon, Minu G.; Hosany, Amit; Journal of the Indian Chemical Society; vol. 81; nb. 7; (2004); p. 547 - 551 View in Reaxys

98 %

With aluminium trichloride, 1-decyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate in acetonitrile, Time= 0.5h, Heating Hajipour; Bagheri; Ruoho; Russian Journal of Organic Chemistry; vol. 42; nb. 6; (2006); p. 844 - 848 View in Reaxys

98 %

With sodium periodate, [bmim]PF6, C15H27ON3 (1+)*PF6 (1-), sodium bromide in water, Time= 15h, T= 20 °C Lei, Ming; Hu, Rui-Jun; Wang, Yan-Guang; Tetrahedron; vol. 62; nb. 38; (2006); p. 8928 - 8932 View in Reaxys

98 %

With 1,4-diaza-bicyclo[2.2.2]octane, 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl, oxygen, 1,3-di(4-pyridyl)propane, copper(II) perchlorate in dimethyl sulfoxide, Time= 2h, T= 20 °C , p= 760Torr Jiang, Nan; Ragauskas, Arthur J.; Journal of Organic Chemistry; vol. 71; nb. 18; (2006); p. 7087 - 7090 View in Reaxys

98 %

With potassium hydroxide, PS-resin, potassium hexacyanoferrate(III), 4-(benzyloxycarbonyl)-2,2,6,6-tetramethylpiperidine-1-oxyl in water, toluene, Time= 2h, T= 20 °C Yoshitomo, Kashiwagi; Chiba, Shinya; Anzai, Jun-ichi; New Journal of Chemistry; vol. 27; nb. 11; (2003); p. 1545 - 1549 View in Reaxys

98 %

With N-methyl-2-indolinone, tetrapropylammonium perruthennate, 1-ethyl-3-methylimidazolium hexafluorophosphate in dichloromethane, Time= 0.5h, T= 20 °C Ley; Ramarao; Smith; Chemical Communications; nb. 21; (2001); p. 2278 - 2279 View in Reaxys

98 %

With [hydroxy(tosyloxy)iodo]benzene, Time= 0.0166667h, microwave irradiation Lee, Jong Chan; Lee, Ji Young; Lee, Seung Jun; Tetrahedron Letters; vol. 45; nb. 25; (2004); p. 4939 - 4941 View in Reaxys

98 %

With NTPPPODS in acetonitrile, Time= 0.0333333h, Reflux Lakouraj, Moslem Mansour; Tajbakhsh, Mahmood; Ramzanian-Lehmali, Farhad; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 183; nb. 6; (2008); p. 1388 - 1395 View in Reaxys

98 %

With air, T= 313 °C Della Pina, Cristina; Falletta, Ermelinda; Rossi, Michele; Journal of Catalysis; vol. 260; nb. 2; (2008); p. 384 386 View in Reaxys

98 %

With oxygen, isobutyraldehyde in acetonitrile, Time= 3.5h, T= 50 °C , p= 760.051Torr Rana, Bharat S.; Jain, Suman L.; Singh, Bhawan; Bhaumik, Asim; Sain, Bir; Sinha, Anil K.; Dalton Transactions; vol. 39; nb. 33; (2010); p. 7760 - 7767

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

15/438

2018-03-11 22:07:32


View in Reaxys 98 %

With rhodium(III) chloride hydrate, oxygen, triethylamine, Time= 20h, T= 97.84 °C , p= 15201Torr Guo, Huajun; Liu, Wei-Dong; Yin, Guochuan; Applied Organometallic Chemistry; vol. 25; nb. 11; (2011); p. 836 842 View in Reaxys

98 %

With dihydrogen peroxide in water, acetonitrile, Time= 1.16667h, T= 90 °C Fazaeli, Razieh; Aliyan, Hamid; Poorgholam, Mohammad Reza; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 42; nb. 6; (2012); p. 805 - 810 View in Reaxys

98.8 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C24H32Cl2CuN2O3Si2, potassium carbonate in water, acetonitrile, Time= 48h, T= 50 °C , Catalytic behavior, Reagent/catalyst, Time Soroceanu, Alina; Cazacu, Maria; Shova, Sergiu; Turta, Constantin; Kozisek, Jozef; Gall, Marian; Breza, Martin; Rapta, Peter; Mac Leod, Tatiana C. O.; Pombeiro, Armando J. L.; Telser, Joshua; Dobrov, Anatolie A.; Arion, Vladimir B.; European Journal of Inorganic Chemistry; nb. 9; (2013); p. 1458 - 1474 View in Reaxys

98 %

With chromium(VI) oxide in neat (no solvent), Time= 0.00833333h, T= 20 °C , Reagent/catalyst, Time, Temperature He, Ai; Zhang, Jie; Zheng, Wenjin; Huang, Chen; Zhang, Changhe; Huang, Lihong; Lou, Ji-Dong; Research on Chemical Intermediates; vol. 39; nb. 3; (2013); p. 1015 - 1020 View in Reaxys

98 %

With dihydrogen peroxide, bromine in water, ethyl acetate, Time= 4h, Reflux Amati, Alessandro; Dosualdo, Gabriele; Zhao, Lihua; Bravo, Anna; Fontana, Francesca; Minisci, Francesco; Bjorsvik, Hans-Rene; Organic Process Research and Development; vol. 2; nb. 4; (1998); p. 261 - 269 View in Reaxys

98 %

General procedure for the catalytic oxidation of alcohols: General procedure: A 50 mL roundbottomed flask was charged with alcohol (1 mmol), palladium catalyst(0.1 mol percent), acetonitrile (10 mL), and H2O2 30percent (5 mmol). The mixture wasstirred at 80 C for the required time. After completion, the catalyst wasseparated by filtration and washed the residual solid with the same reactionsolvent. The filtrate was diluted with water (20 mL) and extracted with ether(3 20 mL) and dried over Na2SO4. After evaporation of the solvent underreduced pressure, the residue was chromatographed (silica gel, ethyl acetate/hexane, 1:9) to obtain the desired products. The products separated werecharacterized by FTIR, GC–MS, 1H NMR spectroscopy and compared with theauthentic samples. With dihydrogen peroxide in acetonitrile, Time= 2h, T= 80 °C , Reagent/catalyst, Solvent, Temperature Sahu, Debojeet; Sarmah, Chandan; Das, Pankaj; Tetrahedron Letters; vol. 55; nb. 23; (2014); p. 3422 - 3425 View in Reaxys

98 %

Oxidation of the benzylic alcohols: general procedure General procedure: A 25-mL round bottomed flask with 2 mL of CH3CN equipped with a magnetic stirrer and reflux condenser was charged with 0.01 mmol catalyst and 5 mmol aqueous hydrogen peroxide (30percent). The mixture was stirred and then 1 mmol alcohol was added. The biphasic mixture was stirred at 90 C for the required time. Progress of the reaction was followed by aliquots withdrawn directly from the reaction mixture analyzed by GC usinginternal standard. After completion of the reaction, the mixture was treated with a 10percent sodium hydrogensulte solution to decompose the unreacted hydrogen peroxide and then with 10percent sodium hydroxide. The product was extracted with n-butyl-ether. The pure product was obtained by distillation or silica gel columnchromatography (hexane/ethyl acetate, 10/1). With dihydrogen peroxide in acetonitrile, Time= 0.333333h, T= 90 °C , Green chemistry, Catalytic behavior, Temperature, Solvent, Reagent/catalyst Fazaeli, Razieh; Aliyan, Hamid; Foroushani, Somaieh Parishani; Mohagheghian, Zahra; Turkish Journal of Chemistry; vol. 38; nb. 3; (2014); p. 372 - 380 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

16/438

2018-03-11 22:07:32


98 %

With C30H24AgBr4N8 (1+)*AgBr2 (1-), N-benzyl-trimethylammonium hydroxide in toluene, Time= 12h, T= 20 °C , Molecular sieve, Schlenk technique, Reagent/catalyst, Temperature, Time, Solvent Han, Lei; Xing, Ping; Jiang, Biao; Organic Letters; vol. 16; nb. 13; (2014); p. 3428 - 3431 View in Reaxys

98 %

With oxygen in toluene, Time= 1h, T= 100 °C , Catalytic behavior, Reagent/catalyst Xu, Chunli; Wang, Zhen; Huangfu, Xiuting; Wang, Hanfei; RSC Advances; vol. 4; nb. 52; (2014); p. 27337 27345 View in Reaxys

98 %

With tert.-butylhydroperoxide in water, acetonitrile, Time= 3h, T= 50 °C , Catalytic behavior, Temperature, Solvent Shilpa; Gayathri; Transition Metal Chemistry; vol. 38; nb. 1; (2013); p. 53 - 62 View in Reaxys

98 %

With dihydrogen peroxide, Time= 5h, T= 80 °C , Green chemistry, Catalytic behavior, Temperature, chemoselective reaction Rana, Surjyakanta; Maddila, Suresh; Pagadala, Ramakanth; Parida; Jonnalagadda, Sreekantha B.; Catalysis Communications; vol. 59; (2014); p. 73 - 77 View in Reaxys

98 %

With oxygen in benzene, T= 150 °C , p= 5250.53Torr Chaudhuri, Sangeeta Roy; Hartwig, Jan; Kupracz, Lukas; Kodanek, Torben; Wegner, Jens; Kirschning, Andreas; Advanced Synthesis and Catalysis; vol. 356; nb. 17; (2014); p. 3530 - 3538 View in Reaxys

98 %

General Procedure for the Catalytic Oxidation of Alcohols General procedure: A 50 mL round bottomed flask was charged with alcohol(1 mmol), catalyst (0.2 molpercent), acetonitrile (10 mL) andH2O2 30percent (5 mmol). The mixture was stirred at 70 °C for the required time in air. The progress of the reaction was monitored by TLC (SiO2 gel). After completion, the reaction mixture was extracted with ether (3 20 mL) and dried over Na2SO4. After evaporation of the solvent under reduced pressure, the residue was chromatographed (silica gel, ethylacetate/ hexane, 1:5). Removal of solvent and usual work upgave the desired aldehydes or ketones, which were identified by comparing spectral data (IR, 1H NMR and Mass Spectra)with those of authentic compounds reported in literature. With [FeCl3(η1-P-(bis[2-(diphenylphosphino)phenyl]ether))(η2-P,P-(bis[2-(diphenylphosphino)phenyl]ether))], dihydrogen peroxide in acetonitrile, Time= 2h, T= 70 °C , Reagent/catalyst, Temperature, Solvent Sahu, Debojeet; Banik, Biplab; Borah, Malabika; Das, Pankaj; Letters in Organic Chemistry; vol. 11; nb. 9; (2014); p. 671 - 676 View in Reaxys

98 %

Typical procedure for the formation of aldehydes (3a-q) A test tube equipped with a magnetic stirring bar was charged with 1 (5 mg, 0.005 mmol, 0.25 molpercent), TEMPO (16 mg, 0.10 mmol, 5 molpercent), and K2CO3 (69 mg, 0.50 mmol, 25 molpercent). Alcohols (2a-q, 2.0 mmol), H2O (5 mL) and H2O2 (30percent, 1 mL) were added. The mixed light green solution was stirred at 60°C for 12 h, cooled to room temperature, and then extracted by Et2O (3 × 5mL). The organic layers were combined, washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. On elution with petroleum ether and ethyl acetate, the crude product was further purified by column chromatography on silica. All aldehyde products synthesized in this work are known and confirmed by 1H NMR spectra. Benzaldehyde (3a) Colorless oil; yield: 208mg, 98percent; 1H NMR (400 MHz, CDCl3, ppm): δ 9.99 (s, 1H), 7.86 (d, J=7.2Hz, 2H), 7.60 (t, J=7.6Hz, 1H), 7.50 (t, J=7.6Hz, 2H); 13C NMR (100 MHz, CDCl3, ppm): δ 192.18, 136.23, 134.28, 129.52, 128.83. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C40H54CuN4O5 (2+)*2I(1-), dihydrogen peroxide, potassium carbonate in water, Time= 12h, T= 60 °C , Reagent/catalyst, Temperature, Time Gao, Jun; Ren, Zhi-Gang; Lang, Jian-Ping; Journal of Organometallic Chemistry; vol. 792; (2015); p. 88 - 92; Art.No: 18908 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

17/438

2018-03-11 22:07:32


98 %

9 : 2.2 General procedure for the dehydrogenation of benzylic alcohols using Ag/ZnO nanoparticles General procedure: A mixture of alcohol (1 mmol), KOH (1 mmol), and 0.005 g Ag/ZnO nanoparticles (2) (containing 8×10−5g Ag) in toluene (2 mL) was stirred at 100 °C for the appropriate time. The reaction was monitored by thin layer chromatography (TLC) or GC. After completion of the reaction, the reaction mixture was diluted with EtOAc and centrifuged to remove the catalyst. The filtrate was extracted with water, the organic layer dried over CaCl2 and evaporated under reduced pressure. The resulting product was purified by column chromatography on silica-gel to afford the pure product. All compounds are known and were characterized by comparison of their physical and spectroscopic data with the already described in the literature. With potassium hydoxide in toluene, Time= 8h, T= 100 °C Hosseini-Sarvari, Mona; Ataee-Kachouei, Tahereh; Moeini, Fatemeh; Materials Research Bulletin; vol. 72; (2015); p. 98 - 105 View in Reaxys

98 %

With sulfuric acid, dihydrogen peroxide, sodium bromide in 1,4-dioxane, water, T= 70 °C , Flow reactor, Green chemistry Liu, Chengkou; Fang, Zheng; Yang, Zhao; Li, Qingwen; Guo, Shiyu; Zhang, Kai; Ouyang, Pingkai; Guo, Kai; Tetrahedron Letters; vol. 56; nb. 44; (2015); p. 5973 - 5976 View in Reaxys

98 %

With oxygen, Time= 16h, T= 30 °C , p= 760.051Torr , Irradiation Zavahir, Sifani; Xiao, Qi; Sarina, Sarina; Zhao, Jian; Bottle, Steven; Wellard, Mark; Jia, Jianfeng; Jing, Liqiang; Huang, Yiming; Blinco, James P.; Wu, Haishun; Zhu, Huai-Yong; ACS Catalysis; vol. 6; nb. 6; (2016); p. 3580 - 3588 View in Reaxys

98 %

With Au(at)Cu(II)-metal-organic framework in toluene, T= 110 °C , Solvent, Temperature Wang, Jing-Si; Jin, Fa-Zheng; Ma, Hui-Chao; Li, Xiao-Bo; Liu, Ming-Yang; Kan, Jing-Lan; Chen, Gong-Jun; Dong, Yu-Bin; Inorganic Chemistry; vol. 55; nb. 13; (2016); p. 6685 - 6691 View in Reaxys

98%

With dihydrogen peroxide in water, ethyl acetate, Time= 0.833333h, T= 50 - 55 °C , Catalytic behavior, Solvent, Reagent/catalyst Keypour, Hassan; Saremi, Shokoufeh Ghahri; Veisi, Hojat; Azadbakht, Reza; RSC Advances; vol. 6; nb. 80; (2016); p. 77020 - 77029 View in Reaxys

98 %

With [2,2]bipyridinyl, Iron(III) nitrate nonahydrate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, acetic acid, Time= 0.5h, T= 80 °C , p= 760.051Torr Lagerblom, Kalle; Wrigstedt, Pauli; Keskiväli, Juha; Parviainen, Arno; Repo, Timo; ChemPlusChem; vol. 81; nb. 11; (2016); p. 1160 - 1165 View in Reaxys

98 %

Aerobic Oxidation of Alcohols 1a–o; Typical Procedure General procedure: Cu-PdNPs/bio-silica catalyst (80 mg) and TEMPO (5 mg, 0.03 mmol)in toluene (3 mL). The reaction flask was purged and filled with oxygen(1 atm) and heated at 110 °C overnight. The reaction mixture was then centrifuged and the supernatant was removed. The solvent was evaporated in vacuo, and the crude product was purified by flash column chromatography (silica gel; hexane/EtOAc). The recovered solid catalyst was washed with toluene (3 × 2 mL) and dried in an oven(100 °C, 4 h) for its reuse. The following known compounds includedin Table 2 were characterized by comparison of their chromatographicand spectroscopic data (FTIR, 1H NMR, 13C NMR, and MS) with those described previously. Benzaldehyde (2a)22Yield: 52 mg (0.49 mmol, 98percent); colorless oil.IR (neat): 2820, 2738, 1703, 1204, 828, 746, 688 cm–1. 1H NMR (300 MHz, CDCl3): δ = 10.05 (s, 1 H), 7.93–7.90 (m, 2 H), 7.66(m, 1 H), 7.58–7.55 (m, 2 H).13C NMR (75 MHz, CDCl3): δ = 192.4, 136.4, 134.4, 129.7, 129.0.MS: m/z = 106 (100) [M]+, 105 (94), 78 (16), 77 (93), 52 (10), 51 (37),50 (18). With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in toluene, T= 110 °C , p= 760.051Torr , Reagent/ catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

18/438

2018-03-11 22:07:32


Buxaderas, Eduardo; Graziano-Mayer, Marilyn; Volpe, María Alicia; Radivoy, Gabriel; Synthesis (Germany); vol. 49; nb. 6; (2017); p. 1387 - 1393; Art.No: SS-2016-M0473-OP View in Reaxys 98 %

4.5 General Procedure for Aerobic Alcohol Oxidation General procedure: The alcohol oxidation reaction was performed by taking10 mg PdNpmont K-10 catalyst, 1 mmol alcohol and3 ml water in a 50 ml round bottom flask under aerobiccondition. The mixture was stirred at room temperatureup to the required time. The progress of the reaction wasmonitored by taking thin layer chromatography (TLC).After completion of the reaction, stirring was stopped and the catalyst was subjected to centrifugation and the residualsolid after filtration was washed with water (4 ml) threetimes. To this filtrate 10 ml ether was added and extractedthe product with ether. The resultant organic phases wasdried over anhydrous Na2SO4,filtered and evaporatedunder reduced pressure. The residue was subjected to silicagel column chromatography (ethyl acetate–hexane, 2:8) toobtain the desired products. With montmorillonite K-10 supported palladium nanoparticles, air in water, Time= 5h, T= 20 °C , Catalytic behavior, Reagent/catalyst, Temperature, Solvent Gogoi, Nibedita; Bordoloi, Porismita; Borah, Geetika; Gogoi, Pradip K.; Catalysis Letters; vol. 147; nb. 2; (2017); p. 539 - 546 View in Reaxys

98 %

2.4 Reaction Conditions General procedure: In a typical process, benzyl alcohol (1 mmol), Cat.(0.5 mmol), 30 percent aq H2O2 (2 mmol) were mixed and H2O(5 mL) was then added. The reaction mixture was refluxedat 80–85 °C for 28 h. The progress of the reaction wasmonitored by the TLC with samples taken periodically.After the completion of the reaction, the system cooledto room temperature. The catalyst was filtered and the filtrateextracted three times with Et2O. The organic layerwas dried over anhydrous MgSO4 and evaporated underreduced pressure. The product was purified by columnchromatograph to give benzaldehyde (98 percent yield). The nextrun was performed under identical reaction conditions. Theproducts were recognized by comparing experimental datawith authentic samples. With dihydrogen peroxide in water, T= 80 °C , Catalytic behavior, Temperature, Solvent Hashemian, Saeedeh; Sedrpoushan, Alireza; Eshbala, Fereshteh Hosseini; Catalysis Letters; vol. 147; nb. 1; (2017); p. 196 - 203 View in Reaxys

98 %

6 : Example 6: Strengthening of Oxidative Oxidation of Benzyl Alcohol by Tetraethylammonium Perfluorooctane Sulfonate (1) In a 50 ml flask, 0.216 g (2 mmol) of benzyl alcohol, 3 ml of deionized water, 0.06 g (0.094 mmol) of tetraethylammonium perfluorooctane sulfonate (TEAPOSF) Stir for 5 min to dissolve the surfactant, stand-by. (2) In a 50 ml flask, 0.0244 g (0.2 mmol) of 4-dimethylaminopyridine, 0.01 g (0.1 mmol) of cuprous chloride, 4.5 ml of deionized water, After dissolving the solid in a nitrogen atmosphere,Stop the nitrogen, To obtain complex solution, stand-by. (3) 4.5 ml of the complex solution obtained in step (2) and 2.5 ml of a TEMPO (0.04 M) solution were added to the flask (1) in step (1) In the air atmosphere, 20 deg C under the conditions of reaction 40min, After the reaction, The reaction solution was subjected to liquid separation, The resulting lower oil phase was washed with saturated sodium chloride solution, Dried over anhydrous sodium sulfate, To obtain an oxidation product of benzaldehyde 0.208 g, Yield 98percent GC content of 99percent; The resulting aqueous layer of the upper layer was extracted with ether, The solvent is distilled off to recover the fluorosurfactant. With dmap, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, perfluorooctanesulfonic acid, tetraethylammonium salt, copper(l) chloride in water, Time= 0.666667h, T= 20 °C , Reagent/catalyst Patent; Zhejiang University of Technology; Wang, Jianli; Chen, Xianbo; Zhang, Qi; (10 pag.); CN106316730; (2017); (A) Chinese View in Reaxys

98 %

General procedure for the oxidation of alcohols tocarbonyl compounds General procedure: The alcohol (1 mmol) was added to a mixture of TBHP(1 mmol) and VO(ephedrine)2MNPs (50 mg) in PEG(1 mL), and then the mixture was refluxed at 80 C for thetime specified. The progress was monitored by TLC (EtOAc/n-hexane, 1/2). After completion of the reaction, the catalystwas separated from the product by an external magnet(within 5 s), and the mixture was washed with EtOAc(25 mL) and decanted. The decanted mixturewas washedwith 30percent NaOH (5 mL) and the organic layer was dried overanhydrous Na2SO4. The evaporation of EtOAc underreduced pressure gave the pure products in 85e98percent yields.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

19/438

2018-03-11 22:07:32


With tert.-butylhydroperoxide, Time= 3h, T= 80 °C , Green chemistry, Catalytic behavior, Temperature Rostami, Amin; Pourshiani, Omid; Darvishi, Neda; Atashkar, Bahareh; Comptes Rendus Chimie; vol. 20; nb. 4; (2017); p. 435 - 439 View in Reaxys 98 %

With Iron(III) nitrate nonahydrate, oxygen, 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,2-dichloro-ethane, Time= 3h, T= 60 °C , Schlenk technique, Green chemistry, Catalytic behavior, Mechanism, Reagent/catalyst, Solvent, Time, Temperature Hu, Yongke; Chen, Lei; Li, Bindong; Catalysis Communications; vol. 103; (2018); p. 42 - 46 View in Reaxys

98 %

2.6.2. Catalytic oxidation by [MnL(Cl)(H2O)] The homogeneous catalyst (0.01 mmol) was suspended in solution of substrates (1 mmol)in CH3CN (5 ml). Then the mixture was allowed to equilibrate at 60 °C. We added dierentamounts of PhI(OAc)2 (as illustrated in footnote of each table) in the mixture with stirring.The stirring was continued for ve hours at 60 °C in air. Upon completion diethyl ether wasused to extract the organic products and 1H-NMR analysis was performed. With [bis(acetoxy)iodo]benzene, C17H14Cl5MnN2O3 in acetonitrile, T= 20 °C , Green chemistry, Catalytic behavior, Reagent/catalyst Chakraborty, Aratrika; Chattopadhyay, Tanmay; Journal of Coordination Chemistry; vol. 70; nb. 19; (2017); p. 3293 - 3307 View in Reaxys

97 %

With bis-trimethylsilanyl peroxide, tris(triphenylphosphine)ruthenium(II) chloride in dichloromethane, Time= 2h, T= 25 °C Kanemoto, Shigekazu; Oshima, Koichiro; Matsubara, Seijiro; Takai, Kazuhiko; Nozaki, Hitosi; Tetrahedron Letters; vol. 24; nb. 21; (1983); p. 2185 - 2188 View in Reaxys

97 %

With bis-trimethylsilanyl peroxide, tris(triphenylphosphine)ruthenium(II) chloride in dichloromethane, Time= 20h Kanemoto, Shigekazu; Matsubara, Seijiro; Takai, Kazuhiko; Oshimara, Koichiro; Utimoto, Kiitiro; Nozaki, Hitosi; Bulletin of the Chemical Society of Japan; vol. 61; (1988); p. 3607 - 3612 View in Reaxys

97 %

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide, Time= 0.25h, Ambient temperature Frigerio, Marco; Santagostino, Marco; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 8019 - 8022 View in Reaxys

97 %

With tert.-butylhydroperoxide, [(N,N',N"-trimethyl-1,4,7-triazacyclononane)Ru(CF3CO2)3*H2O] in dichloromethane, 1,2-dichloro-ethane, Time= 20h, T= 20 °C , Catalytic oxidation Fung, Wai-Hong; Yu, Wing-Yiu; Che, Chi-Ming; Journal of Organic Chemistry; vol. 63; nb. 9; (1998); p. 2873 2877 View in Reaxys

97 %

With 1,4-dibenzyl-1,4-diazoniabicyclo[2.2.2]octane chlorochromate in acetonitrile, Time= 0.25h, Heating xxx; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 39; nb. 11; (2000); p. 863 - 866 View in Reaxys

97 %

With oxygen, Pd nanoparticles, polystyrene-poly(ethylene glycol) resin in water, Time= 1.5h, p= 760Torr , Heating Uozumi, Yasuhiro; Nakao, Ryu; Angewandte Chemie - International Edition; vol. 42; nb. 2; (2003); p. 194 - 197 View in Reaxys

97 %

With potassium permanganate, aluminum polysilicate in toluene, Time= 0.5h, T= 70 - 80 °C Lou, Ji-Dong; Zhu, Li-Yun; Wang, Lan-Zhou; Monatshefte fur Chemie; vol. 135; nb. 1; (2004); p. 31 - 34 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

20/438

2018-03-11 22:07:32


97 %

With [(H2DABCO)2(HDABCO)2(Br)2(Br3)4] in dichloromethane, water, Time= 4h, T= 20 °C Heravi, Majid M.; Derikvand, Fatemeh; Ghassemzadeh, Mitra; Neumueller, Bernhard; Tetrahedron Letters; vol. 46; nb. 37; (2005); p. 6243 - 6245 View in Reaxys

97 %

With sodium dichromate, Time= 0.333333h, T= 20 °C Lou, Ji-Dong; Gao, Chun-Ling; Ma, Yi-Chun; Huang, Li-Hong; Li, Li; Tetrahedron Letters; vol. 47; nb. 3; (2006); p. 311 - 313 View in Reaxys

97 %

With KMnO4 on aluminum silicate, Time= 0.666667h, T= 20 °C Lou, Ji-Dong; Gao, Chun-Ling; Li, Li; Fang, Zhi-Gang; Monatshefte fur Chemie; vol. 137; nb. 8; (2006); p. 1071 1074 View in Reaxys

97 %

With ferric nitrate, Time= 0.25h, T= 80 °C , Product distribution, Further Variations: Temperatures, Reagents, Pressures, time Namboodiri, Vasudevan V.; Polshettiwar, Vivek; Varma, Rajender S.; Tetrahedron Letters; vol. 48; nb. 50; (2007); p. 8839 - 8842 View in Reaxys

97 %

1 Stage 1: With dimethyl sulfoxide in ethyl acetate, T= 0 °C Stage 2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide in ethyl acetate, Time= 3h, T= 0 °C Patent; CLARIANT GMBH; WO2005/102978; (2005); (A1) German View in Reaxys

97 %

B.12 : EXAMPLE 12 EXAMPLE 12 Method for oxidation of benzyl alcohol: Oxygen gas (25 ml min-1) was continuously bubbled through a solution of benzyl alcohol (5 mmol), polystyrene supported [meso-(2,6-dichlorophenyl)porphinato] Iron (II) (corresponding to 0.056 mol percent of metalloporphyrin) in toluene (25 ml). Ascorbic acid (15 mmol) was added to reaction mixture at intervals of 2 hours till maximum conversion of reactant to product was achieved). The reaction mixture was vigorously stirred at 65° C. and the progress of the reaction was monitored by TLC. After stirring the reaction mixture for 4 hrs, it was concentrated to half. Addition of equal volume of methanol precipitated the catalyst that was filtered and the filtrate was evaporated to dryness to give the product. The product was purified by column chromatography and characterized by physical constants and spectroscopic data (IR, 1H-NMR and mass spectra). Yield: 0.52 g (97percent). With oxygen, ascorbic acid in toluene, Time= 4h, T= 65 °C Patent; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; US2006/167313; (2006); (A1) English View in Reaxys

97 %

With potassium bromate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, hydroxylamine hydrochloride, oxygen in dichloromethane, Time= 2h, T= 50 °C , p= 2250.23 - 3000.3Torr , Autoclave Yang, Guanyu; Wang, Wei; Zhu, Weimin; An, Cunbin; Gao, Xinqin; Song, Maoping; Synlett; nb. 3; (2010); p. 437 - 440 View in Reaxys

97 %

With sodium periodate, manganese(II) 5,10,15,20-tetrakis(N-ethylpyridinium-4-yl)porphyrin in water, toluene, Time= 1.5h, T= 30 °C Ren, Qing-Gang; Chen, Shao-Yun; Zhou, Xian-Tai; Ji, Hong-Bing; Bioorganic and Medicinal Chemistry; vol. 18; nb. 23; (2010); p. 8144 - 8149

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

21/438

2018-03-11 22:07:32


View in Reaxys 97 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, hydroxylamine, oxygen in water, 1,2-dichloro-ethane, Time= 4h, T= 80 °C , p= 2250.23Torr , Autoclave Wertz, Sebastian; Studer, Armido; Advanced Synthesis and Catalysis; vol. 353; nb. 1; (2011); p. 69 - 72 View in Reaxys

97 %

With bis-triphenylphosphine-palladium(II) chloride, potassium carbonate, benzyl chloride, Time= 20h, T= 60 °C , Inert atmosphere, chemoselective reaction Liu, Chao; Tang, Shan; Zheng, Liwei; Liu, Dong; Zhang, Heng; Lei, Aiwen; Angewandte Chemie - International Edition; vol. 51; nb. 23; (2012); p. 5662 - 5666 View in Reaxys

97 %

With sulfuric acid, oxygen, sodium nitrite in tetrachloromethane, cyclohexane, Time= 2h, T= 60 °C , Ionic liquid, Solvent, Time, Concentration Zhu, Jie; Wang, Peng-Cheng; Ming, Lu; Synthetic Communications; vol. 43; nb. 14; (2013); p. 1871 - 1881 View in Reaxys

97 %

With Fe3O4/SiO2 Magnetic nanoparticles coated carboxymethyl-β-CD in water, Time= 1.5h, T= 50 °C , Reagent/ catalyst, Temperature, Concentration, chemoselective reaction Zhu, Jie; Wang, Peng-Cheng; Lu, Ming; Journal of the Brazilian Chemical Society; vol. 24; nb. 1; (2013); p. 171 176 View in Reaxys

97 %

With dihydrogen peroxide, benzyltrimethylazanium tribroman-2-uide in water, acetonitrile, Time= 1h, T= 60 °C , Green chemistry Dey, Madhudeepa; Dhar, Siddhartha Sankar; Kalita, Mukul; Synthetic Communications; vol. 43; nb. 12; (2013); p. 1734 - 1742 View in Reaxys

97 %

With potassium hydoxide in N,N-dimethyl-formamide, Time= 4h, T= 20 °C Zhang, Qi; Cai, Shuangfei; Li, Linsen; Chen, Yifeng; Rong, Hongpan; Niu, Zhiqiang; Liu, Junjia; He, Wei; Li, Yadong; ACS Catalysis; vol. 3; nb. 7; (2013); p. 1681 - 1684 View in Reaxys

97 %

With tert.-butylnitrite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, boron trifluoride diethyl etherate in dichloromethane, Time= 1.5h, Inert atmosphere, Reflux, Solvent, Temperature, Time Holan, Martin; Jahn, Ullrich; Organic Letters; vol. 16; nb. 1; (2014); p. 58 - 61 View in Reaxys

97 %

With dmap, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper diacetate in neat (no solvent), Time= 24h, T= 25 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Temperature Guan, Mingyu; Wang, Chao; Zhang, Jingyu; Zhao, Yingsheng; RSC Advances; vol. 4; nb. 90; (2014); p. 48777 48782 View in Reaxys

97 %

With hydrogenchloride, tert.-butylnitrite, TEMPOL, oxygen, chloranil in neat (no solvent), Time= 5h, T= 20 °C , p= 760.051Torr , Green chemistry, Reagent/catalyst Dong, Yanli; Zhao, Xiaomei; Liu, Renhua; Chinese Journal of Chemistry; vol. 33; nb. 9; (2015); p. 1019 - 1023 View in Reaxys

97 %

General condition for alcohol oxidation Complex 3a (7.4mg, 9.5μmol, 5molpercent), 1,2-dichlorobenzene (3mL), and the appropriate amount of [Ce(NH3)6] (NO3)2 dissolved in MeCN (0.5mL) were stirred at reflux for 15min. Benzyl alcohol (20μL, 190μmol) was then added. Aliquots (0.05mL) were taken from the mixture at selected intervals, diluted with CDCl3 (0.5mL) and conversions were determined by 1H NMR spectroscopy.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

22/438

2018-03-11 22:07:32


With ammonium cerium (IV) nitrate, dicarbonyl-(η4-3,4-bis(4-methoxyphenyl)-2,5-diphenylcyclopenta-2,4-dienone) (1,3-dimethyl-4-phenyl-1,2,3-triazolylidene)ruthenium in 1,2-dichloro-benzene, acetonitrile, Time= 24h, T= 150 °C , Catalytic behavior, Reagent/catalyst, Time Cesari, Cristiana; Mazzoni, Rita; Müller-Bunz, Helge; Albrecht, Martin; Journal of Organometallic Chemistry; vol. 793; (2015); p. 256 - 262; Art.No: 18922 View in Reaxys 97 %

With 1,1,1,3',3',3'-hexafluoro-propanol, oxygen, nitric acid, Time= 22h, T= 20 °C Možina, Štefan; Stavber, Stojan; Iskra, Jernej; European Journal of Organic Chemistry; vol. 2017; nb. 3; (2017); p. 448 - 452 View in Reaxys

97.6 %

With nickel dichloride in water, Time= 6h, T= 20 °C , pH= 9, Inert atmosphere, Irradiation, Reagent/catalyst, pH-value Zhao, Lei-Min; Meng, Qing-Yuan; Fan, Xiang-Bing; Ye, Chen; Li, Xu-Bing; Chen, Bin; Ramamurthy, Vaidhyanathan; Tung, Chen-Ho; Wu, Li-Zhu; Angewandte Chemie - International Edition; vol. 56; nb. 11; (2017); p. 3020 3024; Angew. Chem.; vol. 129; nb. 11; (2017); p. 3066 - 3070,5 View in Reaxys

97 %

General procedure for the oxidation of alcohols General procedure: A 10 mL side-armed round bottomed flask equipped witha magnetic stirring bar and a balloon filled with air was chargedwith alcohol (1 mmol), catalyst PdTiC (25 mg) and acetonitrile(2 mL). The reaction mixturewas exposed to visible light irradiationusing 20 W domestic bulb (Fig. 3) and the progress of reaction wasmonitored using TLC. After the completion of the reaction, thePdTiC catalyst was separated using a centrifuge and the productwas isolated by extracting with ethyl acetate, dried over sodiumsulfate, concentrated under reduced pressure and characterized. With palladium nanoparticle grafted titanium cluster, air in acetonitrile, Time= 8h, Irradiation Verma, Sanny; Nasir Baig; Nadagouda, Mallikarjuna N.; Varma, Rajender S.; Tetrahedron; vol. 73; nb. 38; (2017); p. 5577 - 5580 View in Reaxys

97 %

With dihydrogen peroxide in water, Time= 2h, T= 60 °C Soleimani, Ebrahim; Yaesoobi, Nadieh; Ghasempour, Hamid Reza; Applied Organometallic Chemistry; vol. 32; nb. 2; (2018); Art.No: E4006 View in Reaxys

96 %

With silica gel, copper(II) nitrate in tetrachloromethane, Time= 1h, Zn(NO3)2 Nishiguchi, Takeshi; Asano, Fumi; Tetrahedron Letters; vol. 29; nb. 48; (1988); p. 6265 - 6266 View in Reaxys

96 %

With sodium hydroxide, potassium ferrate(VI), N-benzyl-N,N,N-triethylammonium chloride in benzene, Time= 0.1h, T= 25 °C Kwan Soo Kim; Young Kil Chang; Sun Kun Bae; Chi Sun Hahn; Synthesis; nb. 10; (1984); p. 866 - 868 View in Reaxys

96 %

With potassium permanganate, sulfuric acid, triethylamine in chloroform, Ambient temperature Li, Wen-Shan; Liu, Lilian Kao; Synthesis; nb. 4; (1989); p. 293 - 295 View in Reaxys

96 %

With tetrabutylammomium bromide, dihydrogen peroxide, [Ru3O(OAc)6(MeOH)3](1+)*AcO(1-) in dichloromethane, Time= 2h Wynne; Lloyd; Witsil; Mushrush; Stalick; Organic Preparations and Procedures International; vol. 32; nb. 6; (2000); p. 588 - 592 View in Reaxys

96 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, periodic acid in dichloromethane, Time= 0.166667h, T= 20 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

23/438

2018-03-11 22:07:32


Kim, Sung Soo; Nehru, Kasi; Synlett; nb. 4; (2002); p. 616 - 618 View in Reaxys 96 %

With α,α,α-trifluorotoluene, oxygen, Ru*Co(2+)*2OH(1-)*CeO2, Time= 1h, T= 60 °C , atmospheric pressure Ji, Hongbing; Mizugaki, Tomoo; Ebitani, Kohki; Kaneda, Kiyotomi; Tetrahedron Letters; vol. 43; nb. 40; (2002); p. 7179 - 7183 View in Reaxys

96 %

With air, Na6.3Fe0.9[AlMo11O39]*2H2O in toluene, Time= 1h, T= 80 °C , atmospheric pressure Wang, Jianmin; Yan, Liang; Qian, Guang; Wang, Xiaolai; Tetrahedron Letters; vol. 47; nb. 40; (2006); p. 7171 7174 View in Reaxys

96 %

With hydrogen bromide, sodium bromide in chloroform, T= 20 °C , Electrochemical reaction Raju, Thasan; Manivasagan, Sankar; Revathy, Balachandran; Kulangiappar, Kumarasamy; Muthukumaran, Arunachalam; Tetrahedron Letters; vol. 48; nb. 21; (2007); p. 3681 - 3684 View in Reaxys

96 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, tert.-butylnitrite, oxygen in 1,2-dichloro-ethane, Time= 2h, p= 1500.15Torr , Autoclave, Heating He, Xijun; Shen, Zhenlu; Mo, Weimin; Sun, Nan; Hu, Baoxiang; Hu, Xinquan; Advanced Synthesis and Catalysis; vol. 351; nb. 1-2; (2009); p. 89 - 92 View in Reaxys

96 %

With dimethyl sulfoxide, N-ethyl-N,N-diisopropylamine, trifluoroacetic anhydride in dichloromethane, T= 70 °C , Automated microreactor, Large scale reaction, Swern-Moffatt oxidation Nieuwland, Pieter J.; Koch, Kaspar; Van Harskamp, Noud; Wehrens, Ron; Van Hest, Jan C. M.; Rutjes, Floris P. J. T.; Chemistry - An Asian Journal; vol. 5; nb. 4; (2010); p. 799 - 805 View in Reaxys

96 %

With tert.-butylhydroperoxide in acetonitrile, Time= 6h, T= 80 °C Behera, Gobinda Chandra; Parida; Applied Catalysis A: General; vol. 413-414; (2012); p. 245 - 253 View in Reaxys

96 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, potassium tert-butylate, copper(ll) bromide in water, acetonitrile, Time= 4h, T= 25 °C , air Hu, Zhenzhong; Kerton, Francesca M.; Applied Catalysis A: General; vol. 413-414; (2012); p. 332 - 339 View in Reaxys

96 %

With Mn3O4 in N,N-dimethyl-formamide, Time= 4h, T= 80 °C , γ-irradiation Sun, Hua-Yin; Hua, Qing; Guo, Feng-Feng; Wang, Zhi-Yong; Huang, Wei-Xin; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 569 - 573 View in Reaxys

96 %

With manganese dioxide supported on aluminum silicate in dichloromethane, Time= 12h, Reflux Huang, Li-Hong; Ma, Yi-Chun; Zhang, Changhe; Wang, Qiang; Zou, Xiao-Nan; Lou, Ji-Dong; Synthetic Communications; vol. 42; nb. 22; (2012); p. 3377 - 3382 View in Reaxys

96 %

2.3 General procedures for the oxidation of alcohols General procedure: To a 25 mL round-bottom flask, ionic liquid (5.6 mmol), Mn(OAc)2 (0.025 molpercent), alcohol (3 mmol), and n-heptane (6 mL) were added. De-ionized water (0.5 mL) was added to lower the viscosity of the mixture. The resulting solution was then kept stirring vigorously. Under ambient conditions, aqueous hydrogen peroxide (6× 60 μL, 35 wt.percent in water) was injected into the reaction mixture in 3 min intervals over 20 min. After the reaction had been completed, the n-heptane solution (upper layer) was carefully decanted from the ionic liquid medium. In order to completely extract the aldehyde from the ionic liquid with residual n-heptane, additional n-heptane (2× 5 mL) was added and the combined organic solution was then dried over anhydrous sodium sulfate. After the removal of solvent under vacuum, the aldehyde was isolated as a colourless liquid and characterized by GC–MS

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

24/438

2018-03-11 22:07:32


and 1H NMR. The n-heptane collected was reused in catalysis and extraction process. It was found that the use of nheptane, n-hexane, n-pentane, or petroleum ether (40–60 °C) as the extraction phase in the catalysis showed no observable difference as these solvents are immiscible with the ionic liquid. However, heptane was chosen because it is considered as a greener alternative solvent for chemical processes [20]. With dihydrogen peroxide, manganese(II) acetate in n-heptane, water, Time= 0.333333h, T= 25 °C , Ionic liquid, Solvent, chemoselective reaction Wong, Wing-Leung; Ho, Kam-Piu; Lee, Lawrence Yoon Suk; So, Ming-Him; Chan, Tak Hang; Wong, KwokYin; Applied Catalysis A: General; vol. 453; (2013); p. 244 - 249 View in Reaxys 96 %

Aerobic oxidation of benzyl alcohols A mixture of K2CO3 (1 mmol) and the catalyst (52 mg, ∼3 molpercent of Pd2+) in toluene (5 ml) was prepared in a two necked flask. The flask was evacuated and refilled with pure oxygen. To this solution, the alcohol (1 mmol, in 1 ml toluene) was injected and the resulting mixture was stirred at 80 °C under an oxygen atmosphere. After completion of reaction, the reaction mixture was filtered off and the catalyst rinsed twice with CH2Cl2 (5 ml). The excess of solvent was removed under reduced pressure to give the corresponding carbonyl compounds. With oxygen, potassium carbonate in toluene, Time= 24h, T= 80 °C , Concentration, Temperature, Reagent/catalyst, Time Alizadeh; Khodaei; Kordestania; Beygzadeh; Journal of Molecular Catalysis A: Chemical; vol. 372; (2013); p. 167 - 174 View in Reaxys

96 %

The catalytic oxidation of alcohol was carried out in a magnetically stirredglass reaction tube fitted with a reflux condenser. A typical procedure was asfollows using benzyl alcohol as model substrate: benzyl alcohol (2 mmol) andRu(bbp)(pydic) (2 103 mmol, 0.1 mol percent based substrate) were added into areaction tube. The reactor containing this mixture was heated to 60 C in an oilbath under vigorous stirring, and then 30percent H2O2 (10 mmol) was slowlydropped in. The resulting system was stirred at 60 C for 60 min. At the end ofreaction, the resulting products and unreacted substrate were extracted bydichloromethane three times. The extracted liquid mixture was analyzed byGC and GC–MS. GC analyses were performed on a Shimadzu GC-2010 pluschromatography equipped with Rtx-5 capillary column(30 m 0.25 mm 0.25 lm). GC–MS analyses were recorded on a ShimadzuGCMS-QP2010 equipped with Rxi-5 ms capillary column(30 m 0.25 mm 0.25 lm). With C26H16N6O4Ru, dihydrogen peroxide, Time= 1h, T= 60 °C , Solvent Zhou, Xian-Tai; Ji, Hong-Bing; Liu, Sheng-Gui; Tetrahedron Letters; vol. 54; nb. 29; (2013); p. 3882 - 3885 View in Reaxys

96 %

oxidation of allylic and benzylic alcohol General procedure: Chloramine-T (0.5 equiv) was added to a solution of K2[OsO2 (OH)4] (3 molpercent) in tBuOH/H2O (1:1) followed by the addition of alcohol (1.0 mmol) and kept on stirring till completion (confirmed by TLC). The reaction was quenched by adding sodium sulphite(Na2SO3) and stirred for 30 min. The mixture after extraction with ethyl acetate (twice), usualworkup and purification over silica gel column using Hexane:EtOAc (95:5) afforded pure products. With potassium osmate, chloroamine-T in water, tert-butyl alcohol, Time= 0.75h, T= 20 °C , Temperature, chemoselective reaction Devari, Shekaraiah; Deshidi, Ramesh; Kumar, Manjeet; Kumar, Arvind; Sharma, Simmi; Rizvi, Masood; Kushwaha, Manoj; Gupta, Ajai Prakash; Shah, Bhahwal Ali; Tetrahedron Letters; vol. 54; nb. 48; (2013); p. 6407 6410 View in Reaxys

96 %

The procedure for the oxidation of benzyl alcohol is as follows: General procedure: A mixture of H2O (5 mL) and CH2Cl2 (5 mL) wasadded to the chlorinated polymeric beads (2 g). (The unchlorinated beads were obtained from HaloSource, Inc. The unchlorinated beads were chlorinated by soaking the beads in bleach solution, with pH adjusted to 7 by additionof AcOH, for an hour. Then, the chlorinated beads were filtered and dried in air.) After addition of TEMPO (10 mg,0.064 mmol) and benzyl alcohol (0.2 g, 1.8 mmol), NaHCO3(0.5 g) was added to the mixture. The mixture was stirred at r.t. for 3 h and filtered. The residue on the filter

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

25/438

2018-03-11 22:07:32


paper was washed with H2O (20 mL) and CH2Cl2 (10 mL), and the organic phase of the filtrate was separated, dried over MgSO4, and filtered. The solvent was removed under vacuum to obtain benzaldehyde. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium hydrogencarbonate in dichloromethane, water, Time= 3h, T= 20 °C , Green chemistry, chemoselective reaction Akdag, Akin; Öztürk, Perihan; Synlett; vol. 24; nb. 18; (2013); p. 2451 - 2453; Art.No: ST-2013-D0669-L View in Reaxys 96 %

With oxygen in water, Time= 4h, T= 80 °C , pH= 5, Green chemistry, Time, pH-value Nabid, Mohammad Reza; Bide, Yasamin; Aghaghafari, Elham; Rezaei, Seyed Jamal Tabatabaei; Catalysis Letters; vol. 144; nb. 2; (2014); p. 355 - 363 View in Reaxys

96 %

With [Imim-PEG1000-TEMPO][CuCl2 -] in neat (no solvent), Time= 12h, T= 60 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Solvent, Temperature Wang, Zhao-Gang; Jin, Yong; Cao, Xiao-Hua; Lu, Ming; New Journal of Chemistry; vol. 38; nb. 9; (2014); p. 4149 - 4154 View in Reaxys

96 %

With dmap, 9-azabicyclolt;3.3.1gt;nonane-N-oxyl, copper(l) chloride in water, Time= 5h, T= 20 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Solvent Zhang, Guoqi; Yang, Chengxiong; Liu; Li, Li; Golen, James A.; Rheingold, Arnold L.; RSC Advances; vol. 4; nb. 106; (2014); p. 61907 - 61911 View in Reaxys

96%

With oxygen, Azobenzene, sodium bromide in 1,4-dioxane, Time= 24h, T= 80 °C Liu, Chengkou; Fang, Zheng; Yang, Zhao; Li, Qingwen; Guo, Shiyu; Guo, Kai; RSC Advances; vol. 5; nb. 97; (2015); p. 79699 - 79702 View in Reaxys

96 %

With oxygen in dodecane, toluene, Time= 9h, T= 84.84 °C , Catalytic behavior, Reagent/catalyst, Temperature Srivastava, Rajendra; Sarmah, Bhaskar; Satpati, Biswarup; RSC Advances; vol. 5; nb. 33; (2015); p. 25998 26006 View in Reaxys

96 %

2.5. General procedure for Cu(II) complex catalyzed aerobic oxidation of alcohol toaldehyde General procedure: Here, we have reported aerobic oxidation of alcohol to aldehyde using 3. In this method,substrate (4 mmol), 5 molpercent Cu(II) complex, and ammonium persulfate (5 mmol) wereadded to 20 mL acetonitrile. The reaction mixture was stirred at room temperature. Theconversion takes place within 2 min, and the progress of the reaction was monitored byTLC. The product was extracted with EtOAc and purified by column chromatography. Thereaction scheme is shown in scheme 2. With ammonium peroxydisulfate, C48H36Cu2N4O8S2 in acetonitrile, Time= 0.0333333h, T= 20 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Solvent Sarma, Kuladip; Devi, Namita; Kalita, Mukul; Sarma, Bipul; Barman, Pranjit; Journal of Coordination Chemistry; vol. 68; nb. 20; (2015); p. 3685 - 3700 View in Reaxys

96 %

Catalytic Experiments The oxidation reactions were carried out in a100 mL flat-bottomed flask. In a typical run, benzylalcohol (0.2 mL), K2FeO4 (4 mmol), acetic acid(0.3 mL), 20 mL of cyclohexane as a solvent and 0.5 gof freshly calcined zeolite were used. The samples ofreaction mixture were filtered and analyzed using Shimadzugas chromatograph (GC-14C) equipped with aflame photometric detector (FPD). A capillary column(30 m × 0.32 mm × 0.30 μm) was used. The followingtemperature program was employed: 60°C(3 min), from 60 to 280°C with a slope of 15°C/min,maintained for 8 min. With potassium ferrate(VI), acetic acid in cyclohexane, Time= 4h, T= 30 °C , Molecular sieve, Green chemistry, Catalytic behavior, Reagent/catalyst, Temperature, Time

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

26/438

2018-03-11 22:07:32


Wang, Yuan-Yuan; Song, Hua; Song, Hua-Lin; Jin, Zai-Shun; Russian Journal of Physical Chemistry A; vol. 90; nb. 10; (2016); p. 1931 - 1935 View in Reaxys 96 %

General procedure for oxidation of some benzylic alkoholswith (1) General procedure: Benzyl alkohol (1 mmol) was dissolved in CH3CN (10 mL) in a25 mL round bottomed flask equipped with a condensor and amagnetic stirrer. Title oxidant (1mmol, 1.30 g) was added underreflux conditions. The progress of the reactionwasmonitored byTLC(eluent: n-hexane/EtOAc 7:3).After completion of the reaction,the mixture was filtered and the solvent was evaporated.The resulted crude product was purified on a silica-gel (20 ×20 cm) plate (n-hexane/EtOAc 4:1). Pure carbonyl compoundswere obtained in 87–98percent yields, which were characterized bycomparison with authentic samples (Scheme 1). With 1,2-ethandiylbis(triphenylphosphonium) peroxodisulfate dihydrate in acetonitrile, Time= 0.0833333h, Reflux Salmasi; Salimi; Gholizadeh; Abolghasempour; Garrison, Jered C.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; nb. 10; (2016); p. 1380 - 1387 View in Reaxys

96 %

With [(η5-Cp*)Ir(1-benzyl-3-phenylselenomethyl-1,3-dihydrobenzoimidazole-2-selenone)Cl][PF6], potassium tert-butylate in toluene, Time= 6h, T= 80 °C , Reagent/catalyst Sharma, Alpesh K.; Joshi, Hemant; Bhaskar, Renu; Singh, Ajai K.; Dalton Transactions; vol. 46; nb. 7; (2017); p. 2228 - 2237 View in Reaxys

96 %

General procedure for oxidation of alcohols General procedure: In a 10-mL round-bottom flask equipped with O2-filled balloon (~1 atm.), a mixture of alcohol (1 mmol), absolute ethanol (3 mL) and 10 mg of catalyst 4 (3.2 molpercent) was stirred at room temperature. After the completion of the reactions that monitored by thin layer chromatography(TLC), the catalyst was filtered off and the reaction mixture was extracted to CH2Cl2and were purified with silica gel plate chromatography (Scheme 2). The oxidation of primary alcohols proceeds to aldehyde stage and was not observed any carboxylic acid product identified by TLC.The reactions also were performed in the absence of catalyst or in the absence of oxidant in the same conditions. With oxygen in ethanol, Time= 0.5h, T= 20 °C , p= 760.051Torr , Green chemistry, Catalytic behavior, Temperature, Solvent Kazemnejadi, Milad; Shakeri, Alireza; Mohammadi, Mohammad; Tabefam, Marzieh; Journal of the Iranian Chemical Society; vol. 14; nb. 9; (2017); p. 1917 - 1933 View in Reaxys

96%

4 :General procedure: To 10 mL of a microwave tube was added benzyl alcohol (0.5 mmol, 61.2 mg) and triphenylmethanol (0.5 mmol,(0.015 mmol, 11 mg) was added, the reaction mixture was heated to 120 ° C with a microwave reactor, and the reaction was stirred for 60 minutes. After completion of the reaction, the reaction product was separated by flash column chromatography to obtain the desired product I, 92percent.Substitution of 37.0 mg of Ph3PAuNTf2 for 11 mg of Ph3PAuNTf2,In the same manner as in Example 1,The target compound I,Yield 96percent. With triphenylmethyl alcohol, triphenylphosphinegold(I) bis(trifluoromethanesulfonyl)imidate, Time= 1h, T= 120 °C , Microwave irradiation Patent; Shenyang Pharmaceutical University; Liu Yongxiang; Cheng Maosheng; Wang Xiaoyu; Du Chuan; Shi Hui; Wang Yanshi; Liu Yang; (8 pag.); CN104817441; (2017); (B) Chinese View in Reaxys

96 %

General procedure to prepare carbonyl compounds 2a–v. 2,2,6,6-Tetramethylpiperidine 1-oxyl (TEMPO, 9.4 mg,0.06 mmol, 3 mol percent), 2,2′-bipyridyl (9,4 mg, 0.06 mmol,3 mol percent), [Cu(CN)4]OTf (22.6 mg, 0.06 mmol, 3 mol percent) and1-methylimidazole (NMI, 11.5 mg, 11.2 μL, 0.14 mmol,7 mol percent) were placed in a zirconia-milling beaker (45 mL)equipped with four balls (two balls × 5 mm , two balls ×12 mm ) of the same material. The jar was sealed and ballmilled for 1 min. Then, benzyl alcohol (216.3 mg, 207 μL,2.0 mmol), NaCl (1.0 g) together with other two zirconia balls(12 mm ) were added and the reaction mixture was subjectedto grinding for further 10 minutes overall (two cycles of5 minutes each). The first milling cycle was followed by a breakof 2 min leaving in the meantime the uncovered jar in open air.The progress of the reaction was monitored by TLC analysis(heptane/AcOEt 9:1 v/v) and GC–MS analysis on an aliquot ofthe crude. Upon completion

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

27/438

2018-03-11 22:07:32


of the ball milling process, the jarwas opened, the milling balls were removed and the resultingcrude product (adsorbed on NaCl) was then easily transferredinto a separating funnel filled with an aqueous 10percent citric acidsolution (20 mL). The aqueous phase was extracted withcyclopentyl methyl ether (or alternatively with AcOEt)(3 × 15 mL). The combined organic fractions were washed withH2O (25 mL) and brine (25 mL), then dried over Na2SO4, andconcentrated in vacuo to give benzaldehyde in high yield (195 mg, 92percent) and good purity (>93percent by GC analysis). Alternatively, after completion of the reaction, the resulting crudeproduct (adsorbed on NaCl) can be also easily purified by ashort column chromatography on silica gel using heptane/ethylacetate (9:1 v/v) as the eluents to afford pure aldehyde 2b inhigh yield (202 mg, 95percent) as a colourless liquid. With 1-methyl-1H-imidazole, [2,2]bipyridinyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate, sodium chloride in neat (no solvent), Milling, Green chemistry, Concentration Porcheddu, Andrea; Colacino, Evelina; Cravotto, Giancarlo; Delogu, Francesco; De Luca, Lidia; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 2049 - 2055 View in Reaxys 96 %

With silver nano particles dispersed dispersed water extract of fly ash, Time= 4h, T= 70 °C , Inert atmosphere, Green chemistry, Temperature Bhuyan, Bishal; Paul, Arijita; Devi, Meghali; Dhar, Siddhartha Sankar; RSC Advances; vol. 8; nb. 3; (2018); p. 1313 - 1319 View in Reaxys

96 %

10 With phosphoric acid in water, toluene, Time= 18h, T= 25 °C , pH= 3.4, Inert atmosphere, Irradiation Patent; 国立大学法人名古屋大学; Noyori Yoshiharu; Saito Susumu; Naka Hiroshi Shi; Ryuu Jigun; Kudo Akihiko; (12 pag.); JP5991521; (2016); (B2) Japanese View in Reaxys

95 %

With iodobenzene, tetrabutyl-ammonium chloride, palladium diacetate in N,N-dimethyl-formamide, Time= 48h, Ambient temperature Choudary, B. M.; Reddy, N. Prabhakar; Kantam, M. Lakshmi; Jamil, Zafar; Tetrahedron Letters; vol. 26; nb. 50; (1985); p. 6257 - 6258 View in Reaxys

95 %

With zinc dichromate(VI) in dichloromethane, Time= 0.1h, Ambient temperature Firouzabadi, H.; Sardarian, A. R.; Moosavipour, H.; Afshari, G. M.; Synthesis; nb. 4; (1986); p. 285 - 288 View in Reaxys

95 %

With sulfuric acid, oxygen, sodium nitrite in hexane, Time= 1h, or heptane Levina, A. B.; Trusov, S. R.; J. Gen. Chem. USSR (Engl. Transl.); vol. 60; nb. 8.2.; (1990); p. 1932 - 1933,1726 View in Reaxys

95 %

With bis(2,2'-bipyridyl) copper(II) permanganate in dichloromethane, Time= 0.25h, Ambient temperature Firouzabadi, H.; Sardarian, A. R.; Naderi, M.; Vessal, B.; Tetrahedron; vol. 40; nb. 23; (1984); p. 5001 - 5004 View in Reaxys

95 %

With nitric acid in nitromethane, Time= 1.7h, T= 60 °C Gasparrini, F.; Giovannoli, M.; Misiti, D.; Natile, G.; Palmieri, G.; Synthetic Communications; vol. 18; nb. 1; (1988); p. 69 - 76 View in Reaxys

95 %

With cerous hydroxide in benzene, Time= 0.5h, Heating Firouzabadi, H.; Iranpoor, N.; Synthetic Communications; vol. 14; nb. 9; (1984); p. 875 - 882 View in Reaxys

95 %

With trislt;trinitratocerium(IV)gt; paraperiodate in benzene, Time= 0.5h, Heating

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

28/438

2018-03-11 22:07:32


Firouzabadi, H.; Iranpoor, N.; Hajipoor, G.; Toofan, J.; Synthetic Communications; vol. 14; nb. 11; (1984); p. 1033 - 1042 View in Reaxys 95 %

With lt;Ce(NO3)3gt;2CrO4 in benzene, Time= 0.5h, Heating Firouzabadi, H.; Iranpoor, N.; Parham, H.; Tootan, J.; Synthetic Communications; vol. 14; nb. 7; (1984); p. 631 638 View in Reaxys

95 %

With barium ferrate(VI) in benzene, Time= 0.8h, Heating Firouzabadi, Habib; Mohajer, Daryoush; Entezari-Moghadam, Mohsen; Bulletin of the Chemical Society of Japan; vol. 61; (1988); p. 2185 - 2190 View in Reaxys

95 %

With chromium (VI) oxide in toluene, Time= 1h, Heating Lee, Ross A.; Donald, Dennis S.; Tetrahedron Letters; vol. 38; nb. 22; (1997); p. 3857 - 3860 View in Reaxys

95 %

With 4 A molecular sieve, polymer supported perruthenate, 4-methylmorpholine N-oxide in dichloromethane, Time= 48h, Ambient temperature Hinzen, Berthold; Ley, Steven V.; Journal of the Chemical Society - Perkin Transactions 1; nb. 13; (1997); p. 1907 1908 View in Reaxys

95 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, [bis(acetoxy)iodo]benzene in dichloromethane, Time= 0.5h De Mico, Antonella; Margarita, Roberto; Parlanti, Luca; Vescovi, Andrea; Piancatelli, Giovanni; Journal of Organic Chemistry; vol. 62; nb. 20; (1997); p. 6974 - 6977 View in Reaxys

95 %

With lt;Ce(NO3)2gt;2CrO4 in benzene, Time= 0.5h, Heating, reaction in CH2Cl2; mild oxidation of benzylic alcohols to aldehydes and ketones, Product distribution Firouzabadi, H.; Iranpoor, N.; Parham, H.; Tootan, J.; Synthetic Communications; vol. 14; nb. 7; (1984); p. 631 638 View in Reaxys

95 %

With barium ferrate(VI) in benzene, Time= 0.8h, Heating, Product distribution Firouzabadi, Habib; Mohajer, Daryoush; Entezari-Moghadam, Mohsen; Bulletin of the Chemical Society of Japan; vol. 61; (1988); p. 2185 - 2190 View in Reaxys

95 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, [bis(acetoxy)iodo]benzene in dichloromethane, Time= 0.5h, various alcohols under different reaction conditions, Product distribution, Mechanism De Mico, Antonella; Margarita, Roberto; Parlanti, Luca; Vescovi, Andrea; Piancatelli, Giovanni; Journal of Organic Chemistry; vol. 62; nb. 20; (1997); p. 6974 - 6977 View in Reaxys

95 %

With Amberlyst A-27 supported permanganate in dichloromethane Caldarelli, Marina; Habermann, Joerg; Ley, Steven V.; Journal of the Chemical Society - Perkin Transactions 1; nb. 2; (1999); p. 107 - 110 View in Reaxys

95 %

With potassium permanganate, zirconium(IV) oxychloride in diethyl ether, Time= 3.5h, T= 20 °C Firouzabadi; Fakoorpour; Hazarkhani; Synthetic Communications; vol. 31; nb. 24; (2001); p. 3859 - 3862 View in Reaxys

95 %

With modified o-iodoxybenzoic acid in water, Time= 3h, T= 60 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

29/438

2018-03-11 22:07:32


Thottumkara, Arun P; Vinod, Thottumkara K; Tetrahedron Letters; vol. 43; nb. 4; (2002); p. 569 - 572 View in Reaxys 95 %

With hydrogen bromide, dimethyl sulfoxide, Time= 4h, T= 100 °C Li, Chunbao; Xu, Yanli; Lu, Ming; Zhao, Zhuxuan; Liu, Lanjun; Zhao, Zheyuan; Cui, Yi; Zheng, Pengwu; Ji, Xioujie; Gao, Guangjie; Synlett; nb. 12; (2002); p. 2041 - 2042 View in Reaxys

95 %

With potassium perrhuthenate in dichloromethane, Time= 24h, T= 20 °C Wu, Daniel L.; Wight, Andrea P.; Davis, Mark E.; Chemical Communications; nb. 6; (2003); p. 758 - 759 View in Reaxys

95 %

With tetramethylammonium monofluorochromate(VI) in dichloromethane, Time= 0.666667h, T= 20 °C Mahjoub, Ali Reza; Ghammami, Shahriare; Kassaee, Mohammad Zaman; Tetrahedron Letters; vol. 44; nb. 24; (2003); p. 4555 - 4557 View in Reaxys

95 %

With sodium dichromate, sulfuric acid, silica gel in dichloromethane, Time= 0.25h, T= 20 °C Mirjalili, BiBi Fatemeh; Zolfigol, Mohamad Ali; Bamoniri, Abdolhamid; Zarei, Amin; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 178; nb. 8; (2003); p. 1845 - 1849 View in Reaxys

95 %

Stage 1: With dimethylsulfide, N,N'-dibromo-N,N'-(1,2-ethanediyl)bis(p-toluenesulfonamide) in dichloromethane, Time= 3h, T= -15 °C Stage 2: With triethylamine in dichloromethane, T= 20 °C Ghorbani-Vaghei, Ramin; Khazaei, Ardeshir; Tetrahedron Letters; vol. 44; nb. 40; (2003); p. 7525 - 7527 View in Reaxys

95 %

With sodium dichromate, sulfuric acid, silica gel, Time= 0.5h, T= 20 °C , Product distribution, Further Variations: Reagents Mirjalili, Bibi Fatemeh; Zolfigol, Mohamad Ali; Bamoniri, Abdolhamid; Zarei, Amin; Journal of the Chinese Chemical Society; vol. 51; nb. 3; (2004); p. 509 - 512 View in Reaxys

95.5 %

With 4-methylmorpholine N-oxide, [RuCl2(AsPh3)2('mono basic bidentate Shiff base ligand')] in dichloromethane, Time= 3h, Heating, Product distribution, Further Variations: Catalysts Venkatachalam; Ramesh; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 61; nb. 9; (2005); p. 2081 - 2087 View in Reaxys

95 %

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione, Time= 1h, T= 60 °C Moorthy, Jarugu Narasimha; Singhal, Nidhi; Venkatakrishnan; Tetrahedron Letters; vol. 45; nb. 28; (2004); p. 5419 - 5424 View in Reaxys

95 %

With nitric acid, phosphorus pentoxide, silica gel, Time= 0.0166667h Hajipour, Abdol R.; Guo, Lian-Wang; Ruoho, Arnold E.; Molecular Crystals and Liquid Crystals; vol. 456; nb. 1; (2006); p. 85 - 93 View in Reaxys

95 %

With hydrogenchloride, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium nitrite in dichloromethane, water, Time= 10h, T= 20 °C , p= 760.051Torr , in air Wang, Xinliang; Liu, Renhua; Jin, Yu; Liang, Xinmiao; Chemistry - A European Journal; vol. 14; nb. 9; (2008); p. 2679 - 2685 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

30/438

2018-03-11 22:07:32


95 %

5 :8.9mg (0.03mmol) of 2-iodo-5-methylbenzenesulfonic acid, prepared by Preparation Example 2, 2.04g (3.3mol) of powdered Oxone (registered trademark) and 324mg (3mmol) of benzyl alcohol were added to 3.75ml acetonitrile, and the mixture was heated at 70 C while being stirred for one hour. The later treatment was carried out in the same way as in Example 1, and then benzaldehyde was obtained. The yield of the obtained benzaldehyde was determined and the result is shown in Table 1. With potassium peroxymonosulfate, 2-Iodo-5-methylbenzenesulfonic acid in acetonitrile, Time= 1h, T= 70 °C Patent; National University Corporation Nagoya University; EP2085373; (2009); (A1) English View in Reaxys

95 %

With triphenylmethylphosphonium dichromate, Time= 0.05h, T= 20 °C , Neat (no solvent), chemoselective reaction Hajipour, Abdol R.; Safaei, Somayeh; Ruoho, Arnold E.; Synthetic Communications; vol. 39; nb. 20; (2009); p. 3687 - 3692 View in Reaxys

95 %

With hydrogen bromide, potassium nitrate, sodium bromide in dichloromethane, water, Electrochemical reaction Zhang, Li; Zha, Zhenggen; Wang, Zhiyong; Fu, Shengquan; Tetrahedron Letters; vol. 51; nb. 10; (2010); p. 1426 - 1429 View in Reaxys

95 %

With sodium tetrahydroborate, 1 Pd/C, water, oxygen, potassium carbonate in ethanol, Time= 0.33h, T= 20 °C An, Gwangil; Ahn, Hyunseok; De Castro, Kathlia A.; Rhee, Hakjune; Synthesis; nb. 3; (2010); p. 477 - 485; Art.No: F19009SS View in Reaxys

95 %

With N,N'-(1,2-phenylene)bis(salicylaldimidato)manganese(III) chloride, tetra-n-butylammonium hydrogen monopersulfate in acetonitrile, Time= 0.05h, T= 25 °C Rezaeifard, Abdolreza; Jafarpour, Maasoumeh; Nasseri, Mohammad Ali; Haddad, Reza; Helvetica Chimica Acta; vol. 93; nb. 4; (2010); p. 711 - 717 View in Reaxys

95 %

With sulfuric acid, oxygen, sodium nitrite in dichloromethane, Time= 2h, T= 20 °C , p= 3750.38Torr , Autoclave Sheng, Xuebin; Ma, Hong; Chen, Chen; Gao, Jin; Yin, Guochuan; Xu, Jie; Catalysis Communications; vol. 11; nb. 15; (2010); p. 1189 - 1192 View in Reaxys

95 %

With hexamethylenebis(N-methylimidazolium) dichlorochromate, Time= 0.25h, T= 80 °C Hosseinzadeh, Rahman; Mohadjerani, Maryam; Tajbakhsh, Mahmood; Nouzarian, Mahboobe; Synthetic Communications; vol. 41; nb. 12; (2011); p. 1725 - 1732 View in Reaxys

95 %

With dipotassium peroxodisulfate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, iodobenzene, trifluoroacetic acid in water, acetonitrile, Time= 1h, T= 40 °C Zhu, Chenjie; Ji, Lei; Wei, Yunyang; Monatshefte fur Chemie; vol. 141; nb. 3; (2010); p. 327 - 331 View in Reaxys

95 %

With oxygen, pyridium nitrate, Time= 4h, T= 110 °C , p= 750.075Torr , neat (no solvent) Shi, Shenyi; Kong, Aiguo; Zhao, Xinhua; Shan, Yongkui; Synthetic Communications; vol. 41; nb. 20; (2011); p. 3066 - 3070 View in Reaxys

95 %

With 1-methyl-1H-imidazole, [2,2]bipyridinyl, tetrakis(actonitrile)copper(I) hexafluorophosphate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in acetonitrile, Time= 3h, T= 20 °C Hoover, Jessica M.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 133; nb. 42; (2011); p. 16901 - 16910 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

31/438

2018-03-11 22:07:32


95 %

With morpholinium fluorochromate(VI) absorbed on wet silica gel in hexane, Time= 0.333333h, T= 20 °C Sayyed-Alangi, S. Zahra; Sajjadi-Ghotbabadi; Baei, Mohammed T.; Naderi, Sahar; E-Journal of Chemistry; vol. 8; nb. 2; (2011); p. 815 - 818 View in Reaxys

> 95 %

With 4-Methylimidazole, bis-[(trifluoroacetoxy)iodo]benzene in 2,2,2-trifluoroethanol, Time= 2h, T= 25 °C Chen, Yiyun; Kamlet, Adam S.; Steinman, Jonathan B.; Liu, David R.; Nature Chemistry; vol. 3; nb. 2; (2011); p. 146 - 153 View in Reaxys

95 %

With oxygen, potassium carbonate in toluene, Time= 4h, T= 100 °C Zhang, Guofu; Wang, Yong; Wen, Xin; Ding, Chengrong; Li, Ying; Chemical Communications; vol. 48; nb. 24; (2012); p. 2979 - 2981 View in Reaxys

95 %

With poly(1,4-phenylene-2,5-pyridinedicarboxyamide) supported periodic acid in acetonitrile, Time= 1.6h, Reflux Pourali, Ali Reza; Tabaean, Mehrosadat; Nazifi, S. Mohamad Reza; Chinese Chemical Letters; vol. 23; nb. 1; (2012); p. 21 - 24 View in Reaxys

95 %

2.2. Oxidation of alcohols under ultrasonic condition: a general procedure General procedure: A mixture of alcohol (10 mmol), Ni(NO3)2*6H2O (2.908 g, 10 mmol), I2 (1.3 g, 10 mmol) and water (2 mL) were sonicated in a sonic bath working at 35 kHz (constant frequency) maintained at 25 °C by circulating water. After completion of the reaction (Table 5, monitored on TLC), the product was taken into diethyl ether (10 mL), the organic matter was washed with sat. NaHCO3 (2.5 mL), water (5 mL) and then dried over anhydrous Na2SO4. The organic layer was evaporated in a fume hood to get almost pure aldehyde. The crude was then subjected to silica gel column chromatography to get the pure product. All the products were characterized by IR, GC– mass spectral analysis; and the physical properties were compared with the properties of authentic samples. With nickel(II) nitrate hexahydrate, iodine in water, Time= 0.0333333h, T= 25 °C , Sonication, Time, Reagent/catalyst, Solvent Pasha, Mohamed Afzal; Nagashree, Shrivatsa; Ultrasonics Sonochemistry; vol. 20; nb. 3; (2013); p. 810 - 814 View in Reaxys

95 %

With oxygen, Time= 1h, T= 380 °C , Catalytic behavior, Reagent/catalyst Zhao, Guofeng; Hu, Huanyun; Chen, Wei; Jiang, Zheng; Zhang, Shuo; Huang, Jun; Lu, Yong; Catalysis Science and Technology; vol. 3; nb. 2; (2013); p. 404 - 408 View in Reaxys

95 %

With oxygen in toluene, Time= 1h, T= 90 °C , Catalytic behavior Verma, Sanny; Tripathi, Deependra; Gupta, Piyush; Singh, Raghuvir; Bahuguna, Gajendra Mohan; Shivakumar K; Chauhan; Saran, Sandeep; Jain, Suman L.; Dalton Transactions; vol. 42; nb. 32; (2013); p. 11522 - 11527 View in Reaxys

95 %

With manganese dioxide supported on kieselguhr in neat (no solvent), Time= 3h, T= 50 - 55 °C , Milling Zhu, Li-Yun; Lou, Zhiyuan; Lin, Jianan; Zheng, Wenjin; Zhang, Changhe; Lou, Ji-Dong; Research on Chemical Intermediates; vol. 39; nb. 9; (2013); p. 4287 - 4292 View in Reaxys

95 %

With potassium hydoxide in o-xylene, Time= 2.25h, T= 20 °C , Reagent/catalyst, Solvent, Concentration, Time Shaabani, Ahmad; Keshipour, Sajjad; Hamidzad, Mona; Seyyedhamzeh, Mozhdeh; Journal of Chemical Sciences; vol. 126; nb. 1; (2014); p. 111 - 115 View in Reaxys

95 %

With C26H30ClN3RhS(1+)*F6P(1-), potassium tert-butylate in acetone, Time= 6h, T= 80 °C , Schlenk technique, Inert atmosphere, Oppenauer Oxidation, Catalytic behavior, Reagent/catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

32/438

2018-03-11 22:07:32


Saleem, Fariha; Rao, Gyandshwar Kumar; Kumar, Arun; Mukherjee, Goutam; Singh, Ajai K.; Organometallics; vol. 33; nb. 9; (2014); p. 2341 - 2351 View in Reaxys 95 %

With 1,10-Phenanthroline, copper(II) oxide in toluene, Time= 24h, T= 110 °C Zhang, Wu; Guo, Fei; Wang, Fei; Zhao, Na; Liu, Liang; Li, Jia; Wang, Zhenghua; Organic and Biomolecular Chemistry; vol. 12; nb. 30; (2014); p. 5752 - 5756 View in Reaxys

> 95 %

With sodium hypochlorite, C186H204N12O36, sodium hydrogencarbonate, potassium bromide in dichloromethane, water, Time= 0.5h, T= 0 - 15 °C , pH= 8.6 Beejapur, Hazi Ahmad; Campisciano, Vincenzo; Franchi, Paola; Lucarini, Marco; Giacalone, Francesco; Gruttadauria, Michelangelo; ChemCatChem; vol. 6; nb. 8; (2014); p. 2419 - 2424 View in Reaxys

95 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, [{Cu(NO3)}(μ-3-(6-(1H-pyrazol-1-yl)pyridin-2-yl)pyrazol-1-ide)]2, oxygen in water, Time= 24h, T= 30 °C Tan, Da-Wei; Xie, Jing-Bo; Li, Qi; Li, Hong-Xi; Li, Jun-Chi; Li, Hai-Yan; Lang, Jian-Ping; Dalton Transactions; vol. 43; nb. 37; (2014); p. 14061 - 14071 View in Reaxys

95 %

4 : 4.1.2. The oxidation of primary alcohols. General procedure: A round-bottom flask was charged with alcohol (2 mmol), CuOTf (0.1 mmol, 0.05 equiv) (S)-5(pyrrolidin-2-yl)-1H-tetrazole (0.1 mmol, 0.05 equiv), TEMPO (0.1 mmol, 0.05 equiv), DMAP (0.15 mmol, 0.075 equiv) and CH3CN (5 ml). The reaction mixture was stirred at 25 °C open to air until the completion of the reaction, as monitored by TLC. After completion, CH3CN was evaporated under vacuum. The residue was then diluted with CH2Cl2 (5 ml) and filtered through a plug of silica gel to afford the desired product. With dmap, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper(I) triflate, 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole in acetonitrile, Time= 1h, T= 25 °C , Catalytic behavior, chemoselective reaction Liu, Yangyang; Xie, Aming; Li, Junjian; Xu, Xiao; Dong, Wei; Wang, Boliang; Tetrahedron; vol. 70; nb. 52; (2014); p. 9791 - 9796 View in Reaxys

95 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [{(MeOH)Cu(OAc)}(μ-k2:k1-2-(3-(pyridin-2-yl)-1H-pyrazol-1yl)acetic acid(-H))]2*0.5H2O, tetraethylammonium iodide, oxygen, potassium carbonate in water, Time= 24h, T= 40 °C , p= 760.051Torr Xie, Jing-Bo; Bao, Jia-Jing; Li, Hong-Xi; Tan, Da-Wei; Li, Hai-Yan; Lang, Jian-Ping; RSC Advances; vol. 4; nb. 96; (2014); p. 54007 - 54017 View in Reaxys

> 95 %

With (diacetoxyiodo)benzene in dichloromethane, Time= 0.7h, T= 20 °C Beejapur, Hazi Ahmad; Campisciano, Vincenzo; Giacalone, Francesco; Gruttadauria, Michelangelo; Advanced Synthesis and Catalysis; vol. 357; nb. 1; (2015); p. 51 - 58 View in Reaxys

95 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, cesium hydroxide, {[(2-(sulfonylquinlium-8-yloxy)phthalic acid-2H)2Cu4(4,4′-bipyridine)4]·2H2O}n·2nH2O in acetonitrile, Time= 12h, T= 80 °C , Reagent/catalyst, Solvent, Temperature Feng, Xun; Xu, Chen; Wang, Zhi-Qiang; Tang, Si-Fu; Fu, Wei-Jun; Ji, Bao-Ming; Wang, Li-Ya; Inorganic Chemistry; vol. 54; nb. 5; (2015); p. 2088 - 2090 View in Reaxys

95 %

With ammonium cerium (IV) nitrate in neat (no solvent), Time= 6h, T= 50 °C , Green chemistry Wang, Zhao-Gang; Xia, Yong-Gen; Jin, Yong; Lu, Ming; Applied Organometallic Chemistry; vol. 29; nb. 2; (2015); p. 109 - 112 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

33/438

2018-03-11 22:07:32


95 %

With oxygen in toluene, T= 80 °C , p= 8250.83Torr , Inert atmosphere Mannel, David S.; Stahl, Shannon S.; Root, Thatcher W.; Organic Process Research and Development; vol. 18; nb. 11; (2014); p. 1503 - 1508 View in Reaxys

95 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper(II) ferrite, oxygen in water, Time= 24h, T= 100 °C , Sealed tube, Schlenk technique, Green chemistry, Catalytic behavior, Solvent, Temperature, Time Zhu, Xiao; Yang, Daoshan; Wei, Wei; Jiang, Min; Li, Lulu; Zhu, Xiangbing; You, Jinmao; Wang, Hua; RSC Advances; vol. 4; nb. 110; (2014); p. 64930 - 64935 View in Reaxys

95 %

With oxygen, potassium hydoxide in toluene, Time= 12h, T= 100 °C , p= 760.051Torr , Reagent/catalyst Yang, Huimin; Cui, Xinjiang; Deng, Youquan; Shi, Feng; RSC Advances; vol. 4; nb. 104; (2014); p. 59754 59758 View in Reaxys

95 %

General Procedure for the Oxidation of Alcohols To a 10 mL round-bottom flask, Imim-PEG1000-TEMPO (0.5mmol), AuCl3 (0.5 mmol) and benzyl alcohol (10 mmol) were successively added with vigorous stiring. The reaction was allowed to proceed at 60 °C and monitored by TLC. Upon completion, the reaction mixture was cooled to r.t. and extracted three times by adding Et2O. The organic phase was dried over anhydrous MgSO4, filtered, and evaporated under reduced pressure to give benzaldehyde (95percent yield). All products had spectroscopic data consistent with the as signed structures. With gold(III) chloride in neat (no solvent), Time= 6h, T= 60 °C , Green chemistry, Reagent/catalyst, Temperature, Concentration Wang, Zhao-Gang; Xu, Kui; Shen, Meng-Nan; Lu, Ming; Synlett; vol. 25; nb. 17; (2014); p. 2459 - 2462; Art.No: ST-2014-D0594-L View in Reaxys

95 %

With oxygen in N,N-dimethyl-formamide, Time= 4h, T= 80 °C , Catalytic behavior, Reagent/catalyst, chemoselective reaction Zhi, Jian; Mitchell, Sharon; Pérez-Ramírez, Javier; Reiser, Oliver; ChemCatChem; vol. 7; nb. 17; (2015); p. 2585 - 2589 View in Reaxys

95 %

With tert-butylethylene, [IrBr(1,5-cyclooctadiene)((1-methylimidazolyl)(2-methoxybenzyl))], caesium carbonate in toluene, Time= 24h, T= 110 °C , Inert atmosphere, Oppenauer Oxidation, Catalytic behavior, Reagent/catalyst, Temperature, Solvent Jiménez, M. Victoria; Fernández-Tornos, Javier; Modrego, F. Javier; Pérez-Torrente, Jesús J.; Oro, Luis A.; Chemistry - A European Journal; vol. 21; nb. 49; (2015); p. 17877 - 17889 View in Reaxys

95 %

With potassium carbonate in toluene, Time= 3h, T= 70 °C , Reagent/catalyst, Temperature Atashin, Hassan; Malakooti, Reihaneh; Journal of the Chinese Chemical Society; vol. 61; nb. 9; (2014); p. 1039 1044 View in Reaxys

95 %

2.4 Typical procedure for the oxidation of benzylalcohol General procedure: Benzylalcohol (0.1 g, 1.0 mmol) was added to a two-necked flask equipped with a gas bubbling tube containing colloidal of Co(II)-EDANC (0.2 g) and KOH (0.5 mmol) in o-xylene (5mL). Air was bubbled at arate of 5mL/min into the reaction mixture and the progress of the reaction was followed by thin-layer chromatography (TLC). Upon completion, Co(II)-EDANC was separated by filtration and washed with CH3CN (2 × 5mL). The filtrate solvent was evaporated under vacuum and benzylalcohol was purified with column chromatography with n-hexane:ethylacetate (2:1) in 95percent yield. With potassium hydoxide in o-xylene, Time= 2.25h, T= 20 °C , Reagent/catalyst, Solvent Shaabani, Ahmad; Keshipour, Sajjad; Hamidzad, Mona; Seyyedhamzeh, Mozhdeh; Journal of Chemical Sciences; vol. 126; nb. 1; (2014); p. 111 - 115

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

34/438

2018-03-11 22:07:32


View in Reaxys 95 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in aq. phosphate buffer, acetonitrile, Time= 24h, T= 20 °C , pH= 6, Enzymatic reaction Rouhani, Shamila; Rostami, Amin; Salimi, Abdollah; RSC Advances; vol. 6; nb. 32; (2016); p. 26709 - 26718 View in Reaxys

95 %

With 1-methyl-1H-imidazole, copper(l) iodide, C20H25N4O2 in acetonitrile, Time= 5h, T= 25 °C Wang, Lianyue; Bie, Zhixing; Shang, Sensen; Lv, Ying; Li, Guosong; Niu, Jingyang; Gao, Shuang; RSC Advances; vol. 6; nb. 41; (2016); p. 35008 - 35013 View in Reaxys

95 %

General procedure for the oxidation of alcohols General procedure: A mixture of aryl alcohol (1 mmol) and [FemDMMerA]Y (100 mg) in solvent(5 mL) was refluxed in oil bath. After completion of the reaction as monitored byTLC, the reaction mixture was filtered to remove insoluble SILP catalyst.Evaporation of solvent in vacuuo followed by column chromatography over silicagel using petroleum ether/ethyl acetate (95:5 v/v) afforded pure aldehydes. With ferrocene-labeled Merrifield resin-supported ionic liquid ([FemDMMerA]RuO4) in tetrahydrofuran, Time= 3h, Reflux, Green chemistry, Catalytic behavior, Reagent/catalyst, Solvent Kurane, Rajanikant; Bansode, Prakash; Khanapure, Sharanabasappa; Salunkhe, Rajashri; Rashinkar, Gajanan; Research on Chemical Intermediates; vol. 42; nb. 12; (2016); p. 7807 - 7821 View in Reaxys

95 %

With C24H22N6Ni, sodium hydroxide in toluene, Time= 16h, T= 70 °C , Schlenk technique, Reagent/catalyst, Solvent Sikari, Rina; Sinha, Suman; Jash, Upasona; Das, Siuli; Brandao, Paula; De Bruin, Bas; Paul, Nanda D.; Inorganic Chemistry; vol. 55; nb. 12; (2016); p. 6114 - 6123 View in Reaxys

95 %

24 : dehydrogenation oxidation reaction by the synthesis of benzaldehyde of benzylalcohol dehydrated toluene 270mL eggplant flask of 500mL, benzyl alcohol 8.648g (80mmol), and the complex 1 0.85mg (0.0016mmol, 0 .002 molpercent), and the mixture was stirred under reflux conditions for 48 hours.After adding toluene to make it homogeneous, the reaction solution was analyzed by GC, and it was confirmed that the corresponding benzaldehyde was formed at a yield of 95percent.Since this reaction showed a high catalyst rotational speed (TON = 47, 500), the utility of the present invention was shown. With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) in toluene, Time= 48h, Reflux, Solvent Patent; KANTO CHEM CO INC; YAMAGUCHI, RYOHEI; FUJITA, KENICHI; (38 pag.); JP2015/83544; (2015); (A) Japanese View in Reaxys

95 %

With tert.-butylhydroperoxide, H2O*2C2H3O2 (1-)*C22H14N2O4 (2-)*2Cu(2+) in neat (no solvent), Time= 2h, T= 45 °C , Temperature, Solvent, Reagent/catalyst Aryanejad, Sima; Bagherzade, Ghodsieh; Farrokhi, Alireza; Inorganic Chemistry Communications; vol. 81; (2017); p. 37 - 42 View in Reaxys

95 %

Aerobic oxidation of alcohols General procedure: A mixture of K2CO3 (1mmol) and the catalyst (10mg) in toluene (5mL) was prepared in a two necked flask. The flask was evacuated and refilled with pure oxygen. To this solution, the alcohol (1mmol, in 1mL toluene) was injected and the resulting mixture was stirred at 80°C under an oxygen atmosphere. After completion of reaction, the reaction mixture was filtered off and the catalyst rinsed twice with CH2Cl2 (5mL). The excess of solvent was removed under reduced pressure to give the corresponding carbonyl compounds. With oxygen, potassium carbonate in toluene, Time= 12h, T= 80 °C , Green chemistry, Catalytic behavior, Reagent/ catalyst Veisi, Hojat; Hemmati, Saba; Qomi, Mahnaz; Tetrahedron Letters; vol. 58; nb. 44; (2017); p. 4191 - 4196 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

35/438

2018-03-11 22:07:32


95 %

With boron trifluoride diethyl etherate, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in acetonitrile, Time= 0.05h, T= 20 °C , Solvent, Reagent/catalyst Jiang, Heming; Sun, Tian-Yu; Wang, Xiao; Xie, Yaoming; Zhang, Xinhao; Wu, Yun-Dong; Schaefer, Henry F.; Organic Letters; vol. 19; nb. 24; (2017); p. 6502 - 6505 View in Reaxys

95 %

With tert.-butylhydroperoxide, 3Ni(2+)*2C22H14N2O4 (2-)*2C2H3O2 (1-)*6H2O in neat (no solvent), Time= 1h, T= 65 °C , Catalytic behavior, Solvent, Temperature, Reagent/catalyst Aryanejad, Sima; Bagherzade, Ghodsieh; Farrokhi, Alireza; Applied Organometallic Chemistry; vol. 32; nb. 2; (2018); Art.No: E3995 View in Reaxys

94 %

With tert.-butylhydroperoxide, polystyrene-bound phenylselenic acid in tetrachloromethane, Time= 24h, Heating Taylor, Richard T.; Flood, Lawrence A.; Journal of Organic Chemistry; vol. 48; nb. 26; (1983); p. 5160 - 5164 View in Reaxys

94 %

With oxygen, 2,2,6,6-tetramethyl-piperidine-N-oxyl, copper(l) chloride in N,N-dimethyl-formamide, Time= 4h, T= 25 °C Semmelhack, M. F.; Schmid, Christopher R.; Cortes, David A.; Chou, Chuen S.; Journal of the American Chemical Society; vol. 106; nb. 11; (1984); p. 3374 - 3376 View in Reaxys

94 %

With quinolinium monofluorochromate(VI) in dichloromethane, Time= 0.5h Chaudhuri, Mihir K.; Chettri, Shiv K.; Lyndem, Synjukta; Paul, Pradip C.; Srinivas, Pendyala; Bulletin of the Chemical Society of Japan; vol. 67; nb. 7; (1994); p. 1894 - 1898 View in Reaxys

94 %

With aluminum oxide, [bis(acetoxy)iodo]benzene, Time= 0.0166667h, microwave sonication Varma, Rajender S.; Dahiya, Rajender; Saini, Rajesh K.; Tetrahedron Letters; vol. 38; nb. 40; (1997); p. 7029 7032 View in Reaxys

94 %

With 1,4-butanediol dimethylacrylate crosslinked polyacenaphthylene supported t-butyl chromate in chloroform, Time= 21h, T= 30 °C Geethakumari; Sreekumar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 37; nb. 4; (1998); p. 331 - 337 View in Reaxys

94 %

With aluminum oxide, [bis(acetoxy)iodo]benzene, Time= 0.0166667h, T= 80 °C , Irradiation Varma, Rajender S.; Saini, Rajesh K.; Dahiya, Rajender; Journal of Chemical Research - Part S; nb. 3; (1998); p. 120 - 121 View in Reaxys

94 %

With 4-benzyl-pyridine; dichromate in dichloromethane, Time= 0.5h, Ambient temperature, 2-benzylpyridinium dichromate (2-BPDC); other alcohols, Product distribution Akamanchi; Lyer; Meenakshi; Synthetic Communications; vol. 21; nb. 3; (1991); p. 419 - 425 View in Reaxys

94 %

With aluminum oxide, potassium permanganate in neat (no solvent), Time= 0.00833333h Hajipour, Abdol Reza; Mallakpour, Shadpour E.; Imanzadeh, Gholamhasan; Chemistry Letters; nb. 2; (1999); p. 99 - 100 View in Reaxys

94 %

With 1-butyl-3-methylimidazolium chloride, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione, Time= 0.25h, T= 20 °C Karthikeyan, Ganesan; Perumal, Paramasivan T.; Synlett; nb. 14; (2003); p. 2249 - 2251 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

36/438

2018-03-11 22:07:32


94 %

With m-iodosylbenzoic acid, sodium hydrogencarbonate, ruthenium trichloride, Time= 1h, T= 20 °C Yusubov, Mekhman S.; Gilmkhanova, Marina P.; Zhdankin, Viktor V.; Kirschning, Andreas; Synlett; nb. 4; (2007); p. 563 - 566 View in Reaxys

94 %

With bisacetoxybromate(I) resin in toluene, Time= 24h, T= 40 °C Bruenjes, Marco; Sourkouni-Argirusi, Georgia; Kirschning, Andreas; Advanced Synthesis and Catalysis; vol. 345; nb. 5; (2003); p. 635 - 642 View in Reaxys

94 %

With urea hydrogen peroxide adduct, 1-butyl-3-methylimidazolium Tetrafluoroborate, magnesium bromide, Time= 2h, T= 60 °C Heel, Joong Park; Jong, Chan Lee; Synlett; nb. 1; (2009); p. 79 - 80 View in Reaxys

94 %

With copper(II) choride dihydrate, oxygen, caesium carbonate in toluene, Time= 12h, T= 40 °C Liang, Lei; Rao, Guodong; Sun, Hao-Ling; Zhang, Jun-Long; Advanced Synthesis and Catalysis; vol. 352; nb. 14-15; (2010); p. 2371 - 2377 View in Reaxys

94 %

With acetic acid, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in acetonitrile, Time= 5h, T= 20 °C Lin, Cheng-Kun; Lu, Ta-Jung; Tetrahedron; vol. 66; nb. 51; (2010); p. 9688 - 9693 View in Reaxys

94 %

With oxygen, lithium perchlorate in dichloromethane, T= 20 °C , Inert atmosphere, Electrolysis Magdesieva; Dolganov; Latyshev; Yakimanskii; Goikhman; Podeshvo; Lukashev; Russian Journal of Organic Chemistry; vol. 47; nb. 1; (2011); p. 62 - 65 View in Reaxys

94 %

With dihydrogen peroxide in water, Time= 8h, T= 89.84 °C Ding, Yong; Zhao, Wei; Ma, Bao-Chun; Qiu, Wen-Yuan; Canadian Journal of Chemistry; vol. 89; nb. 1; (2011); p. 13 - 18 View in Reaxys

94.7 %

22 :Example 22 (Synthesis of benzaldehyde using a tungsten compound: sodium tungstate was used); In a glassmade vessel equipped with a thermometer, a temperature controller, a dropping device and a stirring device were charged 79 ml of xylene, 108.14 g (1.00 mol) of benzylalcohol, 3.30 g (0.01 mol) of sodium tungstate*dihydrate (Na2WO4*2H2O) and 3.40 g (0.01 mol) of tetrabutyl ammonium hydrogen sulfate. Then, 4.68 g (0.03 mol) of sodium dihydrogen phosphate and 7.16 g (0.02 mol) of disodium hydrogen phosphate were mixed and a pH of the reaction mixture was adjusted to 6.0. Next, an inner temperature of the reaction mixture was maintained from 94 to 95°C, and 80.38 g (1.34 mol) of 60percent aqueous hydrogen peroxide was added dropwise to the mixture with 18.00 g (0.3 mol)/hr, while maintaining the pH of the reaction mixture to 5.5 to 6.5 by using 8 mol/L aqueous sodium hydroxide solution. After completion of the reaction, the resulting reaction mixture was cooled to room temperature, and the organic layer was separated as a solution. The resulting organic layer solution was washed with 1 mol/L sodium hydroxide solution, and the solvent, xylene was distilled off under reduced pressure. The resulting concentrate (crude benzaldehyde) was purified by distillation (66°C/2.5 kPa) to obtain 100.51 g of benzaldehyde as colorless liquid (obtained yield: 94.7percent, based on benzylalcohol). With disodium hydrogenphosphate, sodium dihydrogenphosphate, dihydrogen peroxide, sodium hydroxide, sodium tungstate (VI) dihydrate, tetra(n-butyl)ammonium hydrogensulfate in water, xylene, T= 94 - 95 °C , pH= 5.5 - 6.5 Patent; Ube Industries, Ltd.; EP2351728; (2011); (A1) English View in Reaxys

94 %

With guanidinium chlorochromate, tetrabutylammomium bromide Goswami, Shyamaprosad; Kar, Arnab; Synthetic Communications; vol. 41; nb. 17; (2011); p. 2500 - 2504 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

37/438

2018-03-11 22:07:32


94 %

With C48H51ClN4O8PRu, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Thilagavathi, Natarajan; Jayabalakrishnan, Chinnasamy; Central European Journal of Chemistry; vol. 8; nb. 4; (2010); p. 842 - 851 View in Reaxys

94 %

With tetra‐n‐butyl‐ammonium oxone, meso-tetraphenylporphyrin iron(III) chloride in water, Time= 0.25h, T= 25 °C , Air Rezaeifard, Abdolreza; Jafarpour, Maasoumeh; Naeimi, Atena; Catalysis Communications; vol. 16; nb. 1; (2011); p. 240 - 244 View in Reaxys

94 %

With iron(III) chloride, nitric acid in acetone, Time= 0.166667h, T= 20 °C , Sonication Naik, Ramesh; Nizam, Aatika; Siddekha, Aisha; Pasha; Ultrasonics Sonochemistry; vol. 18; nb. 5; (2011); p. 1124 - 1127 View in Reaxys

94 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in dichloromethane, Time= 1h, T= 20 °C , chemoselective reaction Zhu, Chenjie; Wei, Yunyang; Advanced Synthesis and Catalysis; vol. 354; nb. 2-3; (2012); p. 313 - 320 View in Reaxys

94 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium carbonate, L-proline, copper(I) bromide in methanol, Time= 5h, T= 20 °C Zhang, Guofu; Han, Xingwang; Luan, Yuxin; Wang, Yong; Wen, Xin; Ding, Chengrong; Chemical Communications; vol. 49; nb. 72; (2013); p. 7908 - 7910 View in Reaxys

94 %

With oxygen, potassium carbonate in toluene, Time= 10h, T= 90 °C , p= 760.051Torr , Concentration, Reagent/catalyst, Solvent, Temperature, Time Zhang, Lei; Li, Pinhua; Yang, Jin; Wang, Min; Wang, Lei; ChemPlusChem; vol. 79; nb. 2; (2014); p. 217 - 222 View in Reaxys

94 %

General procedure General procedure: All reactions were performed in a glass flask slurry reactor connected to an O2 tube for atmosphere control and a condenser for reflux condition. A mixture of alcohol (1mmol), Cs2CO3 (0.5mmol) and 2Au/1CuO– ZnO (0.05g) in water was stirred under oxygen atmosphere in a slurry reactor at total reflux condition. Then the catalyst was recovered by filtration, washed two times with 5ml hot EtOAc, and dried for consecutive reaction runs. The filtrate was quenched with 2M HCl aqueous solution, extracted with EtOAc three times and dried over anhydrous MgSO4. Evaporation of the solvent followed by column chromatography on silica gel afforded the pure products (Table3). With oxygen, caesium carbonate in water, Time= 1h, Reflux, Solvent, Temperature, Time Albadi, Jalal; Alihoseinzadeh, Amir; Razeghi, Abdolhosein; Catalysis Communications; vol. 49; (2014); p. 1 - 5 View in Reaxys

94 %

General procedure for the Swern-type oxidation reaction General procedure: A solution of DMSO (3.0 mmol) in CH2Cl2 (2.0 mL) was added toa solution of 1 (1.2 mmol) in CH2Cl2 (5.0 mL) at 30 C, and themixture was stirred for 20 min at the same temperature. The alcoholsubstrate (1.0 mmol) was added, and the mixture was stirredfor another 20 min before the dropwise addition of Et3N(3.0 mmol). The mixture was subsequently left to warm to room temperature (20 min) and concentrated under reduced pressure.The product was isolated by flash column chromatography. Stage 1: With 7,7-dichlorocyclohepta-1,3,5-triene in dichloromethane, dimethyl sulfoxide, Time= 0.333333h, T= -30 °C , Inert atmosphere, Swern Oxidation Stage 2: With triethylamine in dichloromethane, dimethyl sulfoxide, Time= 0.333333h, T= -30 - 20 °C , Inert atmosphere, Swern Oxidation Nguyen, Thanh Vinh; Hall, Michael; Tetrahedron Letters; vol. 55; nb. 50; (2014); p. 6895 - 6898

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

38/438

2018-03-11 22:07:32


View in Reaxys 94 %

With hexaammonium heptamolybdate tetrahydrate, dihydrogen peroxide in water, methyl cyclohexane, Time= 3h, T= 50 °C , Ionic liquid, Green chemistry Hu, Yu-Lin; Lu, Ming; Ge, Xiu-Tao; Journal of the Iranian Chemical Society; vol. 10; nb. 3; (2013); p. 453 - 460 View in Reaxys

94 %

With tert.-butylhydroperoxide, copper(II) acetate monohydrate, calcium carbonate in acetonitrile, Time= 24h, T= 80 °C Yedage, Subhash L.; Bhanage, Bhalchandra M.; Synthesis (Germany); vol. 47; nb. 4; (2015); p. 526 - 532; Art.No: SS-2014-T0513-OP View in Reaxys

94 %

With dmap, tetrakis(actonitrile)copper(I) hexafluorophosphate, N,N'-di-tert-butylethylenediamine, oxygen in dichloromethane, Time= 1h, T= 20 °C , p= 760.051Torr , Schlenk technique, Molecular sieve, Sealed tube, Reagent/catalyst, Time Xu, Boran; Lumb, Jean-Philip; Arndtsen, Bruce A.; Angewandte Chemie - International Edition; vol. 54; nb. 14; (2015); p. 4208 - 4211; Angew. Chem.; vol. 127; nb. 14; (2015); p. 4282 - 4285,4 View in Reaxys

94 %

2.6 Typical procedure for oxidation of alcohols General procedure: All the reactions were carefully carried out at 40°C in a 25ml flask. In a typical procedure an amount of catalyst along with H2O2 was used for the oxidation process under mild conditions. The oxidation process was monitored by thin layer chromatography technique. With dihydrogen peroxide in water, ethyl acetate, T= 45 °C , Catalytic behavior, Reagent/catalyst, Temperature Judy Azar, Amir Reza; Safaei, Elham; Mohebbi, Sajjad; Materials Research Bulletin; vol. 70; (2015); p. 753 - 761; Art.No: 8227 View in Reaxys

94 %

2.3. General procedure for oxidation of alcohols General procedure: A mixture of S4SiIL or S3PIL (0.05mmol) and alcohol (30mmol) in a 25 mL flask fitted with a reflux condenser was heated to the reactiontemperature, then the required amount of aqueous H2O2 was addeddropwise under stirring. The progress of the reaction was monitored by TLC (GF254 silica gel coloration in phosphomolybdic acid/ethanol for aromatic alcohol, in KMnO4 solution for aliphatic alcohol). After the completion, the reaction mixture was extracted with diethyl ether(3 × 20 mL), solvent was evaporated in a vacuum. The residual was analyzedby gas chromatography (HP 6890) equippedwith a flame ionizationdetector and an SE-54 column. The aqueous phase was subjected torotary evaporation, and then was dried at 85 °C under a vacuum for 8 hto give regenerated ionic liquids. Pure oxidation products were obtainedby column chromatography (petroleum ether-ethyl acetate 9:1 (V/V))and identified by the comparison of their IR and 1H NMR spectra withthose of authentic samples. With O40SiW12 (4-)*4C17H38NO3S(1+), dihydrogen peroxide, Time= 4h, T= 70 °C , Green chemistry, Mechanism, Reagent/catalyst, Temperature Li, Xinzhong; Cao, Rong; Lin, Qi; Catalysis Communications; vol. 69; (2015); p. 5 - 10 View in Reaxys

94 %

With hydrogenchloride, platinum, sodium chloride in chloroform, water, T= 30 °C , Electrolysis Bosco, A. John; Lawrence; Christopher; Radhakrishnan; Joseph Rosario, A. Arul; Raja; Vasudevan; Journal of Physical Organic Chemistry; vol. 28; nb. 9; (2015); p. 591 - 595 View in Reaxys

94 %

With dmap, C25H30F17N5O4S(1-)*K(1+), oxygen, copper(II) sulfate in water, Time= 1h, T= 25 °C , Reagent/catalyst, chemoselective reaction Chen, Ba-Tian; Bukhryakov, Konstantin V.; Sougrat, Rachid; Rodionov, Valentin O.; ACS Catalysis; vol. 5; nb. 2; (2015); p. 1313 - 1317 View in Reaxys

94 %

With bis(quinuclidine)bromine(I) bromide, pyridinium trifluroacetate in chloroform, Time= 8h, T= 40 °C , Kinetics, Temperature

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

39/438

2018-03-11 22:07:32


Laila, Abdulhameed; Monatshefte fur Chemie; vol. 144; nb. 3; (2013); p. 307 - 312 View in Reaxys 94 %

General procedure for oxidation of alcohols Catalytic experiments were carried out in a 5 mL test tube. In a typical procedure, 1 mmol benzyl alcohol, 0.02 mmol nanosize copper(II) complex and 3 mmol 30 percent H2O2 were added. The reaction mixture was stirred for 3 h at 70 °C under solvent-free condition. The reaction products were monitored by thin-layer chromatography (TLC). After the reaction was completed, the pure product was obtained after chromatography on a short column of silica gel. The oxidation products were identified by comparison with authentic samples. With C11H16CuN2O6, dihydrogen peroxide in neat (no solvent), Time= 3h, T= 70 °C , Reagent/catalyst, Temperature, chemoselective reaction Saeednia; Hatefi Ardakani; Pakdin-Parizi; Iranmanesh; Sinaei; Journal of the Iranian Chemical Society; vol. 13; nb. 11; (2016); p. 1963 - 1975 View in Reaxys

94 %

2.2 Catalytic reaction General procedure: In a typical experiment, 4-methoxybenzyl alcohol (12μL, 0.1mmol), Cu-FMOF (11.3mg, 10mmol percent), TEMPO (7.8mg, 0.05mmol) and NaCO3 (10.6mg, 0.1mmol) in 1mL of air saturated acetonitrile were taken in a 15-mL three-necked round-bottom flask. The solution was magnetically stirred for 16h at 75°C under air atmosphere. The progress of the reaction was monitored via gas chromatography (Shimadzu GC-2010AF) involving a Chromopak capillary column and flame ionization detector. The products were further confirmed by using gas chromatography–mass spectroscopy (GC–MS) (Shimadzu GCMS-2010). The concentrations of 4-methoxybenzyl alcohol and 4-methoxybenzylaldehyde were calibrated by external standard method with standard samples (see Fig. S1). With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, {[Cu2(1,2-benzenedicarboxylate)2(1,4-bis(1,2,4-triazol-1-ylmethyl)-2,3,5,6-tetrafluorobenzene)2]·3H2O}n, sodium carbonate in acetonitrile, Time= 16h, T= 75 °C Chen, Sheng-Chun; Lu, Sheng-Nan; Tian, Feng; Li, Nan; Qian, Han-Yu; Cui, Ai-Jun; He, Ming-Yang; Chen, Qun; Catalysis Communications; vol. 95; (2017); p. 6 - 11 View in Reaxys

94 %

With potassium bromide in dichloromethane, Time= 0.166667h, T= 0 °C , pH= 9.1, Catalytic behavior Yu, Wei; Zhou, Minghong; Wang, Tianqi; He, Zidong; Shi, Buyin; Xu, Yang; Huang, Kun; Organic Letters; vol. 19; nb. 21; (2017); p. 5776 - 5779 View in Reaxys

94 %

1.10 Preparative synthesis of compounds 2a,b,d-al (general procedure) General procedure: A solution of corresponding alcohol 1a,b,d-al (8 mmol), nitroxide 4a (0.085 g, 0.4 mmol) and compound 6d (0.097 g, 0.8 mmol) in CH2Cl2 (10 mL) was added to a vigorously stirred solution of NaHCO3 (2.016 g, 24 mmol) in water (10 mL) at 20 °C. Then I2 (4.06 g, 16 mmol) powder was added in one portion to the formed reaction mixture at vigorous stirring and temperature 20-22 °C. The reaction mixture was stirred at 20-22 °C for appropriate time (see Table 1 in the article). Then, a saturated solution of sodium thiosulfate was added to the stirred reaction mixture for discoloration. Organic and aqueous phases were separated and the aqueous phase was then extracted with CH2Cl2 (3×5 mL). Organic phase and the extracts were combined and washed subsequently with saturated aqueous solution of NaCl (5 mL), aqueous solutionof HCl (1percent) saturated with NaCl (3 mL), and then with water (5 mL). The washed extract was dried with anhydrous Na2SO4 and evaporated to dryness to give crude product, which was then purified by vacuum distillation under argon atmosphere or by recrystallization. With 2,4,6-trimethyl-pyridine, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy, iodine, sodium hydrogencarbonate in dichloromethane, water, Time= 1h, T= 20 - 22 °C , Reagent/catalyst Kashparova, Vera P.; Klushin, Victor A.; Zhukova, Irina Yu.; Kashparov, Igor S.; Chernysheva, Daria V.; Il'chibaeva, Irina B.; Smirnova, Nina V.; Kagan, Efim Sh.; Chernyshev, Victor M.; Tetrahedron Letters; vol. 58; nb. 36; (2017); p. 3517 - 3521 View in Reaxys

94 %

With 1-methyl-1H-imidazole, 9-azabicyclolt;3.3.1gt;nonane-N-oxyl, copper(I) bromide in water, Time= 2h, T= 20 °C , Reagent/catalyst Sand, Henning; Weberskirch, Ralf; RSC Advances; vol. 7; nb. 53; (2017); p. 33614 - 33626

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

40/438

2018-03-11 22:07:32


View in Reaxys 93 %

With molecular sieve, oxygen, trans-lt;4But-Hpygt;lt;RuO2Cl3(4But-py)gt; in acetonitrile, Time= 3h, Ambient temperature Dengel, Andrew C.; El-Hendawy, Ahmed M.; Griffith, William P.; O'Mahoney, Caroline A.; Williams, David J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 3; (1990); p. 737 - 742 View in Reaxys

93 %

With sodium hypochlorite, tetrabutylammomium bromide in water, ethyl acetate, Time= 0.5h, Ambient temperature Mirafzal, Gholam A.; Lozeva, Albena M.; Tetrahedron Letters; vol. 39; nb. 40; (1998); p. 7263 - 7266 View in Reaxys

93 %

With molecular sieve, oxygen, trans-lt;4But-Hpygt;lt;RuO2Cl3(4But-py)gt; in acetonitrile, Time= 3h, Ambient temperature, or N-methylmorpholine-N-oxide or other catalyst Dengel, Andrew C.; El-Hendawy, Ahmed M.; Griffith, William P.; O'Mahoney, Caroline A.; Williams, David J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 3; (1990); p. 737 - 742 View in Reaxys

93 %

With sodium carbonate, N,N-didecyl-N,N-dimethylammonium bromide, ruthenium trichloride in tetrachloromethane, Time= 3h, Heating, effect of the catalyst concentration; further aromatic aldehydes, Rate constant Sasson, Yoel; Wiener, Harold; Bashir, Subhi; Journal of the Chemical Society, Chemical Communications; (1987); p. 1574 - 1575 View in Reaxys

93 %

With aluminium trichloride, silver bromate in acetonitrile, Time= 0.5h, Heating, other alcohols, aldehydes, benzylic compounds, and thiols, var. Levis acids, var. solvents, var. time, Product distribution Firouzabadi, Habib; Mohammadpoor-Baltork, Iraj; Bulletin of the Chemical Society of Japan; vol. 68; nb. 8; (1995); p. 2319 - 2326 View in Reaxys

93 %

With barium permanganate, Time= 4h, T= 90 °C , Oxidation Firouzabadi, Habib; Karimi, Babak; Abbassi, Mohammad; Journal of Chemical Research - Part S; nb. 3; (1999); p. 236 - 237 View in Reaxys

93 %

With tetrapropylammonium perruthennate, polymer-supported 4-methylmorpholine-N-oxide, 4 A molecular sieve in dichloromethane, Time= 24h, T= 20 °C Brown; Kerr; Lindsay; Pike; Ratcliffe; Synlett; nb. 8; (2001); p. 1257 - 1259 View in Reaxys

93 %

With air, cryptomelan H-K-OMS-2 in toluene, Time= 4h, T= 110 °C Son, Young-Chan; Makwana, Vinit D.; Howell, Amy R.; Suib, Steven L.; Angewandte Chemie - International Edition; vol. 40; nb. 22; (2001); p. 4280 - 4283 View in Reaxys

93 %

With iodosylbenzene, N,N-ethylenebis(3,5-dichlorosalicylideneiminato)Cr(III)Cl in dichloromethane, Time= 0.5h, T= 20 °C Kim, Sung Soo; Kim, Dong Won; Synlett; nb. 10; (2003); p. 1391 - 1394 View in Reaxys

93 %

With silica chromate, silica gel, Time= 0.333333h, T= 20 °C Zolfigol, Mohammad A.; Shirini, Farhad; Mohammadpoor-Baltork, Iraj; Choghamarani, Arash Gh.; Hajjami, Maryam; Sedaghat, Abdol M.; Mendeleev Communications; nb. 3; (2005); p. 113 - 116 View in Reaxys

93 %

With N-methylpyrrolidine-2-one hydrotribromide in acetonitrile, Time= 2h, Heating

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

41/438

2018-03-11 22:07:32


Joseph, Jomy K.; Jain, Suman L.; Sain, Bir; European Journal of Organic Chemistry; nb. 3; (2006); p. 590 - 594 View in Reaxys 93 %

With ethylenebis(N-methylimidazolium) chlorochromate, Time= 0.0666667h, Microwave irradiation Hosseinzadeh, Rahman; Tajbakhsh, Mahmood; Khaledi, Hamid; Journal of the Chinese Chemical Society; vol. 55; nb. 1; (2008); p. 239 - 243 View in Reaxys

93 %

With Ru(PPh3)(OH)-salen, oxygen in chloroform, Time= 1.5h, T= 20 °C Mizoguchi, Hirotaka; Uchida, Tatsuya; Ishida, Kohichi; Katsuki, Tsutomu; Tetrahedron Letters; vol. 50; nb. 26; (2009); p. 3432 - 3435 View in Reaxys

93 %

With oxovanadium(IV) sulfate, oxygen, sodium nitrite in water, acetonitrile, Time= 2h, T= 80 °C , p= 3750.38Torr Du, Zhongtian; Miao, Hong; Hong, Ma.; Sun, Zhiqiang; Jiping, Ma.; Xu, Jie; Advanced Synthesis and Catalysis; vol. 351; nb. 4; (2009); p. 558 - 562 View in Reaxys

93 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, iodosylbenzene, sodium dodecyl-sulfate, potassium bromide in water, Time= 0.5h, T= 20 °C Zhu, Chenjie; Wei, Yunyang; Ji, Lei; Synthetic Communications; vol. 40; nb. 14; (2010); p. 2057 - 2066 View in Reaxys

93 %

With potassium nitrate in water, Time= 3h, T= 20 °C , Electrolysis Zhang, Li; Zha, Zhenggen; Wang, Zhiyong; Synlett; nb. 13; (2010); p. 1915 - 1918 View in Reaxys

93 %

With oxygen in octanol, Time= 1.2h, T= 70 °C , p= 760.051Torr Liu, Lin; Ma, Juanjuan; Sun, Zhen; Zhang, Jianping; Huang, Jingjing; Li, Shanzhong; Tong, Zhiwei; Canadian Journal of Chemistry; vol. 89; nb. 1; (2011); p. 68 - 71 View in Reaxys

93 %

With 4‐(acetylamino)‐2,2,6,6‐tetramethyl‐1‐oxopiperidinium tetrafluoroborate in water, Time= 6h, Reflux Mamros, Audrey N.; Sharrow, Phillip R.; Weller, William E.; Luderer, Mark R.; Fair, Justin D.; Pazehoski, Kristina O.; Luderer, Matthew R.; Arkivoc; vol. 2011; nb. 5; (2011); p. 23 - 33 View in Reaxys

93 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in dibutyl ether, Time= 7h, T= 65 °C , p= 760.051Torr Chrobok, Anna; Baj, Stefan; Pudlo, Wojciech; Jarzebski, Andrzej; Applied Catalysis A: General; vol. 389; nb. 1-2; (2010); p. 179 - 185 View in Reaxys

93 %

Stage 1: With iron(III) chloride hexahydrate, oxygen, silica gel in toluene, Time= 0.0833333h, Autoclave Stage 2: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in toluene, Time= 7h, T= 80 °C , p= 3750.38Torr , Autoclave Wang, Lianyue; Li, Jun; Lv, Ying; Zhao, Gongda; Gao, Shuang; Applied Organometallic Chemistry; vol. 26; nb. 1; (2012); p. 37 - 43 View in Reaxys

93 %

With tert.-butylhydroperoxide in decane, acetonitrile, Time= 0.333333h, T= 65 °C Mungse, Harshal P.; Verma, Sanny; Kumar, Neeraj; Sain, Bir; Khatri, Om P.; Journal of Materials Chemistry; vol. 22; nb. 12; (2012); p. 5427 - 5433 View in Reaxys

93 %

With oxygen in dichloromethane, Green chemistry, Reagent/catalyst Ionita, Petre; RSC Advances; vol. 3; nb. 44; (2013); p. 21218 - 21221

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

42/438

2018-03-11 22:07:32


View in Reaxys 93 %

General procedure for the oxidation of alcohols General procedure: A vial was charged with alcohol (1 mmol), IBX (1.2 mmol, 1.2 equiv) and 2 wt percent GMPGS-2000/H2O solution (5 mL). The mixture was stirred for 24 h at 25 °C and filtered. The solid was washed with CH2Cl2 and the filtrate was extracted with CH2Cl2 (3×10 mL). Then, the organic phase was combined and dried with anhydrous Na2SO4, evaporated to dryness. The crude product was purified was purified by column chromatography on silica gel eluted with (petroleum ether/EtOAc) to afford the desired product. With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in water, Time= 24h, T= 25 °C , Micellar solution Xie, Aming; Zhou, Xiangxiang; Feng, Liandong; Hu, Xinyu; Dong, Wei; Tetrahedron; vol. 70; nb. 21; (2014); p. 3514 - 3519 View in Reaxys

93 %

General Procedure for the Oxidation of Alcohol General procedure: Alcohol (1 mmol), water (1 mL), and CoFe2O4 MNPs (11.8mg, 5 mol percent) were added to a round-bottomed flask. The reaction mixture was stirred for the two minutes, and then oxone (0.6 mmol) was added in three portions. The reaction mixture was placed at room temperature and stirred for the specified time (Table 5). The reaction was followed by TLC (EtOAc-cyclohexane, 2:10). After the completion of the reaction, the product was extracted in dichloromethane. The solvent was evaporated under reduced pressure to give the corresponding aromatic products. Purification of the residue using plate chromatography (silica gel) provided the pure carbonyl compounds. The aliphatic products in dichloromethane was dried with anhydrous MgSO4 and detected by GC-FID. Stage 1: With cobalt ferrite in water, Time= 0.0333333h Stage 2: With oxone(R) in water, Time= 0.333333h, T= 20 °C Sadri, Fariba; Ramazani, Ali; Massoudi, Abdolhossain; Khoobi, Mehdi; Azizkhani, Vahid; Tarasi, Roghayeh; Dolatyari, Leila; Min, Bong-Ki; Bulletin of the Korean Chemical Society; vol. 35; nb. 7; (2014); p. 2029 - 2032 View in Reaxys

93 %

With oxygen in water, Time= 6h, T= 80 °C , p= 760.051Torr , Catalytic behavior, Temperature, Reagent/catalyst Sahu, Debojeet; Silva, Ana Rosa; Das, Pankaj; RSC Advances; vol. 5; nb. 96; (2015); p. 78553 - 78560 View in Reaxys

93 %

2.2 General procedure for the oxidation of benzylalcohols mediated by TEMPO and molecular oxygen General procedure: To a stirred solution of benzyl alcohol (0.5 mmol) in dry toluene, TEMPO (0.5 mmol), potassium carbonate (1.5 mmol) and silica functionalized copper (II) catalyst (0.2 g) was added. The reaction mixture was stirred a 110C in an atmosphere of oxygen and monitored through TLC. When the reaction got completed, the reaction mixture was cooled to room temperature and was filtered. The residue was washed with water followed by EtOAc (3×10mL). The filtrate was washed with brine solution and finally the product was obtained after the removal of solvent under reduced pressure followed by passing through column of silica and elution with EtOAc: pet ether (1:100). With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, potassium carbonate in toluene, Time= 3h, T= 110 °C , Green chemistry Sharma, Pankaj; Gupta, Monika; Gupta, Rajive; Gupta, Manjulla; Journal of Chemical Sciences; vol. 127; nb. 8; (2015); p. 1485 - 1489 View in Reaxys

93 %

With tert.-butylhydroperoxide in water, Time= 3h, T= 60 °C Patnam, Padma L.; Bhatt, Mukesh; Singh, Raghuvir; Saran, Sandeep; Jain, Suman L.; RSC Advances; vol. 6; nb. 65; (2016); p. 60888 - 60895 View in Reaxys

93 %

Oppenauer Oxidation of Alcohols Using In(i-OPr)3; General Procedure General procedure: To a screw tube in a glovebox was added In(Oi-Pr)3 (29.2 mg, 0.1 mmol). The tube was then sealed and removed from the glovebox, and CHCl3 (1 mL), alcohol (0.5 mmol), and pivalaldehyde (280 μL, 2.5 mmol) were added under N2 in this order. After stirring the mixture at r.t. for 3 h, H2O (1.0 mL) was added to the reaction mixture, which was then extracted with EtOAc. The organic phase was dried (Na2SO4), and evaporated under reduced pressure. The crude material was purified by silica gel column chromatography (Table 2 and Scheme 2).

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

43/438

2018-03-11 22:07:32


With indium isopropoxide, pivalaldehyde in chloroform, Time= 3h, T= 20 °C , Glovebox, Sealed tube, Inert atmosphere, Oppenauer Oxidation Ogiwara, Yohei; Ono, Yuji; Sakai, Norio; Synthesis (Germany); vol. 48; nb. 23; (2016); p. 4143 - 4148; Art.No: SS-2016-F0462-OP View in Reaxys 93 %

22 :Benzyl alcohol and 1.10g (10.1mmol), tetrabutylammonium bromide, 0.161g (0.50mmol), TEMPO 0.0160g (0.10mmol) and the m- dichlorobenzene (GC internal standard) in a reaction vessel and dissolved in 1.22g of dichloromethane 30mL input, and performing the oxidation reaction under stirring after cooling the liquid temperature in the reaction vessel to the 5 , the crystal was added with stirring 1.99g (12.1mmol) of sodium hypochlorite pentahydrate, it was raised to room temperature and then the ice bath was removed It was.In the same manner as in Example 1. After 1 hour from the start of the oxidation reaction was confirmed that bar internal standard analysis by GC, the benzaldehyde is produced in a yield of 93percent. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium hypochlorite pentahydrate, tetrabutylammomium bromide in dichloromethane, T= 5 - 20 °C Patent; NIPPON LIGHT METAL COMPANY, LIMITED; TOMOHIDE, OKADA; TOMOTAKE, ASAWA; YUKIHIRO, SUGIYAMA; (9 pag.); KR2015/26729; (2015); (A) Korean View in Reaxys

93 %

With [Ru2Cl2(3,6-di{3-[(1-ethyl-5-methylpyrazol-3-yl)methyl]-1-imidazoliumyl}pyridazine)(p-cymene)2]*2(PF6), dihydrogen peroxide in acetonitrile, Time= 2h, T= 60 °C , Catalytic behavior, Reagent/catalyst Chen, Chao; Ni, Shengliang; Zheng, Qing; Yu, Meifang; Wang, Hangxiang; European Journal of Inorganic Chemistry; vol. 2017; nb. 3; (2017); p. 616 - 622 View in Reaxys

93 %

Typical procedure for the study of catalytic properties General procedure: To investigate the catalytic activity of complex (3), oxidation of primary alcohols into the corresponding carbonyl compounds was carried out [32]. Benzyl alcohol was selected as a model substratefor oxidation process. As an initial test, different amounts of complex from 0.01 to 0.05 g in acetonitrile solvent were mixed with 30 μL of hydrogen peroxide (30percent) as an oxidant and benzyl alcohol(0.5 mmol, 0.05 g) was added to the mixture at room temperature. Also, the reaction was run in the absence of catalyst. Then, bychanging of parameters such as the amount of oxidant from 30to 65 lL and temperature from 20 to 70 °C, optimized conditionsfor oxidation of benzyl alcohol to benzaldehyde was evaluated. After finding the optimized conditions for benzyl alcohol, oxidation of its derivatives and hexanol (0.5 mmol substrate) were studied inthe same way. The reaction progress was monitored by TLC in aregular alternative time. After completion of the reactions and removing of the solvent, the hemogeneous catalyst was separated from the reaction mixture by addition of water (5.0 mL). Then, the organic phase was separated by addition of chloroform (10.0 mL)and dried over Na2SO4. The product was purified by chromatographyon silica gel (ratio of eluent: hexane/ethyl acetate from 1:10 to1:5). Yields were obtained by weighting of isolated products. All products were known by MS and 1H NMR spectroscopy [9,24]. With [Cu(6-(2-carboxylatophenylcarbamoyl)picolinate)](4-dimethylaminopyridine)*3H2O, dihydrogen peroxide in acetonitrile, T= 45 °C , Temperature Abdolmaleki, Sara; Ghadermazi, Mohammad; Inorganica Chimica Acta; vol. 461; (2017); p. 221 - 232 View in Reaxys

93 %

With (6,8,15,17-tetramethyl-7H,16H-5,9,14,18-tetraaza-dibenzo[b,i]-cyclotetradecenato(2-)-k(4)-N,N',N'',N''')nickel(II), sodium t-butanolate in 5,5-dimethyl-1,3-cyclohexadiene, Time= 7h, T= 85 °C , Inert atmosphere, Schlenk technique, Sealed tube, Catalytic behavior, Reagent/catalyst, Solvent Parua, Seuli; Das, Siuli; Sikari, Rina; Sinha, Suman; Paul, Nanda D.; Journal of Organic Chemistry; vol. 82; nb. 14; (2017); p. 7165 - 7175 View in Reaxys

93 %

With C12H17N2O(1-)*Cu(2+)*N3 (1-), dihydrogen peroxide in acetonitrile, Time= 2h, T= 80 °C , Temperature Liu, Li-Jun; Inorganic and Nano-Metal Chemistry; vol. 47; nb. 6; (2017); p. 956 - 960 View in Reaxys

93 %

4.4 General procedure for the catalytic oxidation

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

44/438

2018-03-11 22:07:32


General procedure: The following oxidation of benzyl alcohol represents the general procedure. A mixture of nitrosotetrazolium salt (1, 3.6mg, 0.011mmol), concentrated HNO3 (16μL, 0.21mmol), and benzyl alcohol (3b, 22mg, 0.20mmol) was stirred in MeCN (2.0mL) at room temperature for 1.3h in the presence of n-cetane (tR=5.4min) as an internal standard. At intervals, aliquots were analyzed by GC after passing through a SiO2 column (eluting with CH2Cl2). The yield of 4b (tR=4.5min) was calculated to be 93percent based on a calibration curve using an authentic sample. In the case of 2-adamantanol (4g), the yield was calculated by 1H NMR based on the peaks of 2.63ppm (2H of 4g) using n-cetane (0.88ppm, 6H) as a standard. With 5-nitroso-1,3-diphenyltetrazolium tetrafluoroborate, nitric acid in acetonitrile, Time= 1.3h, T= 20 °C Matsukawa, Yuta; Hirashita, Tsunehisa; Araki, Shuki; Tetrahedron; vol. 73; nb. 42; (2017); p. 6052 - 6056 View in Reaxys 93 %

With cobaltocene, C18H11Cl3FeN4 (1-), sodium hydroxide in toluene, Time= 4h, T= 75 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst Sinha, Suman; Das, Siuli; Sikari, Rina; Parua, Seuli; Brandaõ, Paula; Demeshko, Serhiy; Meyer, Franc; Paul, Nanda D.; Inorganic Chemistry; vol. 56; nb. 22; (2017); p. 14084 - 14100 View in Reaxys

92 %

With hydrogenchloride, 3-chloro-benzenecarboperoxoic acid in N,N-dimethyl-formamide, Time= 0.0833333h, Ambient temperature Kim, Hyoung Rae; Jung, Ji Hun; Kim, Jae Nyong; Ryu, Eung K.; Synthetic Communications; vol. 20; nb. 5; (1990); p. 637 - 640 View in Reaxys

92 %

With (1,10-phenanthroline)H2CrOCl5 in dichloromethane, Time= 2h, T= 25 °C Chakraborty, T. K.; Chandrasekaran, S.; Tetrahedron Letters; vol. 21; (1980); p. 1583 - 1586 View in Reaxys

92 %

With potassium hydroxide, dipotassium peroxodisulfate, potassium ruthenate, adogen 464 in dichloromethane, Time= 3h, Ambient temperature Kim, Kwan Soo; Kim, Sung Jung; Song, Yang Heon; Hahn, Chi Sun; Synthesis; nb. 11; (1987); p. 1017 - 1018 View in Reaxys

92 %

With barium permanganate in acetonitrile, Time= 0.25h, Heating Firouzabadi, H.; Mottghinejad, E.; Seddighi, M.; Synthesis; nb. 5; (1989); p. 378 - 380 View in Reaxys

92 %

With selenium(IV) oxide, bis-{4-methoxy-phenyl}-selenoxyde in 1,4-dioxane, Time= 24h, Heating Ogura, Fumio; Otsubo, Tetsuo; Ariyoshi, Kimio; Yamaguchi, Hachiro; Chemistry Letters; (1983); p. 1833 - 1834 View in Reaxys

92 %

With 1-Chloro-1H-indole-2,3-dione in benzene, Time= 24h, Irradiation Berti, Corrado; Greci, Lucedio; Synthetic Communications; vol. 11; nb. 9; (1981); p. 681 - 686 View in Reaxys

92 %

With montmorillonite K 10 clay supported iron(III) nitrate (clayfen), Time= 0.00416667h, microwave (900 Watts) irradiation at ca. 65 deg C Varma, Rajender S.; Dahiya, Rajender; Tetrahedron Letters; vol. 38; nb. 12; (1997); p. 2043 - 2044 View in Reaxys

92 %

With bromine, nickel(II) benzoate in acetonitrile, Time= 4h, T= 20 °C , selective oxidation of alcohols Doyle, Michael P.; Dow, Robert L.; Synthetic Communications; vol. 10; nb. 11; (1980); p. 881 - 888 View in Reaxys

92 %

With 3-carboxypyridinium chlorochromate on alumina in dichloromethane, Time= 1h, Ambient temperature

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

45/438

2018-03-11 22:07:32


Heravi, Majid M.; Kiakoojori, Reza; Mirza-Aghayan, Maryam; Tabar-Hydar, Kourosh; Bolourtchian, Mohammad; Monatshefte fur Chemie; vol. 130; nb. 3; (1999); p. 481 - 483 View in Reaxys 92 %

With ammonium chlorochromate on montmorillonite K-10 in dichloromethane, Time= 1h, Ambient temperature Heravi, Majid M.; Kiakojoori, Reza; Tabar-Hydar, Kourosh; Monatshefte fur Chemie; vol. 130; nb. 4; (1999); p. 581 - 583 View in Reaxys

92 %

With zeolite HZSM-5 supported iron(III) nitrate, Time= 0.00277778h Heravi, Majid M.; Ajami, Dariush; Aghapoor, Kuoumars; Ghassemzadeh, Mitra; Chemical Communications; nb. 9; (1999); p. 833 - 834 View in Reaxys

92 %

With (NO3)3CeBrO3 in acetonitrile, Time= 2.5h, Heating Shirini; Tajik; Aliakbar; Akbar; Synthetic Communications; vol. 31; nb. 5; (2001); p. 767 - 770 View in Reaxys

92 %

With laccase, 2,2,6,6-tetramethyl-piperidine-N-oxyl, oxygen in water, Time= 24h, T= 20 °C , pH= 4.5 Fabbrini, Maura; Galli, Carlo; Gentili, Patrizia; Macchitella, Daniele; Tetrahedron Letters; vol. 42; nb. 43; (2001); p. 7551 - 7553 View in Reaxys

92 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, ammonium cerium(IV) nitrate, oxygen in acetonitrile, Time= 2h, T= 82 °C Kim, Sung Soo; Jung, Hyun Chul; Synthesis; nb. 14; (2003); p. 2135 - 2137 View in Reaxys

92 %

With 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl, [bmim]PF6, dihydrogen peroxide, hydrogen bromide, Time= 2h, T= 40 °C , Product distribution, Further Variations: Solvents, Reagents Jiang, Nan; Ragauskas, Arthur J.; Tetrahedron Letters; vol. 46; nb. 19; (2005); p. 3323 - 3326 View in Reaxys

92 %

With triethylammonium fluorochromate(VI) in dichloromethane, Time= 0.666667h, Heating Ghammamy; Hashemzadeh; Mazareey; Russian Journal of Organic Chemistry; vol. 41; nb. 12; (2005); p. 1752 1754 View in Reaxys

92 %

With tetra-n-propylammonium bromate in ethanol, Time= 1h, Heating Deb, Dibakar; Das, Satya Sandhya; Nath, Utpal; Das, Pranab J.; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 43; nb. 6; (2004); p. 1360 - 1362 View in Reaxys

92 %

With oxygen, caesium carbonate, [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, carbon in toluene, Time= 3h, T= 110 °C , p= 760.051Torr Choi, Eunjung; Lee, Chongmok; Na, Youngim; Chang, Sukbok; Organic Letters; vol. 4; nb. 14; (2002); p. 2369 2371 View in Reaxys

92 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, Oxone, tetrabutyl-ammonium chloride in dichloromethane, Time= 12h, T= 20 °C , Oxidation, Product distribution, Further Variations: Solvents, Reagents Bolm, Carsten; Magnus, Angelika S.; Hildebrand, Jens P.; Organic Letters; vol. 2; nb. 8; (2000); p. 1173 - 1175 View in Reaxys

92 %

With N -hydroxyphthalimide, oxygen, 3-chlorobenzoate, cobalt(II) acetate in acetonitrile, Time= 2h, T= 20 °C Minisci, Francesco; Punta, Carlo; Recupero, Francesco; Fontana, Francesca; Pedulli, Gian Franco; Chemical Communications; nb. 7; (2002); p. 688 - 689

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

46/438

2018-03-11 22:07:32


View in Reaxys 92 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, tetra-n-butylammonium hydrogen monopersulfate, Time= 0.5h, T= 60 °C , Ionic liquid Zhu, Chenjie; Ji, Lei; Wei, Yunyang; Catalysis Communications; vol. 11; nb. 12; (2010); p. 1017 - 1020 View in Reaxys

92 %

With [Ru(CO)(PPh3)2L4], 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Thilagavathi; Manimaran; Priya, N. Padma; Sathya; Jayabalakrishnan; Applied Organometallic Chemistry; vol. 24; nb. 4; (2010); p. 301 - 307 View in Reaxys

92 %

With VO(O-i-Pr)(8-hydroxyquinolinate)2, triethylamine, Time= 24h, T= 100 °C , Neat (no solvent) Hanson, Susan K.; Wu, Ruilian; Silks, L. A. Pete; Organic Letters; vol. 13; nb. 8; (2011); p. 1908 - 1911 View in Reaxys

92 %

With copper(II) chloride monohydrate, oxygen, silica gel in octanol, Time= 3h, T= 50 °C , p= 760.051Torr , Ionic liquid Liu, Lin; Ma, Juanjuan; Xia, Jiyin; Li, Luodan; Li, Chunlong; Zhang, Xiaobo; Gong, Junyan; Tong, Zhiwei; Catalysis Communications; vol. 12; nb. 5; (2011); p. 323 - 326 View in Reaxys

92 %

With iodosylbenzene sulfate, β‐cyclodextrin in water, Time= 2h, T= 60 °C , chemoselective reaction Zhu, Chenjie; Wei, Yunyang; Catalysis Letters; vol. 141; nb. 4; (2011); p. 582 - 586 View in Reaxys

92 %

(i) Procedure for alcohols not containing acid-sensitive groups. General procedure: To a mixture of alcohol in dry DMSO (10 volume) was added 1 equiv of polymer bromide and the reaction mixture was stirred at room temperature for a given period of time (Table 1). After the completion of the reaction, the reaction mixture was filtered and the polymer bed washed with DMSO. Combined DMSO layers were quenched with ice-water mixture and extracted with ether. The ether layer was given water wash, brine wash, dried over anhydrous sodium sulphate, and concentrated to get the pure carbonyl compounds. All the products were characterized by NMR and MS analysis. With Br3 (1-)*C10H15NPol(1+), dimethyl sulfoxide, Time= 4h, T= 20 °C Prasanna; Mohanaraju; Tetrahedron Letters; vol. 52; nb. 51; (2011); p. 6971 - 6973 View in Reaxys

92 %

With manganese dioxide supported on graphite in dichloromethane, Time= 10h, Reflux Lou, Ji-Dong; Lu, Xiu Lian; Huang, Li-Hong; Wang, Qiang; Zou, Xiao-Nan; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 41; nb. 10; (2011); p. 1342 - 1345 View in Reaxys

92 %

With oxygen in toluene, Time= 4h, T= 79.84 °C Kantam, M. Lakshmi; Reddy, R. Sudarshan; Pal, Ujjwal; Sudhakar; Venugopal; Ratnam, K. Jeeva; Figueras; Chintareddy, Venkat Reddy; Nishina, Yuta; Journal of Molecular Catalysis A: Chemical; vol. 359; (2012); p. 1 - 7 View in Reaxys

92%

With O40PW12 (3-)*C30H60N3 (3+), dihydrogen peroxide in water, Time= 1h, T= 90 °C He, Ying; Ma, Xiaoyun; Lu, Ming; Arkivoc; vol. 2012; nb. 8; (2012); p. 187 - 197 View in Reaxys

92%

With Pd2(azobenzene)2Cl2, oxygen in ethanol, N,N-dimethyl-formamide, Time= 3.66667h, T= 50 °C , p= 0Torr , Pressure Sharma, Varsha; Sagar, Priyanka; Rohit; Journal of the Indian Chemical Society; vol. 89; nb. 4; (2012); p. 463 469

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

47/438

2018-03-11 22:07:32


View in Reaxys 92 %

General Procedure for the Catalytic Oxidation.In a 50 mL roundbottom flask, the substrate (1.0 mmol) was combined with complex 8 (8.3 mg, 0.020 mmol) and NEt3 (14 μL, 0.10 mmol). The mixture was dissolved in 1,2-dichloroethane (2 mL) under air, and the flask equipped with a stir bar and an air condenser. The flask was heated with stirring in an oil bath at 60° C. for 24 h under air. To isolate the product, the solvent was removed under vacuum, and the dark residue was extracted with ethyl acetate/hexanes (3:7), filtered through a plug of silica gel, and the solvent removed under vacuum. With triethylamine, VO(O-i-Pr)(8-hydroxyquinolinate)2 in 1,2-dichloro-ethane, Time= 24h, T= 60 °C Patent; LOS ALAMOS NATIONAL SECURITY, LLC; US2012/232279; (2012); (A1) English View in Reaxys

92 %

With tert.-butylhydroperoxide, thiourea S,S-dioxide in dodecane, acetonitrile, Time= 4h, T= 65 °C Verma, Sanny; Singh, Raghuvir; Tripathi, Deependra; Gupta, Piyush; Bahuguna, Gajendra Mohan; Jain, Suman L.; RSC Advances; vol. 3; nb. 13; (2013); p. 4184 - 4188 View in Reaxys

92 %

Oxidation of alcohols 10 to carbonyl compounds 11 General procedure: A 25 mL round bottom flask was charged with alcohol (1.0 mmol), catalyst (0.02 equiv.), MeCN (5 mL), TBHP (1.5 M solution in dodecane; 1.5 equiv.) and then stirred at 65 °C for 1 h. According to Table 2, all reactions require 1 h. At the end of the reaction, the catalyst was filtered at room temperature over membrane filter paper and reused for subsequent runs. The filtrate so obtained was concentrated under reduced pressure and the residue was dissolved in dichloromethane (20 mL). The organic layer was washed with brine solution (10 mL 3×). The organic layer was dried over anhydrous MgSO4 and then, concentrated under reduced pressure. Product was purified by column chromatography over silica gel. The isolated yield of the obtained product was found to be 94percent and the conversion was determined by the GC–MS analysis. The purity of the products was determined by comparing the 1H NMR spectra of the products with those of authentic samples. With tert.-butylhydroperoxide in dodecane, acetonitrile, Time= 1h, T= 65 °C Verma, Sanny; Le Bras, Jean; Jain, Suman L.; Muzart, Jacques; Applied Catalysis A: General; vol. 468; (2013); p. 334 - 340 View in Reaxys

92 %

General procedure: a mixture of benzylalcohol (0.54 g, 5.0 mmol), Cu(OAc)2 (n1 molpercent) and TEMPO (n2 molpercent) in specified solvent (15 mL) was stired at roomtemperature for 3 h. Dichloromethane (15 mL) was added to the resulting mixture. The dichloromethanephase was separated, and the aqueous phase was further extracted with dichloromethane(10 mL × 2). The combined organic layers were dried over anhydrous sodiumsulfate and concentrated to give a residue, which was purified by columnchromatography on silica gel (eluent: petroleum ether/ethyl acetate 10:1) toprovide the desired product benzaldehyde With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper diacetate in water, acetonitrile, Time= 3h, T= 20 °C , Green chemistry, Solvent, Reagent/catalyst Jiang, Jian-An; Du, Jia-Lei; Wang, Zhan-Guo; Zhang, Zhong-Nan; Xu, Xi; Zheng, Gan-Lin; Ji, Ya-Fei; Tetrahedron Letters; vol. 55; nb. 10; (2014); p. 1677 - 1681 View in Reaxys

92 %

With ammonium nitrate, hydrogenchloride, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in water, acetonitrile, Time= 6h, T= 60 °C , Green chemistry, Concentration, Reagent/catalyst, Solvent, Temperature, Time Prebil, Rok; Stavber, Gaj; Stavber, Stojan; European Journal of Organic Chemistry; vol. 2014; nb. 2; (2014); p. 395 - 402 View in Reaxys

92 %

General Procedure for Oxidation of Alcohols General procedure: Aromatic alcohol (1–2 mmol) was dissolved in methanol (or acetone in somecases, 2–4 mL) at room temperature, followed by addition of the aqueous solutionof N-bromosuccinimide (1.5 eq.=alcohol) with continuous stirring. GMP-b-CD (3,100mg=mmol of alcohol) were added in the reaction mixture and stirring was continued.Progress of the reaction was monitored by TLC until the reaction was completed(4–6 h). GMP was separated by filtration after completion of the reaction. Thereaction mixture was extracted with ethyl acetate (45 mL), combined

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

48/438

2018-03-11 22:07:32


organiclayers were dried over Na2SO4, and solvent was removed under reduced pressure.The product was further purified by flash column chromatography and analyzedby NMR spectroscopy. With N-Bromosuccinimide in methanol, water, Time= 4h, T= 20 °C , Green chemistry Tahir, Muhammad Nazir; Qamar, Riaz-Ul; Adnan, Ahmad; Ghaffar, Abdul; Jun, Bong-Hyun; Yu, Jae-Hyuk; Jung, Seunho; Synthetic Communications; vol. 44; nb. 5; (2014); p. 589 - 599 View in Reaxys 92 %

With octanol, C35H58CrN5O3*2CH4O, dihydrogen peroxide in acetonitrile, Time= 5h, T= 80 °C , Catalytic behavior, Reagent/catalyst, Solvent, Temperature Noshiranzadeh, Nader; Bikas, Rahman; Slepokura, Katarzyna; Mayeli, Mina; Lis, Tadeusz; Inorganica Chimica Acta; vol. 421; (2014); p. 176 - 182 View in Reaxys

92 %

5.4 : 3. Typical procedure for alcohol oxidation General procedure: The oxidation process was carried out under identical condi-tions with special care. The oxidation of alcohols was carried outwith H2O2in the presence of different synthesized catalysts atatmospheric pressure and temperature of 50C. With dihydrogen peroxide, T= 50 °C , p= 760.051Torr Judy-Azar, Amir-Reza; Mohebbi, Sajjad; Journal of Molecular Catalysis A: Chemical; vol. 397; (2015); p. 158 - 165 View in Reaxys

92 %

With oxygen in toluene, Time= 3h, T= 110 °C , Temperature, Time, Solvent Wang; Xu; Catalysis Letters; vol. 144; nb. 11; (2014); p. 1919 - 1929 View in Reaxys

92 %

4.1. General Procedure for Heck Coupling and the Oxidationof Alcohols General procedure: A typical reaction was carried out as follows: bromobenzene(1a) (1.0 mmol), alkene (1.5 mmol), HCOONa (1.5mmol), 50 mg of wool-Pd complex catalyst (Pd 11.74 percent),were added to 15 mL aqueous media (PEG-400 = 33 mg) ina 25 mL beaker, and stirred at 80 °C under ambient conditions.After the completion of the reaction, the catalyst was filtrated, washed and dried. Subsequently, 40 mg of the solidcatalyst, benzyl alcohol (0.2 mmol), K2CO3 (0.2 mmol) were stirred in 15 mL aqueous media (PEG-400 = 33 mg), atmosphericair was used as the source of molecular oxygen at 60°C for 24 h, and the oxidation monitored by TLC. After completion, an extraction with ethyl acetate was performed.The organic layer was dried under reduced pressure to givethe desired crude product. Analytically pure products were obtained by column chromatography using petroleum ether and ethyl acetate as eluent. Formation of products and consumptionof substrates were monitored by GC. The identity of products was determined either by comparison with authentic samples using GC or by NMR analysis. The conversion and product selectivity were determined using GC analysis. With potassium carbonate in water, Time= 24h, T= 60 °C Wu, Shang; Zhang, Hong; Wang, Yanbin; Su, Qiong; Lei, Ziqiang; Wu, Lan; Letters in Organic Chemistry; vol. 11; nb. 10; (2014); p. 774 - 779 View in Reaxys

92 %

Oxidation of benzyl alcohol General procedure: In a typical procedure, catalyst (4 molpercent) and periodic acid(1.5 mmol/3 equiv) were stirred with 10 ml of water taken in a RBflask. The substrate (0.5 mmol/1 equiv) was added slowly to thestirred solution/ suspension. Stirring continued for required time atroom temperature until complete conversion was achieved. The catalystwas then separated magnetically from the reaction mixture. Theproduct was extracted with diethyl ether and purified by columnchromatographyusing n-hexane: ethanol (4:1) as eluent to give the aldehyde.The separated catalyst was washed with ethanol and dried in ahot air oven. With hematite, periodic acid in water, Time= 1h Paul, Bappi; Bhuyan, Bishal; Purkayastha, Debraj Dhar; Dhar, Siddhartha Sankar; Catalysis Communications; vol. 69; (2015); p. 48 - 54 View in Reaxys

92 %

Typical procedure for the oxidation of primary alcohols.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

49/438

2018-03-11 22:07:32


General procedure: A 5-mL two-necked, round-bottom flask equipped with a magnetic stirrer and an oxygen balloon was charged in succession with 0.0106 g(0.05 mmol) of Cu(OTf), 0.0078 g (0.05 mmol) of TEMPO, 0.0136 g (0.04 mmol) of benzoxazine ligand L, and 1 mL of methylene chloride. The corresponding alcohol, 1 mmol, was then added at 25°C under stirring, and oxygen from the balloon was introduced through a three-way valve. The progress of the reaction was monitored by GLC using a suitable column. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, 6,8-di(tert-butyl)-3-[2-(1H-imidazol-4-yl)ethyl]-3,4-dihydro-2H-1,3-benzoxazine, oxygen, copper(I) triflate in dichloromethane, Time= 7h, T= 25 °C , Catalytic behavior, Reagent/catalyst, Solvent, Temperature Zhang; Huang; Lü; Cao; Zhao; Russian Journal of General Chemistry; vol. 85; nb. 8; (2015); p. 1965 - 1972; Zh. Obshch. Khim. View in Reaxys 92 %

With tert.-butylnitrite, oxygen, 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine, acetic acid in acetonitrile, Time= 4h, T= 20 °C , Irradiation, Reagent/catalyst, Solvent Samanta, Suvendu; Biswas, Papu; RSC Advances; vol. 5; nb. 102; (2015); p. 84328 - 84333 View in Reaxys

92 %

With sodium periodate in water, acetonitrile, Time= 1.33333h, T= 20 °C Saffar-Teluri, Ali; RSC Advances; vol. 5; nb. 86; (2015); p. 70577 - 70585 View in Reaxys

92 %

With potassium carbonate in water, dimethyl sulfoxide, Time= 0.5h, T= 60 °C , Reagent/catalyst, Solvent Dehghan, Mahsa; Motaharinejad, Atieh; Saadat, Mostafa; Ahdenov, Reza; Babazadeh, Mirzaagha; Hosseinzadeh-Khanmiri, Rahim; RSC Advances; vol. 5; nb. 112; (2015); p. 92335 - 92343 View in Reaxys

92 %

With oxygen, nitrosonium tetrafluoroborate in dichloromethane, Time= 2h, T= 20 °C Shakir, Ahmed Juwad; Paraschivescu, Codruta; Matache, Mihaela; Tudose, Madalina; Mischie, Alice; Spafiu, Felicia; Ionita, Petre; Tetrahedron Letters; vol. 56; nb. 49; (2015); p. 6878 - 6881 View in Reaxys

92 %

With [OsV(O)(2,2’:6’,2’’:6’’,2’’’-quaterpyridine)(4-picoline)Cl](PF6)2 in acetonitrile, T= 23 °C , Inert atmosphere Liu, Yingying; Ng, Siu-Mui; Lam, William W. Y.; Yiu, Shek-Man; Lau, Tai-Chu; Angewandte Chemie - International Edition; vol. 55; nb. 1; (2016); p. 288 - 291; Angew. Chem.; vol. 128; nb. 1; (2016); p. 296 - 299,4 View in Reaxys

92 %

2.4. General Procedure for the Oxidation under Microwave Irradiation General procedure: The substrate (1mmol) and 1.5–2 mmol oxidant were mixed. To this mixture 0.5 mL CH2Cl2 was added. The mixture was subjected to microwave irradiation (1000 W). Upon completion of the reaction, extraction with ether (3 × 25mL) and evaporation of the solvent gave the corresponding carbonyl compounds. The products formed were analyzed by their 2,4-dinitrophenylhydrazone derivatives.The precipitated 2,4-DNP was filtered off, weighed, and recrystallized from ethanol. With 1,1,3,3-tetramethylguanidinium fluorochromate in dichloromethane, Time= 0.00111111h, Microwave irradiation, Reagent/catalyst, Solvent Şendil, Kivilcim; Özgün, H. Beytiye; Üstün, Ebru; Journal of Chemistry; vol. 2016; (2016); Art.No: 3518102 View in Reaxys

92 %

Typical procedure for the oxidation of alcohols General procedure: A solution of BTC (0.41 g, 1.39 mmol) in dry CH2Cl2 (5 mL) was cooled in an ice-salt bath under an atmosphere of N2. A solution of I (1.24 g, 4.17 mmol) in dry CH2Cl2 (5 mL) was added dropwise for 0.5 h, at −15 °C. Stirring was continued for 0.5 h, and a solution of benzyl alcohol (0.3 g, 2.78 mmol) in dry CH2Cl2 (5 mL) was added dropwise for 0.5 h, at−15 °C. After stirring for 0.5 h, Et3N (0.84 g, 8.34 mmol) was added slowly while the temperature should be controlled below −15 °C. When the reaction was completed, 10percent HCl solution in water was added dropwise until the pH of the reaction solution reached 2 under ice bath. The mixture was extracted with nhexane or petroleum ether (10 mL x 2),decanted. The product was acquired after organic layer was concentrated and purified by flash chromatography (SiO2; n-hexane). (0.27 g, 92percent). The water layer was used for the recovery of V and the excess I.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

50/438

2018-03-11 22:07:32


Stage 1: With bis(trichloromethyl) carbonate, 4-(2-(2-(methylsulfinyl)ethyl)-4-nitrophenyl)morpholine in dichloromethane, Time= 1h, T= -15 °C , Inert atmosphere, Swern Oxidation Stage 2: With triethylamine in dichloromethane, T= -15 °C , Inert atmosphere, Swern Oxidation, Temperature, Reagent/catalyst Ye, Xiaojing; Fu, Hongliang; Ma, Jiahao; Zhong, Weihui; Synthetic Communications; vol. 46; nb. 10; (2016); p. 885 - 892 View in Reaxys 92 %

1 :In a 1OO mL single-necked flask, a magnet, 3 mmo1 benzyl alcohol, 3 mol percent TEMPO, 2 mol percent copper bromide and 0.88 neutral alumina together into a single-necked flask, the bottle is sealed with plastic wrap (fresh film left hole). Start the single-mouth bottle at the bottom of the strong magnetic stirrer for mixing, start the timer. After the reaction, the organic material was extracted with ethyl acetate, the organic phase was washed with water and brine, respectively, dried over anhydrous magnesium sulfate, the organic phase was then subjected to GC analysis (benzyl alcohol conversion 100percent, the selectivity of benzaldehyde is 100percent). Finally, then rinsed obtained product was purified by 300-400 mesh silica column. The yield of benzaldehyde is 92percent. With aluminum oxide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper(ll) bromide, Green chemistry, Reagent/catalyst Patent; Jinan University; WANG, QIU FEN; ZHENG, GENG XIU; ZHAO, JING JING; YANG, QIAN; JIANG, SHOU XIANG; XU, YAN; ZHAN, FU XU; (6 pag.); CN104193600; (2016); (B) Chinese View in Reaxys

92 %

With 1-methyl-1H-imidazole, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate, 2-[N-methyl-N-(pyridin-2-yl)amino]pyridine in acetonitrile, Time= 2h, T= 30 °C Marais, Lindie; Burés, Jordi; Jordaan, Johan H. L.; Mapolie, Selwyn; Swarts, Andrew J.; Organic and Biomolecular Chemistry; vol. 15; nb. 33; (2017); p. 6926 - 6933 View in Reaxys

92%

1 : Example 1: In a 150 mL thick-walled pressure tube equipped with a magnetic stirrer,In an air atmosphere,To the system was added benzyl alcohol (i.e., R1 in formula (I) H) 1.0 mmol (108.1 mg)Ammonia (1.6 x 10-2 mol / L) 5.0 mL,5 molpercent (9.5 mg) of cuprous iodide,TEMPO 5 molpercent (7.8 mg),100 & lt; 0 & gt; C for 12 h,After the reaction is over,The reaction solution was cooled to room temperature,And extracted with ethyl acetate (3 x 5.0 mL). The organic layers were combined and concentrated in vacuo to remove ethyl acetate to give the crude product. The crude product was purified by column chromatography(Petroleum ether: ethyl acetate = 10: 1) to give the pure desired product.The yield of 97.6 mg was 92percent. With ammonium hydroxide, copper(l) iodide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, Time= 15h, T= 100 °C Patent; Zhejiang University of Technology; Zhang Guofu; Zhao Yiyong; Zhang Guihua; Ding Chengrong; Lv Jinghui; Yu Yidong; (10 pag.); CN106905097; (2017); (A) Chinese View in Reaxys

92.4 %

3.2. Catalytic oxidation of alcohols General procedure: The oxidation of benzyl alcohol with O2 was acted as a probe reactionto estimate the activities of as-synthesized catalysts. In order toget the optimum reaction conditions of Co-NG, different parameterssuch as solvent, reaction temperature, reaction time and dosage ofcatalyst were investigated. It was found that the best solvent should beDMF, the optimal dosage of catalyst should be 5 mg, the suitable reactiontemperature should be controlled at 130 °C, and the reasonablereaction time should be 5 h. (Table S1, and Fig. S13) When air is used asthe oxidant instead of oxygen, the benzyl alcohol conversion increasesfrom 47.4percent to 68.3percent as the air flow increases from 20 mL min−1 to80 mL min−1. But the catalytic efficiency is still lower than that usingoxygen as the oxidant. With the optimized experimental conditions, Co-NG and Co-G-750were examined as potential catalysts for the aerobic oxidation of benzylalcohol. It can be seen that the reaction hardly occurred without anycatalyst (Table 2). Only 10.8percent of benzyl alcohol conversion was obtainedwhen using GO as the catalyst. To investigate the influence ofnitrogen-doping temperature on the catalytic activity, a series of Co-NGcatalysts were prepared by controlling the annealing temperaturevarying from 550 °C to 850 °C. The catalytic performance of thesematerials in the oxidation benzyl alcohol to benzaldehyde were evaluated(Table 2, Entry 2–5). It was evident that Co-NG-750 (containing0.4 wtpercent Co) performed better catalytic activity and higher turnoverfrequency (as high as 544 h−1) than the others. For example, the TOF ofCo-NG was 42.8 times higher than that of Co3O4/CMK-3 and 406 timeshigher times than Co3O4/RGO-N. Co-N-C catalyst synthesized by pyrolysisof Co(NO3)3 and nicarbazine showed a conversion of

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

51/438

2018-03-11 22:07:32


less than10percent after reaction for one hour in the oxidation of benzyl alcohol,which was much lower than that of Co-NG-750 (50.1percent) [28]. With oxygen in N,N-dimethyl-formamide, Time= 5h, T= 130 °C , Solvent, Reagent/catalyst Li, Min; Wu, Shujie; Yang, Xiaoyuan; Hu, Jing; Peng, Ling; Bai, Lu; Huo, Qisheng; Guan, Jingqi; Applied Catalysis A: General; vol. 543; (2017); p. 61 - 66 View in Reaxys 92 %

2.7. General procedure of oxidation of alcohols General procedure: The alcohol (1 mmol), catalyst (20 mg), PhI(OAc)2 (403 mg,1.25 mmol) and MgSO4 (about 300 mg) were stirred in ethylene dichloride (EDC, 25 mL) at room temperature until the reaction was complete. The progress of the reaction was monitored by TLC. The reaction mixture was filtered through sintered funneland residue was washed with EDC. Then the EDC layer was washed with water and dried over anhydrous MgSO4. The solvent was removed using rotary evaporator at room temperature under reduced pressure. The crude product was purified by column chromatography over silica gel using ethyl acetate–petroleum ether as eluent. With [bis(acetoxy)iodo]benzene, magnesium sulfate in 1,2-dichloro-ethane, Time= 3h, T= 20 °C Dasgupta, Sanchari; Chakraborty, Aratrika; Chatterjee, Sourav; Chattopadhyay, Tanmay; Inorganica Chimica Acta; vol. 474; (2018); p. 1 - 10 View in Reaxys

91 %

With tert.-butylhydroperoxide, titanium(IV) isopropylate in dichloromethane, Time= 24h, T= 20 °C , molecular sieves Krohn, Karsten; Khanbabaee, Karamali; Rieger, Hagen; Chemische Berichte; vol. 123; nb. 6; (1990); p. 1357 1364 View in Reaxys

91 %

With Dess-Martin periodane in dichloromethane, Time= 1h, T= 25 °C Dess, D. B.; Martin, J. C.; Journal of Organic Chemistry; vol. 48; nb. 22; (1983); p. 4155 - 4156 View in Reaxys

91 %

With peracetic acid, sodium bromide in acetic acid, Time= 2h, T= 60 °C Morimoto, Takashi; Hirano, Masao; Ashiya, Hiroyuki; Egashira, Hidetaka; Zhuang, Xiumin; Bulletin of the Chemical Society of Japan; vol. 60; nb. 11; (1987); p. 4143 - 4144 View in Reaxys

91 %

With aluminum oxide, ammonium chlorochromate in cyclohexane, Time= 1h, T= 30 °C Zhang, Gui-Sheng; Shi, Qi-Zeng; Chen, Mi-Feng; Cai, Kun; Synthetic Communications; vol. 27; nb. 6; (1997); p. 953 - 956 View in Reaxys

91 %

With isoquinolinium fluorochromate in dichloromethane, Time= 1h, Heating Srinivasan; Stanley, Preethi; Balasubramanian; Synthetic Communications; vol. 27; nb. 12; (1997); p. 2057 2064 View in Reaxys

91 %

With ammonium chlorochromate, silica gel in cyclohexane, Time= 2h, T= 30 °C Zhang, Gui-Sheng; Shi, Qi-Zeng; Chen, Mi-Feng; Cai, Kun; Synthetic Communications; vol. 27; nb. 21; (1997); p. 3691 - 3696 View in Reaxys

91 %

With KMnO4-kieselguhr Reagent in toluene, Time= 1h, T= 70 °C Lou, Ji-Dong; Lou, Wen-Xing; Synthetic Communications; vol. 27; nb. 21; (1997); p. 3697 - 3699 View in Reaxys

91 %

With aluminum oxide, dimethylammonium chlorochromate in cyclohexane, Time= 2h, T= 25 - 30 °C Zhang, Gui-Sheng; Shi, Qi-Zeng; Chen, Mi-Feng; Cai, Kun; Organic Preparations and Procedures International; vol. 30; nb. 2; (1998); p. 215 - 218

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

52/438

2018-03-11 22:07:32


View in Reaxys 91 %

With dipyridinium dichromate, adogen 464, dihydrogen peroxide, sodium carbonate in various solvent(s), Time= 24h, Heating, Oxidation Delaval, Nicolas; Bouquillon, Sandrine; Henin, Francoise; Muzart, Jacques; Journal of Chemical Research Part S; nb. 4; (1999); p. 286 - 287 View in Reaxys

91 %

With nitric acid, ytterbium(III) triflate in 1,2-dichloro-ethane, Time= 0.5h, Heating, Oxidation Barrett, Anthony G. M.; Braddock, D. Christopher; McKinnell, R. Murray; Waller, Francis J.; Synlett; nb. 9; (1999); p. 1489 - 1490 View in Reaxys

91 %

With imidazolium fluorochromate in acetonitrile, Time= 1.5h, T= 20 °C , Oxidation Pandurangan; Rajkumar, G. Abraham; Arabindoo, Banumathi; Murugesan; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 1; (1999); p. 99 - 100 View in Reaxys

91 %

With nitric acid in dichloromethane, Time= 1h, T= 20 °C Strazzolini, Paolo; Runcio, Antonio; European Journal of Organic Chemistry; nb. 3; (2003); p. 526 - 536 View in Reaxys

91 %

With potassium permanganate in various solvent(s), Time= 1h, T= 20 °C Kumar, Anil; Jain, Nidhi; Chauhan; Synthetic Communications; vol. 34; nb. 15; (2004); p. 2835 - 2842 View in Reaxys

91 %

With oxygen, RuHAP in toluene, Time= 24h, T= 90 °C , p= 760.051Torr , Oxidation, Kinetics Yamaguchi, Kazuya; Mori, Kohsuke; Mizugaki, Tomoo; Ebitani, Kohki; Kaneda, Kiyotomi; Journal of the American Chemical Society; vol. 122; nb. 29; (2000); p. 7144 - 7145 View in Reaxys

91 %

With C11H17N2O2, potassium tert-butylate, copper(ll) bromide in water, acetonitrile, T= 20 °C Gartshore, Christopher J.; Lupton, David W.; Advanced Synthesis and Catalysis; vol. 352; nb. 18; (2010); p. 3321 - 3328 View in Reaxys

91 %

With potassium bromide in water, acetonitrile, Time= 10h, T= 20 °C Chen, Jiang-Min; Zeng, Xiao-Mei; Zhdankin, Viktor V.; Synlett; nb. 18; (2010); p. 2771 - 2774 View in Reaxys

91 %

With potassium 12-tungstocobaltate(III) in water, acetonitrile, Time= 0.1h, Microwave irradiation Farhadi; Ansari; Journal of the Iranian Chemical Society; vol. 8; nb. 2; (2011); p. 470 - 476 View in Reaxys

91 %

With [Rh((5-H-dibenzo[a,d]cyclohepten-5-yl)2NH)(PPh3)]OTf, potassium carbonate, Nitrosobenzene in tetrahydrofuran, T= 20 °C Annen, Samuel P.; Gruetzmacher, Hansjoerg; Dalton Transactions; vol. 41; nb. 46; (2012); p. 14137 - 14145 View in Reaxys

91 %

With oxygen in N,N-dimethyl-formamide, Time= 1h, T= 100 °C , p= 760.051Torr , Reagent/catalyst Luan, Yi; Qi, Yue; Gao, Hongyi; Zheng, Nannan; Wang, Ge; Journal of Materials Chemistry A; vol. 2; nb. 48; (2014); p. 20588 - 20596 View in Reaxys

91 %

With [bis(acetoxy)iodo]benzene, magnesium sulfate in 1,2-dichloro-ethane, Time= 4h, T= 45 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

53/438

2018-03-11 22:07:32


Rahaman, Hasimur; Laha, Radha M.; Maiti, Dilip K.; Ghosh, Sujit Kumar; RSC Advances; vol. 5; nb. 43; (2015); p. 33923 - 33929 View in Reaxys 91 %

1 : 4.5. General procedure for the aerobic alcohol oxidation General procedure: Under an air atmosphere, a Schlenk tube was charged with MCM-41-bpy-CuI (40 mg, 0.025 mmol), alcohol (0.5 mmol), TEMPO (4 mg, 0.025 mmol), aqueous ammonia (0.5 mmol, 25e28percent, w/w) and EtOH (1.0 mL). The mixture was stirred at 50 °C for 18-48 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 mL), and filtered. The MCM-41-bpy-CuI complex was washed with EtOH (2*5 mL), and Et2O (5 mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (petroleum/ethyl acetate=15:1 to 10:1) to provide the desired product. With ammonium hydroxide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in ethanol, Time= 22h, T= 50 °C Zhao, Hong; Chen, Qiurong; Wei, Li; Jiang, Yuanyuan; Cai, Mingzhong; Tetrahedron; vol. 71; nb. 46; (2015); p. 8725 - 8731; Art.No: 27151 View in Reaxys

91 %

With potassium carbonate in toluene, Time= 3h, T= 80 °C , Reagent/catalyst Kadam, Mahesh M.; Dhopte, Kiran B.; Jha, Neetu; Gaikar, Vilas G.; Nemade, Parag R.; New Journal of Chemistry; vol. 40; nb. 2; (2016); p. 1436 - 1442 View in Reaxys

91 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [{Cu2(5-phenyl-2,8-bis(2-pyridinyl)-1,9,10-anthyridine) (H2O)4(CH3CN)2}(ClO4)4], oxygen in toluene, Time= 12h, T= 100 °C , Kinetics, Reagent/catalyst, Solvent, Temperature Huang, Da-Wei; Liu, Yi-Hung; Peng, Shie-Ming; Liu, Shiuh-Tzung; Organometallics; vol. 35; nb. 2; (2016); p. 151 - 158 View in Reaxys

91.1 %

With oxygen, Time= 4h, p= 760.051Torr , Irradiation, Sealed tube, Catalytic behavior, Kinetics, Reagent/catalyst Chen, Yu; Li, Weizun; Wang, Jingyu; Yang, Qian; Hou, Qidong; Ju, Meiting; RSC Advances; vol. 6; nb. 74; (2016); p. 70352 - 70363 View in Reaxys

90 %

With alumina supported chromium(VI) oxide in hexane, Time= 24h, Ambient temperature Hirano, Masao; Kuroda, Hisanori; Morimoto, Takashi; Bulletin of the Chemical Society of Japan; vol. 63; nb. 8; (1990); p. 2433 - 2434 View in Reaxys

90 %

With bislt;benzyltriethylammoniumgt; dichromate in N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 4h, T= 60 80 °C Hishmat; El Ebrashi; El Naem; Abd El Rahman; Synthesis; vol. No. 12; (1982); p. 1075 - 1077 View in Reaxys

90 %

With tripropylammonium fluorochromate (VI) in dichloromethane, Time= 0.75h Chamchaang, W.; Prankprakma, V.; Tarnchompoo, B.; Thebtaranonth, C.; Thebtaranonth, Y.; Synthesis; nb. 7; (1982); p. 579 - 580 View in Reaxys

90 %

With isocyanate de chlorosulfonyle, dimethyl sulfoxide, triethylamine in dichloromethane, Time= 1.5h, T= -78 °C Olah, George A.; Vankar, Yashwant D.; Arvanaghi, Massoud; Synthesis; nb. 2; (1980); p. 141 - 142 View in Reaxys

90 %

With trans-{dioxoruthenium(VI)(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)propylenediamine)}(perchlorate)2 in acetonitrile, Time= 1h, T= 25 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

54/438

2018-03-11 22:07:32


Che, Chi-Ming; Tang, Wai-Tong; Li, Chi-Keung; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 12; (1990); p. 3735 - 3739 View in Reaxys 90 %

With sodium hypochlorite, sodium stearate, Time= 16h, Ambient temperature Jursic, Branko; Synthesis; nb. 11; (1988); p. 868 - 871 View in Reaxys

90 %

With potassium nitrososulfonate, adogen 464 in benzene, Time= 12h Morey, Jeronimo; Dzielenziak, Adam; Saa, Jose Manuel; Chemistry Letters; (1985); p. 263 - 264 View in Reaxys

90 %

With tetrakis(pyridine)silver dichromate in benzene, Time= 3h, Heating Firouzabadi, H.; Sardarian, A.; Gharibi, H.; Synthetic Communications; vol. 14; nb. 1; (1984); p. 89 - 94 View in Reaxys

90 %

With tetra(n-butyl)ammonium dichromate(VI) in dichloromethane, Time= 3h, Heating Santaniello, Enzo; Ferraboschi, Patrizia; Synthetic Communications; vol. 10; nb. 1; (1980); p. 75 - 82 View in Reaxys

90 %

With dinitrogen tetraoxide, ferric nitrate in dichloromethane, Ambient temperature, further oxidizing agent, further conditions and solvents Iranpoor, Nasser; Firouzabadi, Habib; Zolfigol, Mohammad Ali; Bulletin of the Chemical Society of Japan; vol. 71; nb. 4; (1998); p. 905 - 908 View in Reaxys

90 %

With alumina supported chromium(VI) oxide in hexane, Time= 24h, Ambient temperature, other aromatic alcohols Hirano, Masao; Kuroda, Hisanori; Morimoto, Takashi; Bulletin of the Chemical Society of Japan; vol. 63; nb. 8; (1990); p. 2433 - 2434 View in Reaxys

90 %

With N-iodo-succinimide in benzene, Time= 2h, Irradiation, var. alcohols, var. irradiat. times, Product distribution Beebe, T. R.; Adkins, R. L.; Bogardus, C. C.; Champney, B.; Hii, P. S.; et al.; Journal of Organic Chemistry; vol. 48; nb. 18; (1983); p. 3126 - 3128 View in Reaxys

90 %

With potassiuim nitrosodisulfonate, adogen 464 in benzene, Time= 12h, Mechanism Morey, Jeronimo; Dzielenziak, Adam; Saa, Jose Manuel; Chemistry Letters; (1985); p. 263 - 264 View in Reaxys

90 %

With benzyltriphenylphosphonium peroxymonosulfate, Time= 0.166667h, Oxidation Hajipour, Abdol Reza; Mallakpour, Shadpour E.; Adibi, Hadi; Chemistry Letters; nb. 5; (2000); p. 460 - 461 View in Reaxys

90 %

With DDB in acetonitrile, Time= 1h, Heating Shirini; Tajik; Jalili; Synthetic Communications; vol. 31; nb. 19; (2001); p. 2885 - 2889 View in Reaxys

90 %

With ammonium dichromate(VI), silica gel, iodic acid, Time= 0.166667h, T= 20 °C , Product distribution, Further Variations: Reaction partners, Solvents Shirini; Zolfigol; Azadbar; Russian Journal of Organic Chemistry; vol. 37; nb. 11; (2001); p. 1600 - 1602 View in Reaxys

90 %

With chromium(VI) oxide, Time= 3h Lou, Ji-Dong; Xu, Zhi-Nan; Tetrahedron Letters; vol. 43; nb. 35; (2002); p. 6095 - 6097 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

55/438

2018-03-11 22:07:32


90.5 %

With bentonite clay, nitric acid in hexane, Time= 3.5h, Heating Bahulayan, Damodaran; Narayan, Gopinathan; Sreekumar, Vellalath; Lalithambika, Malathy; Synthetic Communications; vol. 32; nb. 23; (2002); p. 3565 - 3574 View in Reaxys

90 %

With sodium bromate, Nafion-Ce(IV), Nafion-H in water, acetonitrile, Time= 4h, Heating Yamoto, Takehiko; Shinoda, Naoki; Journal of Chemical Research, Synopses; nb. 8; (2002); p. 400 - 402 View in Reaxys

90 %

With poly[4-(diacetoxyiodo)styrene], 2,2,6,6-tetramethyl-piperidine-N-oxyl in acetone, Time= 2h, T= 20 °C Sakuratani, Kenji; Togo, Hideo; Synthesis; nb. 1; (2003); p. 21 - 23 View in Reaxys

90 %

With butyltriphenylphosphonium chlorochromate in acetonitrile, Time= 0.666667h, Heating, Product distribution, Further Variations: Solvents Hajipour, Abdol R.; Mallakpour, Shadpour E.; Malakoutikhah, Morteza; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 42; nb. 1; (2003); p. 195 - 198 View in Reaxys

90 %

With pyridine, tetra-n-butylammonium hydrogen monopersulfate, Mn(meso-tetraphenylporphyrin)OAc in acetonitrile, Time= 0.0833333h, T= 25 °C , Product distribution, Further Variations: Reagents, Solvents Rezaeifard, Abdolreza; Jafarpour, Maasoumeh; Moghaddam, Gholamreza Kardan; Amini, Fatemeh; Bioorganic and Medicinal Chemistry; vol. 15; nb. 8; (2007); p. 3097 - 3101 View in Reaxys

90 %

With tert.-butylhydroperoxide, iron(III)phthalocyanine chloride, acetic acid, Time= 1h, T= 20 °C Filipan-Litvic, Mirela; Litvic, Mladen; Vinkovic, Vladimir; Bioorganic and Medicinal Chemistry; vol. 16; nb. 20; (2008); p. 9276 - 9282 View in Reaxys

90 %

With dipotassium peroxodisulfate, molybdenum trioxide in water, acetonitrile, Time= 0.68h, Reflux Shirini; Yazdanbakhsh; Pop-Kiadeh, M. Mahdavi; Abedini; Journal of Chemical Research; nb. 7; (2008); p. 409 411 View in Reaxys

Ca. 90 %

With C36H40Cu2N6O2 (2+) in acetone, T= -70 °C Matsumoto, Takahiro; Ohkubo, Kei; Honda, Kaoru; Yazawa, Akiko; Furutachi, Hideki; Fujinami, Shuhei; Fukuzumi, Shunichi; Suzuki, Masatatsu; Journal of the American Chemical Society; vol. 131; nb. 26; (2009); p. 9258 - 9267 View in Reaxys

90 %

With sodium hypochlorite, 4-({[4-(triphenylphosphonio)benzyl]oxy}carbonyl)oxy-2,2,6,6-tetramethylpiperidin-1-oxyl perchlorate, sodium hydrogencarbonate, potassium bromide in dichloromethane, water, Time= 0.0833333h, pH= 8.9 Roy, Marie-Noelle; Poupon, Jean-Christophe; Charette, Andre B.; Journal of Organic Chemistry; vol. 74; nb. 22; (2009); p. 8510 - 8515 View in Reaxys

90 %

With hydrogen bromide, oxygen, sodium nitrite in water, acetonitrile, Time= 24h, T= 70 °C Uyanik, Muhammet; Fukatsu, Ryota; Ishihara, Kazuaki; Chemistry - An Asian Journal; vol. 5; nb. 3; (2010); p. 456 - 460 View in Reaxys

90%

8 : Manufacture of benzaldehyde Benzyl alcohol (2.0g, 18.5mmol), potassium carbonate (1.5g, 11.1mmol), 4-hydroxy TEMPO (31mg, 0.19mmol), tetrabutylammonium bromide (0.5g, 1.9mmol) and MTBE (15ml) were put in a 50-ml egg plant type flask. The suspension was cooled to less 10°C in an ice bath and thereto was added NCS (2.7g, 20.4mmol) divided in three portions.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

56/438

2018-03-11 22:07:32


The insoluble materials were filtered off and the filtrate was washed with 5percent aqueous sodium bicarbonate solution. The crude product was purified by distillation to give benzaldehyde (1.77g, yield 90percent). With N-chloro-succinimide, TEMPOL, tetrabutylammomium bromide, potassium carbonate in tert-butyl methyl ether, T= 10 °C Patent; DAISO CO., LTD.; EP1666441; (2006); (A1) English View in Reaxys 90 %

With [Mn(IV)(O)(BQCN)(H2O)](2+) in water, acetonitrile, T= 0 °C , Inert atmosphere, Kinetics, Concentration Sawant, Sarvesh C.; Wu, Xiujuan; Cho, Jaeheung; Cho, Kyung-Bin; Kim, Sun Hee; Seo, Mi Sook; Lee, YongMin; Kubo, Minoru; Ogura, Takashi; Shaik, Sason; Nam, Wonwoo; Angewandte Chemie - International Edition; vol. 49; nb. 44; (2010); p. 8190 - 8194 View in Reaxys

90 %

With bromine, oxygen, potassium nitrate in acetonitrile, Time= 24h, T= 50 °C , chemoselective reaction Yuan, Yu; Shi, Xiao; Liu, Wei; Synlett; nb. 4; (2011); p. 559 - 564; Art.No: W17710ST View in Reaxys

90 %

With trichloroisocyanuric acid in water, Time= 1h, T= 20 °C , Ionic liquid Lee, Jong Chan; Kim, Jimi; Lee, Seung Bae; Chang, Soon-Uk; Jeong, Yeon Jin; Synthetic Communications; vol. 41; nb. 13; (2011); p. 1947 - 1951 View in Reaxys

90 %

With tert.-butylhydroperoxide in decane, acetonitrile, Time= 3h, T= 65 °C Verma, Sanny; Nandi, Mahasweta; Modak, Arindam; Jain, Suman L.; Bhaumik, Asim; Advanced Synthesis and Catalysis; vol. 353; nb. 11-12; (2011); p. 1897 - 1902 View in Reaxys

90 %

With tert.-butylhydroperoxide, manganese(III) 5,10,15-tris(pentafluorophenyl)perbromocorrolate in water, benzene, Time= 12h, T= 25 °C Bose, Suranjana; Pariyar, Anand; Biswas, Achintesh Narayan; Das, Purak; Bandyopadhyay, Pinaki; Catalysis Communications; vol. 12; nb. 6; (2011); p. 446 - 449 View in Reaxys

90 %

With C10H6BrClN4O2PdS, 4-methylmorpholine N-oxide in dichloromethane, Time= 2h, Reflux Ramasubramanian, Ayaloor Subramanian; Bhat, Badekai Ramachandra; Dileep, Ramakrishna; Rani, Sandya; Journal of the Serbian Chemical Society; vol. 76; nb. 1; (2011); p. 75 - 83 View in Reaxys

90 %

With ammonium cerium (IV) nitrate, 1-hexyl-3-methylimidazolium hydrogen sulphate, Time= 0.416667h, T= 80 °C , neat (no solvent), chemoselective reaction Hajipour; Khazdooz; Ruoho; Journal of the Iranian Chemical Society; vol. 8; nb. 2; (2011); p. 382 - 387 View in Reaxys

90 %

With manganese(IV) oxide, manganese(II) nitrate tetrahydrate, dibenzoyl peroxide in hexane, Time= 0.166667h, T= 70 °C , p= 760.051Torr , chemoselective reaction Massah, Ahmad Reza; Kalbasi, Roozbeh Javad; Azadi, Mohammad; Comptes Rendus Chimie; vol. 15; nb. 5; (2012); p. 428 - 436 View in Reaxys

90 %

General procedure: Alcohol (1 mmol) and NaOCl (ca. 13percent, 5 mL) were dissolved in HFIP (1 mL) and was stirred at 25-30 °C in a vial for 3 h. After completion of the reaction as indicated by TLC, the HFIP was separated by distillation and then the mixture was extracted with diethyl ether (3 x 25 mL). The combined organic layers were washed with H2O and dried over MgSO4. The solvent was removed under vacuum, and the residue was purified bychromatography. All the products were characterized by comparison of their physical and spectral data with those of authentic samples. With sodium hypochlorite in 1,1,1,3',3',3'-hexafluoro-propanol, Time= 3h, T= 25 - 30 °C , chemoselective reaction

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

57/438

2018-03-11 22:07:32


Khaksar, Samad; Talesh, Saeed Mohammadzadeh; Journal of Fluorine Chemistry; vol. 140; (2012); p. 95 - 98 View in Reaxys 90 %

With sodium perborate tetrahydrate, sulfuric acid, potassium bromide in water, T= 80 °C Han, Mikyoung; Jeong, Ku Sun; Lee, Jong Chan; Bulletin of the Korean Chemical Society; vol. 33; nb. 7; (2012); p. 2405 - 2406 View in Reaxys

90 %

With modified polyacrylamide-supported chlorochromate in cyclohexane, Time= 3h, T= 20 °C Tamami, Bahman; Heiran, Roghayeh; Montazer, Elham Riazi; Journal of the Serbian Chemical Society; vol. 77; nb. 5; (2012); p. 685 - 697 View in Reaxys

90%

With C32H18CuN4O6*H2O, dihydrogen peroxide in water, acetonitrile, Time= 2h, T= 20 °C , Reagent/catalyst, Concentration, Time Shoair, Abdel Ghany F.; Journal of Coordination Chemistry; vol. 65; nb. 20; (2012); p. 3511 - 3518 View in Reaxys

90%

With aluminium dodecatungstophosphate, dihydrogen peroxide in water, acetonitrile, Time= 0.583333h, T= 90 °C , Reflux, Solvent, Concentration, Reagent/catalyst Aliyan, Hamid; Fazaeli, Razieh; Habibollah, Nasibeh; Journal of the Korean Chemical Society; vol. 56; nb. 5; (2012); p. 591 - 596 View in Reaxys

90 %

With dihydrogen peroxide in water, acetonitrile, Time= 0.833333h, T= 25 °C , Solvent, Temperature, Reagent/catalyst, Concentration, Time Eshtiagh-Hosseini, Hossein; Tabari, Taymaz; Takjoo, Reza; Eshghi, Hossein; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 43; nb. 3; (2013); p. 264 - 272 View in Reaxys

90 %

With sodium hydrogensulfate monohydrate, iodic acid in water, acetonitrile, Time= 1.5h, Reflux Khademian, Mohsen; Khademian, Maryam; Rahimnejad, Mostafa; Mokhtarian, Nader; Asian Journal of Chemistry; vol. 25; nb. 5; (2013); p. 2927 - 2928 View in Reaxys

90 %

With C21H19ClN3RuSe(1+)*F6P(1-), 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, T= 80 °C , Reagent/ catalyst Saleem, Fariha; Rao, Gyandshwar Kumar; Kumar, Arun; Mukherjee, Goutam; Singh, Ajai K.; Organometallics; vol. 32; nb. 13; (2013); p. 3595 - 3603 View in Reaxys

90 %

2.5 Procedure for the catalytic oxidation of benzyl alcohol To a solution of benzyl alcohol (5 mmol), the catalyst [Cu2(L)(μ-OH)](ClO4)2 (0.0125 mmol) 4 molpercent and 30 percent H2O2 5 mL were added and the mixture was vigorously stirred at 70 °C for 1 h. After, the mixture was poured into water and the product was extracted with dichloromethane and dried over Na2SO4. The solvent was removed and the product was purified by column chromatography. The product was characterized by IR and 1H NMR spectra. With C35H32ClCu2N2O7S2 (1+)*ClO4 (1-)*H2O, dihydrogen peroxide, Time= 1h, T= 70 °C Pattanayak, Poulami; Pratihar, Jahar Lal; Patra, Debprasad; Brandao, Paula; Mal, Dasarath; Felix, Vitor; Polyhedron; vol. 59; (2013); p. 23 - 28 View in Reaxys

90 %

With tert.-butylhydroperoxide in acetonitrile, Time= 0.333333h, Reflux, Catalytic behavior, Temperature, Solvent Massah, Ahmad Reza; Kalbasi, Roozbeh Javad; Kaviyani, Somayeh; RSC Advances; vol. 3; nb. 31; (2013); p. 12816 - 12825 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

58/438

2018-03-11 22:07:32


90 %

General procedure for aerobic benzyl alcohol oxidation General procedure: Typical aerobic oxidation processes were carried out in atwo-necked round-bottom flask with 10.0 mM of benzyl alcoholor substituted benzyl alcohol in 100.0 L NaOH (1 N), catalystCu2O/Au (3.0 mg), and water (15.6 mL) with oxygen purging andstirring at 80C for 5 h. The reaction mixture was then quenchedwith 0.1 M HCl and, extracted with ethyl acetate and the organiclayer was dried over anhydrous MgSO4. The crude product was thenanalyzed by1H-NMR and gas chromatography-mass spectrometry(GC-MS). With oxygen, sodium hydroxide in water, Time= 5h, T= 80 °C , Catalytic behavior, Reagent/catalyst Prasad, K. Sudhakara; Noh, Hui-Bog; Reddy, S. Subba; Reddy, A. Eswar; Shim, Yoon-Bo; Applied Catalysis A: General; vol. 476; (2014); p. 72 - 77 View in Reaxys

90 %

With [VO(2-chloro-N'-(5-fluoro-2-hydroxybenzylidene)benzohydrazide-H2)(OMe)(MeOH)]*MeOH, dihydrogen peroxide, sodium hydrogencarbonate in acetonitrile, Time= 5h, T= 60 °C , Reagent/catalyst Yang, Kui-Hua; Transition Metal Chemistry; vol. 39; nb. 4; (2014); p. 469 - 475 View in Reaxys

90 %

With C18H26Cl2Cu3N4O10, dihydrogen peroxide in neat (no solvent), Time= 6h, T= 100 °C Borthakur, Rosmita; Asthana, Mrityunjaya; Saha, Mithu; Kumar, Arvind; Pal, Amarta Kumar; RSC Advances; vol. 4; nb. 41; (2014); p. 21638 - 21643 View in Reaxys

90%

in toluene, Time= 3h, T= 110 °C , Catalytic behavior Ganesh Babu; Krishnamoorthi; Thiruneelakandan; Karvembu; Catalysis Letters; vol. 144; nb. 7; (2014); p. 1245 - 1252 View in Reaxys

90 %

2.5. Procedure for catalytic oxidation of benzyl alcohol derivatives General procedure: To a solution of benzyl alcohol derivative (Eq. (4)) (5 mmol), in 10 mL acetonitrile catalyst [Cu2(L)2(NO3)2] (0.002 mmol), and 50percent H2O2 (5 mL) was added and the mixture was refluxed at 80 °C for 2 h. The mixture was then poured into water and the product was extracted with dichloromethane and dried over Na2SO4. The solvent was removed and the product was purified by column chromatography. The product was characterized by IR and 1H NMR spectra. With C48H36Cu2N4O8S2, dihydrogen peroxide in acetonitrile, Time= 2h, T= 80 °C , p= 760.051Torr Pattanayak, Poulami; Pratihar, Jahar Lal; Patra, Debprasad; Brandao, Paula; Felix, Vitor; Inorganica Chimica Acta; vol. 418; (2014); p. 171 - 179 View in Reaxys

90 %

With C12H12N2O6Zn, hydrogen bromide, dihydrogen peroxide, trifluoroacetic acid in tetrahydrofuran, water, Time= 6h, T= 20 °C , Catalytic behavior, Reagent/catalyst, Temperature, Time Enthaler, Stephan; Wu, Xiao-Feng; Weidauer, Maik; Irran, Elisabeth; Doehlert, Peter; Inorganic Chemistry Communications; vol. 46; (2014); p. 320 - 323 View in Reaxys

90 %

With oxygen in octanol, Time= 6.5h, T= 65 °C , Reagent/catalyst, Solvent Liu, Lin; Liu, Dong; Xia, Zhiwei; Gao, Jiulin; Zhang, Tianlin; Ma, Juanjuan; Zhang, Dongen; Tong, Zhiwei; Monatshefte fur Chemie; vol. 144; nb. 2; (2013); p. 251 - 254 View in Reaxys

90 %

With oxygen, triethylamine in water, Time= 0.3h, T= 100 °C , p= 30003Torr , Flow reactor, Green chemistry Osako, Takao; Torii, Kaoru; Uozumi, Yasuhiro; RSC Advances; vol. 5; nb. 4; (2015); p. 2647 - 2654 View in Reaxys

90 %

With tetrabutylammomium bromide, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in water, Time= 1h, T= 20 °C , Green chemistry

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

59/438

2018-03-11 22:07:32


Liu, Yangyang; Xie, Aming; Cao, Meiping; Feng, Liandong; Wang, Boliang; Asian Journal of Chemistry; vol. 27; nb. 2; (2015); p. 587 - 590 View in Reaxys 90 %

With silver nanoparticle deposited layered double hydroxides (Ag NPs-LDH) in para-xylene, T= 110 °C , Catalytic behavior Islam; Borah; Acharya; RSC Advances; vol. 5; nb. 17; (2015); p. 13239 - 13245 View in Reaxys

90 %

General Procedures for the Copper-Catalyzed Primary BenzylicAlcohol Oxidation under Air in Water (pMethylbenzylAlcohol) General procedure: A mixture of p-methylbenzyl alcohol (1.0 mmol), N-phenylglycine(0.0076 g, 0.05 mmol), CuBr2 (0.0112 g, 0.05 mmol),Na2CO3 (0.1060 g, 1.0 mmol), TEMPO (0.0078 g, 0.05 mmol),H2O (3.0 mL) were added to a 100 mL Schlenk tube, which wasvigorously stirred in air under reflux for 0.5 h. After the reaction,the product was extracted with CH2Cl2 (3 × 2.0 mL). Thecombined organic phase was washed with H2O (3.0 mL) anddried over anhydrous MgSO4. After concentration undervacuum, the residue was purified by column chromatography toafford pmethylbenzaldehyde.Isolated yield: 0.1080 g (90percent). With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium carbonate, N-Phenylglycine, copper(ll) bromide in water, Time= 1h, Reflux, Schlenk technique Zhang, Guofu; Lei, Jie; Han, Xingwang; Luan, Yuxin; Ding, Chengrong; Shan, Shang; Synlett; vol. 26; nb. 6; (2015); p. 779 - 784 View in Reaxys

90 %

With N -hydroxyphthalimide, oxygen in acetonitrile, Time= 16h, T= 70 °C , Catalytic behavior, Solvent, Temperature, Reagent/catalyst Jafarpour, Maasoumeh; Rezaeifard, Abdolreza; Yasinzadeh, Vahid; Kargar, Hossein; RSC Advances; vol. 5; nb. 48; (2015); p. 38460 - 38469 View in Reaxys

90 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, dimethyl 3-methyl-9-oxo-7(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-2,4-di(pyridin-2-yl)-3,7-diazabicyclo-[3.3.1]nonane-1,5-dicarboxylate, copper(I) bromide in water, Time= 5h, T= 20 °C , Green chemistry Ang, Wei Jie; Chng, Yong Sheng; Lam, Yulin; RSC Advances; vol. 5; nb. 99; (2015); p. 81415 - 81428 View in Reaxys

90%

2.4 Oxidation Procedure General procedure: To a solution of the alcohol (0.5 mmol) and complex (scheme 1; 0.01 mmol) in ethanol (5 mL) was added tBuOOH (0.5 mmol), and the reaction mixture was stirred in air at 80°C for the required time. GC monitored the reaction progress and the yields of the products. Further purification was achieved by silica chromatography. With tert.-butylhydroperoxide, [((E)-1-(((2-hydroxypropyl)imino)methyl)naphthalen-2-olato)Cu(μ2-Cl)2Cu((E)-1-(((2hydroxypropyl)imino)methyl)naphthalen-2-olato)]*1.5(methanol) in ethanol, Time= 1h, T= 80 °C , Time Naeimi, Atena; Saeednia, Samira; Yoosefian, Mehdi; Rudbari, Hadi Amiri; Nardo, Viviana Mollica; Journal of Chemical Sciences; vol. 127; nb. 7; (2015); p. 1321 - 1328 View in Reaxys

90 %

General Experimental Procedure for the Oxidation of Alcohols: General procedure: To a solution of the alcohol (1.0 mmol) and hydrogen peroxide(5.0 mmol, 30percent aq) was added BiBr3 (10 molpercent). The reactionmixture was stirred at 70 °C for 10–40 min, and thereaction mixture was extracted with dichloromethane (2 × 5mL). The combined organic layers were washed with saturatedbrine (2 × 5 mL) and dried with anhydrous MgSO4. After evaporationof the solvent, the residue was purified by flash columnchromatography (SiO2; CH2Cl2–hexane, 3:2) to afford the purecarbonyl compound. With bismuth(III) bromide, dihydrogen peroxide in water, Time= 0.5h, T= 70 °C , Green chemistry Han, Mi-Kyung; Kim, Sohwa; Kim, Sung Tae; Lee, Jong Chan; Synlett; vol. 26; nb. 17; (2015); p. 2434 - 2436; Art.No: ST-2015-U0545-L View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

60/438

2018-03-11 22:07:32


90 %

General experimental procedure for the oxidationreaction General procedure: Substrate (5 mmol) and ZPFe (0.5 mol percent) were added intoa 25 cm3 two-necked flask. It was heated in an oil bath to50 °C and then, 30 percent H2O2 (0.015 mol) was added slowlywith continuous stirring for the specified time. The reactionprogress was monitored by GC. At the end, the reactionmixture was cooled to room temperature and then, thecatalyst was removed from the reaction mixture by centrifuge.After that, the organic layer was separated from theaqueous phase by extraction with n-hexane and dried overanhydrous CaCl2. The identity of reaction products wasconfirmed by FT-IR, GC–MS, and 1H NMR. With dihydrogen peroxide in neat (no solvent), Time= 0.25h, T= 50 °C , Catalytic behavior, Time, Solvent, Temperature Hajipour, Abdol Reza; Karimi, Hirbod; Masti, Amir; Monatshefte fur Chemie; vol. 147; nb. 2; (2016); p. 413 - 423 View in Reaxys

90 %

With 3-(6-(3,5-dimethyl-1H-pyrazol-1-yl)pyridin-2-yl)-1-(2-((1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)oxy)-2-oxoethyl)-1H-imidazol-3-ium iodide, oxygen, sodium carbonate, copper(I) bromide, Time= 24h, T= 50 °C , Ionic liquid Guo, Bin; Xue, Jiang-Yan; Li, Hong-Xi; Tan, Da-Wei; Lang, Jian-Ping; RSC Advances; vol. 6; nb. 57; (2016); p. 51687 - 51693 View in Reaxys

90 %

With tetrabutylammomium bromide, oxygen, acetic acid, sodium nitrite, Time= 2h, T= 70 °C , Green chemistry Sheykhan, Mehdi; Moafi, Hadi Fallah; Abbasnia, Masoumeh; RSC Advances; vol. 6; nb. 56; (2016); p. 51347 51355 View in Reaxys

90 %

General procedure for selective oxidation of alcohols General procedure: A typical experimental procedure was as follows: alcohol (1 mmol) as substrate wasadded to the dioxo-Mo(VI) Schiff base complex (0.02 mmol). Then, tert-BuOOH(1 mmol, 70 percent aqueous solution) was added and the mixture was stirred at roomtemperature (25 C). The progress of the reaction was monitored by thin-layerchromatography (TLC) (eluent n-hexane:ethyl acetate, various ratios). After thereaction was completed, the residue was washed with a minimal volume of CH2Cl2. The solvent was then evaporated, and the pure product was obtained afterchromatography on a silica gel column. With tert.-butylhydroperoxide, MoO2{N((CH3)C6H4)CHC6H4O}2 in water, Time= 2h, T= 25 °C , Solvent, Reagent/ catalyst Hatefi-Ardakani, Mehdi; Saeednia, Samira; Pakdin-Parizi, Zahra; Rafeezadeh, Mahdieh; Research on Chemical Intermediates; vol. 42; nb. 10; (2016); p. 7223 - 7230 View in Reaxys

90 %

With dihydrogen peroxide in water, Time= 0.35h, Reflux, Green chemistry, Solvent Mirsafaei, Razieh; Heravi, Majid M.; Hosseinnejad, Tayebeh; Ahmadi, Shervin; Applied Organometallic Chemistry; vol. 30; nb. 10; (2016); p. 823 - 830 View in Reaxys

90 %

Oxidation of alcohols to carbonyl compounds General procedure: A solution of the organic compounds (Table-1, 10 mmol) in 10 mL of dichloromethane was added to 3,4-dihydroisoquinolinium chlorochromate (Table-1, 1:1 ratio; 3.94 g, 10 mmol and 1:3 ratio; 11.83 g, 30 mmol). The mixture was stirred magnetically at room temperature until the complete consumption of the substrate. The progress of the reaction was monitored by TLC analysis. After completion of the reaction, 50 mL of water was added to the reaction mixture and extracted with ether (3 x 20 mL). The combined organic layer was dried over MgSO4 and evaporated on a rotary evaporator under reduced pressure. Then the product was chromatographed over silica gel using ethyl acetate-hexane (1:4) as the eluent to separate the product. After evaporation of the solvent, the fairly pure solid were crytstallized out the liquid carbonyl compounds were derivatized with 2,4-dinitrophenylhydrazine. The melting points of solid compounds such as benzil, benzophenone, 3-oxocholestorol, 1-menthone, 1-indanone, tetralone, 10-anthraquinone and phenanthrene-9,10-quinone were checked and these compounds were identified by spectral data like IR and 1H NMR. With DIQCC in dichloromethane, Time= 0.5h, T= 20 °C Ozen, Recep; Asian Journal of Chemistry; vol. 26; nb. 18; (2014); p. 6081 - 6083

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

61/438

2018-03-11 22:07:32


View in Reaxys 90 %

With tert.-butylhydroperoxide, C12H17Cl2CuN3O in acetonitrile, Time= 14h, T= 24.84 °C , Catalytic behavior, Reagent/catalyst, Solvent, Time Bhattacharjee, Aradhita; Halder, Shibashis; Ghosh, Koushik; Rizzoli, Corrado; Roy, Partha; New Journal of Chemistry; vol. 41; nb. 13; (2017); p. 5696 - 5706 View in Reaxys

90 %

With Oxone in water, Time= 1.08333h, T= 20 °C , Reagent/catalyst, Solvent Ramazani, Ali; Khoobi, Mehdi; Sadri, Fariba; Tarasi, Roghayeh; Shafiee, Abbas; Aghahosseini, Hamideh; Joo, Sang Woo; Applied Organometallic Chemistry; vol. 32; nb. 1; (2018); Art.No: E3908 View in Reaxys

89 %

With oxygen, sodium bromide, cobalt(III) acetate in acetic acid, Time= 2h, T= 60 °C , effect of presence and absence NaBr at various mole ratios, various benzylalcohol derivatives, Mechanism Hirano, Masao; Morimoto, Takashi; Itoh, Keiko; Bulletin of the Chemical Society of Japan; vol. 61; nb. 10; (1988); p. 3749 - 3751 View in Reaxys

89 %

With sodium hypochlorite, 2,2,6,6-tetramethyl-4-(3',3',4',4',5',5',6',6',6'-nonafluorohexyl)-(3'',3'',4'',4'',5'',5'',6'',6'',6''nonafluorohexan)amidepiperidin-1-oxyl, potassium bromide in dichloromethane, Time= 1h, T= 0 °C , aq. buffer Dobbs, Adrian P.; Penny, Mark J.; Jones, Peter; Tetrahedron Letters; vol. 49; nb. 49; (2008); p. 6955 - 6958 View in Reaxys

89 %

With cobalt(II) nitrate hexahydrate, manganese (II) nitrate tetrahydrate, C58H45F51N13O5, oxygen in acetic acid, Time= 2h, T= 40 °C Gheorghe, Alexandru; Chinnusamy, Tamilselvi; Cuevas-Yanez, Erick; Hilgers, Petra; Reiser, Oliver; Organic Letters; vol. 10; nb. 19; (2008); p. 4171 - 4174 View in Reaxys

89 %

With sodium hypochlorite, 2,2,6,6-tetramethyl-4-(3',3',4',4',5',5',6',6',6'-nonafluorohexyl)-(3'',3'',4'',4'',5'',5'',6'',6'',6''nonafluorohexan)amidepiperidin-1-oxyl, sodium hydrogencarbonate, potassium bromide in dichloromethane, Time= 1.33333h, T= 0 - 20 °C , aq. buffer Dobbs, Adrian P.; Jones, Peter; Penny, Mark J.; Rigby, Stephen E.; Tetrahedron; vol. 65; nb. 27; (2009); p. 5271 - 5277 View in Reaxys

89 %

With diethylammonium chlorochromate, acetic acid in water, T= 24.84 °C , Darkness, Kinetics Singh, Balgar; Mahajan, Simpy; Jasrotia, Vikas S.; Sharma, Madhu; Sheikh; Kalsotra; Journal of the Indian Chemical Society; vol. 86; nb. 5; (2009); p. 528 - 530 View in Reaxys

89 %

With 1,8-diazabicyclo[5.4.0]undec-7-ene hydrobromide-perbromide in dichloromethane, water, Time= 1.45h, T= 20 °C , chemoselective reaction Bakavoli, Mehdi; Rahimizadeh, Mohammad; Eshghi, Hossein; Shiri, Ali; Ebrahimpour, Zahra; Takjoo, Reza; Bulletin of the Korean Chemical Society; vol. 31; nb. 4; (2010); p. 949 - 952 View in Reaxys

89 %

With Py3PMo12O40, dihydrogen peroxide, Aliquat 336 in water, Time= 3h, T= 70 °C Tundo, Pietro; Romanelli, Gustavo P.; Vazquez, Patricia G.; Arico, Fabio; Catalysis Communications; vol. 11; nb. 15; (2010); p. 1181 - 1184 View in Reaxys

89 %

Oxidation of p-chlorobenzyl alcohol (Table 1, entry 5). Typical procedure: To a solution of p-chlorobenzyl alcohol (143.4 mg, 1.01 mmol) in CH2Cl2 (10 mL) was added Kbirnessite (2.98 g). The reaction mixture was stirred at 30 °C for 7 h. Black precipitate was removed by filtration over celite. The filtrate was concentrated to give crude p-benzaldehyde, which was purified through flash chromatography (silica gel/hexane-EtOAc) to give 2c in 90percent yield (129.1 mg).

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

62/438

2018-03-11 22:07:32


With K-birnessite MnO2 in dichloromethane, Time= 2h, T= 30 °C Kamimura, Akio; Nozaki, Yuichiro; Ishikawa, Shingo; Inoue, Ryota; Nakayama, Masaharu; Tetrahedron Letters; vol. 52; nb. 4; (2011); p. 538 - 540 View in Reaxys 89 %

With bis(tetrabutylammonium) manganate, Time= 0.166667h, T= 20 °C Ellis, Rhys; Lee, Kee-Han; Ainsworth, Matthew; Kerr, Alexander; Viseux, Eddy M. E.; Synlett; vol. 23; nb. 9; (2012); p. 1371 - 1373 View in Reaxys

89 %

With tert.-butylhydroperoxide in decane, Time= 6h, T= 80 °C , Reagent/catalyst Gawande, Manoj B.; Branco, Paula S.; Nogueira, Isabel D.; Ghumman, C. Amjad A.; Bundaleski, Nenad; Santos, Aderito; Teodoro, Orlando M.N.D.; Luque, Rafael; Green Chemistry; vol. 15; nb. 3; (2013); p. 682 - 689 View in Reaxys

89 %

The oxidation of alcohols was carried out under O2 in a 50-mL two-necked, round-bottom flask equipped with a magnetic stirrer. Typically, Fe2(SO4)3 (0.25 mmol) and TMHPO (0.25 mmol) were added to the flask, followed by 15 mL of a CH3CN/H2O (1:2) solvent mixture. After stirring for 5 min, the alcohol (5 mmol) was added, followed by NaNO2 (0.25 mmol). The resulting mixture was stirred at room temperature and 1 atm pressure of oxygen. When the reactions were completed, the reaction mixture was transferred to a separating funnel and extracted with dichloromethane. The organic layer was dried over anhydrous Na2SO4 and concentrated and further purified by flash chromatography to give the desired product. With iron(III) sulfate, TEMPOL, oxygen, sodium nitrite in water, acetonitrile, Time= 8h, T= 20 °C , p= 760.051Torr Shi, Xiang-Jun; Qian, Jie; Tan, Fan-Fan; Yu, Chuan-Ming; Journal of Chemical Research; vol. 37; nb. 7; (2013); p. 398 - 401 View in Reaxys

89 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, sodium hypochlorite, tetrabutylammomium bromide, sodium hydrogencarbonate in dichloromethane, water, Time= 0.0122222h, T= 0 °C , Solvent, Time Hampton, Philip D.; Whealon, Matthew D.; Roberts, Lisa M.; Yaeger, Andrew A.; Boydson, Rick; Organic Process Research and Development; vol. 12; nb. 5; (2008); p. 946 - 949 View in Reaxys

89 %

With C34H37N4O6Ru2 (1+)*Cl(1-), potassium hydoxide in toluene, Time= 6h, T= 70 °C , Schlenk technique, Inert atmosphere, Catalytic behavior, Solvent, Reagent/catalyst, Temperature Dutta, Indranil; Sarbajna, Abir; Pandey, Pragati; Rahaman, S. M. Wahidur; Singh, Kuldeep; Bera, Jitendra K.; Organometallics; vol. 35; nb. 10; (2016); p. 1505 - 1513 View in Reaxys

89 %

With Cu/OMS-2 in toluene, Time= 20h, T= 90 °C , Reagent/catalyst Meng, Xu; Bi, Xiuru; Wang, Yanmin; Chen, Gexin; Chen, Baohua; Jing, Zhenqiang; Zhao, Peiqing; Catalysis Communications; vol. 89; (2017); p. 34 - 39 View in Reaxys

89 %

Sample Microwave Oxidation Reaction BNA (0.1043 g, 0.490 mmol) and 4 mL sulfolane were added to a 10 mL microwave tube. Benzyl alcohol (0.1 mL, 0.962 mmol) was then added to the reaction mixture. The microwave tube was then heated in a microwave reactor for 5 minutes at 190 C. The colorless solution turned dark brown. An aliquot was removed and placed in d6-DMSO. Tollen's test indicated formation of aldehyde. 1H NMR peaks of benzaldehyde in d6-DMSO were observed: 10.02 (1H, s), 7.94 (2H, d), 7.72 (1H, t), 7.65 (2H, t) . ESI-MS: M+1= 107, and GC/MS M+ = 106 also confirmed benzaldehyde formation. To quantify product formation, a 1H NMR was taken before the reaction as well as after the microwave reaction. Each time, 0.10 mL of the total reaction mixture was added to 1.00 mL d6-DMSO that was spiked with an internal standard (para-dimethoxybenzene, p-DMB). The spiked d6-DMSO was created by adding 0.0254 g pDMB to 15.0 mL of d6-DMSO in order to obtain a 1:1 molar ratio between p-DMB and the NAD+ models. With N-benzylpyridinium bromide in sulfolane, Time= 0.0833333h, T= 190 °C , Microwave irradiation, Reagent/catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

63/438

2018-03-11 22:07:32


Jensen, Anton W.; Moore, John M.; Kimble, MaryEllen V.; Ausmus, Alex P.; Dilling, Wendell L.; Tetrahedron Letters; vol. 57; nb. 50; (2016); p. 5636 - 5638 View in Reaxys 89.5 %

3.3. Alcohols oxidation catalyzed by 1 and 2 General procedure: Complexes 1 and 2, as well as their precursor Cu(OAc)2H2O,were tested as homogeneous catalysts for the oxidation of selectedalcohols (benzyl alcohol, 1-phenylethanol or cyclohexanol) to thecorresponding aldehyde or ketones, using aqueous t-BuOOH(TBHP) as oxidizing agent, under typical conditions of 40–60 C,low power (10–25 W) microwave (MW) irradiation, 0.25–1 h ofreaction time and in a solvent- and additive-free medium (Scheme 2). The eventual organo-catalytic ability of the acyclicSchiff base H2L was also tested. The catalytic results obtained atthe optimized reaction conditions are displayed in Table 2. With tert.-butylhydroperoxide, 2C14H11NO5S(2-)*C3H7NO*2Cu(2+)*C10H8N2*H2O, Time= 0.5h, T= 40 - 60 °C , Microwave irradiation, Reagent/catalyst Hazra, Susanta; Martins, Luísa M.D.R.S.; Guedes da Silva, M. Fátima C.; Pombeiro, Armando J.L.; Inorganica Chimica Acta; vol. 455; (2017); p. 549 - 556 View in Reaxys

89 %

4.2 General procedure for the synthesis of 59 benzylaldehyde To a 10mL round bottom flask, the mixture of 12 benzylalcohol 1a (1.0mmol, 0.104mL) and Cu2(ophen)2 (0.05mmol, 26mg,) in 60 CH3CN (4mL), was stirred in oil bath at 60°C under oxygen atmosphere (oxygen ball). The reaction was monitored and conversions were determined by GC–MS. With Cu2(ophen)2, oxygen in acetonitrile, Time= 12h, T= 60 °C , Green chemistry Zhang, Lingjuan; Liu, Jie; Zhang, Fuqiang; Zhang, Xian-Ming; Journal of Catalysis; vol. 354; (2017); p. 78 - 83 View in Reaxys

89 %

General procedure: Benzyl alcohol (0.05g, 0.5mmol), was added to a mixture of 15percent H2O2 (0.3 g, 8.83mmol), complex [MoO2)2(slsch)(H2O)2] (0.01g, 0.017mmol) in acetonitrile solution in 50mL round bottom flask. The mixture was first stirred at ambient temperature for 20mins and then the temperature was raised to 70°C for 2h. The crude product was separated by a separating funnel and dried over anhydrous sodium sulfate. The oxidized product was purified by column chromatography to afford benzaldehyde. The isolated product was ascertained by comparison with the authentic sample using 1H and 13C NMR spectroscopies. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C18H18Mo2N4O10, dihydrogen peroxide in acetonitrile, Time= 3h, T= 20 - 70 °C , Temperature, Solvent, Reagent/catalyst Kurbah, Sunshine Dominic; Kumar, Arvind; Syiemlieh, Ibanphylla; Asthana; Lal, Ram A.; Inorganic Chemistry Communications; vol. 86; (2017); p. 39 - 43 View in Reaxys

89 %

With dihydrogen peroxide, Time= 0.5h, T= 60 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Temperature Karimi, Hirbod; Journal of the Chinese Chemical Society; vol. 62; nb. 7; (2015); p. 604 - 613 View in Reaxys

88 %

With dimethyl sulfoxide, triethylamine, trichloromethyl chloroformate in dichloromethane Takano, Seiichi; Inomata, Kohei; Tomita, Shun'ichi; Yanase, Masashi; Samizu, Kyiohiro; Ogasawara, Kunio; Tetrahedron Letters; vol. 29; nb. 50; (1988); p. 6619 - 6620 View in Reaxys

88 %

With manganese dioxide on silica gel, Time= 0.00555556h, Irradiation Varma, Rajender S.; Saini, Rajesh K.; Dahiya, Rajender; Tetrahedron Letters; vol. 38; nb. 45; (1997); p. 7823 7824 View in Reaxys

88 %

With quinolinium monofluorochromate(VI) in dichloromethane, Time= 2.5h, Heating, further temperature (room) and reagent (pyridinium fluorochromate)

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

64/438

2018-03-11 22:07:32


Rajkumar, G. Abraham; Arabindoo, Banumathi; Murugesan, V.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 37; nb. 6; (1998); p. 596 - 598 View in Reaxys 88 %

With iodine, oxygen in acetonitrile, Time= 5h, T= 20 °C , Irradiation Farhadi, Saeid; Zabardasti, Abedien; Babazadeh, Zaynab; Tetrahedron Letters; vol. 47; nb. 50; (2006); p. 8953 8957 View in Reaxys

88 %

With tert.-butylhydroperoxide, bis(4-cyanopyridine)copper(II) chloride complex in water, acetonitrile, Time= 3h, p= 760.051Torr , Heating Sarmah, Purabi; Barman, Rama K.; Purkayastha, Pratyush; Bora, Sanchay J.; Phukan, Prodeep; Das, Birinchi K.; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 48; nb. 5; (2009); p. 637 - 644 View in Reaxys

88 %

With pyridine, C22H16CoN2O8, oxygen in water, Time= 4h, T= 80 °C , pH= 11.5 Seyedi, Seyed Mohammad; Sandaroos, Reza; Zohuri, Gholam Hossein; Chinese Chemical Letters; vol. 21; nb. 11; (2010); p. 1303 - 1306 View in Reaxys

88 %

4.4. A typical example for alcohol oxidation General procedure: The reaction was carried out in a 150 mL Teflon-lined 316 L stainless steel autoclave and a magnetic stirrer. A mixture of 0.1 mmol of PdCl2, 0.2 mmol of NaOAc, 2 mmol of 2-octanol and 4 mL of DMA were placed in the 150 mL Teflon-lined 316 L stainless steel autoclave and stirred for 5 min. Then, 0.1 MPa of O2 was introduced. The mixture was stirred for 4 h at 60 °C. After the reaction, the reactor was quickly cooled to room temperature. The excess of O2 was depressurized slowly. GC analysis of the solution using biphenyl as an internal standard gave a 89percent yield of 2-octanone with >99percent selectivity. Stage 1: With sodium acetate, palladium dichloride in ISOPROPYLAMIDE, Time= 0.0833333h, Autoclave Stage 2: With oxygen in ISOPROPYLAMIDE, Time= 4h, T= 60 °C , p= 750.075Torr , Autoclave Wang, Lian-Yue; Li, Jun; Lv, Ying; Zhang, Heng-Yun; Gao, Shuang; Journal of Organometallic Chemistry; vol. 696; nb. 20; (2011); p. 3257 - 3263 View in Reaxys

88 %

2.7. General procedure for the oxidation of alcohols General procedure: A mixture of the aromatic alcohol (0.5 mmol), catalyst 4a (0.002 mmol) and 30percent H2O2 (5 equiv.) was added to a roundbottom flask containing 10 mL of acetonitrile. The total mixture was stirred at 70 °C for 4 h. The reaction was monitored by TLC. After completion of the reaction, the solvent was removed, theorganic phase was separated and dried over Na2SO4, and the product was purified by column chromatography (hexane/ethyl acetate).Yields were determined by weighing the isolated products, which were characterized by 1H NMR and IR spectroscopy (Table 5). With C36H27CuN8O2, dihydrogen peroxide in acetonitrile, Time= 4h, T= 70 °C Pattanayak, Poulami; Pratihar, Jahar Lal; Patra, Debprasad; Brandao, Paula; Felix, Vitor; Chattopadhyay, Surajit; Polyhedron; vol. 79; (2014); p. 43 - 51 View in Reaxys

88 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, {[Cu(BTPMPA)(OH2)(OTf)]OTf}, oxygen, potassium carbonate in toluene, acetonitrile, Time= 5h, T= 27 °C Dharmalingam, Sivanesan; Koo, Eunhae; Yoon, Sungho; Park, Gyoosoon; Bulletin of the Korean Chemical Society; vol. 35; nb. 3; (2014); p. 715 - 720 View in Reaxys

88 %

General procedure for oxidation of alcohol: General procedure: In a typical experiment, 1 mmol 1-phenyl ethanol and 10 mol percent (25.30 mg) VOSO4.5H2O (purchased from Loba Chemie, molecular weight 253.08) in 2 ml CH3CN/H2O (1:1) in a round bottomed flask. To this mixture 2 equiv 70percent TBHP (aqueous) was added and stirred at room temperature for the time specified in Table 1. The progress of the reaction was monitored by TLC. After the completion of the reaction, the mixture was ex-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

65/438

2018-03-11 22:07:32


tracted with ethyl acetate (3 x 20 mL) three times. The ethyl acetate layer was dried with anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetatehexane as the eluent. Formation of the product was confirmed by comparing FTIR spectra, 1H NMR spectra, 13C NMR spectra, melting point measurement and GC-MS with authentic compounds. With tert.-butylhydroperoxide, vanadyl(IV) sulphate pentahydrate in water, acetonitrile, Time= 3h, T= 20 °C , Green chemistry Sarmah, Gayatri; Bharadwaj, Saitanya K.; Dewan, Anindita; Gogoi, Ankur; Bora, Utpal; Tetrahedron Letters; vol. 55; nb. 36; (2014); p. 5029 - 5032 View in Reaxys 88 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, 6C8H4O4 (2-)*4HO(1-)*6Ce(4+)*4O(2-), oxygen in acetonitrile, Time= 24h, T= 110 °C , p= 4500.45Torr , Catalytic behavior, Reagent/catalyst, Time Lammert, Martin; Wharmby, Michael T.; Smolders, Simon; Bueken, Bart; Lieb, Alexandra; Lomachenko, Kirill A.; De Vos, Dirk; Stock, Norbert; Chemical Communications; vol. 51; nb. 63; (2015); p. 12578 - 12581 View in Reaxys

88 %

With C22H21ClN3RuS2 (1+)*F6P(1-), potassium carbonate, 4-methylmorpholine N-oxide in dichloromethane, acetonitrile, Time= 3h, T= 60 °C , Catalytic behavior, Reagent/catalyst Saleem, Fariha; Rao, Gyandshwar K.; Kumar, Satyendra; Singh, Mahabir Pratap; Singh, Ajai K.; Dalton Transactions; vol. 44; nb. 44; (2015); p. 19141 - 19152 View in Reaxys

88 %

With (carbonyl)chloro(hydrido)tris(triphenylphosphine)ruthenium(II), oxygen in toluene, Time= 18h, T= 90 °C , p= 760.051Torr , Molecular sieve, Sealed tube Ray, Ritwika; Chandra, Shubhadeep; Maiti, Debabrata; Lahiri, Goutam Kumar; Chemistry - A European Journal; vol. 22; nb. 26; (2016); p. 8814 - 8822 View in Reaxys

87 %

With trimethylammonium chlorochromate, 4 A molecular sieve, acetic acid in 1,2-dichloro-ethane, Time= 2h, Heating Acharya, Shrinivas P.; Rane, Ramakrishna A.; Synthesis; nb. 2; (1990); p. 127 - 128 View in Reaxys

87 %

With chromium(VI) oxide in dimethyl sulfoxide, Time= 4h, Ambient temperature Lou; Synthetic Communications; vol. 22; nb. 5; (1992); p. 767 - 772 View in Reaxys

87 %

With sodium tungstate, dihydrogen peroxide, tricaprylmethylammonium hydrogen sulfate in water, Time= 3h, T= 90 °C Sato, Kazuhiko; Takagi, Junko; Aoki, Masao; Noyori, Ryoji; Tetrahedron Letters; vol. 39; nb. 41; (1998); p. 7549 - 7552 View in Reaxys

87 %

With dihydrogen peroxide, tricaprylmethylammonium hydrogen sulfate, sodium tungstate in water, Time= 3h, T= 90 °C , Oxidation Sato, Kazuhiko; Aoki, Masao; Takagi, Junko; Zimmermann, Klaus; Noyori, Ryoji; Bulletin of the Chemical Society of Japan; vol. 72; nb. 10; (1999); p. 2287 - 2306 View in Reaxys

87 %

With chromium(VI) oxide, tert.-butylhydroperoxide, silica gel in dichloromethane, Time= 0.166667h, microwave irradiation, Oxidation Singh; Sharma; Chhibber; Kaur; Kad; Synthetic Communications; vol. 30; nb. 21; (2000); p. 3941 - 3945 View in Reaxys

87 %

With iron(III) chloride, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy, oxygen, sodium nitrite in 1,2-dichloroethane, Time= 10h, T= 50 °C , p= 3000.3Torr , Autoclave

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

66/438

2018-03-11 22:07:32


Yin, Weili; Chu, Changhu; Lu, Qiongqiong; Tao, Jianwei; Liang, Xinmiao; Liu, Renhua; Advanced Synthesis and Catalysis; vol. 352; nb. 1; (2010); p. 113 - 118 View in Reaxys 87 %

With pyridine, oxygen, palladium diacetate in toluene, Time= 2.5h, T= 100 °C , p= 26618.1Torr , Inert atmosphere Ye, Xuan; Johnson, Martin D.; Diao, Tianning; Yates, Matthew H.; Stahl, Shannon S.; Green Chemistry; vol. 12; nb. 7; (2010); p. 1180 - 1186 View in Reaxys

87 %

With C30H25N3OPPd, 4-methylmorpholine N-oxide in dichloromethane, Time= 2.5h, Reflux Dileep; Bhat, Badekai Ramachandra; Applied Organometallic Chemistry; vol. 24; nb. 9; (2010); p. 663 - 666 View in Reaxys

87 %

Open air oxidation of alcohols General procedure: Open air oxidation of alcohols An initial set of experiments was performed by placing CuSO4·5H2O (0.03 mmol from stock solution of 50 mg/mL in H2O) and salicylaldimine (0.06 mmol) into a 100 mL two-neck round-bottom flask fitted with a condenser and a magnetic stirring bar. The reaction mixture was diluted with 5 mL of distilled water and heated at 80 °C for 15 min to ensure the complex formation. After cooling to room temperature, 0.15 mmol of TEMPO was introduced into the solution which was heated at desired temperature for 5 min. Benzyl alcohol (3 mmol) was then added into the solution. The catalysis was carried out for 1.5 h and then the aqueous solution was extracted with ethyl acetate (3 mL * 3 mL). For quantitative analysis, 0.5 mL of ethyl acetate extraction was placed in a sample vial and diluted with 1 mL of ethyl acetate. 100 μL of acetophenone (0.86 mmol) was used as internal standard. The sample was analyzed by GC (Agilent 6890 chromatograph, Agilent 19091J-413 capillary column 0.32 mm * 30 m * 0.25 μm, FID detector). GC-MS method was used for identification of the products (Agilent 6890 N equipped with Agilent 5973 mass selective detector, HP 19091 L-102 capillary columns, 200 mm * 24 m * 0.31 μm). All oxidation experiments were done three times and the reported conversions are average values of the nearest two. To determine isolated yield the reaction mixture after ethyl acetate extraction was dried with anhydrous MgSO4. The solvent was evaporated after filtration and the resulting residue was purified by silica gel column chromatography. Isolated product was identified by 1H, 13C NMR and FT-IR spectroscopy (see below). Prior to column chromatography, a small portion of the residue was taken into a NMR tube and was dissolved in 0.5 mL of CDCl3. Beside of the GC method 1H NMR was also used to analyze conversion by integrating the aldehyde and the corresponding alcohol peak areas. Benzaldehyde. Oxidation of benzyl alcohol (324 mg, 3 mmol) gave benzaldehyde as pale yellow liquid (278 mg, isolated yield 87percent, conversion quantitative and selectivity > 99percent). Eluent n-hexane:ethyl acetate = 50:1. 1H NMR (200 MHz, CDCl3, TMS): δH: 7.47-7.61 (m, 4H, Ar-H), 7.86 (d, 1H, J = 6.8 Hz, Ar-H), 10.00 (s, 1H, CH=O) ppm. 13C NMR (50 MHz, CDCl3): δC: 128.0, 128.7, 133.4, 135.3, 191.3 ppm. IR (cm-1): 1696 (υC=O). With copper(ll) sulfate pentahydrate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, (1-methylethyl)(2-hydroxy-3,5di(t-butyl)phenyl)methylimine in water, Time= 1.83333h, T= 20 - 80 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Temperature, Time Ahmad, Jahir Uddin; Raeisaenen, Minna T.; Kemell, Marianna; Heikkilae, Mikko J.; Leskelae, Markku; Repo, Timo; Applied Catalysis A: General; vol. 449; (2012); p. 153 - 162 View in Reaxys

87 %

With dihydrogen peroxide, Time= 2h, T= 80 °C , Green chemistry Pagadala, Ramakanth; Maddila, Suresh; Rana, Surjyakanta; Jonnalagadda, Sreekantha B.; RSC Advances; vol. 4; nb. 13; (2014); p. 6602 - 6607 View in Reaxys

87 %

2.5. Typical procedure for alcohol oxidation

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

67/438

2018-03-11 22:07:32


General procedure: The reaction mixture of Primary or secondary alcohol (1 mmol),RuIIICl2 (AsPh3)2 (Ph-DPMP) Schiff base complex (0.1 mmol), NMO(1.1 mmol) and dichloromethane (2 mL) was stirred at room temperature.The filtrate obtained was evaporated under reduced pressureand the residual mass was dissolved in a mixture of ethylacetate/hexane (1:4) and then passed through a short column ofsilica gel using hexane/ethyl acetate (4:1) as eluent. Removal ofsolvent and usual workup gave the corresponding aldehydes andketones, which were identified by comparing their physical andspectral data with those of authentic compounds reported in literature[27]. With RuCl2(AsPh3)2(Ph-DPMP), 4-methylmorpholine N-oxide in dichloromethane, Time= 0.75h, T= 20 °C , Solvent, Temperature Raja, K. Kanmani; Indra Gandhi; Lekha; Easwaramoorthy; Rajagopal; Journal of Molecular Structure; vol. 1060; nb. 1; (2014); p. 49 - 57 View in Reaxys 87 %

General procedure: The liquid phase catalytic oxidations were carried out under ambient condition in a 25 mL round bottom flask equipped with a magnetic stirrer and immersed in a thermostated oil bath at 60 ± 1 °C. H2O2 (3 mmol) was added to the flask containing the catalyst (1 mg) and a representative alkene, namely cyclohexene (1 mmol) in the required solvent (3 mL). The course of the reaction was monitored using a gas chromatograph equipped with a capillary column and a flame ionization detector. The oxidation products were identified by comparing their retention times with those of authentic samples or alternatively by 1H NMR and GC-Mass analyses. Yields based on the added substrate were determined by a calibration curve. With [VO(3-hydroxy-N’-(2-hydroxybenzylidene)-2-naphthohydrazide(-2H))(benzohydroxamate)]*EtOH, dihydrogen peroxide, sodium hydrogencarbonate in acetonitrile, Time= 5h, T= 60 °C , Reagent/catalyst Yang, Kui-Hua; Acta Chimica Slovenica; vol. 61; nb. 3; (2014); p. 629 - 636 View in Reaxys

87.65 %

2.4. Catalytic Test The oxidation of benzyl alcohol using spinel MnFe2O4NFs and MnFe2O4 NPs catalysts was carried out in a batchreactor operated under atmospheric conditions. 10 molesof oxidant (H2O2 were added along with 1 g of nanosizedcatalysts (MnFe2O4 NFs and MnFe2O4 NPs) and the contentswere heated at 80 C in an acetonitrile medium for10 h in a three necked round bottom flask equipped witha reflux condenser and thermometer. The oxidized productsafter the catalytic reaction are collected and studiedusing Agilent GC spectrometer. The column used for thestudy was a DB wax column (capillary column) of length30 mm and helium was used as the carrier gas. The yieldsof the carbonyl compounds formed were calculated by thefollowing formula,7 With dihydrogen peroxide in acetonitrile, Time= 10h, T= 80 °C , Inert atmosphere, Reagent/catalyst Jacintha, A. Mary; Manikandan; Chinnaraj; Antony, S. Arul; Neeraja; Journal of Nanoscience and Nanotechnology; vol. 15; nb. 12; (2015); p. 9732 - 9740 View in Reaxys

87 %

With C29H33FeN5O3 (2+)*2CF3O3S(1-) in acetonitrile, Time= 24h, Kinetics, Mechanism Rana, Sujoy; Dey, Aniruddha; Maiti, Debabrata; Chemical Communications; vol. 51; nb. 77; (2015); p. 14469 14472 View in Reaxys

87 %

With Au NCs/TiO2, dihydrogen peroxide, oxygen in toluene, Time= 16h, T= 90 °C , p= 750.075Torr , Reagent/catalyst Giorgi, Pascal D.; Miedziak, Peter J.; Edwards, Jennifer K.; Hutchings, Graham J.; Antoniotti, Sylvain; ChemCatChem; vol. 9; nb. 1; (2017); p. 70 - 75 View in Reaxys

87 %

General procedure for aerobic oxidation of alcohols in water General procedure: To a 48 mL tube, were added Cu(II) or Cu(I) salt (0.05 mmol), PEG-PyTa (0.025 mmol) and H2O (3.0 mL). The mixture was stirred for 30 min at room temperature and a clear dark-blue solution was observed. Then alcohols (1.0 mmol), TEMPO (0.05 mmol), and K2CO3 (0.2 mmol) were sequentially added, followed by connecting a balloon of oxygen. The reaction mixture was stirred at room temperature until the reaction completed based on GC analysis. After that, the reaction mixture was extracted with MTBE (3 mL×3) and the extracts were combined, dried over anhydrous Na2SO4 and concentrated under vacuum. Finally, the residue was purified by flash chromatography on silica to afford the desired aldehydes.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

68/438

2018-03-11 22:07:32


With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C110H202N8O47, oxygen, copper(II) bis(trifluoromethanesulfonate), potassium carbonate in water, Time= 6h, T= 20 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Time, Temperature Sun, Nan; Zhang, Xiaonan; Jin, Liqun; Hu, Baoxiang; Shen, Zhenlu; Hu, Xinquan; Catalysis Communications; vol. 101; (2017); p. 5 - 9 View in Reaxys 86 %

With potassium dichromate in various solvent(s), Time= 4h, T= 90 - 100 °C Santaniello, Enzo; Ferraboschi, Patrizia; Synthesis; nb. 8; (1980); p. 646 - 647 View in Reaxys

86 %

With 1,10-Phenanthroline, oxygen, potassium carbonate, copper(l) chloride in benzene, Time= 2h, Heating Jallabert, C.; Riviere, H.; Tetrahedron; vol. 36; nb. 82; (1980); p. 1191 - 1194 View in Reaxys

86 %

With ferric(III) bromide, dihydrogen peroxide, Time= 24h, T= 20 °C Martin, Sandra E.; Garrone, Analia; Tetrahedron Letters; vol. 44; nb. 3; (2003); p. 549 - 552 View in Reaxys

86 %

With tert.-butylhydroperoxide, resin-PPh2-Co(PPh3)2Cl2 in dichloromethane, water, Time= 4h, Heating, Oxidation Leadbeater, Nicholas E.; Scott, Kathryn A.; Journal of Organic Chemistry; vol. 65; nb. 15; (2000); p. 4770 - 4772 View in Reaxys

86.8 %

5B; 11 With trichloroisocyanuric acid, tetrabutylammomium bromide, water, potassium carbonate, ruthenium trichloride in ethyl acetate, Time= 1 - 3h, T= 20 - 45 °C , Product distribution / selectivity Patent; Nagase & Co., Ltd.; Nagase Chemtex Corporation; JP2005/75784; (2005); (A) Japanese View in Reaxys

86 %

With 1-methyl-1H-imidazole, carbon dioxide, oxygen, copper(l) chloride, Time= 2h, T= 60 °C , p= 52505.3Torr , Autoclave, neat (no solvent) Miao, Cheng-Xia; He, Liang-Nian; Wang, Jin-Quan; Gao, Jian; Synlett; nb. 20; (2009); p. 3291 - 3294 View in Reaxys

86.6 %

With C40H39BrN4O2PRu, oxygen in dichloromethane, Time= 6h, T= 20 °C Priya, N. Padma; Arunachalam; Sathya; Jayabalakrishnan; Journal of Coordination Chemistry; vol. 63; nb. 8; (2010); p. 1440 - 1450 View in Reaxys

86 %

With [(ruthenium(II)chloride(carbonyl)(triphenylphosphine)2)2(C12H8(NC(CH3)CHC(O)NHC6H5)(NC(CH3)C6H4O))], oxygen in dichloromethane, Time= 6h, T= 20 °C Sathya, Nagarajan; Raja, Gunasekaran; Jayabalakrishnan, Chinnasamy; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 41; nb. 1; (2011); p. 81 - 90 View in Reaxys

86 %

With ammonium nitrate in dichloromethane, Time= 0.416667h, T= 20 °C , Inert atmosphere Zarei, Amin; Bulletin of the Korean Chemical Society; vol. 33; nb. 7; (2012); p. 2149 - 2155 View in Reaxys

86.8 %

With ruthenium(III) chloride trihydrate, trichloroisocyanuric acid, tetrabutylammomium bromide, potassium carbonate in water, ethyl acetate, T= 25 - 45 °C , Green chemistry Yamaoka, Hidenori; Moriya, Narimasa; Ikunaka, Masaya; Organic Process Research and Development; vol. 8; nb. 6; (2004); p. 931 - 938 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

69/438

2018-03-11 22:07:32


86 %

With diphenyl phosphoryl azide, (1,3-bis(4-((4-((3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indolin]-1'-yl)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2,6-diisopropylphenyl)imidazolidin-2-ylidene)copper(I) chloride, oxygen in ethylene glycol, ethyl acetate, Time= 12h, T= 80 °C , p= 760.051Torr , Schlenk technique Zhang, Guodong; Lang, Rui; Wang, Wenlong; Lv, Hui; Zhao, Liyuan; Xia, Chungu; Li, Fuwei; Advanced Synthesis and Catalysis; vol. 357; nb. 5; (2015); p. 917 - 922 View in Reaxys

86.4 %

A general procedure for the oxidation of benzylic alcohols follows To a mixture of benzyl alcohol (0.5 mL, 4.84 mM) and 30percent aqueous hydrogen peroxide(0.5 mL, 4.63 mM), the complex [CuZn(bz)3(bpy)2]BF4 (20 mg, 0.22 mM) was added andstirred at 70 °C for 6 h and the reaction mixture was extracted with dichloromethane. Theorganic phase was dried over anhydrous sodium sulfate. Evaporation of dichloromethanegave a crude mixture for 1H NMR analysis, then was purified by column chromatographyto afford benzaldehyde, whose identity was ascertained by comparison with authenticsample and IR, 1H NMR, and 13C NMR. With [CuZn(bz)3(bpy)2]BF4, dihydrogen peroxide in water, Time= 6h, T= 70 °C Koch; Kumar; Borthakur; Ozukum; Lal; Journal of Coordination Chemistry; vol. 68; nb. 2; (2015); p. 229 - 240 View in Reaxys

86 %

With N -hydroxyphthalimide, oxygen in acetonitrile, Time= 3h, T= 70 °C , p= 760.051Torr , Irradiation, Green chemistry, Reagent/catalyst Jafarpour, Maasoumeh; Kargar, Hossein; Rezaeifard, Abdolreza; RSC Advances; vol. 6; nb. 30; (2016); p. 25034 - 25046 View in Reaxys

86 %

With [Cu6(pyridine-2-thiolate)6], potassium hydoxide in toluene, Time= 24h, T= 70 °C , Schlenk technique, Glovebox, Inert atmosphere Tan, Da-Wei; Li, Hong-Xi; Zhang, Meng-Juan; Yao, Jian-Lin; Lang, Jian-Ping; ChemCatChem; vol. 9; nb. 6; (2017); p. 1113 - 1118 View in Reaxys

86 %

18 : Example 18: [Cu6 (pyt) 6]Catalytic dehydrogenation of benzaldehyde In the glove box, the benzyl alcohol (1.0 mmol), [Cu6 (Pyt)6 ] (0.1 mmol), KOH (1.0 mmol) is added to the test tube with the magnetic coil in the has, then adding 2.0 ml dry toluene solvent. After the sealed reaction tube, is taken out of the glove box. Toward the nozzle leads into the small and stable and low production, stable air flow after such as, for 70 °C reaction under 24 h; after the reaction, extracted with ethyl acetate (3 × 5 ml), the combined organic phase, dried with anhydrous sodium sulfate, filtered, concentrated filtrate for rotary evaporator, and then separating and purifying column law silica gel chromatography, to obtain the target product (yield 86percent) benzaldehyde With [Cu6(SC5H4N)6], potassium hydoxide in toluene, Time= 24h, T= 70 °C , Glovebox, Inert atmosphere Patent; Soochow University; Li, Hongxi; Tan, Dawei; Li, Haiyan; Lang, Jianping; (15 pag.); CN106588957; (2017); (A) Chinese View in Reaxys

85 %

With iodosylbenzene, tris(triphenylphosphine)ruthenium(II) chloride in dichloromethane, Time= 0.5h, Ambient temperature Mueller, Paul; Godoy, Jose; Tetrahedron Letters; vol. 22; nb. 25; (1981); p. 2361 - 2364 View in Reaxys

85 %

With lt;PPh4gt;2lt;Mo2O3(O2)4gt; in dichloromethane, Time= 3h, Ambient temperature Campbell, Nicholas J.; Dengel, Andrew C.; Edwards, Catherine J.; Griffith, William P.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1989); p. 1203 - 1208 View in Reaxys

85 %

With zinc(II) chlorosulphate in dichloromethane, Time= 0.0833333h, Ambient temperature Firouzabadi, H.; Sharifi, A.; Synthesis; nb. 10; (1992); p. 999 - 1002 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

70/438

2018-03-11 22:07:32


85 %

With pyridine, 3-carboxypyridinium dichromate in dichloromethane, Time= 0.416667h, T= 0 °C , other ratio of reagents, time and temperature, Product distribution Cossio, Fernando P.; Lopez, Concepcion M.; Palomo, Claudio; Tetrahedron; vol. 43; nb. 17; (1987); p. 3963 3974 View in Reaxys

85 %

With nicotinium dichromate in pyridine, dichloromethane, Time= 0.416667h, Ambient temperature, other reagents, solvent, reaction time, Product distribution Lopez, C.; Gonzalez, A.; Cossio, F. P.; Palomo, C.; Synthetic Communications; vol. 15; nb. 13; (1985); p. 1197 1212 View in Reaxys

85 %

With Jones reagent on silica in dichloromethane Ali; Wiggin; Synthetic Communications; vol. 31; nb. 9; (2001); p. 1389 - 1397 View in Reaxys

85 %

With sodium bromate, sodium dihydrogenphosphate, iron(III) chloride in water, acetonitrile, Time= 6h, T= 25 °C Shaabani; Ajabi; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 40; nb. 2; (2001); p. 148 - 151 View in Reaxys

85 %

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran, Time= 0.5h, T= 60 °C Ozanne, Aurelie; Pouysegu, Laurent; Depernet, Dominique; Francois, Bruno; Quideau, Stephane; Organic Letters; vol. 5; nb. 16; (2003); p. 2903 - 2906 View in Reaxys

85 %

With barium dichromate(VI) in acetonitrile, Time= 4h, Heating Mottaghinejad, Enayatollah; Shaafi; Ghasemzadeh; Tetrahedron Letters; vol. 45; nb. 48; (2004); p. 8823 - 8824 View in Reaxys

85 %

2.4 : FIG. 2 With mIBX in water, Time= 3h, T= 60 °C , Reactivity Patent; Vinod, Thottumkara K.; Thottumkara, Arun P.; US2004/30187; (2004); (A1) English View in Reaxys

85 %

With dihydrogen peroxide in water, acetonitrile, Time= 3h, T= 50 °C Mardur; Gokavi; Journal of the Iranian Chemical Society; vol. 7; nb. 2; (2010); p. 441 - 446 View in Reaxys

85 %

With manganese(II) nitrate hexahydrate, copper(II) nitrate trihydrate, acetic acid in α,α,α-trifluorotoluene, Time= 1h, T= 50 °C , In air, chemoselective reaction Tucker-Schwartz, Alexander K.; Garrell, Robin L.; Chemistry - A European Journal; vol. 16; nb. 42; (2010); p. 12718 - 12726 View in Reaxys

85 %

(a) General procedure for oxidation of benzylic alcohol: (a) General procedure: 1-phenylethanol (0.122 gm, 1.0 mmol), vanadium polyoxometalates[C7H7N(CH3)3]3V10O28H3*3H2O] (0.073 g, 0.05 mmol) and PTSA*H2O (0.095 g, 0.5 mmol) were mixed at room temperature, ground thoroughly in a mortar until the mixture became homogeneous. The yellow colour of the mixture became green instantaneously on grinding, indicating progress of the reaction. The reaction mixture was diluted with ether (30 mL) and washed with water (20 mL). The organic layer was washed with brine (3 *20 mL), dried over anhydrous Na2SO4, concentrated, and finally purified by column chromatography on silica, using ethyl acetate/ petroleum ether (1:9) as the eluent to obtain acetophenone in 97percent yield. 1H NMR (CDCl3, 300 MHz): d 7.9-8.2 (m, 2H), 7.4-7.7 (m, 3H), 2.6 (s, 3H); 13C NMR (CDCl3, 75.5 MHz): d 197.4, 136.9, 134.2, 129.3, 129.9, 26.5; IR (KBr): 1688 cm-1

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

71/438

2018-03-11 22:07:32


With toluene-4-sulfonic acid in water, Time= 0.0166667h, T= 20 °C Dewan, Anindita; Sarma, Tridib; Bora, Utpal; Kakati, Dilip K.; Tetrahedron Letters; vol. 52; nb. 20; (2011); p. 2563 - 2565 View in Reaxys 85 %

With N-(1-oxo-2,2,6,6-tetramethylpiperidin-4-yl)-benzoylamide, sodium hydrogencarbonate, potassium iodide in dichloromethane, water, T= 20 - 25 °C , pH= 8.6, Electrochemical reaction Kagan; Kashparova; Zhukova; Kashparov; Russian Journal of Applied Chemistry; vol. 83; nb. 4; (2010); p. 745 747 View in Reaxys

85 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, calcium methylate in acetonitrile, T= 0 - 20 °C Reddy, Sabbasani Rajasekhara; Stella, Selvaraj; Chadha, Anju; Synthetic Communications; vol. 42; nb. 23; (2012); p. 3493 - 3503 View in Reaxys

85 %

With Pyridine-2,6-dicarboxylic acid, dihydrogen peroxide, trifluoroacetic acid, zinc dibromide in tetrahydrofuran, water, Time= 16h, T= 20 °C Wu, Xiao-Feng; Chemistry - A European Journal; vol. 18; nb. 29; (2012); p. 8912 - 8915 View in Reaxys

85 %

With 2,5,8-trichlorotris(triazolo)benzene, Time= 0.25h Thottempudi, Venugopal; Forohor, Farhad; Parrish, Damon A.; Shreeve, Jean'Ne M.; Angewandte Chemie - International Edition; vol. 51; nb. 39; (2012); p. 9881 - 9885 View in Reaxys

85 %

With copper dichloride in tetrahydrofuran, Time= 2h, T= 80 °C , chemoselective reaction Lokhande, Pradeep D.; Waghmare, Smita R.; Gaikwad, Harsh; Hankare; Journal of the Korean Chemical Society; vol. 56; nb. 5; (2012); p. 539 - 541 View in Reaxys

85 %

With ammonium cerium (IV) nitrate in water, acetonitrile, Time= 24h, T= 20 °C El Kadiri, Moulay Youness; El Ghachtouli, Sanae; Guillot, Regis; Billon, Laurianne; Charlot, Marie-France; Framery, Eric; Andrioletti, Bruno; Aukauloo, Ally; ChemSusChem; vol. 5; nb. 11; (2012); p. 2147 - 2150 View in Reaxys

85 %

With dihydrogen peroxide in water-d2, Time= 0.583333h, T= 20 °C Eshtiagh-Hosseini, Hossein; Tabari, Taymaz; Eshghi, Hossein; Asian Journal of Chemistry; vol. 25; nb. 6; (2013); p. 3307 - 3312 View in Reaxys

85 %

3.1. Oxidation of benzhydrol 1a in the presence of substoichiometric amounts of activated MnO2: preparation of benzophenone 2 (Table 1, entry 6). General procedure#10; General procedure: Benzhydrol 1 (0.3831 g, 2.08 mmol) was dissolved in toluene (15 mL) and activated MnO2 (purchased from Aldrich, 0.106 g, 1.92 mmol, 50 mg/mmol) was added to the solution. The reaction mixture was heated at 110 °C under oxygen atmosphere for 4 h. Supernatant of the reaction mixture was scooped by pipet. Additional toluene (5 mL) was added to solid residue and washed the solid then the supernatant was scooped by pipet. This washing procedure was repeated for four times. All of toluene solution was combined and concentrated. Crude product was purified by flash chromatography (silica gel/hexane-EtOAc 3:1) to give 2 in 98percent yield (0.373 g, 2.05 mmol). MnO2 residue was examined for the recycling use of the oxidant (Scheme 4, see below). With manganese(IV) oxide, oxygen in toluene, Time= 4h, T= 110 °C , Green chemistry, Time Kamimura, Akio; Komatsu, Hiroyuki; Moriyama, Takaaki; Nozaki, Yuichiro; Tetrahedron; vol. 69; nb. 29; (2013); p. 5968 - 5972 View in Reaxys

85 %

With dipotassium peroxodisulfate, sodium chloride in acetonitrile, Time= 0.0833333h, Reflux, Green chemistry, chemoselective reaction

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

72/438

2018-03-11 22:07:32


Badri, Rashid; Alizadeh-haddad, Alireza; Adlu, Maryam; Mohammadi, Mohammad Kazem; Bulletin of the Chemical Society of Ethiopia; vol. 27; nb. 1; (2013); p. 131 - 136 View in Reaxys 85 %

With [ZnCu2(disalicylaldehyde succinoyldihydrazone)(NO3)2(H2O)8]2H2O, dihydrogen peroxide in neat (no solvent), Time= 10h, T= 100 °C , Green chemistry, Solvent Borthakur, Rosmita; Asthana, Mrityunjaya; Kumar, Arvind; Koch, Angira; Lal; RSC Advances; vol. 3; nb. 45; (2013); p. 22957 - 22962 View in Reaxys

85 %

2.2 General procedure for selective oxidation of alcohols to corresponding carbonyl compounds General procedure: A mixture of primary or secondary alcohol (1.0 mmol), TEMPO (0.05 mmol), L-N2O2 (0.05 mmol), and cupric acetate (0.05 mmol) in 1-butyl-3-methyl-3 H-imidazol-1-ium tetrafluoroborate [bmim][BF4] (1.5 mL) was stirred at 40 °C for 4–10 h. The progress of reaction was monitored by TLC, final product was isolated by extraction with diethyl ether and purified by column chromatography using 5percent ethyl acetate in hexane on silica gel as solid support. The pure product isolated by column chromatography was weighed after drying to calculate the isolated yield. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, L-7202, copper diacetate, 1-butyl-3-methylimidazolium Tetrafluoroborate, Time= 4h, T= 40 °C , Green chemistry Sah, Ajay K.; Soni, Kiran; Catalysis Communications; vol. 28; (2012); p. 120 - 123 View in Reaxys

85 %

With Oxone in ethanol, Time= 0.5h, T= 20 °C , Catalytic behavior, Reagent/catalyst, Solvent Nasseri, Mohammad Ali; Mohammadinezhad, Arezou; Salimi, Mehri; Journal of the Iranian Chemical Society; vol. 12; nb. 1; (2015); p. 81 - 86 View in Reaxys

85 %

Typical procedure for the oxidation alcohols to aldehydes and ketones using periodic acid catalyzed by SCOCC General procedure: A solution of acetonitril (10 mL, 1mmol) and periodic acid was placed in flask and stir for the 15 min. Then, a mixture of alcohols (1mmol) and S-COCC (1percentmmol) was added and the resulting mixture was stirred at room temperature for a suitable period (Table 3) and completion of the reaction investigated byTLC (n-hexane/EtOAc; 2:1) analysis. Then, EtOAc (20ml) was subjoined to the reaction mixture and after being washed with water/sodium solfite (1:1), the mixture was filtered off. The solvent was vaporized and produced pure products. With sym-collidinium chlorochromate, periodic acid in acetonitrile, Time= 0.0833333h, T= 20 °C Shiri, Lotfi; Sheikh, Davood; Sheikhi, Masoome; Revue Roumaine de Chimie; vol. 59; nb. 10; (2014); p. 825 834 View in Reaxys

85 %

With cobalt(II)-meso-tetra(4-carboxyphenyl)porphyrin on TiO2/WO3 nanohybrid in acetonitrile, Time= 1h, T= 30 °C , UV-irradiation, Solvent, Reagent/catalyst Safaei, Elham; Mohebbi, Sajjad; Journal of Materials Chemistry A; vol. 4; nb. 10; (2016); p. 3933 - 3946 View in Reaxys

85 %

General procedure for oxidation of alcohols General procedure: Catalytic experiments were carried out in a 5-mL test tube. In a typical procedure, to 1 mmol benzyl alcohol in 1 ml solvent, 2 molpercent (0.02 g) of γ-Fe2O3-MoO2L and 2 mmolof 30 percent H2O2 was added. The reaction mixture was stirred for 3 h at 80 C. The reaction products were monitored byTLC or GC. After completion of the reaction, the mixture was diluted with EtOAc. The catalyst was separated by an external magnet, washed with EtOAc, dried and reused for a consecutive run under the same reaction conditions. Evaporation of the solvent from the filtrate under reduced pressure gave the crude products, which were then purified by chromatography on silica gel eluted with n-hexane/EtOAc (2:1). With dihydrogen peroxide in ethanol, Time= 3h, T= 80 °C , Temperature, Reagent/catalyst, Solvent Saeednia; Ardakani, M. Hatefi; Parizi, Z. Pakdin; Hafshejani, M. Tavakoli; Transition Metal Chemistry; vol. 41; nb. 7; (2016); p. 767 - 774 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

73/438

2018-03-11 22:07:32


85 %

With N -hydroxyphthalimide, oxygen in ethyl acetate, Time= 3h, T= 70 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst, Solvent Rezaeifard, Abdolreza; Khoshyan, Ashkan; Jafarpour, Maasoumeh; Pourtahmasb, Mehrdad; RSC Advances; vol. 7; nb. 26; (2017); p. 15754 - 15761 View in Reaxys

85 %

With 4,4'-bipyridine, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper(I) bromide in acetonitrile, T= 80 °C , Temperature Lee, Darren S.; Amara, Zacharias; Clark, Charlotte A.; Xu, Zeyuan; Kakimpa, Bruce; Morvan, Herve P.; Pickering, Stephen J.; Poliakoff, Martyn; George, Michael W.; Organic Process Research and Development; vol. 21; nb. 7; (2017); p. 1042 - 1050 View in Reaxys

85 %

With tert.-butylhydroperoxide in acetonitrile, Time= 1h, T= 70 °C , Irradiation, Catalytic behavior, Reagent/catalyst, Temperature, Solvent Askari, Parvin; Mohebbi, Sajjad; New Journal of Chemistry; vol. 42; nb. 3; (2018); p. 1715 - 1724 View in Reaxys

84 %

With sodium bromite in water, Time= 10h, Ambient temperature Kageyama, Toshifumi; Kawahara, Shuji; Kitamura, Kohji; Ueno, Yoshio; Okawara, Makoto; Chemistry Letters; (1983); p. 1097 - 1100 View in Reaxys

84 %

With hydrogen bromide, dihydrogen peroxide in dichloromethane, Time= 4h, T= 60 °C Dakka, Jihad; Sasson, Yoel; Bulletin de la Societe Chimique de France; nb. 4; (1988); p. 756 View in Reaxys

84 %

With dihydrogen peroxide, lt;NMe4gt;3lt;(MePO3)lt;MePO2(OH)gt;W6O13(O2)4(OH)2(OH2)gt;*4H2O, Time= 3h, T= 70 °C Griffith, William P.; Parkin, Bernardeta C.; White, Andrew J. P.; Williams, David J.; Journal of the Chemical Society, Chemical Communications; nb. 21; (1995); p. 2183 - 2184 View in Reaxys

84 %

With γ-picolinium chlorochromate, silica gel in dichloromethane, Time= 1.5h, T= 20 °C Salehi; Khodaei; Yazdanipoor; Polish Journal of Chemistry; vol. 77; nb. 10; (2003); p. 1281 - 1286 View in Reaxys

84 %

With dmap, [2,2]bipyridinyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, copper(I) bromide in acetonitrile, Time= 1h, T= 20 °C , Schlenk technique Könning, Daniel; Olbrisch, Tobias; Sypaseuth, Fanni D.; Tzschucke, C. Christoph; Christmann, Mathias; Chemical Communications; vol. 50; nb. 39; (2014); p. 5014 - 5016 View in Reaxys

84 %

General procedure: All of the reactions were carried out at 100 °C under reflux in a 25 mL flask equipped with a magnetic stirrer. 30percent H2O2 solution was added to a mixture of alcohol (5mmol) and the catalyst (8 molpercent). The reaction solutions in all cases were vigorously stirred using magnetic stirrers, and an oil bath was used to achieve the desired reaction temperature. After completion (TLC), the reaction mixture was cooled to room temperature and filtered. Filtrate was extracted with ethylacetate (3×10 mL) and the combined organic extract was washed with water (3×10mL), brine (10 mL) and dried over anhydrous Na2SO4. After removing the solvent, the crude product was purified by column chromatography over silica gel (60–120 mesh) using ethyl acetate and hexane as eluent to afford the pure products 2a–l. With C26H34Cu2N6O18Zn, dihydrogen peroxide in water, Time= 12h, T= 100 °C , Green chemistry, Catalytic behavior, Solvent, Reagent/catalyst, Temperature Borthakur, Rosmita; Asthana, Mrityunjaya; Kumar, Arvind; Lal, Ram A.; Inorganic Chemistry Communications; vol. 46; (2014); p. 198 - 201

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

74/438

2018-03-11 22:07:32


View in Reaxys 84 %

With potassium carbonate in toluene, Time= 4.83333h, T= 85 - 90 °C , p= 760.051Torr , Schlenk technique, Inert atmosphere, Sonication, Green chemistry, Time Wang, Dong; Deraedt, Christophe; Salmon, Lionel; Labrugère, Christine; Etienne, Laetitia; Ruiz, Jaime; Astruc, Didier; Chemistry - A European Journal; vol. 21; nb. 17; (2015); p. 6501 - 6510 View in Reaxys

84 %

With 2,2,2-trifluoroethanol, chloro-(pentamethylcyclopentadienyl)-{5-methoxy-2-{1-[(4-methoxyphenyl)imino-N]ethyl}phenyl-C}-iridium(lll), potassium carbonate, Time= 12h, T= 100 °C , Inert atmosphere, Sealed tube Zou, Qingzhu; Wang, Chao; Smith, Jen; Xue, Dong; Xiao, Jianliang; Chemistry - A European Journal; vol. 21; nb. 27; (2015); p. 9656 - 9661 View in Reaxys

84.1 %

With aluminum oxide, bis(2,2'-bipyridine)([2,2'-bipyridine]-5,5'-dicarboxylic acid)ruthenium(II) dichloride, oxygen in acetonitrile, Time= 12h, p= 750.075Torr , Irradiation, Reagent/catalyst Leow, Wan Ru; Ng, Wilson Kwok Hung; Peng, Tai; Liu, Xinfeng; Li, Bin; Shi, Wenxiong; Lum, Yanwei; Wang, Xiaotian; Lang, Xianjun; Li, Shuzhou; Mathews, Nripan; Ager, Joel W.; Sum, Tze Chien; Hirao, Hajime; Chen, Xiaodong; Journal of the American Chemical Society; vol. 139; nb. 1; (2017); p. 269 - 276 View in Reaxys

83 %

With 1-(benzoylamino)-3-methylimidazolium chlorochromate in dichloromethane, Time= 20h, Heating, oxidation of various allylic and benzylic alcohols with a new selective reagent; effect of temperature, of amount of reagent, and of reaction time Martinez, Yolanda; De Las Heras, Maria A.; Vaquero, Juan J.; Garcia-Navio, Jose L.; Alvarez-Builla, Julio; Tetrahedron Letters; vol. 36; nb. 46; (1995); p. 8513 - 8516 View in Reaxys

83 %

With C51H43ClN3O2P2Ru, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Thilagavathi; Manimaran; Jayabalakrishnan; Journal of Coordination Chemistry; vol. 63; nb. 7; (2010); p. 1252 1262 View in Reaxys

83 %

With tert.-butylhydroperoxide, Cu2(μ-O2CC6H5)4(4-Etpy)2 in methanol, water, Time= 3h, T= 65 °C Sarmah, Purabi; Das, Birinchi K.; Phukan, Prodeep; Catalysis Communications; vol. 11; nb. 10; (2010); p. 932 935 View in Reaxys

83.8 %

With C98H78Br4N2O2P4Ru2, oxygen in dichloromethane, Time= 6h, T= 20 °C , p= 760.051Torr Manimaran, Arumugam; Jayabalakrishnan, Chinnasamy; Applied Organometallic Chemistry; vol. 24; nb. 2; (2010); p. 71 - 81 View in Reaxys

83 %

With potassium phosphate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, Cu2(phenanthroline)2(μ-Cl)2Cl2, oxygen in acetonitrile, Time= 2h, T= 20 °C Hossain, Md. Munkir; Shyu, Shin-Guang; Advanced Synthesis and Catalysis; vol. 352; nb. 17; (2010); p. 3061 3068 View in Reaxys

83 %

With N-Bromosuccinimide, L-proline in water, Time= 2h, T= 20 °C Liu, Xiuhong; Wu, Jun; Shang, Zhicai; Synthetic Communications; vol. 42; nb. 1; (2012); p. 75 - 83 View in Reaxys

83 %

Stage 1: With copper(I) bromide in acetonitrile, Time= 0.05h, T= 20 °C , Inert atmosphere Stage 2: With N,N'-di-tert-butyldiaziridinone in acetonitrile, Time= 5h, T= 60 °C Zhu, Yingguang; Zhao, Baoguo; Shi, Yian; Organic Letters; vol. 15; nb. 5; (2013); p. 992 - 995

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

75/438

2018-03-11 22:07:32


View in Reaxys 83 %

Typical procedure for the oxidation of 1-phenyl-ethanol General procedure: 1-Phenyl-ethanol (0.14 g, 1.00 mmol) was added to a two-necked flask equipped with a gas bubbling tube containing colloidal of CoPcCell (0.05 g) and KOH (0.25 mmol) in o-xylene (5 mL) at room temperature. The mixture was stirred at room temperature under O2 atmosphere provided with a balloon. The progress of the reaction was followed by thin layer chromatography (TLC). Upon completion, CoPcCell was separated by filtration and washed with acetone (5 mL). Acetophenone was isolated from the mixture using column chromatography with n-hexane in 90percent yield. With 6-((cobalt(II) 4,9,16,23-tetraaminephthalocyanin-4-yl))cellulose, oxygen, potassium hydoxide in o-xylene, Time= 8.5h, T= 20 °C , Green chemistry Shaabani, Ahmad; Keshipour, Sajjad; Hamidzad, Mona; Shaabani, Shabnam; Journal of Molecular Catalysis A: Chemical; vol. 395; (2014); p. 494 - 499 View in Reaxys

83.4 %

With tert.-butylhydroperoxide, Time= 1h, T= 100 °C , Microwave irradiation, Reagent/catalyst Dias Ribeiro de Sousa Martins, Luísa Margarida; Carabineiro, Sónia Alexandra Correia; Wang, Jiawei; Rocha, Bruno Gonçalo Martins; Maldonado-Hódar, Francisco José; Latourrette de Oliveira Pombeiro, Armando José; ChemCatChem; vol. 9; nb. 7; (2017); p. 1211 - 1221 View in Reaxys

82 %

With potassium permanganate, Tris(3,6-dioxaheptyl)amine in dichloromethane, Time= 3h, Ambient temperature McKillop, Alexander; Mills, Lester S.; Synthetic Communications; vol. 17; nb. 6; (1987); p. 647 - 656 View in Reaxys

82 %

With dodecane, potassium chlorochromate on alumina in tetrachloromethane, Time= 2h, Ambient temperature, further solvents Carlsen, Per H. J.; Husbyn, Mette; Braenden, Jon E,; Eliason, Robert; Acta Chemica Scandinavica; vol. 43; nb. 5; (1989); p. 485 - 488 View in Reaxys

82 %

With quinolinium chlorochromate(VI) in dichloromethane, Time= 8h, Heating, further solvent: DMF Srinivasan; Ramesh; Madhulatha; Balasubramanian; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 35; nb. 5; (1996); p. 480 - 481 View in Reaxys

82 %

With potassium dichromate in dimethyl sulfoxide, Time= 3h, T= 90 - 100 °C , also in polyethylene glycol 400, various molar ratios, Product distribution Santaniello, Enzo; Ferraboschi, Patrizia; Synthesis; nb. 8; (1980); p. 646 - 647 View in Reaxys

82 %

With trimethylaluminum in toluene, Time= 0.5h, T= 20 °C , Oppenauer oxidation Graves, Christopher R.; Zeng, Bi-Shun; Nguyen, SonBinh T.; Journal of the American Chemical Society; vol. 128; nb. 39; (2006); p. 12596 - 12597 View in Reaxys

82 %

With oxygen in 1,4-dioxane, Time= 6h, T= 80 °C Lee, Chan Woo; Jin, Sung Ho; Yoon, Koo Sik; Jeong, Han Mo; Chi, Ki-Whan; Tetrahedron Letters; vol. 50; nb. 5; (2009); p. 559 - 561 View in Reaxys

82 %

With C65H55ClN4O5P2Ru, 4-methylmorpholine N-oxide in chloroform, Time= 3h, T= 20 °C Balasubramian; Raju; Chinnusamy; Journal of the Indian Chemical Society; vol. 86; nb. 6; (2009); p. 570 - 576 View in Reaxys

82 %

With oxygen in 1,3,5-trimethyl-benzene, Time= 4h, T= 135 °C , p= 760.051Torr

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

76/438

2018-03-11 22:07:32


He, Jinling; Yamaguchi, Kazuya; Mizuno, Noritaka; Chemistry Letters; vol. 39; nb. 11; (2010); p. 1182 - 1183 View in Reaxys 82 %

With C52H40Cl2N3O3P2Ru, 4-methylmorpholine N-oxide in chloroform Raju; Balasubramanian; Jayabalakrishnan; Chinnusamy; Journal of the Indian Chemical Society; vol. 87; nb. 11; (2010); p. 1305 - 1311 View in Reaxys

82 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, C30H34Cu2N2O12, Time= 4h, T= 20 °C , Ionic liquid Soni, Kiran; Kumar, Anil; Sah, Ajay K.; Catalysis Communications; vol. 17; (2012); p. 95 - 98 View in Reaxys

82 %

With tert.-butylhydroperoxide, Co(0.137)Fe3O4(0.863) in water, Time= 5h, T= 80 °C Gawande, Manoj B.; Rathi, Anuj; Nogueira, Isabel D.; Ghumman; Bundaleski; Teodoro; Branco, Paula S.; ChemPlusChem; vol. 77; nb. 10; (2012); p. 865 - 871 View in Reaxys

82 %

With tert.-butylhydroperoxide in water, Time= 5h, T= 80 °C Gawande, Manoj B.; Rathi, Anuj; Nogueira, Isabel D.; Ghumman; Bundaleski; Teodoro; Branco, Paula S.; Collection of Czechoslovak Chemical Communications; vol. 77; nb. 10; (2012); p. 865 - 871 View in Reaxys

82 %

General Procedure General procedure: A mixture of benzylic alcohol (1.0mmol), urea hydrogen peroxide (1.5 mmol) and calciumchloride (0.5 mmol) was stirred in PEGDME250 (2 mL) at 70oC for 4 h. After cooling the mixture to room temperature theproduct is extracted into diethyl ether (3 × 20 mL), washedwith water and dried over MgSO4. The combined etherextracts were concentrated under reduced pressure and thecrude product was purified by flash column chromatography(ethyl acetate/n-hexane = 1:3, v/v) to give the desired carbonylcompound. With urea hydrogen peroxide adduct, calcium chloride, Time= 4h, T= 70 °C Ha, Su Jeong; Jung, Eun-Young; Kim, Won Mi; Lee, Jong Chan; Bulletin of the Korean Chemical Society; vol. 35; nb. 2; (2014); p. 629 - 630 View in Reaxys

82 %

Catalytic studies General procedure: In a Pyrex flask equipped with a magnet bar, a solution of the alcohol (5 mmol) in acetonitrile (10 mL) was prepared. To this solution PTA/Si-imid Si-MNPs (50 mg) was added and purged with O2 and joined through an inlet tube to a balloon filled with O2 before irradiation.The suspension was vigorously stirred and irradiated with a high pressure 400 W mercury lamp using a cut-off Pyrex filter at room temperature. The progress of the reaction was monitored by TLC. At the end of the reaction the organic layer was simply decanted by means of an external magnet. The decanted solution was purified on a silica-gel plate or a silica-gel column to obtain the pure product. The identities of the products were confirmed by FT-IR and 1H NMR spectral data. With oxygen in acetonitrile, Time= 1.5h, T= 20 °C , Irradiation, Green chemistry, chemoselective reaction Afshari, Mozhgan; Gorjizadeh, Maryam; Afshar, Ghazal; Oriental Journal of Chemistry; vol. 29; nb. 4; (2013); p. 1675 - 1681 View in Reaxys

82 %

General procedure for the oxidation General procedure: A mixture of benzhydrol (1 mmol, 0.184 g), isobutyraldehyde (1.5 mmol, 0.108 g), and catalyst (1 mol percent 0.01 mmol) in acetonitrile (15 mL) was heated at 60 °C under stirring by using an oxygen balloon. The progress of the reaction was monitored by thin layer chromatography on silica gel. On completion, the reaction mixture was cooled to room temperature and centrifuged to separate the catalyst. The product was identified with GCMS. The solvent was removed under reduced pressure and the product was obtained by passing it through a short column of silica gel using EtOAc–hexane (1:9) as eluent. The identity of the product was confirmed by comparing the physical and spectral data (1H and 13C NMR) with the reported compound. The recovered catalyst was dried at 50 °C for 2 h and can be reused for recycling experiments. With oxygen, isovaleraldehyde in acetonitrile, Time= 4h, T= 65 °C , Catalytic behavior

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

77/438

2018-03-11 22:07:32


Panwar, Vineeta; Kumar, Pawan; Ray, Siddharth S.; Jain, Suman L.; Tetrahedron Letters; vol. 56; nb. 25; (2015); p. 3948 - 3953 View in Reaxys 82 %

With [MnIII(2-((2-(2-(2-(2-hydroxybenzylideneamino)phenylamino)propylamino)phenylimino)methyl)phenolato)]Cl, dihydrogen peroxide in acetonitrile, Time= 2h, Reflux Azadbakht, Reza; Amini Manesh, Abbas; Malayeri, Mahdieh; Dehghani, Behzad; New Journal of Chemistry; vol. 39; nb. 8; (2015); p. 6459 - 6464 View in Reaxys

82 %

2.3. Catalytic Oxidation of Benzyl Alcohol to Benzaldehyde General procedure: All reactions were carried out in two-neck flask (50.0mL) fitted with a condenser. Benzyl alcohol (1.08 mL, 10mmol) and 1 molpercent of -Fe2O3 nanofibers were added to theflask. The reaction mixture was stirred at 70 oC. H2O2 (30Wtpercent in water, 3.0 mL, 3eq) was added continuously with asyringe pump during 12 h. Completion of reaction was monitoredby TLC. The mixture was cooled to room temperatureand the catalyst was removed from the mixture by applyingan external magnet. CH2Cl2 was added and the aqueous layerwas extracted. The organic layer was dried over MgSO4. Thesolvent was removed in vacuum and then the product wasisolated by flash chromatography with ethyl acetate/hexaneas eluent. With iron(III) oxide, dihydrogen peroxide in water, Time= 12h, T= 70 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Solvent Ziyadi, Hakimeh; Heydari, Akbar; Nikbakht, Fatemeh; Letters in Organic Chemistry; vol. 12; nb. 8; (2015); p. 598 - 604 View in Reaxys

82 %

With iron vanadate, urea hydrogen peroxide adduct in acetonitrile, Time= 3h, T= 50 °C , Catalytic behavior, Reagent/catalyst, Solvent, Concentration, chemoselective reaction Heydari, Akbar; Sheykhan, Mehdi; Sadeghi, Masoud; Radfar, Iman; Inorganic and Nano-Metal Chemistry; vol. 47; nb. 2; (2017); p. 248 - 255 View in Reaxys

81 %

With Clay-Supported Iron(III) Nitrate in pentane, Time= 1.5h, p= 100Torr Cornelis, Andre; Laszlo, Pierre; Synthesis; nb. 10; (1980); p. 849 - 850 View in Reaxys

81 %

With lutidine N-oxide, dioxo(tetramesitylporphyrinato)ruthenium(VI) in benzene, Ambient temperature Higuchi; Ohtake; Hirobe; Tetrahedron Letters; vol. 32; nb. 50; (1991); p. 7435 - 7438 View in Reaxys

81 %

With sodium bromate, NaHCO3 buffer pH:10, sodium carbonate, ruthenium trichloride in water, 1,2-dichloro-ethane, Time= 1.5h, T= 70 °C Kanemoto, Shigekazu; Tomioka, Hiroki; Oshima, Koichiro; Nozaki, Hitosi; Bulletin of the Chemical Society of Japan; vol. 59; (1986); p. 105 - 108 View in Reaxys

81 %

With potassium dichromate in N,N-dimethyl-formamide, Time= 2h, T= 100 °C Lou, Ji-Dong; Lu, Li-Huang; Liu, Wei; Synthetic Communications; vol. 27; nb. 21; (1997); p. 3701 - 3703 View in Reaxys

81 %

With isoquinolinium dichromate in dichloromethane, Time= 6h, Heating, Oxidation Srinivasan; Akila; Caroline; Balasubramanian; Synthetic Communications; vol. 28; nb. 12; (1998); p. 2245 - 2251 View in Reaxys

81 %

With oxygen in toluene, Time= 12h, T= 110 °C Kantam, M. Lakshmi; Yadav, Jagjit; Laha, Soumi; Sreedhar, Bojja; Bhargava, Suresh; Advanced Synthesis and Catalysis; vol. 350; nb. 16; (2008); p. 2575 - 2582 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

78/438

2018-03-11 22:07:32


81 %

With dihydrogen peroxide in water, acetonitrile, Time= 5h, T= 60 °C , p= 760.051Torr Monfared, Hassan Hosseini; Alavi, Sohaila; Farrokhi, Afsaneh; Vahedpour, Morteza; Mayer, Peter; Polyhedron; vol. 30; nb. 11; (2011); p. 1842 - 1848 View in Reaxys

81 %

With dihydrogen peroxide in acetonitrile, Time= 12h, T= 60 °C , chemoselective reaction Zhu, Jie; Wang, Peng Cheng; Lu, Ming; New Journal of Chemistry; vol. 36; nb. 12; (2012); p. 2587 - 2592 View in Reaxys

81 %

General Procedure. General procedure: To a stirred solution of a benzylic alcohol (1.0 mmol) in 1 mL [bmim]BF4 was added 65percent nitric acid (0.5 mmol) and copper(II) bromide (0.5 mmol). The reaction mixture was stirred in the air at 60 °C for 4 h and the reaction monitored by TLC for the complete consumption of the benzylic alcohol. The solution was cooled to room temperature and the product is extracted into ethyl acetate (2 20 mL), washed with water and dried over MgSO4. After removal of the solvent under reduced pressure, the crude product was purified by flash chromatography (ethyl acetate/n-hexane = 1:5, v/v) to yield the desired carbonyl compound. With nitric acid, copper(ll) bromide, Time= 4h, T= 60 °C , Ionic liquid, Reagent/catalyst, Solvent Lim, Chae Mi; Ha, Su Jeong; Lee, Jong Chan; Bulletin of the Korean Chemical Society; vol. 33; nb. 12; (2012); p. 4258 - 4260 View in Reaxys

81 %

With Tributylphosphine oxide, oxygen, sodium acetate, palladium diacetate in toluene, T= 80 °C , p= 750.075Torr , Molecular sieve Gowrisankar, Saravanan; Neumann, Helfried; Goerdes, Dirk; Thurow, Kerstin; Jiao, Haijun; Beller, Matthias; Chemistry - A European Journal; vol. 19; nb. 47; (2013); p. 15979 - 15984 View in Reaxys

81 %

With potassium carbonate in toluene, Time= 4h, T= 40 °C , Reagent/catalyst, Solvent, Temperature Karami, Kazem; Naeini, Nasrin Haghighat; Eigner, Vaclav; Dusek, Michal; Lipkowski, Janusz; Hervés, Pablo; Tavakol, Hossein; RSC Advances; vol. 5; nb. 124; (2015); p. 102424 - 102435 View in Reaxys

81 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C34H51CeN5O8, oxygen in acetonitrile, Time= 28h, T= 85 °C , p= 760.051Torr , Molecular sieve, Schlenk technique, Inert atmosphere Paul, Mitali; Shirase, Satoru; Morimoto, Yuma; Mathey, Laurent; Murugesapandian, Balasubramanian; Tanaka, Shinji; Itoh, Shinobu; Tsurugi, Hayato; Mashima, Kazushi; Chemistry - A European Journal; vol. 22; nb. 12; (2016); p. 4008 - 4014 View in Reaxys

81 %

Stage 1: With nickel(II) chloride hexahydrate, cadmium sulphide in acetonitrile, Time= 0.00277778h, Schlenk technique, Sonication, Inert atmosphere Stage 2: in acetonitrile, Time= 24h, T= 20 °C , Irradiation, Inert atmosphere, Schlenk technique Chai, Zhigang; Zeng, Ting-Ting; Li, Qi; Lu, Liang-Qiu; Xiao, Wen-Jing; Xu, Dongsheng; Journal of the American Chemical Society; vol. 138; nb. 32; (2016); p. 10128 - 10131 View in Reaxys

80 %

With oxoperoxobis(N-phenylbenzohydroxamato)molybdenum-VI in 1,2-dichloro-ethane, Time= 7h, T= 85 °C Tomioka, Hiroki; Takai, Kazuhiko; Oshima, Koichiro; Nozaki, Hitosi; Toriumi, Koshiro; Tetrahedron Letters; vol. 21; (1980); p. 4843 - 4846 View in Reaxys

80 %

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,4-dioxane, Time= 90h, Ambient temperature Becker, Hans-Dieter; Bjoerk, Anders; Adler, Erich; Journal of Organic Chemistry; vol. 45; nb. 9; (1980); p. 1596 1600 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

79/438

2018-03-11 22:07:32


80 %

With t-BuOSmI2, pivalaldehyde in tetrahydrofuran, Time= 24h, T= 65 °C , Product distribution Namy, J. L.; Souppe, J.; Collin, J.; Kagan, H. B.; Journal of Organic Chemistry; vol. 49; nb. 11; (1984); p. 2045 2049 View in Reaxys

80 %

With perchloric acid, N-chlorobenzotriazole in water, acetic acid, T= 39.9 °C , Ea, ΔS(excit.), ΔG(excit.); varying concentrations of benzyl alcohol, CBT, and acid; other acid; other temperatures; effect of added chloride ions at 30 deg C., Thermodynamic data, Rate constant Rangadurai, A.; Thiagarajan, V.; Venkatasubramanian, N.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 21; nb. 1; (1982); p. 42 - 45 View in Reaxys

80 %

With 4,5-dihydro-4(5)-oxo-5(4)-imino-1H-pyrrololt;2,3-fgt;quinoline-2,7,9-tricarboxylic acid 2,9-dimethyl ester Ca-nitrate salt in dimethyl sulfoxide, acetonitrile, Time= 24h, T= 25 °C , var. of reagent, Product distribution Itoh, Shinobu; Huang, Xin; Kawakami, Hirokatsu; Komatsu, Mitsuo; Ohshiro, Yoshiki; Fukuzumi, Shunichi; Journal of the Chemical Society, Chemical Communications; nb. 20; (1995); p. 2077 - 2078 View in Reaxys

80 %

With (phthalocyaninato)iron(II), zirconium phosphate, oxygen, hydroquinone, tris(triphenylphosphine)ruthenium(II) chloride in water, N,N-dimethyl-formamide, Time= 3h, T= 20 °C , p= 760Torr Villemin, Didier; Hammadi, Mohamed; Hachemi, Messaoud; Synthetic Communications; vol. 32; nb. 10; (2002); p. 1501 - 1515 View in Reaxys

80 %

With potassium carbonate, Time= 4h, T= 20 °C Lou, Ji-Dong; Xu, Zhi-Nan; Tetrahedron Letters; vol. 43; nb. 49; (2002); p. 8843 - 8844 View in Reaxys

80 %

With air, ferric(III) bromide, ferric nitrate in acetonitrile, Time= 24h, T= 20 °C Martin, Sandra E; Suarez, Dario F; Tetrahedron Letters; vol. 43; nb. 25; (2002); p. 4475 - 4479 View in Reaxys

80 %

With C23H23ClN3RuSe2 (1+)*F6P(1-), 4-methylmorpholine N-oxide in dichloromethane, Reflux Das, Dipanwita; Singh, Pradhumn; Prakash, Om; Singh, Ajai K.; Inorganic Chemistry Communications; vol. 13; nb. 11; (2010); p. 1370 - 1373 View in Reaxys

80 %

Typical experimental procedure for the synthesis of Piperonal: (entry 4, Table 1) In a typical experimental procedure a mixture of benzo[d][1,3]dioxol-5-ylmethanol (1 mmol, 152 mg), NaIO4 (1 mmol, 213 mg) in 2 ml of DCM was taken in an open round bottomed flask at room temperature and then NH2OH*HCl (1.5 mmol, 105 mg) was added by portion for 5 min. After completion (TLC), the reaction mixture was diluted with a 1:1 mixture of water/DCM (10 mL) and washed with 10percent (w/v) Na2S2O3 (3 .x. 5 ml). Then the combined organic layer was dried over anhydrous Na2SO4. Evaporation of solvent furnished the crude product which was subjected to column chromatography using ethyl acetate-petroleum ether (1:10) to obtain the analytically pure product as a white solid (122 mg, 80percent). With sodium periodate, hydroxylamine hydrochloride in dichloromethane, T= 20 °C , chemoselective reaction Majee, Adinath; Kundu, Shrishnu Kumar; Santra, Sougata; Hajra, Alakananda; Tetrahedron Letters; vol. 53; nb. 33; (2012); p. 4433 - 4435 View in Reaxys

80 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in toluene, Time= 16h, T= 80 °C , Catalytic behavior, Reagent/catalyst Samanta, Suvendu; Das, Sudipto; Samanta, Partha Kumar; Dutta, Supriya; Biswas, Papu; RSC Advances; vol. 3; nb. 42; (2013); p. 19455 - 19466 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

80/438

2018-03-11 22:07:32


80 %

Catalytic Studies General procedure: In a typical run, a 25 mL flask was charged with catalyst (100 mg), acetonitrile (5 mL), alcohol (1 mmol), and H2O2 (3 mmol). This mixture was heated in an oil bath at 70°C and the progress of the reaction was monitored by TLC. At the end of the reaction, the catalyst was simply collected using a magnetic bar and the reaction mixture was then transferred out of the flask. The decanted solution was purified on a silica-gel plate or a silicagel column to obtain the pure product. The structures of the products were established on the basis of their spectral analysis (IR, 1H NMR). With dihydrogen peroxide in acetonitrile, Time= 2h, T= 70 °C , chemoselective reaction Afshari, Mozhgan; Gorjizadeh, Maryam; Nazari, Simin; Naseh, Mohammad; Oriental Journal of Chemistry; vol. 29; nb. 4; (2013); p. 1523 - 1530 View in Reaxys

80 %

2.2 Catalytic reaction General procedure: An oven dried flask was charged with Fe3O4 (0.030g) and benzoin (0.127g, 0.6 mmol). To the flask toluene (3.0mL) was added and heated to 80°C with magnetic stirring. After completion of the reaction (monitored by TLC and UV–Visible spectroscopy), the reaction mixture was cooled to rt, and the catalyst was magnetically removed and washed several times with toluene. With iron(III) oxide in toluene, Time= 12h, T= 80 °C , Green chemistry Shaikh, Melad; Satanami, Mansingh; Ranganath, Kalluri V.S.; Catalysis Communications; vol. 54; (2014); p. 91 93 View in Reaxys

80 %

2.2 Catalytic reaction An oven dried flask was charged with Fe3O4 (0.030 g) and benzoin (0.127 g, 0.6 mmol). To the flask toluene (3.0 mL) was added and heated to 80 °C with magnetic stirring. After completion of the reaction (monitored by TLC and UV– Visible spectroscopy), the reaction mixture was cooled to rt, and the catalyst was magnetically removed and washed several times with toluene. With iron oxide in toluene, Time= 12h, T= 80 °C Shaikh, Melad; Satanami, Mansingh; Ranganath, Kalluri V.S.; Catalysis Communications; vol. 54; (2014); p. 91 93 View in Reaxys

80 %

With oxygen in toluene, UV-irradiation, Catalytic behavior, Kinetics, Reagent/catalyst Li, Ang; Wang, Tuo; Chang, Xiaoxia; Cai, Weiting; Zhang, Peng; Zhang, Jijie; Gong, Jinlong; Chemical Science; vol. 7; nb. 2; (2016); p. 890 - 895 View in Reaxys

80%

2.5 Procedure for the catalytic oxidation of benzylalcohol A mixture of benzyl alcohol (0.5 mmol), catalyst[(L 2a )2Cu] (4 molpercent) or [(L 2b )2Cu] (4 molpercent) and 30percentH2O2 (5 equiv.) was taken in 10mL acetonitrile solvent in a round bottom flask. The mixture was vigorouslystirred at 70°C for 1 h. The reaction was monitored byTLC. After completion of the reaction, the solvent wasremoved, the organic phase was separated and driedover Na2SO4 and the product was purified by columnchromatography (hexane/ethyl acetate). Yields weredetermined by weighing the isolated product, whichwas characterized by 1H NMR and IR spectroscopy. With C54H46CuN8O6, dihydrogen peroxide in acetonitrile, Time= 1h, T= 70 °C , Reagent/catalyst Mondal, Palash; Parua, Sankarprasad; Pattanayak, Poulami; Das, Uttam; Chattopadhyay, Surajit; Journal of Chemical Sciences; vol. 128; nb. 5; (2016); p. 803 - 813 View in Reaxys

79 %

With 2,2'-bipyridinium chlorochromate in dichloromethane, Time= 2.5h Guziec, Frank S.; Luzzio, Frederick A.; Synthesis; nb. 9; (1980); p. 691 - 694 View in Reaxys

79 %

With tert.-butylhydroperoxide, CrO3 (3-)*La(3+), Time= 2.5h, T= 90 °C , neat (no solvent)

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

81/438

2018-03-11 22:07:32


Singh, Savita J.; Jayaram, Radha V.; Synthetic Communications; vol. 42; nb. 3; (2012); p. 299 - 308 View in Reaxys 79.4 %

With Ni3(PW12O40)2*26H2O, dihydrogen peroxide, Time= 3.5h, T= 90 °C , Neat (no solvent) Tian, Wei; Hou, Yang; Wang, Xiaoguang; Lu, Bin; Zhao, Jingxiang; Cai, Qinghai; Chinese Journal of Chemistry; vol. 30; nb. 2; (2012); p. 433 - 437 View in Reaxys

79%

With copper phthalocyanine, tetra-n-butylammonium hydrogen monopersulfate in water, T= 85 °C , Green chemistry Kheirjou, Somayyeh; Kheirjou, Ramin; Rezayan, Ali Hossein; Shakourian-Fard, Mehdi; Mahmoudi Hashemi, Mohammad; Comptes Rendus Chimie; vol. 19; nb. 3; (2016); p. 313 - 318 View in Reaxys

78 %

With manganese(IV) oxide in hexane, Time= 5h, Ambient temperature Tsuboi, Sadao; Ishii, Naomi; Sakai, Takashi; Tari, Isao; Utaka, Masanori; Bulletin of the Chemical Society of Japan; vol. 63; nb. 7; (1990); p. 1888 - 1893 View in Reaxys

78 %

With pyridinium bromochromate in chloroform, Time= 3h, Heating, other alcohols Narayanan, N.; Balasubramanian, T. R.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 228 - 229 View in Reaxys

78 %

With 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate in dichloromethane, Time= 0.05h, Microwave irradiation, Oxidation Hajipour, Abdol Reza; Mallakpour, Shadpour E.; Khoee, Sepideh; Synlett; nb. 5; (2000); p. 740 - 742 View in Reaxys

78 %

With aluminium trichloride, benzyltriphenylphosphonium periodate in acetonitrile, Time= 1.5h, Heating Hajipour; Mallakpour; Samimi; Synlett; nb. 11; (2001); p. 1735 - 1738 View in Reaxys

78.8%

10 :REFERENCE EXAMPLE 10 The experiment was conducted in the same manner as in Reference Example 9, except that 15 mg of compound (12) obtained in Reference Example 7 (2,2,6,6-tetramethylpiperidine-1-oxyl-4-yl group: 0.08 mmol) was used instead of compound (14) and 37.24 g (10 mmol) of the 2.0percent by weight aqueous solution of sodium hypochlorite was used. As a result, by the reaction, benzaldehyde was produced with yield of 78.8percent (based on benzyl alcohol). With sodium hypochlorite, C41H76N4O8, sodium hydrogencarbonate, potassium bromide in dichloromethane, water, Time= 1h, T= 0 - 2 °C , pH= 8.6, Product distribution / selectivity Patent; Shiomi, Yasuhiro; Uno, Osamu; Ohta, Akio; Sunakami, Takeshi; US2005/124807; (2005); (A1) English View in Reaxys

78 %

With bis-(2,4,6-trimethylpyridinium) dichromate in acetonitrile, Time= 0.166667h, Reflux, chemoselective reaction Shiri, Lotfi; Ghorbani-Choghamarani, Arash; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 184; nb. 2; (2009); p. 492 - 498 View in Reaxys

78 %

With [2,2]bipyridinyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, 1,8-diazabicyclo[5.4.0]undec-7-ene, copper(ll) bromide in acetonitrile, Time= 0.7h, T= 20 °C , Kinetics, Reagent/catalyst Kumpulainen, Esa T. T.; Koskinen, Ari M. P.; Chemistry - A European Journal; vol. 15; nb. 41; (2009); p. 10901 10911 View in Reaxys

78 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, trans-[Ru(Mes-NP)2(CH3CN)2](BF4)2 in 1,2-dichloro-ethane, toluene, Time= 6h, T= 80 °C , Inert atmosphere

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

82/438

2018-03-11 22:07:32


Saha, Biswajit; Rahaman, S. M. Wahidur; Sinha, Arup; Bera, Jitendra K.; Australian Journal of Chemistry; vol. 64; nb. 5; (2011); p. 583 - 589 View in Reaxys 78 %

With C17H16Cl2N3O2RuS, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux, Catalytic behavior, Reagent/catalyst Pramanik, Ajoy Kumar; Mondal, Tapan Kumar; Inorganica Chimica Acta; vol. 411; (2014); p. 106 - 112 View in Reaxys

78 %

General procedure: All reactions were carried out in a glass reactor (∼50 mL) withbenzyl alcohol (1 mmol) as model substrate. The optimized amountof nano catalyst (0.04 g), H2O2(30 wtpercent in water) was added tothe reaction mixture and vigorously stirred at optimized reactionconditions. The aliquots of the reaction mixture were analysedby GC. With dihydrogen peroxide in neat (no solvent), Time= 2h, T= 80 °C , Catalytic behavior, Reagent/catalyst Bhat, Pooja B.; Rajarao, Ravindra; Sahajwalla, Veena; Bhat, Badekai Ramachandra; Journal of Molecular Catalysis A: Chemical; vol. 409; (2015); p. 42 - 49 View in Reaxys

78 %

With o-iodosobenzoic acid, oxygen in dimethyl sulfoxide, Time= 24h, T= 80 °C , Green chemistry, Solvent Bindu, Vittam Hima; Parvathaneni, Sai Prathima; Rao, Vaidya Jayathirtha; Catalysis Letters; vol. 147; nb. 6; (2017); p. 1434 - 1440 View in Reaxys

78.9 %

With dihydrogen peroxide in acetonitrile, Time= 2h, T= 80 °C , Catalytic behavior, Temperature, Time Li, Qichen; Zhang, Lingling; Wang, Xiaozhong; Xu, Gang; Chen, Yingqi; Dai, Liyan; RSC Advances; vol. 7; nb. 59; (2017); p. 37467 - 37473 View in Reaxys

77 %

With manganese(IV) oxide, Time= 48h Lou, Ji-Dong; Xu, Zhi-Nan; Tetrahedron Letters; vol. 43; nb. 35; (2002); p. 6149 - 6150 View in Reaxys

77 %

With silica gel, Dess-Martin periodane, Time= 0.0333333h, microwave irradiation Heravi, Majid M.; Sangsefidi, Ladan; Oskooie, Hossein A.; Ghassemzadeh, Mitra; Tabar-Hydar, Koroush; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 178; nb. 4; (2003); p. 707 - 709 View in Reaxys

77 %

With C26H22N2O6Ru, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Molecular sieve, Reflux Abdel Aziz, Ayman A.; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 41; nb. 4; (2011); p. 384 - 393 View in Reaxys

77 %

With oxygen, acetic acid, carbonic acid dimethyl ester, 2,3-dicyano-5,6-dichloro-p-benzoquinone, sodium nitrite, Time= 10h, T= 18 °C , Irradiation, Sealed tube Walsh, Katie; Sneddon, Helen F.; Moody, Christopher J.; Organic Letters; vol. 16; nb. 19; (2014); p. 5224 - 5227 View in Reaxys

77 %

With air, MnO2 nanowires on amine functionalized graphite nanosheet in 1,4-dioxane, Time= 16h, T= 100 °C Chakravarty; Sengupta; Basu; Mukherjee; De; RSC Advances; vol. 5; nb. 112; (2015); p. 92585 - 92595 View in Reaxys

76 %

With sodium bromite, 4-benzoxy-2,2,6,6-tetramethylpiperidine-N-oxyl, sodium hydrogencarbonate in dichloromethane, water, Time= 4h, Ambient temperature Inokuchi, Tsutomo; Matsumoto, Sigeaki; Nishiyama, Tokio; Torii, Sigeru; Journal of Organic Chemistry; vol. 55; nb. 2; (1990); p. 462 - 466 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

83/438

2018-03-11 22:07:32


76 %

With tetrahexylammonium chloride, dihydrogen peroxide, lt;NBu4gt;lt;(Ph2PO2)(WO(O2)2)2gt; in benzene, Time= 3h, T= 75 °C Gresley, N. Melanie; Griffith, William P.; Parkin, Bernardeta C.; White, Andrew J. P.; Williams, David J.; Journal of the Chemical Society - Dalton Transactions; nb. 10; (1996); p. 2039 - 2045 View in Reaxys

76 %

With N -hydroxyphthalimide in ethyl acetate, Time= 0.25h, T= 70 °C , Irradiation Jafarpour, Maasoumeh; Feizpour, Fahimeh; Rezaeifard, Abdolreza; RSC Advances; vol. 6; nb. 60; (2016); p. 54649 - 54660 View in Reaxys

76 %

With nickel(II) ferrite in toluene, Time= 6h, T= 120 °C , Green chemistry Payra, Soumen; Saha, Arijit; Banerjee, Subhash; RSC Advances; vol. 6; nb. 57; (2016); p. 52495 - 52499 View in Reaxys

75 %

With bichromate of bis(triphenylphosphino)methane in dichloromethane, Time= 12h, T= 25 °C Cristau, Henri-Jean; Torreilles, Eliane; Morand, Philippe; Christol, Henri; Tetrahedron Letters; vol. 27; nb. 16; (1986); p. 1775 - 1776 View in Reaxys

75 %

With bichromate of bis(triphenylphosphino)methane in dichloromethane, Time= 12h, T= 25 °C , Heating, other temperature and reaction time; variation of ratio of the reactants, Product distribution Cristau, Henri-Jean; Torreilles, Eliane; Morand, Philippe; Christol, Henri; Tetrahedron Letters; vol. 27; nb. 16; (1986); p. 1775 - 1776 View in Reaxys

75 %

With sodium hypochlorite, water, potassium bromide, 1-hydroxy-2,2,6,6-tetramethylpiperidine silica-support, ethynodiol in dichloromethane, Time= 0.5h, T= 0 °C , pH= 9.1, Oxidation Bolm, Carsten; Thomas, Fey; Chemical Communications; nb. 18; (1999); p. 1795 - 1796 View in Reaxys

75 %

With bis(collidine)bromine(I) hexafluorophosphate in dichloromethane, Time= 2.5h, T= 20 °C Rousseau; Robin; Tetrahedron Letters; vol. 41; nb. 46; (2000); p. 8881 - 8885 View in Reaxys

75 %

With γ-picolinium chlorochromate in dichloromethane, Time= 0.333333h, T= 20 °C Khodaie; Salehi; Goodarzi; Synthetic Communications; vol. 31; nb. 8; (2001); p. 1253 - 1256 View in Reaxys

75 %

With oxygen, phosphotungstic acid, silica gel in acetonitrile, Time= 2.5h, T= 20 °C , UV-irradiation Farhadi, Saeid; Afshari, Mozhgan; Maleki, Mansoureh; Babazadeh, Zaynab; Tetrahedron Letters; vol. 46; nb. 49; (2005); p. 8483 - 8486 View in Reaxys

75 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, sodium hypochlorite, silica gel, potassium bromide in dichloromethane, Time= 1h, T= 0 °C , pH= 9.1, Anelli oxidation Fey, Thomas; Fischer, Holger; Bachmann, Stefan; Albert, Klaus; Bolm, Carsten; Journal of Organic Chemistry; vol. 66; nb. 24; (2001); p. 8154 - 8159 View in Reaxys

75.51 %

With 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, T= 20 °C Raju; Balasubramanian; Chinnusamy; Asian Journal of Chemistry; vol. 22; nb. 9; (2010); p. 7318 - 7326 View in Reaxys

75 %

With potassium superoxide, tetraethylammonium bromide in N,N-dimethyl-formamide, Time= 0.025h, Inert atmosphere, Microwave irradiation, Concentration, Solvent

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

84/438

2018-03-11 22:07:32


Raghuvanshi, Raghvendra Singh; Singh, Yogendra; Journal of the Indian Chemical Society; vol. 90; nb. 8; (2013); p. 1255 - 1257 View in Reaxys 75 %

2.3. Catalytic experiments General procedure: The liquid phase oxidation was carried out in an ACE pressure tube filled with oxygen. Water suspension of Au NPs-rGO composites (8.1 mg in 2 mL), benzyl alcohol (1 mmol) and K2CO3 (3 mmol) were placed in a glass ACE pressure tube (10 mL) with a magnetic stirrer bar. The tube was sealed with a rubber O-ring and threaded Teflon seal under O2, and the entire mixture was vigorously stirred at 130 °C (bath temperature) for 4 h. The reaction mixture was cooled to room temperature and the organic product was extracted with ethyl acetate (3 × 10 mL). The aqueous phase was separated and could be used consecutively for another three times for the oxidation of benzyl alcohols (1st recycle 73percent, 2nd recycle 74percent and 3rd recycle 70percent benzaldehyde was obtained). The upper organic phase was dried and concentrated under reduced pressure. The product was purified by column chromatography. With oxygen, potassium carbonate in water, Time= 4h, Sealed tube, Heating, Catalytic behavior, Temperature, Time Sharma, Ponchami; Darabdhara, Gitashree; Reddy, Tallapareddy Muralikrishna; Borah, Ashwini; Bezboruah, Pranjal; Gogoi, Pranjal; Hussain, Najrul; Sengupta, Pinaki; Das, Manash R.; Catalysis Communications; vol. 40; (2013); p. 139 - 144 View in Reaxys

75 %

General procedure for oxidation of alcohols in solution General procedure: In a round-bottomed flask (25 mL) equipped with a magnetic stirrer andcondenser, a solution of alcohols (1 mmol) and DMSO (0.2 mol percent) in CH3CN(5 mL) was prepared. TTN/Silica gel (0.834 g which contain 1 mmol TTN) andAlCl3 (0.75 mmol) was added to the solution and the mixture was refluxed forthe appropriate times as indicated in Table 1.The progress of the reaction was followed by TLC (CCl4/EtOAC: 4/1).After completion, the reaction mixture was filtrate and the solid material waswashed with CH3CN (10 mL). The filtrate was evaporated and the resultingcrude material was purified by column chromatography on silica gel to affordthe pure product. With aluminum (III) chloride, dimethyl sulfoxide in acetonitrile, Time= 0.583333h, Reflux, chemoselective reaction Manesh, Abbas Amini; Nazari, Tahereh; Journal of the Chilean Chemical Society; vol. 60; nb. 3; (2015); p. 3001 3004 View in Reaxys

75 %

With C17H19FeN5O5 (1-)*C8H20N(1+) in water, acetonitrile, T= 30 °C , pH= 7, Kinetics, Catalytic behavior, Reagent/ catalyst, pH-value Pattanayak, Santanu; Jasniewski, Andrew J.; Rana, Atanu; Draksharapu, Apparao; Singh, Kundan K.; Weitz, Andrew; Hendrich, Michael; Que, Lawrence; Dey, Abhishek; Sen Gupta, Sayam; Inorganic Chemistry; vol. 56; nb. 11; (2017); p. 6352 - 6361 View in Reaxys

74 %

27 :In a screwed test tube, 1.00 g of fluorapatite (FAp) and 0.060 g (0.010 mmol) of a catalyst (CetylPy)10[H2W12O42] were weighed, and 0.108 g (1.00 mmol) of benzylalcohol was added to a solid mixture composed of them, and the mixture was stirred well. Further, 0.11 mL (1.0 mmol) of 31percent aqueous hydrogen peroxide was added and the mixture was stirred well, then, allowed to stand still at 25° C. After 24 hours at 25° C., benzaldehyde was produced with a yield of 74percent. With fluorapatite, dihydrogen peroxide, (CetylPy)10[H2W12O42] in water, Time= 24h, T= 25 °C Patent; OSAKA UNIVERSITY; US2010/113807; (2010); (A1) English View in Reaxys

74 %

With C2H6O*C6H6*C41H33As2Cl2N2O4Ru, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Sukanya, Duraiswamy; Raja, Duraisamy Senthil; Bhuvanesh, Nattamai S.P.; Natarajan, Karuppannan; Polyhedron; vol. 30; nb. 6; (2011); p. 1108 - 1113 View in Reaxys

74 %

With C43H30ClN3O2PRu, oxygen, 4-methylmorpholine N-oxide in dichloromethane, Time= 6h, Reflux, chemoselective reaction

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

85/438

2018-03-11 22:07:32


Manimaran, Arumugam; Chinnusamy, Vaiyapuri; Jayabalakrishnan, Chinnasamy; Applied Organometallic Chemistry; vol. 25; nb. 2; (2011); p. 87 - 97 View in Reaxys 73.6 %

7 :Operating as described in example 1 , 10.8 g (0.1 mols) of benzyl alcohol are EPO <DP n="8"/>reacted, in 100 g toluene, with 6.0 g (0.29 rnols) of p-formaldehyde in the presence of 2.04 g (0.01 mois) of aluminium protoxide.After cooling and adding 300 m. of an aqueous 1 M sodium hydroxide solution, the phases are separated and the organic solution evaporated under vacuum (at25°C/21 mbar) to obtain a crude reaction product containing benzaidehyde with a73.6percent GC yield and a conversion of 83.1 percent. With formaldehyd, aluminium protoxide in toluene, Time= 2h, Heating / reflux Patent; ENDURA S.P.A.; WO2007/12641; (2007); (A1) English View in Reaxys

73 %

With bis-triphenylphosphine-palladium(II) chloride, potassium carbonate, Desyl chloride in tetrahydrofuran, Time= 20h, T= 65 - 70 °C , Inert atmosphere, Schlenk technique Liu, Chao; Tang, Shan; Lei, Aiwen; Chemical Communications; vol. 49; nb. 13; (2013); p. 1324 - 1326 View in Reaxys

73 %

Benzaldehyde (2a); Typical Procedure for Optimization ofCopper/Imidazolium/TEMPO-Catalyzed Aerobic Oxidation of Benzylic Alcohols A 30-mL Schlenk tube was evacuated and filled with O2 (purity>99.99percent). Benzyl alcohol (2 mmol), Cu powder (Aladdin product, 200 mesh, purity 99.9percent), imidazolium salt, and TEMPO in distilled H2O (4 mL) were added and the mixture was stirred at 35 °C under an O2 atmosphere by connecting an O2 balloon for the required time. The mixture was extracted with CH2Cl2 (3 × 10 mL). The combined extracts were dried (MgSO4). The conversion was measured using anisole as the internal standard by a capillary gas chromatography. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C20H36N5 (3+)*3Br(1-), oxygen, copper in water, Time= 6h, T= 35 °C , Schlenk technique, Reagent/catalyst Chen, Congyan; Liu, Bo; Chen, Wanzhi; Synthesis (Germany); vol. 45; nb. 24; (2013); p. 3387 - 3391; Art.No: SS-2013-H0531-OP View in Reaxys

73 %

With C32H31ClN4OPRuS(1+)*F6P(1-), 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux, Catalytic behavior, Reagent/catalyst Sarkar, Shyamal Kumar; Jana, Mahendra Sekhar; Mondal, Tapan Kumar; Sinha, Chittaranjan; Applied Organometallic Chemistry; vol. 28; nb. 8; (2014); p. 641 - 651 View in Reaxys

72 %

With tetrabutylammonium periodite, lt;RuO2(bipy)lt;IO3(OH)3gt;gt;*1.5H2O in dichloromethane, water, Time= 4h, Ambient temperature Bailey, Alan J.; Griffith, William P.; White, Andrew J. P.; Williams, David J.; Journal of the Chemical Society, Chemical Communications; nb. 16; (1994); p. 1833 - 1834 View in Reaxys

72 %

With aluminum oxide, bromine in dichloromethane, Oxidation Love, Brian E.; Nguyen, Binh T.; Synthetic Communications; vol. 30; nb. 5; (2000); p. 963 - 970 View in Reaxys

72%

With C26H29ClN5ORu(1+)*CF3O3S(1-), potassium carbonate, methoxybenzene in N,N-dimethyl acetamide, Time= 4h, T= 110 °C , Reagent/catalyst, Solvent Donnelly, Kate F.; Segarra, Candela; Shao, Li-Xiong; Suen, Rachelle; Müller-Bunz, Helge; Albrecht, Martin; Organometallics; vol. 34; nb. 16; (2015); p. 4076 - 4084 View in Reaxys

72 %

With nitrobenzene in acetonitrile, Time= 0.483333h, Irradiation, Flow reactor

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

86/438

2018-03-11 22:07:32


Nakamura; Yoshida; Kuwahara; Katayama; Journal of Photochemistry and Photobiology A: Chemistry; vol. 322-323; (2016); p. 35 - 40 View in Reaxys 72 %

General procedure for the oxidative reaction General procedure: Caution. tert-Butyl hydroperoxide is an exceptionally dangerous chemical that is highly reactive, flammable, and toxic. It is corrosive to skin and mucous membranes and causes respiratory distress when inhaled. A solution of secondary alcohol (1 mmol) and 70percent TBHP (6 or 10 equiv.) was stirred at 100 °C for 24 h. The reaction mixture was quenched with the saturated solution of sodium thiosulfate (5 mL) and extracted with dichloromethane (3 x 10 mL). The combined dichloromethane extracts were dried over anhydrous Na2SO4 and filtered, and then the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE or PE/EtOAc as the eluent to obtain the desired products. With tert.-butylhydroperoxide in water, Time= 24h, T= 100 °C Wu, Jianglong; Liu, Yan; Ma, Xiaowei; Liu, Ping; Gu, Chengzhi; Dai, Bin; Synthetic Communications; vol. 46; nb. 21; (2016); p. 1747 - 1758 View in Reaxys

71 %

With 4-methylmorpholine N-oxide, tetrapropylammonium perruthennate in dichloromethane, Time= 0.5h, Ambient temperature Griffith, William P.; Ley, Steven V.; Whitcombe, Gwynne P.; White, Andrew D.; Journal of the Chemical Society, Chemical Communications; (1987); p. 1625 - 1627 View in Reaxys

71 %

With quinoxalinium dichromate, acetic acid in dichloromethane, Time= 2h, T= 20 °C Degirmenbasi, Nebahat; Oezguen, Beytiye; Monatshefte fur Chemie; vol. 133; nb. 11; (2002); p. 1417 - 1421 View in Reaxys

71 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, 1,1'-binaphthalene-2,2'-diamine, oxygen, copper(II) bis(trifluoromethanesulfonate) in nitromethane, Time= 22h, T= 20 °C Alamsetti, Santosh Kumar; Mannam, Sreedevi; Mutupandi, Pandi; Sekar, Govindasamy; Chemistry - A European Journal; vol. 15; nb. 5; (2009); p. 1086 - 1090 View in Reaxys

71.93 %

With [(RuCl(CO)(PPh3)2)2(4,6-diacetylresorcinato)], 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Krishnamoorthy; Sathyadevi; Deepa; Dharmaraj; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 77; nb. 1; (2010); p. 258 - 263 View in Reaxys

71 %

Catalytic oxidation reactions by Ni(II) Schiff base complexes: General procedure: Catalytic oxidation of alcohols to corresponding carbonyl compounds by Ni(II) Schiff base complexes was carried out in the presence of oxygen atmosphere at ambient temperature (Scheme-III). A typical reaction using the complexes [Ni(L)(PPh3)] as a catalyst and alcohols as substrates ata 1:100 molar ratio is described as follows. A solution of Ni(II) Schiff base complexes (0.01 mmol) in 20 cm3 CH2Cl2 was added to the solution of alcohol (1 mmol) under 1 atm oxygen atmosphere at ambient temperature. The solution mixture was stirred at room temperature for 6 h and the solvent was then evaporated from the mother liquor under reduced pressure.The residue was then extracted with petroleum ether (60-80 °C) (20 cm3) and the carbonyl compounds were treated with 2,4dinitrophenyl hydrazine, methanol and few drops of sulphuric acid. The yellow colour product obtained is quantified as 2,4-dinitrophenylhydrazone derivatives [5-7]. With C32H23N2NiO2P, oxygen in dichloromethane, Time= 6h, T= 20 °C , p= 760.051Torr , Green chemistry, Reagent/ catalyst Madaselvi; Padma Priya; Jeyaraj; Arun Paul; Kalaivani; Shahul Meeran; Arunachalam; Asian Journal of Chemistry; vol. 28; nb. 8; (2016); p. 1682 - 1686 View in Reaxys

71%

A solution of complex 1 (0.01mmol) in CH2Cl2 (25mL) was added to the mixture containing PhCH2OH (1mmol), NMO (3mmol) and molecular sieves. The reaction mixture was refluxed and conversion of PhCH2OH to PhCHO was moni-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

87/438

2018-03-11 22:07:32


tored taking the reaction mixture at 10min time interval. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was then extracted with diethyl ether, concentrated to ≈1mL. Conversions were determined by GC instrument equipped with a flame ionization detector (FID) using a HP–5 column of 30m length, 0.53mm diameter and 5.00μm film thickness. The column, injector and detector temperatures were 200, 250 and 250°C respectively. The carrier gas was N2 (UHP grade) at a flow rate of 30mL/min. The injection volume of sample was 2μL. The oxidation products were identified by GC co-injection with authentic samples. No significant conversion was observed after 50min. All other alcohols were oxidized by refluxing the reaction mixture for 1h and conversions were monitored following the identical protocol. With C16H12Cl2N2O3RuS, 4-methylmorpholine N-oxide in dichloromethane, Time= 1h, T= 4 °C , Molecular sieve, Reflux Roy, Puspendu; Mondal, Apurba Sau; Pramanik, Ajoy Kumar; Mondal, Tapan Kumar; Journal of Organometallic Chemistry; vol. 828; (2017); p. 1 - 9 View in Reaxys 71 %

With 3.0percent Pd nanoparticle loaded magnetic SBA-15 catalyst, Time= 9h, T= 85 °C , Catalytic behavior, Reagent/catalyst Li, Yingying; Huang, Jiale; Hu, Xijun; Lam, Frank Leung-Yuk; Wang, Wenju; Luque, Rafael; Journal of Molecular Catalysis A: Chemical; vol. 425; (2016); p. 61 - 67 View in Reaxys

70 %

With tetrabutylammomium bromide in α,α,α-trifluorotoluene, Time= 3h, T= 20 °C , Inert atmosphere Matsumoto, Kazutsugu; Iwata, Toshiaki; Suenaga, Masahiro; Okudomi, Masayuki; Nogawa, Masaki; Nakano, Mariko; Sugahara, Ai; Bannai, Yuta; Baba, Kenji; Heterocycles; vol. 81; nb. 11; (2010); p. 2539 - 2553 View in Reaxys

70 %

With BrO3 (1-)*C12H24KO6, T= 115 °C Song, Yingying; Jing, Huanwang; Li, Bo; Bai, Dongsheng; Chemistry - A European Journal; vol. 17; nb. 31; (2011); p. 8731 - 8738 View in Reaxys

70 %

With tert.-butylhydroperoxide in decane, dichloromethane, Time= 16h, T= 20 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst, Time Huang, Enrique Kwan; Cheung, Wai-Man; Chan, Ka-Wang; Lam, Frank Leung-Yuk; Hu, Xijun; Zhang, QianFeng; Williams, Ian D.; Leung, Wa-Hung; European Journal of Inorganic Chemistry; nb. 16; (2013); p. 2893 - 2899 View in Reaxys

70 %

3.2. Experimental procedure General procedure: The continuous ow microreactor system was assembled as shown in Figure 1. The Me2SO, activator, and benzyl alcohol were loaded into HPLC pumps with appropriate ow rates. After a stable period of 10 min, the effluent was collected in a separation funnel through which we could observe the color and layering by controlling the valve. Then effluent was finally collected into a continuously stirred ask containing an excess amount of triethylamine. The temperatures were kept constant by a water bath with constant circulation temperatures and a thermostat magnetism agitator. All of the reactions were monitored offline by GC-MS; the yields and selectivities were calculated by the method of area normalization. Upon completion of the reaction, the mixture of triethylamine and effluent was washed with 5percent HCl and the organic layer was separated. Then the organic layer was washed 2 or 3 times until the mixture in the separation funnel reached neutral. In the process, the aqueous layers were always extracted twice with dichloromethane. At last, the organic layers were collected together and dried by anhydrous MgSO4 for 4 h. The final product, benzaldehyde, was obtained after filtration and reduced pressure distillation. Stage 1: With oxalyl dichloride, dimethyl sulfoxide, T= 15 °C , Flow reactor, Swern Oxidation Stage 2: With triethylamine, T= 15 °C , Flow reactor, Swern Oxidation, Temperature Zhu, Lin; Xu, Xiaohui; Zheng, Fuping; Turkish Journal of Chemistry; vol. 42; nb. 1; (2018); p. 75 - 85 View in Reaxys

68 %

With tetrabutylammonium chlorochromate in chloroform, Time= 18h, Ambient temperature Santaniello, Enzo; Milani, Fulvia; Casati, Rosangela; Synthesis; nb. 9; (1983); p. 749 - 751

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

88/438

2018-03-11 22:07:32


View in Reaxys 68 %

With manganese(IV) oxide, Pyridine-2,6-dicarboxylic acid in water, acetonitrile, Time= 20h, T= 20 °C , various carboxylic acid, Product distribution Achremowicz, Lucjan; Mlochowski, Jacek; Mora, Czeslaw; Skarzewski, Jacek; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 735 - 742 View in Reaxys

68 %

With [RuCl(PPh3)2(L1)], 4-methylmorpholine N-oxide in dichloromethane, Time= 5h, Reflux Priyarega; Tamizh, M Muthu; Karvembu; Prabhakaran; Natarajan; Journal of Chemical Sciences; vol. 123; nb. 3; (2011); p. 319 - 325 View in Reaxys

68.85 %

With oxygen in water, Time= 6h, T= 90 °C , Inert atmosphere Sun, Daohua; Zhang, Genlei; Jiang, Xinde; Huang, Jiale; Jing, Xiaolian; Zheng, Yanmei; He, Jing; Li, Qingbiao; Journal of Materials Chemistry A; vol. 2; nb. 6; (2014); p. 1767 - 1773 View in Reaxys

68 %

With tert.-butylhydroperoxide, potassium phosphate, benzamidine monohydrochloride, copper diacetate in 1,2-dichloro-ethane, Time= 12h, T= 20 °C Guo, Wei; Huang, Kunbo; Ji, Fanghua; Wu, Wanqing; Jiang, Huanfeng; Chemical Communications; vol. 51; nb. 42; (2015); p. 8857 - 8860 View in Reaxys

67 %

With C17H25N2Se(1+)*Cl(1-), dihydrogen peroxide in water, Time= 24h, T= 60 °C Cheng, Xian Yi; Li, Kang Feng; Wang, Qiao Jian; Wang, Cong Ying; Ying, Tao Kai; Chinese Chemical Letters; vol. 23; nb. 7; (2012); p. 801 - 804 View in Reaxys

67 %

With tert.-butylhydroperoxide in acetonitrile, Time= 0.0833333h, T= 50 °C Gogoi, Nibedita; Begum, Tahshina; Dutta, Smarika; Bora, Utpal; Gogoi, Pradip K.; RSC Advances; vol. 5; nb. 115; (2015); p. 95344 - 95352 View in Reaxys

67 %

Primary alcohols The primary alcohols were converted into their corresponding aldehydes in 21-94 percent yield with turnover 9-33 (Table-1). For 1, the highest yield for oxidation products for the alcohols was obtained with H2O2 as oxidant while for complex 2, t-BuOOH gave better results. The product formation using complex 1 was in the order H2O2 > tBuOOH> O2 while for complex 2 the order was t-BuOOH > H2O2 >O2. Aromatic benzyl alcohols gave better yields with both complexes compared to the aliphatic alcohols due to the fact that the aromatic product is a non-enolisable aldehyde thus reducing the number of possible side products [13]. With C19H15ClFeN3O5, dihydrogen peroxide, Reagent/catalyst Bhowon, Minu Gupta; Jhaumeer-Laulloo, Sabina; Wah, Henri Li Kam; Meetun, Anisha; Mudhoo, Karishma; Asian Journal of Chemistry; vol. 29; nb. 1; (2017); p. 152 - 156 View in Reaxys

66 %

Photocatalytic activity The photocatalytic selective oxidation of benzyl alcohol was performed as the following [7]. A mixture of benzyl alcohol (0.1mmol) and 8mg of catalyst was dissolved in the solvent of benzotrifluoride (1.5mL). The above mixture was transferred into a 10mL Pyrex glass bottle filled with molecular oxygen at a pressure of 0.1MPa and stirred for half an hour to make the catalyst blend evenly in the solution. The suspensions were irradiated by a 300W Xe arc lamp (PLS-SXE 300, Beijing Trusttech Co. Ltd.) with a UV-Cut filter to cut off light of wavelength 420nm. After the reaction, the mixture was centrifuged at 12,000rmp for 20min to completely remove the catalyst particles. The remaining solution was analyzed with an Agilent Gas Chromatograph (GC-7820 fitted with a capillary FFAP analysis column and helium as gas carrier). With ZnIn2S4, oxygen, Time= 3h, p= 750.075Torr , Irradiation, Green chemistry, chemoselective reaction

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

89/438

2018-03-11 22:07:32


Chen, Zhixin; Xu, Jingjing; Ren, Zhuyun; He, Yunhui; Xiao, Guangcan; Catalysis Communications; vol. 41; (2013); p. 83 - 86 View in Reaxys 65 %

With sodium dichromate, sulfuric acid, tetra(n-butyl)ammonium hydrogensulfate in ethyl acetate, Time= 0.0333333h, Ambient temperature Halldin, C.; Langstroem, B.; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 38; nb. 1; (1984); p. 1 - 4 View in Reaxys

65 %

With oxygen in carbon dioxide, Time= 0.00263889h, T= 100 °C , p= 90007.2Torr Jenzer; Sueur; Mallat; Baiker; Chemical Communications; nb. 22; (2000); p. 2247 - 2248 View in Reaxys

65 %

With dihydrogen peroxide, methyltrioxorhenium(VII), sodium bromide in various solvent(s), Time= 3.5h, T= 20 °C Jain, Suman L.; Sharma, Vishal B.; Sain, Bir; Bulletin of the Chemical Society of Japan; vol. 79; nb. 10; (2006); p. 1601 - 1603 View in Reaxys

65 %

With Pyridine-2,6-dicarboxylic acid, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [bis(acetoxy)iodo]benzene, tetrabutylammomium bromide, iron(II) acetate in methanol, Time= 48h, T= 110 °C , Sealed tube, Catalytic behavior, Reagent/catalyst, Solvent Ray, Ritwika; Jana, Rahul Dev; Bhadra, Mayukh; Maiti, Debabrata; Lahiri, Goutam Kumar; Chemistry - A European Journal; vol. 20; nb. 47; (2014); p. 15618 - 15624 View in Reaxys

64 %

15 :Example 15 (An embodiment of the invention described in the above embodiment [1]): Production of benzaldehyde In a 50 ml three-necked flask equipped with a magnetic stirrer, a reflux condenser and a thermometer, 21.6 g (200 mmols) of benzyl alcohol, 10.0 g (67 mmols) of sodium bromate and 20 ml(348 mmols) of acetic acid were charged, and then the resultant mixture was stirred at 75°C for 8 hours. With the processing of the reaction, a small amount of bromine was produced and the temperature of the reaction solution was raised to 80°C. After the completion of the reaction, bromine completely disappeared. The reaction solution was cooled to room temperature and 100 ml of water was added. Under cooling in an ice bath, an aqueous 24percent sodium hydroxide solution was added by several portions so as not to raise the liquid temperature until the pH is adjusted to 11 or higher. The resulting product was extracted in turn with 100 ml of ether and 50 ml of ether, and then the ether phase was washed with saturated saline. The ether phase was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to obtain 19.1 g of an oil. With respect to the components in the oil, the intended benzaldehyde was produced in an area ratio, as determined by gas chromatography, of 89.4percent. This oil was purified by distillation under reduced pressure [112 to 115°C /13.33 KPa (100 mmHg)]to obtain 13.6 g of benzaldehyde. Isolation yield: 64percent. With sodium bromate, acetic acid, Time= 8h, T= 75 - 80 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1661877; (2006); (A1) English View in Reaxys

64.17 %

With C40H32ClN2O2PRu, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, T= 20 °C Manivannan; Manimaran; Arunachalam; Jayabalakrishnan; Chinnusamy; Journal of the Indian Chemical Society; vol. 85; nb. 10; (2008); p. 988 - 995 View in Reaxys

63 %

With chromium(VI) oxide, potassium chloride, tetrabutyl-ammonium chloride, Time= 1.5h Gelbard, Georges; Brunelet, Thierry; Jouitteau, Catherine; Tetrahedron Letters; vol. 21; nb. 48; (1980); p. 4653 4654 View in Reaxys

63 %

With potassium ferrate(VI), K10 clay in pentane, Time= 3h, Ambient temperature Delaude, Lionel; Laszlo, Pierre; Journal of Organic Chemistry; vol. 61; nb. 18; (1996); p. 6360 - 6370 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

90/438

2018-03-11 22:07:32


63 %

With potassium ferrate on K10 montmorillonite in pentane, Time= 3h, Ambient temperature, oxidation of several alcohols and further organic compounds; effect of water content of catalyst in cyclohexane; slow oxidation of solvent Delaude, Lionel; Laszlo, Pierre; Lehance, Pascal; Tetrahedron Letters; vol. 36; nb. 46; (1995); p. 8505 - 8508 View in Reaxys

63.6 %

With oxygen in polyglycol, Time= 12h, T= 130 °C Liu, Wei; Li, Baojun; Gao, Cuiling; Xu, Zheng; Chemistry Letters; vol. 38; nb. 11; (2009); p. 1110 - 1111 View in Reaxys

63 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, L-proline, copper(II) oxide in N,N-dimethyl-formamide, Time= 24h, T= 110 °C Shinde, Mahesh H.; Kshirsagar, Umesh A.; RSC Advances; vol. 6; nb. 58; (2016); p. 52884 - 52887 View in Reaxys

62 %

With C16H13MnNO3*3H2O, dihydrogen peroxide in water, Time= 1h, T= 20 °C , Ionic liquid Rong, Meizhu; Wang, Juan; Shen, Yanping; Han, Jinyu; Catalysis Communications; vol. 20; (2012); p. 51 - 53 View in Reaxys

62 %

With C35H57N2O4V, dihydrogen peroxide in acetonitrile, Time= 4h, T= 70 °C , Kinetics, Catalytic behavior, Concentration, Solvent, Temperature Noshiranzadeh, Nader; Mayeli, Mina; Bikas, Rahman; Slepokura, Katarzyna; Lis, Tadeusz; Transition Metal Chemistry; vol. 39; nb. 1; (2014); p. 33 - 39 View in Reaxys

62 %

With quinolinium chlorochromate(VI) in water, Time= 4h, T= 20 °C Gupta, Neeraj; Thakur, Apoorva; Bhardwaj, Pushpa; New Journal of Chemistry; vol. 38; nb. 8; (2014); p. 3749 3754 View in Reaxys

60 %

With water, fluorine, acetonitrile in chloroform, T= -10 - 0 °C Rozen, Shlomo; Bareket, Yifat; Kol, Moshe; Tetrahedron; vol. 49; nb. 36; (1993); p. 8169 - 8178 View in Reaxys

60 %

With RuCl(OAc)(PPh3)3, Co(salophen)(PPh3), oxygen, hydroquinone in dichloromethane, T= 20 °C , Product distribution Baeckvall, Jan-E.; Chowdhury, Ratan L.; Karlsson, Ulrika; Journal of the Chemical Society, Chemical Communications; nb. 7; (1991); p. 473 - 475 View in Reaxys

60 %

With allyl diethyl phosphate, sodium carbonate, palladium diacetate in N,N-dimethyl-formamide, Time= 2.5h Shvo, Youval; Goldman-Lev, Vered; Journal of Organometallic Chemistry; vol. 650; nb. 1-2; (2002); p. 151 - 156 View in Reaxys

60 %

With 1-hydroxy-4-iodoiodoxol-3(1H)-one in acetone, Time= 3h, Reflux Shah, Azhar-Ul-Haq A.; Khan, Zulfiqar A.; Choudhary, Naila; Lohoelter, Christine; Schaefer, Sascha; Marie, Guillaume P.L.; Farooq, Umar; Witulski, Bernhard; Wirth, Thomas; Organic Letters; vol. 11; nb. 16; (2009); p. 3578 - 3581 View in Reaxys

60 %

With 1,1'-bis-(diphenylphosphino)ferrocene, [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, potassium carbonate, 4- methyl-2-pentanone, Time= 0.5h, Reflux, Schlenk technique, Inert atmosphere, Oppenauer Oxidation Nicklaus, Céline M.; Phua, Pim Huat; Buntara, Teddy; Noel, Sebastien; Heeres, Hero J.; De Vries, Johannes G.; Advanced Synthesis and Catalysis; vol. 355; nb. 14-15; (2013); p. 2839 - 2844 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

91/438

2018-03-11 22:07:32


60 %

General procedure for oxidation of alcohols: General procedure: Oven dried round bottom flask was charged with Eosin Y (5 mmol) alcohol (1 mmol) and 3 equiv. of TBHP (5.5 M in decane) in dry ACN. The resulting mixture was degassed for 15 mins, followed by back filling N2, and then irradiated under Blue LED light (12W, 455 nm) at room temperature (25 oC). After reaction completion monitored through TLC, the mixture was diluted with 15 ml of 10percent NaHCO3 solution, and extracted with EtOAc (3 × 20 ml). The combined organic extracts were washed with brine (20 ml), dried over Na2SO4, and concentrated on vacuo. Purification of the crude product on silica gel using EtOAc:Hexane as solvent system afforded the desired product. With tert.-butylhydroperoxide, eosin y in decane, acetonitrile, Time= 28h, T= 25 °C , Inert atmosphere, Irradiation, Molecular sieve, Green chemistry, chemoselective reaction Devari, Shekaraiah; Rizvi, Masood Ahmad; Shah, Bhahwal Ali; Tetrahedron Letters; vol. 57; nb. 30; (2016); p. 3294 - 3297 View in Reaxys

59.9 %

With pyridine, 1,1'-ditetradecyl-3,3'-methylene-4-diimidazolin-2,2'-diylidene palladium(IV) tetrachloride in chloroformd1, Time= 2h, T= 60 °C , p= 760.051Torr McCall, A. Scott; Kraft, Stefan; Organometallics; vol. 31; nb. 9; (2012); p. 3527 - 3538 View in Reaxys

59 %

General oxidation procedure General procedure: The liquid phase catalytic oxidations were carried out under air(atmospheric pressure) in a 25 mL round bottom flask equippedwith a magnetic stirrer and immersed in a thermostated oil bathat 80 or 60 C. In a typical experiment, a mixture of 30percent H2O2(3 mmol), solvent (3 mL), NaHCO3 (0.25 mmol), chlorobenzene(0.1 g) as internal standard and cis-cyclooctene (1 mmol) wasadded to a flask containing the catalyst 1–8 (1.70 lmol). Thecourse of the reaction was monitored using a gas chromatographequipped with a capillary column and a flame ionization detector.The oxidation products were identified by comparing their retentiontimes with those of authentic samples or alternatively by 1HNMR and GC–Mass analyses. Yields based on the added substratewere determined by a calibration curve. Control reactions werecarried out in the absence of catalyst, H2O2 and NaHCO3 underthe same conditions as the catalytic runs verifying that no products,or only trace yields, were detected. With C22H16N4O8V2, dihydrogen peroxide in acetonitrile, Time= 5h, T= 60 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst Hosseini-Monfared, Hassan; Asghari-Lalami, Nasim; Pazio, Aleksandra; Wozniak, Krzysztof; Janiak, Christoph; Inorganica Chimica Acta; vol. 406; (2013); p. 241 - 250 View in Reaxys

59 %

With 2,2-dimethylbutyric acid, (R,R)-Mn-dpn, dihydrogen peroxide in acetonitrile, T= 0 °C , Inert atmosphere, chemoselective reaction Ottenbacher, Roman V.; Talsi, Evgenii P.; Bryliakov, Konstantin P.; Chemical Record; vol. 18; nb. 1; (2018); p. 78 - 90 View in Reaxys

58 %

3.3. Reaction experiment procedure THe optimal alignment of the Raman probe with the liquid pock-ets on the microreactor chip was carried out using a flow of benzylalcohol (0.02 ml/min) and oxygen (1 ml/min). The coordinates ofthe liquid pockets and the parameters of the Raman acquisition(integration time 100 ms, accumulation number 4, sampling timebetween reactors 0.2 min, sampling time intervals 4–5 min, totalsampling number 50–70) were then input into the Labview pro-gram. The gas and the liquid flow were set to the designated valuesand the reaction was initiated by switching on the heater and start-ing the Raman acquisition. The integration under the diagnosticpeaks at 1000 cm−1and 1700 cm−1was performed by the Labviewprogram and the calculated ratio of the peak areas was displayed.Typical reaction conditions for catalyst evaluation were 0.005 g cat-alyst, 0.008 ml/min of benzyl alcohol, 1 ml/min of O2, 120C and2 bar(g) of back pressure at reactor outlets. With oxygen, Time= 5h, T= 120 °C , p= 1500.15Torr , Flow reactor, Reagent/catalyst, Pressure, Time Cao, Enhong; Brett, Gemma; Miedziak, Peter J.; Douthwaite, John M.; Barrass, Simon; McMillan, Paul F.; Hutchings, Graham J.; Gavriilidis, Asterios; Catalysis Today; vol. 283; (2017); p. 195 - 201 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

92/438

2018-03-11 22:07:32


58 %

2.3. Alcohol oxidation study of catalysts General procedure: To 1 mmol solution of the aromatic alcohol in EDC solvent, 1.25 mmol of PhI(OAc)2 and 300 mg of the MgSO4 along with0.01 mmol of uranium oxide nanoparticles were added. The mixture was stirred about 8 to 10 h at 45 C using TLC to monitor the sequence. After completion of the reaction, it was filtered, the solvent was then evaporated, the crude was purified by column chromatography and the final product was characterized by 1HNMR spectroscopy. With [bis(acetoxy)iodo]benzene, uranium oxide, magnesium sulfate in 1,2-dichloro-ethane, Time= 8h, T= 45 °C Majumder, Ishani; Chatterjee, Sourav; Fischer, Roland C.; Neogi, Swarup Kumar; Mautner, Franz A.; Chattopadhyay, Tanmay; Inorganica Chimica Acta; vol. 462; (2017); p. 112 - 122 View in Reaxys

57 %

With RuHCl(CO)(PPh3)3 complex supported on multiwall carbon nanotubes in toluene, Time= 4h, T= 100 °C , Inert atmosphere, Sealed tube, Reagent/catalyst Ghafouri, Moloud; Moghadam, Majid; Mehrani, Kheirollah; Daneshvar, Anahita; Applied Organometallic Chemistry; vol. 32; nb. 2; (2018); Art.No: E4048 View in Reaxys

56 %

With tert.-butylhydroperoxide in water, Time= 4.5h, T= 60 °C , Green chemistry Rezaeifard, Abdolreza; Farshid, Parisa; Jafarpour, Maasoumeh; Moghaddam, Gholamreza Kardan; RSC Advances; vol. 4; nb. 18; (2014); p. 9189 - 9196 View in Reaxys

54 %

With acrylic acid methyl ester, chlorocarbonylbis(triphenylphosphine)rhodium(I), Time= 0.25h, T= 120 °C , p= 10343Torr , microwave irradiation Takahashi, Masaaki; Oshima, Koichiro; Matsubara, Seijiro; Tetrahedron Letters; vol. 44; nb. 51; (2003); p. 9201 9204 View in Reaxys

54 %

With laccase, N -hydroxyphthalimide, oxygen in various solvent(s), Time= 24h, T= 20 °C , pH= 5 Baiocco, Paola; Barreca, Anna Maria; Fabbrini, Maura; Galli, Carlo; Gentili, Patrizia; Organic and Biomolecular Chemistry; vol. 1; nb. 1; (2003); p. 191 - 197 View in Reaxys

54 %

With oxygen, Time= 2h, p= 750.075Torr , Irradiation, Catalytic behavior, Reagent/catalyst, Time Li, Xiuzhen; Weng, Bo; Zhang, Nan; Xu, Yi-Jun; RSC Advances; vol. 4; nb. 110; (2014); p. 64484 - 64493 View in Reaxys

54 %

2.2. General procedure for the aerobic oxidation of various substrates General procedure: To a dried 45 mL tube equipped with a magnetic stirring, 2 mL acetonitrile, 0.5 mmol substrate and 0.046 mmol NO2 were sequentially added (note: the air in the tube was not removed). Then the reaction tube was sealed and stirred magnetically at a constant-temperature to perform the reaction for 5 h. Once the reaction time was reached, GCanalysis of the mixture provided the GC yields of the products. Then the crude product from another parallel experiment was purified by silicagel chromatography to give the desired product. With Nitrogen dioxide in acetonitrile, Time= 5h, T= 140 °C , p= 760.051Torr , Sealed tube, Catalytic behavior, Solvent, Temperature, Reagent/catalyst Ren, Fangping; Tian, Xinzhe; Ren, Yun-Lai; Zhao, Shuang; Wang, Jianji; Zhao, Bo; Catalysis Communications; vol. 101; (2017); p. 98 - 101 View in Reaxys

53 %

With manganese(IV) oxide, aluminum oxide in acetonitrile, Time= 1.16667h, T= 20 °C Stavrescu, Ruxandra; Kimura, Takahide; Fujita, Mitsue; Vinatoru, Mircea; Ando, Takashi; Synthetic Communications; vol. 29; nb. 10; (1999); p. 1719 - 1726 View in Reaxys

Ca. 53 %

With C16H13MnNO5*H2O, dihydrogen peroxide in water, acetonitrile, Time= 4h, T= 50 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

93/438

2018-03-11 22:07:32


De; Deb; Nath Bhowmik; Dutta Purkayastha; Journal of the Indian Chemical Society; vol. 86; nb. 1; (2009); p. 76 82 View in Reaxys 53 %

Room temperature hydrogen peroxide was chosen and the initialstudy was carried out using benzyl alcohol as substrate(4.63 mmol) and 1.91 equivalent of H2O2 (8.83 mmol) at 70 C inpresence of 0.022 mmol of catalyst (Scheme 1).The oxidation reaction was conducted at 70 C keeping [Cu3(slmh)(l-Cl)2(CH3OH)3]0.5CH3OH:benzyl alcohol:H2O2 molarratio at (1:209.5:398.2) for 12 h. The result reveal that this homotrinuclearcomplex efficiently catalyzes the oxidation of primaryalcohol to the aldehyde in 53percent yield. Fortunately, the usualundesirable further oxidation to acid was not observed at all underthe present reaction condition. In this work, direct selectiveoxidation of benzyl alcohol to benzaldehyde with 30percent H2O2 wasperformed over [Cu3(slmh)(l-Cl)2(CH3OH)3]0.5CH3OH as a catalystwith good benzyl alcohol conversion to benzaldehyde With [Cu3(disalicylaldehydemalonoyldihydrazone)(μ-Cl)2(CH3OH)3]0.5CH3OH, dihydrogen peroxide, Time= 12h, T= 70 °C Koch, Angira; Kumar, Arvind; De, Arjun K.; Phukan, Arnab; Lal, Ram A.; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 129; (2014); p. 103 - 113 View in Reaxys

53 %

With oxygen in toluene, Time= 0.5h, T= 100 °C , Catalytic behavior, Reagent/catalyst, Temperature Du; Jin; Feng; Zhang; He; Li; Catalysis Science and Technology; vol. 5; nb. 6; (2015); p. 3216 - 3225 View in Reaxys

53 %

With tert.-butylhydroperoxide, iron(II) chloride in water, ethyl acetate, T= 120 °C Wang, Shi-Sheng; Fu, Hong; Wang, Guanlin; Sun, Meng; Li, Ya-Min; RSC Advances; vol. 6; nb. 57; (2016); p. 52391 - 52394 View in Reaxys

53 %

2.4. Photocatalytic experiments The reaction setup used for the photocatalytic conversion ofBA to BAL consisted in a circular flat glass reactor (5 cm diame-ter; 1.5 cm thickness; 30 mL total volume), located at 6.5 cm fromthe irradiation source, which was filled with 28 mL of BA aqueoussolution (1.5 mM, initial pH adjusted using H2SO4) and 28 mg of cat-alyst. The system was continuously purged with argon (10 mL min−1) and kept under dark conditions for 15 min. After that period,irradiation was initiated using a UV-LED emitting at 390 nm. Sam-ples were periodically withdrawn for determination of BA and BALconcentration by HPLC-DAD. Light intensity reaching the reactorusing UV-LED was 220 W m−2, determined by using a UV–vis spec-troradiometer (OceanOptics USB2000 +). With ruthenium loaded graphitized-carbon nitride in water, Time= 4h, T= 20 °C , pH= 2, Inert atmosphere, Irradiation, Reagent/catalyst Lima, Maria J.; Tavares, Pedro B.; Silva, Adrián M.T.; Silva, Cláudia G.; Faria, Joaquim L.; Catalysis Today; vol. 287; (2017); p. 70 - 77 View in Reaxys

53 %

(b) Millimolar scale reactions: General procedure: A glass vial fitted with magnetic stirrer and a magnetic bar containing a reaction mixture of alcohol (0.1 mmol), NH4SCN (3 eq.), catalyst (5 molpercent) and 2 ml of solvent. The vial was closed with rubber septum and O2 was bubbling for 15 minutes using needles. The reaction mixture was irradiated under a 23W CFL lamp for a certain time period. Reaction progress was monitored by TLC. After, completion of the reaction, a yellow solid was formed. The reaction mixture of three vials with the same content were combined and filter it through whatman filter paper. The mixture was evaporated under reduced pressure and purified by column chromatography using hexane/ ethyl acetate as eluent. Further, the reaction mixture was run on a GC-MS instrument for characterisation. Yield, conversion and selectivity were calculated using following equations. With 4,5,6,7-tetrachloro-2',4',5',7'-tetraiodofluorescein disodium salt, oxygen, ammonium thiocyanate in acetonitrile, Time= 20h, T= 20 °C , Irradiation Sheriff Shah, Sk; Pradeep Singh; Tetrahedron Letters; vol. 59; nb. 3; (2018); p. 247 - 251 View in Reaxys

52%

With dihydrogen peroxide in acetone, Time= 3h, T= 24.84 °C , Inert atmosphere, Schlenk technique

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

94/438

2018-03-11 22:07:32


Xiang, Jing; Li, Hao; Wu, Jia-Shou; Zeitschrift fur Anorganische und Allgemeine Chemie; vol. 640; nb. 8-9; (2014); p. 1670 - 1674 View in Reaxys 51 %

With tert.-butylhydroperoxide, Rh+(diphos) in methanol, benzene, Time= 50h, T= 70 °C Mueller, Paul; Idmoumaz, Hamid; Journal of Organometallic Chemistry; vol. 345; (1988); p. 187 - 200 View in Reaxys

51 %

With eosin y in dimethyl sulfoxide, Time= 24h, T= 80 °C , Irradiation Li, Jian; Wang, Hongni; Liu, Li; Sun, Jiangtao; RSC Advances; vol. 4; nb. 91; (2014); p. 49974 - 49978 View in Reaxys

51 %

General Procedure for the Oxidative Reaction General procedure: A solution of diphenylmethanol (1 mmol), NBS (1.3equiv.), KOAc (1.5 equiv.) H2O (1.5 mL), and CH2Cl2 (0.5mL) was magnetically stirred in 25 mL flask at room temperaturefor 10 h. The reaction mixture was added into water(10 mL), and extracted with EtOAc (3 × 10 mL). The combinedEtOAc extracts were dried over anhydrous MgSO4,filtrated, and then the solvent was removed under reducedpressure. The residue was purified by the flash columnchromatography on silica gel with PE or PE/EtOAc as theeluent to obtain the desired products. The oxidation productswere identified by GC-MS and 1H NMR. With N-Bromosuccinimide, potassium acetate in dichloromethane, water, Time= 10h, T= 20 °C , Green chemistry Wu, Jianglong; Liu, Yan; Liu, Ping; Gu, Chengzhi; Letters in Organic Chemistry; vol. 14; nb. 4; (2017); p. 254 260 View in Reaxys

50 %

With permanganate adsorbed on alumina in diethyl ether, Time= 1.5h, T= 35 °C Thuy, Vu Moc; Maitte, Pierre; Bulletin des Societes Chimiques Belges; vol. 98; nb. 11; (1989); p. 877 - 878 View in Reaxys

50 %

With [FeIV(O)(N,N-bis(2-pyridylmethyl)bis(2-pyridyl)methylamine)](ClO4)2, scandium tris(trifluoromethanesulfonate) in acetonitrile, T= 24.84 °C , Kinetics, Reagent/catalyst Morimoto, Yuma; Park, Jiyun; Suenobu, Tomoyoshi; Lee, Yong-Min; Nam, Wonwoo; Fukuzumi, Shunichi; Inorganic Chemistry; vol. 51; nb. 18; (2012); p. 10025 - 10036 View in Reaxys

50 %

With dimethyl sulfoxide, potassium hydoxide, Time= 24h, T= 90 °C Saunthwal, Rakesh K.; Patel, Monika; Verma, Akhilesh K.; Journal of Organic Chemistry; vol. 81; nb. 15; (2016); p. 6563 - 6572 View in Reaxys

49 %

With N -hydroxyphthalimide, sodium perchlorate in acetonitrile, electrolytical oxidation, anode potential 0.85 V Masui, Masaichiro; Ueshima, Takahiro; Ozaki, Shigeko; Journal of the Chemical Society, Chemical Communications; nb. 8; (1983); p. 479 - 480 View in Reaxys

49 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [bis(acetoxy)iodo]benzene in dichloromethane, Time= 0.075h, T= 35 °C , Flow reactor, Time, chemoselective reaction Ambreen, Nida; Kumar, Ravi; Wirth, Thomas; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1437 1442 View in Reaxys

48 %

With oxygen, potassium hydoxide, Time= 1h, T= 80 °C , p= 750.075Torr , Autoclave Wolfson, Adi; Ben-Harush, Kfir; Herskowitz, Moti; Kinetics and Catalysis; vol. 51; nb. 1; (2010); p. 63 - 68 View in Reaxys

47 %

With tert.-butylhydroperoxide, C45H52CuN4O3 in decane, acetonitrile, Time= 18h, T= 70 °C Wu, Xianghong; Gorden, Anne E. V.; European Journal of Organic Chemistry; nb. 4; (2009); p. 503 - 509

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

95/438

2018-03-11 22:07:32


View in Reaxys 47 %

8 : Benzyl Alcohol Oxidation in a Plug Flow Reaction Pd/PPhen (20 mg) is mixed with quartz sand (200 mg), and packed into a tube reactor (6 mmxl6O mm). An evaporator for benzyl alcohol is connected to the top of the tube reactot The temperatures of evaporator and reactor are controlled by individual tube ovens. l3enzyl alcohol (0.1 mlh’) is injected through a syringe pump into the evaporator and carried by °2 (50 mLmin’) into the reactot The partial pressure of benzyl alcohol is controlled to be lower than its vapor pressure. The products are collected in a dry-ice cooled tetrahydroffiran solution with a gas outlet to atmosphere. The solutions are analyzed by GC-FID in one hour intervals with dodecane as standard. The results are shown in Table 4. With 5-palladium/activated carbon in neat (no solvent), T= 120 °C , Flow reactor Patent; STUDIENGESELLSCHAFT KOHLE MBH; Schueth, Ferdi; Furstner, Alois; Wang, Feng; (21 pag.); US2017/21342; (2017); (A1) English View in Reaxys

46 %

With heptahydrido bis(tricyclohexylphosphine)rheniume(VII), T= 150 °C , Inert atmosphere Jin, Hongming; Xie, Jin; Pan, Changduo; Zhu, Zhengbo; Cheng, Yixiang; Zhu, Chengjian; ACS Catalysis; vol. 3; nb. 10; (2013); p. 2195 - 2198 View in Reaxys

46 %

With [Mn(bp)(NCS)0.9(NO3)0.1(CH3OH)]*CH3OH, dihydrogen peroxide in acetonitrile, Time= 4h, T= 60 °C , Reagent/ catalyst, Concentration, Temperature, Solvent Noshiranzadeh, Nader; Emami, Marzieh; Bikas, Rahman; Slepokura, Katarzyna; Lis, Tadeusz; Polyhedron; vol. 72; (2014); p. 56 - 65 View in Reaxys

46 %

With iron containing titania supported on zeolite in acetonitrile, Time= 8h, T= 35 °C , p= 750.075Torr , Irradiation Magdziarz, Agnieszka; Colmenares, Juan C.; Chernyayeva, Olga; Kurzydlowski, Krzysztof; Grzonka, Justyna; ChemCatChem; vol. 8; nb. 3; (2016); p. 536 - 539 View in Reaxys

45.5 %

With [Ru(CO)(triphenylarsine)(OC6H4C(CHCHC6H4Cl)O)2], 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, T= 20 °C , Molecular sieve Muthukumar; Viswanathamurthi; Natarajan; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 70; nb. 5; (2008); p. 1222 - 1226 View in Reaxys

45 %

With dihydrogen peroxide, Time= 4h, T= 50 °C , Autoclave, neat (no solvent) Wang, Xiaoli; Wu, Gongde; Wei, Wei; Sun, Yuhan; Transition Metal Chemistry; vol. 35; nb. 2; (2010); p. 213 - 220 View in Reaxys

44.7 %

With ferric sulfate nonahydrate, perchloric acid in water, T= 25 °C , pH= 0.5, Inert atmosphere, Irradiation, Catalytic behavior, pH-value, Concentration, Wavelength Spasiano, Danilo; Marotta, Raffaele; Di Somma, Ilaria; Andreozzi, Roberto; Caprio, Vincenzo; Photochemical and Photobiological Sciences; vol. 12; nb. 11; (2013); p. 1991 - 2000 View in Reaxys

44.5 %

Representative procedure with benzyl alcohol Typically, in the autoclave, benzyl alcohol (2 mmol), NHPI (0.2 mmol), HNO3 (0.4 mmol), and CuBr2 (0.01 mmol) were added in 3 mL acetonitrile at 0 °C. After the autoclave was closed, oxygen was charged to 0.1 MPa. The autoclave was placed in a water bath at 25 °C. The reaction mixture was monitored by GC. When the reaction was finished, the autoclave was carefully depressurized. The reaction mixture was neutralized by 10 percent Na2CO3 and extracted with CH2Cl2 (10 mL * 3). The organic layers were concentrated in vacuo, and the product was further purified by column chromatography over silica gel (n-hexane:ethyl acetate, 10:1) to afford benzaldehyde (95 mg, 44.5 percent yield) as a light-yellow liquid. Purity was confirmed by GC, 1H NMR, and 13C NMR. 1H NMR (400 MHz, CDCl3): d 7.51(t, 3JH,H = 7.2 Hz, 2 H), 7.61 (t, 3JH,H = 7.2 Hz, 1 H), 7.86 (d, 3JH,H = 7.6 Hz, 2H), 9.99 (s, 1 H); 13C NMR (100.6 MHz, CDCl3): d 128.7, 129.4, 134.1, 136.0, 192.0.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

96/438

2018-03-11 22:07:32


With N -hydroxyphthalimide, oxygen, nitric acid, copper(ll) bromide in acetonitrile, Time= 4h, p= 750.075Torr , Autoclave, Catalytic behavior, Reagent/catalyst, chemoselective reaction Chen, Bo; Li, Jun; Yang, Gang; Gao, Shuang; Research on Chemical Intermediates; vol. 41; nb. 6; (2015); p. 3929 - 3936 View in Reaxys 43.7 %

With dihydrogen peroxide in water, Time= 1h, T= 100 °C , Kinetics, Reagent/catalyst, Temperature Xiong, Leisha; Chen, Rong; Chen, Fengxi; RSC Advances; vol. 6; nb. 103; (2016); p. 101048 - 101060 View in Reaxys

41 %

With α,α,α-trifluorotoluene, Time= 20h, UV-irradiation, Reagent/catalyst Koito, Yusuke; Rees, Gregory J.; Hanna, John V.; Li, Molly M. J.; Peng, Yung-Kang; Puchtler, Tim; Taylor, Robert; Wang, Tong; Kobayashi, Hisayoshi; Teixeira, Ivo F.; Khan, M. Abdullah; Kreissl, Hannah T.; Tsang, S. C. Edman; ChemCatChem; vol. 9; nb. 1; (2017); p. 144 - 154 View in Reaxys

40 %

With oxygen, palladium diacetate, Time= 18h, T= 80 °C , p= 750.075Torr , Supercritical conditions, neat (no solvent) Herbert, Matthew; Montilla, Francisco; Galindo, Agustin; Polyhedron; vol. 29; nb. 18; (2010); p. 3287 - 3293 View in Reaxys

40 %

With thallium (III) oxide, sulfuric acid in water, Time= 4h, Reflux Gun'kin; Russian Journal of General Chemistry; vol. 80; nb. 3; (2010); p. 451 - 454 View in Reaxys

40 %

General Procedure General procedure: A mixture of alcohols (1 mmol) and DBDMH or DCDMH (1-1.5 mmol) in a 10 mL round-bottomed flask sealed with a stopper, was stirred in an oil-bath for the appropriate time and temperature (Table 1) under solvent-free condition. Then, as monitored by TLC (eluent n-hexane/acetone 10:2), hot water (10 mL) was added to mixture and stirred magnetically for 10 min. Then, the solution was extracted with (CH2Cl2/water (2 × 10 mL)) and organic phase dried over anhydrous Na2SO4 (1 g). Evaporation of the solvent gave the corresponding carbonyl compounds. Melting points and spectral data of all products are fully consistent with those previously reported. The structures of the products were confirmed from physical and spectroscopic data such as melting points, 1H NMR and 13C NMR spectra, fully consistent with those previously reported.17,18 With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione, Time= 0.75h, Reagent/catalyst Khazaei, Ardeshir; Abbasi, Fatemeh; Kianiborazjani, Maryam; Saednia, Shahnaz; Journal of the Brazilian Chemical Society; vol. 25; nb. 2; (2014); p. 361 - 364 View in Reaxys

39 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, triethylamine, copper(ll) bromide in acetonitrile, Time= 1h, Product distribution, Further Variations: Reagents, Solvents Uber, Jorge Salinas; Vogels, Yorick; Van Den Helder, Dave; Mutikainen, Ilpo; Turpeinen, Urho; Fu, Wen Tian; Roubeau, Olivier; Gamez, Patrick; Reedijk, Jan; European Journal of Inorganic Chemistry; nb. 26; (2007); p. 4197 - 4206 View in Reaxys

38 %

With MoO2(acac) in dimethyl sulfoxide, Time= 10h, T= 100 °C , reactions under var. conditions, Product distribution, Mechanism Lorber, Christian Y.; Pauls, Irene; Osborn, John A.; Bulletin de la Societe Chimique de France; vol. 133; nb. 7-8; (1996); p. 755 - 758 View in Reaxys

38 %

With oxygen, copper(II) acetate monohydrate, palladium dichloride in dimethyl sulfoxide, toluene, Time= 20h, T= 80 °C Wang, Lu; Wang, Yanxia; Liu, Chao; Lei, Aiwen; Angewandte Chemie - International Edition; vol. 53; nb. 22; (2014); p. 5657 - 5661; Angew. Chem.; vol. 126; nb. 22; (2014); p. 5763 - 5767,5 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

97/438

2018-03-11 22:07:32


38 %

With 2,2,6,6-tetramethylpiperidin-1-ol, [{Cu12((2,4,6-trimethylbenzene)-1,3,5-triacetate)8(N,N-dimethylacetamide)4(H2O)8}·8H2O·48H2O], oxygen, sodium carbonate in acetonitrile, Time= 3h, T= 60 °C , Catalytic behavior Paul, Mithun; Adarsh; Dastidar, Parthasarathi; Crystal Growth and Design; vol. 14; nb. 3; (2014); p. 1331 - 1337 View in Reaxys

37 %

With diphenylether, Fe(TAML)Li, [bis(acetoxy)iodo]benzene in acetone, Time= 4h, T= 25 °C , Inert atmosphere, Green chemistry, Catalytic behavior Napoly, Francois; Jean-Gerard, Ludivine; Goux-Henry, Catherine; Draye, Micheline; Andrioletti, Bruno; European Journal of Organic Chemistry; vol. 2014; nb. 4; (2014); p. 781 - 787 View in Reaxys

35.2 %

With pentaaminechlorocobalt(III) dichloride, (2,2':6',2''-terpyridine)(2,2'-bipyridine)aquaruthenium(II) perchlorate in aq. phosphate buffer, Time= 5h, pH= 4.7, Inert atmosphere, Irradiation, Catalytic behavior, Reagent/catalyst Bai, Lichen; Li, Fei; Wang, Yong; Li, Hua; Jiang, Xiaojuan; Sun, Licheng; Chemical Communications; vol. 52; nb. 62; (2016); p. 9711 - 9714 View in Reaxys

34.2 %

With dihydrogen peroxide in water, Time= 1.5h, T= 100 °C , Reagent/catalyst Xiao, Shiwei; Zhang, Chuntao; Chen, Rong; Chen, Fengxi; New Journal of Chemistry; vol. 39; nb. 6; (2015); p. 4924 - 4932 View in Reaxys

34 %

Stage 1: With 1,3,5-Tri-tert-butylbenzene in methanol, Time= 76h, T= 65 °C Stage 2: With C36H78Cu2N6O2 (2+)*2CF3O3S(1-), oxygen in methanol, Temperature Karahalis, Gregory J.; Thangavel, Arumugam; Chica, Bryant; Bacsa, John; Dyer, R. Brian; Scarborough, Christopher C.; Inorganic Chemistry; vol. 55; nb. 3; (2016); p. 1102 - 1107 View in Reaxys

33 %

With oxygen, palladium, Time= 0.5h, T= 55 °C Potekhin, V. V.; Matsura, V. A.; Ukraintsev, V. B.; Russian Journal of General Chemistry; vol. 70; nb. 12; (2000); p. 1939 - 1939; Zhurnal Obshchei Khimii; vol. 70; nb. 12; (2000); p. 2058 - 2058 View in Reaxys

33.0%

11 :REFERENCE EXAMPLE 11 The experiment was conducted in the same manner as in Reference Example 9, except that 15 mg (0.08 mmol) of 4-methoxy-2,2,6,6-tetramethylpiperidine-1-oxyl was used instead of compound (14) and 37.24 g (10 mmol) was used instead of 74.48 g (20 mmol) of the 2.0percent by weight aqueous solution of sodium hypochlorite. As a result, by the reaction, benzaldehyde was produced with yield of 33.0percent (based on benzyl alcohol). With sodium hypochlorite, sodium hydrogencarbonate, 4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical, potassium bromide in dichloromethane, water, Time= 1h, T= 0 - 2 °C , pH= 8.6, Product distribution / selectivity Patent; Shiomi, Yasuhiro; Uno, Osamu; Ohta, Akio; Sunakami, Takeshi; US2005/124807; (2005); (A1) English View in Reaxys

32 %

With laccase from a strain of Trametes villosa, N-Phenylacetohydroxamic acid, oxygen in 1,4-dioxane, water, Time= 24h, T= 20 °C , pH= 5, Enzymatic reaction, Product distribution, Further Variations: Solvents Cantarella, Gaetano; Galli, Carlo; Gentili, Patrizia; New Journal of Chemistry; vol. 28; nb. 3; (2004); p. 366 - 372 View in Reaxys

32 %

General Procedure for the Study of the Substrate Scope of ICl as Oxidant General procedure: Starting alcohols (1.00 g, 1.0 eq) specified in Table 3 were dissolved in 10 mL of dried CH2Cl2 (for substrates in entries 8–20 in Table 3, 30 mL of dried CH2Cl2 was used), and the resulting mixture was stirred in an ice-water bath, followed by addition of Cs2CO3 (3.0 eq). The suspension was stirred at this temperature, and ICl (1.5 eq) dissolved in 2 mL of CH2Cl2 was added dropwise. After addition, the reaction mixture was stirred at room temperature until the reaction completed as indicated by TLC analysis, which was conducted at 0.5-h intervals.The reaction mixture was subjected to aqueous workup described previously to yield the pure carbonyl compounds specified in Table 3.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

98/438

2018-03-11 22:07:32


With Iodine monochloride, caesium carbonate in dichloromethane, Time= 5h, T= 0 - 20 °C , Green chemistry Wei, Peng; Zhang, Datong; Gao, Zhigang; Cai, Wenqing; Xu, Weiren; Tang, Lida; Zhao, Guilong; Synthetic Communications; vol. 45; nb. 12; (2015); p. 1457 - 1470 View in Reaxys 31.9 %

With C56H45N4O3OsP2 (1+)*ClO4 (1-), 4-methylmorpholine N-oxide in dichloromethane, Time= 4h, Reflux, Molecular sieve, Catalytic behavior, Reagent/catalyst Datta, Papia; Sardar, Dibakar; Panda, Uttam; Halder, Ajanta; Manik, Nabin Baran; Chen, Chun-Jung; Sinha, Chittaranjan; Applied Organometallic Chemistry; vol. 30; nb. 5; (2016); p. 323 - 334 View in Reaxys

31.7 %

Benzyl alcohol (BzOH) oxidation reactions with H2O2 were carried out in a glass reactor with a magnetic stirrer and a reflux condenser,immersed in a thermally controlled bath at 70 °C for 7 h. In a typical reaction, benzyl alcohol (Fluka>95percent) (9.11 mmol), was stirred with hydrogen peroxide (H2O2, Riedel de Han, 35 wt.percent in water)(2.28 mmol), using acetonitrile (AcN, Sintorgan, 99.5percent) (91.15 mmol)as solvent and M-M(60) as catalyst (100 mg). Reaction progress was followed taking samples at different times by a lateral tabulation without opening the reactor. Liquid samples were immediately filtered and analyzed by gas chromatography equipped with FID detector (HP-1capillary column) and identified by comparison with known standards. With dihydrogen peroxide in water, acetonitrile, Time= 7h, T= 70 °C , Green chemistry, Catalytic behavior, Reagent/ catalyst Cánepa, Analía L.; Elías, Verónica R.; Vaschetti, Virginia M.; Sabre, Ema V.; Eimer, Griselda A.; Casuscelli, Sandra G.; Applied Catalysis A: General; vol. 545; (2017); p. 72 - 78 View in Reaxys

30 %

With sodium hypochlorite, aluminum oxide, PEGMME-350 in dichloromethane, Time= 24h, Ambient temperature, var. catalysts Sawicki, Robert A.; Tetrahedron Letters; vol. 23; nb. 22; (1982); p. 2249 - 2252 View in Reaxys

30 %

With tetrakis(pyridine)silver dichromate in dichloromethane, Time= 0.3h, other solvent, reaction time, Product distribution Firouzabadi, H.; Sardarian, A.; Gharibi, H.; Synthetic Communications; vol. 14; nb. 1; (1984); p. 89 - 94 View in Reaxys

30.3 %

With oxygen, o-chlorobenzylidene malononitrile, CoNaY, T= 379.85 °C , Product distribution, Further Variations: Catalysts, Temperatures Seiki, Takayuki; Nakato, Asako; Nishiyama, Satoru; Tsuruya, Shigeru; Physical Chemistry Chemical Physics; vol. 5; nb. 17; (2003); p. 3818 - 3826 View in Reaxys

30 %

With α,α,α-trifluorotoluene, zinc(II) oxide, oxygen, Time= 8h, UV-irradiation, Reagent/catalyst Tang, Zi-Rong; Yin, Xia; Zhang, Yanhui; Xu, Yi-Jun; RSC Advances; vol. 3; nb. 17; (2013); p. 5956 - 5965 View in Reaxys

30 %

With [Pd(1,5-cyclooctadiene)Cl(SnCl3)], Time= 3h, T= 110 °C , Mechanism Mohanty, Anuradha; Roy, Sujit; Tetrahedron Letters; vol. 57; nb. 25; (2016); p. 2749 - 2753 View in Reaxys

29.7 %

With potassium permanganate in benzene, Time= 1.5h, T= 20 °C , Irradiation Yamawaki,Junko; Sumi, Shinjiro; Ando, Takashi; Hanafusa, Terukiyo; Chemistry Letters; (1983); p. 379 - 380 View in Reaxys

29 %

With tert.-butylhydroperoxide, (14,28-[1,3-diiminoisoindolinato]phthalocyaninato)Fe(III) in water, Time= 2h, T= 20 °C , Reagent/catalyst, Time

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

99/438

2018-03-11 22:07:32


Peterson, Brian M.; Herried, Morgan E.; Neve, Rachel L.; McGaff, Robert W.; Dalton Transactions; vol. 43; nb. 48; (2014); p. 17899 - 17903 View in Reaxys 28 %

2.3. Catalytic procedures and product analysis General procedure: Oxidation of hydrocarbons substrates was performed in a100 mL glass vessel under dioxygen or argon atmosphere. Typically,the reactor was charged with 1 or 2 mL either neat substrate or 0.1 M substrate solution in MeCN containing 0.1 mM (FePctBu4)2N. The reactions were initiated by addition of 70percent aqueous solution of tBuOOH. The reaction mixture was magnetically stirred at 25, 50 or 60°C for desired time. Reaction products were analyzed by GC–MS and GC directly or using Ph3P method introduced by Shul’pin . Chlorobenzene standard was added as 0.1 M solution prior to analyses. With tert.-butylhydroperoxide, .mu.-nitrido-bis[tetra(tert-butyl)phthalocyaninatoiron] in water, acetonitrile, Inert atmosphere, Catalytic behavior Kudrik, Evgeny V.; Sorokin, Alexander B.; Journal of Molecular Catalysis A: Chemical; vol. 426; (2017); p. 499 505 View in Reaxys

27 %

With ((ethylenediamine)Pd(NO3)2)6(2,4,6-tri(pyridin-4-yl)-1,3,5-triazine)4, oxygen in water, Time= 18h, T= 130 °C , Schlenk technique, Catalytic behavior, Reagent/catalyst Qiu, Xuan; Zhong, Wei; Bai, Cuihua; Li, Yingwei; Journal of the American Chemical Society; vol. 138; nb. 4; (2016); p. 1138 - 1141 View in Reaxys

26 %

With oxygen, potassium carbonate, N,N'-bis(4-aminophenyl)-1,4-benzoquinonediimine, copper(l) chloride in toluene, Time= 24h, T= 90 °C , other reagent, Product distribution Hirao, Toshikazu; Fukuhara, Shinya; Journal of Organic Chemistry; vol. 63; nb. 21; (1998); p. 7534 - 7535 View in Reaxys

26 %

in dimethyl sulfoxide, Time= 2h, T= 160 °C Wang, Zhen-Zhen; Tang, Yu; Tetrahedron; vol. 72; nb. 10; (2016); p. 1330 - 1336 View in Reaxys

25 %

With copper phthalocyanine, tetra-n-butylammonium hydrogen monopersulfate in water, Time= 0.5h, T= 70 °C Rezaeifard, Abdolreza; Jafarpour, Maasoumeh; Naeimi, Atena; Salimi, Mehri; Inorganic Chemistry Communications; vol. 15; (2012); p. 230 - 234 View in Reaxys

24 %

4.5 Oxidation of benzyl alcohols with molecular oxygen General procedure: VOSO4·5H2O (6.3 mg, 0.025 mmol), 4,4′-di-tert-butyl-2,2′-bipyridyl (13.4 mg, 0.05 mmol), and pnitrobenzhydrol (0.05 mmol) were placed in a 25 mL two necked round-bottomed flask, and then water (2.5 mL) was added. Next, the mixture was stirred, and then anhydrous MgSO4 (902.8 mg, 7.5 mmol) was slowly added into the mixture (cooling by ice water). Then, substrate (0.5 mmol) was added into the mixture at room temperature, and the mixture was stirred at 90 °C for the appropriate time under O2 (0.1 MPa, O2 balloon). The yield of the product was confirmed by 1H NMR spectroscopy using 1,2-diphenylethane as the internal standard, after extraction of the reaction mixture with diethyl ether. The product was identified by comparison with the commercially available sample. With magnesium sulphate, 1,1-Diphenylmethanol, vanadyl(IV) sulphate pentahydrate, oxygen, 4,4'-di-tert-butyl-2,2'bipyridine in water, Time= 22h, T= 20 - 90 °C , p= 750.075Torr Marui, Kuniaki; Higashiura, Yuuki; Kodama, Shintaro; Hashidate, Suguru; Nomoto, Akihiro; Yano, Shigenobu; Ueshima, Michio; Ogawa, Akiya; Tetrahedron; vol. 70; nb. 14; (2014); p. 2431 - 2438 View in Reaxys

24 %

With tert.-butylhydroperoxide, H12MnO6 (2+)*2C9H5N4O3S(1-)*4H2O, Time= 1h, T= 150 °C , Microwave irradiation, Catalytic behavior, Reagent/catalyst Mahmudov, Kamran T.; Sutradhar, Manas; Martins, Luísa M. D. R. S.; Guedes da Silva, M. Fátima C.; Ribera, Alice; Nunes, Ana V. M.; Gahramanova, Shahnaz I.; Marchetti, Fabio; Pombeiro, Armando J. L.; RSC Advances; vol. 5; nb. 33; (2015); p. 25979 - 25987

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

100/438

2018-03-11 22:07:32


View in Reaxys 23 %

With 1-ethenyl-4-methylbenzene, oxygen, copper(II) acetate monohydrate, palladium dichloride in dimethyl sulfoxide, toluene, Time= 20h, T= 80 °C Wang, Lu; Wang, Yanxia; Liu, Chao; Lei, Aiwen; Angewandte Chemie - International Edition; vol. 53; nb. 22; (2014); p. 5657 - 5661; Angew. Chem.; vol. 126; nb. 22; (2014); p. 5763 - 5767,5 View in Reaxys

23 %

With carbon monoxide, oxygen, copper(II) acetate monohydrate, palladium dichloride in dimethyl sulfoxide, toluene, Time= 20h, T= 80 °C Wang, Lu; Wang, Yanxia; Liu, Chao; Lei, Aiwen; Angewandte Chemie - International Edition; vol. 53; nb. 22; (2014); p. 5657 - 5661; Angew. Chem.; vol. 126; nb. 22; (2014); p. 5763 - 5767,5 View in Reaxys

23 %

2.3. Photocatalytic activity The photocatalytic activity of g-C3N4-based catalysts wasinvestigated by the selective oxidation of benzyl alcohol with molecular O2 as oxidant under visible light irradiation. In a typicalreaction, photocatalytic activity measurements were carried out ina 25 mL glass reactionflaskfitted with a condenser and a magneticstirrer. The visible-light source for the reaction was provided by a300 W Xenon lamp with a 420 nm cut-offfilter. Benzyl alcohol(1 mmol), the catalyst (50 mg) and trifluorotoluene (10 mL) wereadded to theflask reactor. O2 (pressure ca. 1 bar) collected in arubber bag was connected to the system. The resulting system wasthen stirred at 100 C for 4 h under visible light irradiation. Afterthe reaction, the solid catalyst was separated by centrifugation. Theliquid phase was analyzed by a gas chromatograph (VARIAN 450) with anisole as the internal standard. In addition, different radicalscavengers were used in the controlled photoactivity experiments,which involved -butyl alcohol (TBA, as trapping agent for hydroxylradical species), benzoquinone (BQ, as trapping agent forsuperoxide radical species) and ammonium oxalate (AO, astrapping agent for holes). The amount of the above scavengerswas 1 mmol. With oxygen, Time= 4h, T= 100 °C , p= 750.075Torr , Irradiation Zhang, Ligang; Liu, Di; Guan, Jing; Chen, Xiufang; Guo, Xingcui; Zhao, Fuhua; Hou, Tonggang; Mu, Xindong; Materials Research Bulletin; vol. 59; (2014); p. 84 - 92 View in Reaxys

23 %

With Mg–Al hydrotalcite doped with Fe(3+). Elemental composition: Mg - 29.4percent, Al - 3.05percent, Fe - 11.4percent. in toluene, Time= 24h, T= 110 °C , Inert atmosphere, Catalytic behavior, Reagent/catalyst, Time Bain, John; Cho, Philip; Voutchkova-Kostal, Adelina; Green Chemistry; vol. 17; nb. 4; (2015); p. 2271 - 2280 View in Reaxys

22 %

With C32H25Cl2N6O2Rh2 (1+)*Cl(1-) in water, Time= 12h, T= 100 °C , Sealed tube, Green chemistry, Reagent/catalyst Wang, Xuewei; Wang, Chao; Liu, Yuxuan; Xiao, Jianliang; Green Chemistry; vol. 18; nb. 17; (2016); p. 4605 4610 View in Reaxys

21.73 %

With hydrogenchloride, sodium hexachloroiridate(III), cerium(IV) sulphate, sulfuric acid, acetic acid in water, Time= 3h, T= 100 °C Tandon, Praveen K.; Dwivedi, Priy B.; Singh, Satpal; Synthetic Communications; vol. 39; nb. 11; (2009); p. 1920 1928 View in Reaxys

21 %

With pyridine-2-carbaldehyde, 2-(Aminomethyl)pyridine, iron(II) trifluoromethanesulfonate acetonitrile disolvate, dihydrogen peroxide in acetonitrile, Time= 1.5h, T= 25 °C Olivo, Giorgio; Giosia, Simone; Barbieri, Alessia; Lanzalunga, Osvaldo; Di Stefano, Stefano; Organic and Biomolecular Chemistry; vol. 14; nb. 45; (2016); p. 10630 - 10635 View in Reaxys

20 %

With aluminum oxide, potassium ferrate(VI), copper(II) sulfate in benzene, Time= 5h, Ambient temperature, competition reaction with cyclohexene Kim, Kwan Soo; Song, Yang Heon; Lee, Nam Ho; Hahn, Chi Sun; Tetrahedron Letters; vol. 27; nb. 25; (1986); p. 2875 - 2878

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

101/438

2018-03-11 22:07:32


View in Reaxys 18.1 %

With oxygen, Cu(14)-NaX, rubidium, T= 289.85 °C , p= 760Torr , Catalytic oxidation, Product distribution, Further Variations: Catalysts, Temperatures Tsuruya; Konda; Nishiyama; Physical Chemistry Chemical Physics; vol. 1; nb. 23; (1999); p. 5393 - 5399 View in Reaxys

18 %

With C27H42ClN2PRu, caesium carbonate in 5,5-dimethyl-1,3-cyclohexadiene, Time= 48h, T= 140 °C , Inert atmosphere, Glovebox, Sealed tube Chang, Weihong; Gong, Xue; Wang, Shuizhong; Xiao, Ling-Ping; Song, Guoyong; Organic and Biomolecular Chemistry; vol. 15; nb. 16; (2017); p. 3466 - 3471 View in Reaxys

17.4 %

With Bi2MoO6, Time= 4h, T= 24.84 °C , p= 750.075Torr , Irradiation, Reagent/catalyst, Wavelength Jing, Kaiqiang; Xiong, Jinhua; Qin, Na; Song, Yujie; Li, Liuyi; Yu, Yan; Liang, Shijing; Wu, Ling; Chemical Communications; vol. 53; nb. 61; (2017); p. 8604 - 8607 View in Reaxys

16 %

With oxygen in water, Time= 24h, T= 80 °C , p= 22502.3Torr , pH= 8, Autoclave Kanbak-Aksu; Nahid Hasan; Hagen; Hollmann; Sordi; Sheldon; Arends; Chemical Communications; vol. 48; nb. 46; (2012); p. 5745 - 5747 View in Reaxys

16.8 %

2.3. Vapor-Phase Oxidation of BenzylAlcohol to Benzaldehyde Vapor-phase oxidation of benzyl alcohol to benzaldehyde over α -K5PW11(M·OH2O39 (M = MnII, CoII, NiII, and ZnII) Keggin HPAs was carried out in a continuous-owquartz reactor under atmospheric pressure. Each cata-lyst (0.5 g) charged into a quartz reactor was pretreatedwith a mixed stream of nitrogen (10 ml/min) and oxy-gen (10 ml/min) at 350 C for 1 h. Benzyl alcohol(145 × 10−3 mol/h) was sufciently vaporized by passingthrough a pre-heating zone and it was continuously fedinto the reactor together with a mixed stream of oxygen (10 ml/min) and nitrogen (10 ml/ min). The reaction wascarried out at 330 C for 6 h. Reaction products were peri-odically sampled and analyzed using a gas chromatograph(HP 5890, Hewlett-Packard) equipped with ame ioniza-tion detector (GC-FID). Conversion of benzyl alcohol andyield for benzaldehyde were calculated on the basis of carbon balance. With H2MnO40PW11 (5-)*5K(1+), oxygen, Time= 6h, T= 330 °C , p= 760.051Torr , Inert atmosphere, Flow reactor, Reagent/catalyst Choi, Jung Ho; Kang, Tae Hun; Bang, Yongju; Yoo, Jaekyeong; Jun, Jin Oh; Song, In Kyu; Journal of Nanoscience and Nanotechnology; vol. 14; nb. 11; (2014); p. 8873 - 8878 View in Reaxys

14 %

With gold, oxygen in toluene, Time= 13h, T= 100 °C , p= 760.051Torr Qi, Yue; Luan, Yi; Peng, Xiong; Yang, Ming; Hou, Junying; Wang, Ge; European Journal of Inorganic Chemistry; vol. 2015; nb. 30; (2015); p. 5099 - 5105 View in Reaxys

14 %

With chloro-(pentamethylcyclopentadienyl)-{5-methoxy-2-{1-[(4-methoxyphenyl)imino-N]ethyl}phenyl-C}-iridium(lll), potassium carbonate in 2,2,2-trifluoroethanol, Time= 3h, T= 100 °C Jiang, Xue; Tang, Weijun; Xue, Dong; Xiao, Jianliang; Wang, Chao; ACS Catalysis; vol. 7; nb. 3; (2017); p. 1831 - 1835 View in Reaxys

14 %

General procedure for aerobic catalytic oxidation of benzyl alcohol General procedure: Reactions performed at atmospheric pressure were conducted in a 50mL round bottom flask or in vials of 20mL capacity, at the desired temperature. The catalyst (0.025mmol) and TEMPO (0.05mmol) were first charged to the flask and the toluene (2mL) and the benzyl alcohol (1.0mmol) were then added and the mixture was stirred for the duration of the reaction. When the reaction had finished, the reaction mixture was filtered, added an internal standard (50μl of dodecane) and diethyl ether up to 10mL. The homogenized mixture was analyzed by gas chromatography. At least, two determinations were carried out for each catalytic essay.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

102/438

2018-03-11 22:07:32


With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C30H30CuN4O2 in toluene, Time= 6h, T= 60 °C , p= 760.051Torr , Catalytic behavior, Solvent, Temperature, Reagent/catalyst del Mar Conejo, María; Cantero, Jorge; Pastor, Antonio; Álvarez, Eleuterio; Galindo, Agustín; Inorganica Chimica Acta; vol. 470; (2018); p. 113 - 118 View in Reaxys 13 %

With silver hexafluoroantimonate, C20H30N4NiOS, potassium tert-butylate, oxygen, Time= 20h, T= 24.84 °C , p= 1500.15Torr Kochem, Amélie; Gellon, Gisèle; Jarjayes, Olivier; Philouze, Christian; Du Moulinet D'Hardemare, Amaury; Van Gastel, Maurice; Thomas, Fabrice; Dalton Transactions; vol. 44; nb. 28; (2015); p. 12743 - 12756 View in Reaxys

12 %

With D-glucose, Gluconobacter oxidans DSM 2343, yeast extract in phosphate buffer, Time= 24h, T= 28 °C , pH= 6.3, Enzymatic reaction Villa, Raffaella; Romano, Andrea; Gandolfi, Raffaella; Sinisterra Gago, Jose V.; Molinari, Francesco; Tetrahedron Letters; vol. 43; nb. 34; (2002); p. 6059 - 6061 View in Reaxys

12 %

General Procedure for the direct N-alkylation of amines: General procedure: To a microwave vial (0.5-2.0 mL) was added iron(III) phthalocyanine chloride (10molpercent), tBuOK (2.0 mmol), under an atmosphere. The vial was sealed using vial capsinclude reseal septa and then purged with nitrogen To the vial was added amine (1.0mmol) and alcohol (4.0 mmol) via syringe. The mixture was stirred and heated undermicrowave irradiation for 12 h at 130 °C. After the reaction, the resulting mixture wasfiltered through celite with diethyl ether. The solution was evaporated and theresulting residue was purified by flash column chromatography (EtOAc:Hexane = 1:10)to yield the corresponding N-alkylated amine. With iron(III)phthalocyanine chloride, potassium tert-butylate in neat (no solvent), Time= 12h, T= 130 °C , Inert atmosphere, Microwave irradiation Minakawa, Maki; Okubo, Masataka; Kawatsura, Motoi; Bulletin of the Chemical Society of Japan; vol. 88; nb. 12; (2015); p. 1680 - 1682 View in Reaxys

10 %

With 2-Picolinic acid, manganese(II) perchlorate hexahydrate, dihydrogen peroxide, sodium acetate in [(2)H6]acetone, water, Time= 16h, T= 0 - 20 °C Pijper, Dirk; Saisaha, Pattama; De Boer, Johannes W.; Hoen, Rob; Smit, Christian; Meetsma, Auke; Hage, Ronald; Van Summeren, Ruben P.; Alsters, Paul L.; Feringa, Ben L.; Browne, Wesley R.; Dalton Transactions; vol. 39; nb. 43; (2010); p. 10375 - 10381 View in Reaxys

10 %

With [(TPA-O-allyl)2Fe2(benzoylformate)2](ClO4)2, oxygen in acetonitrile, Time= 24h, T= 20 °C , Reagent/catalyst Sheet, Debobrata; Halder, Partha; Paine, Tapan Kanti; Angewandte Chemie - International Edition; vol. 52; nb. 50; (2013); p. 13314 - 13318; Angew. Chem.; vol. 125; nb. 50; (2013); p. 13556 - 13560 View in Reaxys

10 %

With tert.-butylhydroperoxide, C44H53FeN4O6 in water, Time= 0.5h, T= 80 °C , Microwave irradiation, Reagent/catalyst Sutradhar, Manas; Alegria, Elisabete C. B. A.; Mahmudov, Kamran T.; Guedes Da Silva, M. Fátima C.; Pombeiro, Armando J. L.; RSC Advances; vol. 6; nb. 10; (2016); p. 8079 - 8088 View in Reaxys

8%

With C55H43ClN5P2Ru(1+)*Cl(1-), potassium hydoxide in toluene, Time= 2h, T= 140 °C , Sealed tube Yang, Fa-Liu; Wang, Ying-Hui; Ni, Yong-Feng; Gao, Xiang; Song, Bing; Zhu, Xinju; Hao, Xin-Qi; European Journal of Organic Chemistry; vol. 2017; nb. 24; (2017); p. 3481 - 3486 View in Reaxys

7.8 %

With ammonia, oxygen in water, Time= 1h, T= 149.84 °C , p= 22502.3Torr

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

103/438

2018-03-11 22:07:32


Nie, Renfeng; Shi, Juanjuan; Xia, Shuixin; Shen, Lian; Chen, Ping; Hou, Zhaoyin; Xiao, Feng-Shou; Journal of Materials Chemistry; vol. 22; nb. 35; (2012); p. 18115 - 18118 View in Reaxys 7%

With iron(III) chloride hexahydrate, oxygen, T= 55 °C , Microwave irradiation Wang, Xiaoyu; Du, Chuan; Shi, Hui; Pang, Yadong; Jin, Shengfei; Hou, Yuqian; Wang, Yanshi; Peng, Xiaoshi; Xiao, Jianyong; Liu, Yang; Liu, Yongxiang; Cheng, Maosheng; Tetrahedron; vol. 71; nb. 38; (2015); p. 6744 6748 View in Reaxys

1%

7 : Example 7 Oxidation of Benzyl Alcohol Example 7 Oxidation of Benzyl Alcohol (0314) Oxidations of 1 mM benzyl alcohol with 2 mM H2O2 were carried with 30percent acetonitrile and 10 mM acetate (pH 3-5), phosphate (pH 7) or borate buffer (pH 9) at specified pH values, using 0.01 mg/mL of purified peroxygenase (mature peroxygenase encoded by SEQ ID NO: 1) in a total reaction volume of 1 mL. Reactions were performed at room temperature for 25 minutes and stopped by adding 1 μL of catalase (Terminox Ultra 50L, Novozymes). (0315) Samples were analyzed on an Agilent 1200 HPLC system equipped with a Diode Array Detector (Agilent, Santa Clara Calif., USA) and separated on a Zorbax Stable Bond C18 (2) (80 , 2.1×50 mm, 1.8 μm) column from Phenomenex (Torrance Calif., USA) thermostated at 40° C. Two mobile phases were used: (A) 0.1percent formic acid, and (B) 0.1percent formic acid in acetonitrile. (0316) Separations were run using stepwise gradient starting with 5percent B held for 4 min, then increasing to 100percent B within 6 min with a constant flow rate of 0.5 mL/min. (0317) Benzyl alcohol and its possible oxidation products, benzaldehyde and benzoic acid, were identified and quantified by external calibration using authentic standards, based on their retention times, UV absorbtion spectra (210 nm, 250 nm, and 230 nm respectively). (0318) The peroxygenase oxidised benzyl alcohol yielding a single product, benzaldehyde, as shown in Table 4. [table-us-00005-en] TABLE 4 Comparison of benzaldehyde yields at various pH. Benzaldehyde pH (percent) 3 0.8 5 1.0 7 0 9 0 With Aspergillus carbonarius peroxygenase gene, dihydrogen peroxide in acetonitrile, Time= 0.416667h, T= 20 °C , pH= 5, Enzymatic reaction, Catalytic behavior Patent; Novozymes A/S; Landvik, Sara; Oestergaard, Lars Henrik; Kalum, Lisbeth; (25 pag.); US9404093; (2016); (B2) English View in Reaxys With air, T= 300 °C , Leiten ueber Silberasbest Moureu; Mignonac; Bulletin de la Societe Chimique de France; vol. <4> 29; (1921); p. 99; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 260 View in Reaxys Moureu; Mignonac; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 260; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 171; (1920); p. 652 View in Reaxys With selenium(IV) oxide Astin; Newman; Riley; Journal of the Chemical Society; (1933); p. 393 View in Reaxys With air, T= 400 - 480 °C , Leiten ueber einen Vanadiumpentoxyd-Bimsstein-Katalysator Schorigin; Kisber; Smoljanikowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 2; p. 150; Chem. Zentralbl.; vol. 100; nb. II; (1929); p. 730 View in Reaxys T= 340 °C , Leiten ueber Aluminiumoxyd Adkins; Folkers; Journal of the American Chemical Society; vol. 53; (1931); p. 1422 View in Reaxys With copper Faucounau; Bulletin de la Societe Chimique de France; vol. <5>4; (1937); p. 60,64; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 203; (1936); p. 407 View in Reaxys Dupont; Piganiol; Bulletin de la Societe Chimique de France; vol. <5> 6; (1939); p. 322,326

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

104/438

2018-03-11 22:07:32


View in Reaxys With cobalt Faucounau; Bulletin de la Societe Chimique de France; vol. <5>4; (1937); p. 60,64; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 203; (1936); p. 407 View in Reaxys Dupont; Piganiol; Bulletin de la Societe Chimique de France; vol. <5> 6; (1939); p. 322,326 View in Reaxys With nickel(II) sulphate, alkaline aqueous benzenesulfonate, T= 70 °C , weiteres Reagens: Nickel-Anoden McKee; Heard; ; vol. 65; (1934); p. 301,316 View in Reaxys With cobalt(II) sulfate, alkaline aqueous benzenesulfonate, T= 70 °C , weiteres Reagens: Nickel-Anoden McKee; Heard; ; vol. 65; (1934); p. 301,316 View in Reaxys With air, T= 350 °C , Leiten ueber versilbertes Kupfer Aleksandrowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 10; (1937); p. 105,114; Chem. Zentralbl.; vol. 109; nb. I; (1938); p. 3328 View in Reaxys With air, T= 300 - 350 °C , Leiten ueber einen Kupfer-Silber-Bimsstein-Katalysator Davies; Hodgson; Journal of the Chemical Society; (1943); p. 281 View in Reaxys With 1,2-ethyl dinitrate, oxygen, T= 135 - 145 °C Patent; I.G. Farbenind.; DE539476; (1929); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 782 View in Reaxys With aluminium(III) phenoxide, p-benzoquinone, benzene Yamashita; Matsumura; Nippon Kagaku Kaishi; vol. 64; (1943); p. 506; ; (1947); p. 3753 View in Reaxys With sodium hypobromide Palfray; Metayer; Panouse; Bulletin de la Societe Chimique de France; (1947); p. 766,770 View in Reaxys Panouse; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 223; (1946); p. 745 View in Reaxys With magnesium hypobromite Metayer; Roumens; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 225; (1947); p. 1324 View in Reaxys With calcium(II) nitrate Schorygin; Kisber; Ssmoljaninowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 3; (1930); p. 721,725; Chem. Zentralbl.; vol. 101; nb. II; (1930); p. 3397 View in Reaxys With lead(IV) acetate, benzene, T= 80 °C Criegee; Kraft; Rank; Justus Liebigs Annalen der Chemie; vol. 507; (1933); p. 159,167 View in Reaxys With lead(IV) acetate, acetic acid, T= 80 °C Criegee; Kraft; Rank; Justus Liebigs Annalen der Chemie; vol. 507; (1933); p. 159,167

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

105/438

2018-03-11 22:07:32


View in Reaxys With aluminium benzyl alcoholate, 3-phenyl-propenal Davies; Hodgson; Journal of the Society of Chemical Industry, London; vol. 62; (1943); p. 109 View in Reaxys With air, Leiten ueber eine gluehende Platinspirale Trillat; Bulletin de la Societe Chimique de France; vol. <3> 29; (1903); p. 43 View in Reaxys Leiten durch auf 800-820grad erhitzte Kupferroehren Ipatjew; Chemische Berichte; vol. 35; (1902); p. 1061;; Chemische Berichte; vol. 36; (1903); p. 1997,1998 View in Reaxys With manganese dioxide sulfate, sulfuric acid, T= 40 - 50 °C Patent; Bad. Anilin- u. Sodaf.; DE175295 View in Reaxys With oxygen, platinum Sneeden; Turner; Journal of the American Chemical Society; vol. 77; (1955); p. 190 View in Reaxys With pyridine, tert-butylhypochlorite Grob; Schmid; Helvetica Chimica Acta; vol. 36; (1953); p. 1763,1769 View in Reaxys With pyridine, N-chloro-succinimide Grob; Schmid; Helvetica Chimica Acta; vol. 36; (1953); p. 1763,1769 View in Reaxys Hebbelynck; Martin; Bulletin des Societes Chimiques Belges; vol. 60; (1951); p. 54,65 View in Reaxys With dipotassium peroxodisulfate Horii et al.; Yakugaku Zasshi; vol. 76; (1956); p. 1101; ; (1957); p. 3553 View in Reaxys With selenium(IV) oxide, Erhitzen des Reaktionsprodukts Weygand et al.; Chemische Berichte; vol. 83; (1950); p. 394,398 View in Reaxys With di-tert-butyl chromate Oppenauer; Oberrauch; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 37; (1949); p. 246,259 View in Reaxys With ruthenium tetroxide Berkowitz; Rylander; Journal of the American Chemical Society; vol. 80; (1958); p. 6682 View in Reaxys With carbon dioxide, palladium Wieland; Chemische Berichte; vol. 45; (1912); p. 493 View in Reaxys With aluminium trichloride, chloral Frankforter; Kritchevsky; Journal of the American Chemical Society; vol. 36; (1914); p. 1522 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

106/438

2018-03-11 22:07:32


With ammonia, T= 380 °C , Leiten ueber Thoriumdioxyd Mailhe; Chemiker-Zeitung, Chemische Apparatur; vol. 34; (1910); p. 1184 View in Reaxys Sabatier; Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 153; (1911); p. 162 View in Reaxys With oxygen, T= 320 - 330 °C , p= 30 - 40Torr , Leiten ueber Silberasbest Moureu; Mignonac; Bulletin de la Societe Chimique de France; vol. <4> 29; (1921); p. 99; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 260 View in Reaxys Moureu; Mignonac; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 260; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 171; (1920); p. 652 View in Reaxys With potassium bromate, hydrogen bromide, T= 50 - 80 °C Farkas; Schaechter; Journal of the American Chemical Society; vol. 71; (1949); p. 2828; ; (1948); p. 7313 View in Reaxys T= 300 °C , Leiten ueber fein verteiltes Kupfer Sabatier; Senderens; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 136; (1903); p. 984 View in Reaxys With pyridine, oxygen, copper(II) nitrate Patent; Shell Devel.Co.; US2883426; (1957) View in Reaxys With manganese(IV) oxide Sugasawa; Mizukami; Pharmaceutical Bulletin; vol. 2; (1954); p. 341 View in Reaxys With chromium(VI) oxide, chloro-trimethyl-silane, 1.) CH2Cl2, room temp. 2.) room temp., 45 min., Yield given. Multistep reaction Aizpurua, J. M.; Palomo, Claudio; Tetrahedron Letters; vol. 24; nb. 40; (1983); p. 4367 - 4370 View in Reaxys With iodosylbenzene in benzene, Time= 5h, T= 80 °C , Yield given Barton, Derek H. R.; Godfrey, Christopher R. A.; Morzycki, Jacek W.; Motherwell, William B.; Stobie, Alan; Tetrahedron Letters; vol. 23; nb. 9; (1982); p. 957 - 960 View in Reaxys With zinc(II) cation, oxygen, 2,4,7-trimethyl-10-benzylquinolt;8,7-ggt;pteridine-9,11(7H,10H)-dione, Time= 20h, Irradiation, Yield given Shinkai, Seiji; Nakao, Hideki; Ueda, Kaori; Manabe, Osamu; Tetrahedron Letters; vol. 25; nb. 46; (1984); p. 5295 - 5298 View in Reaxys 20 % Chromat.

With tert.-butylhydroperoxide, bis(acetylacetonate)oxovanadium in benzene, Time= 6h, T= 80 °C Kaneda, Kiyotomi; Kawanishi, Yasuyuki; Jitsukawa, Koichiro; Teranishi, Shiichiro; Tetrahedron Letters; vol. 24; nb. 45; (1983); p. 5009 - 5010 View in Reaxys

21 % Chromat.

With 2-Diazobenzophenon-Kation, 2,4,6-trifluoromethylpyridine, RuL3 (2+) in acetonitrile, Time= 1h, Irradiation Cano-Yelo, Herminia; Deronzier, Alain; Tetrahedron Letters; vol. 25; nb. 48; (1984); p. 5517 - 5520

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

107/438

2018-03-11 22:07:32


View in Reaxys 100 % Chromat.

With aluminum oxide, potassium ferrate(VI), copper(II) sulfate in benzene, Time= 2h, Ambient temperature Kim, Kwan Soo; Song, Yang Heon; Lee, Nam Ho; Hahn, Chi Sun; Tetrahedron Letters; vol. 27; nb. 25; (1986); p. 2875 - 2878 View in Reaxys

92 % Chromat.

With osmium(VIII) oxide, acetic acid in diethyl ether, Time= 30h, Ambient temperature Maione, Anna Maria; Romeo, Aurelio; Synthesis; nb. 11; (1984); p. 955 - 957 View in Reaxys With diphenylantimony(III) bromide, bromine, 1.) benzene, 2 h, room temp., 2.) 10 min, Yield given. Multistep reaction Yaozeng Huang; Yanchang Shen; Chen Chen; Synthesis; nb. 6/7; (1985); p. 651 - 652 View in Reaxys With hydrogenchloride, ammonium molybdate in dimethyl sulfoxide, Time= 4h, Heating, Yield given Sur, Bimanesh; Adak, Mohini Mohan; Pathak, Tanmoy; Hazra, Banasri; Banerjee, Amalendu; Synthesis; nb. 6/7; (1985); p. 652 - 654 View in Reaxys

98 % Chromat.

With N-iodo-succinimide, tetra-(n-butyl)ammonium iodide in dichloromethane, Time= 1h, Ambient temperature Hanessian, Stephen; Wong, David Hin-chor; Therien, Michel; Synthesis; nb. 5; (1981); p. 394 - 396 View in Reaxys With N-Bromosuccinimide, perchloric acid in acetic acid, T= 40 °C , other equiv of oxidant, other equiv of substrate, other temperature, with or without HgCl2, Hg(ClO4)2, succinimide, various times Gopalakrishnan, G.; Pai, B. R.; Venkatasubramanian, N.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 19; nb. 4; (1980); p. 293 - 296 View in Reaxys With trans-lt;Ru(VI)(dmpipy)2O2gt;lt;ClO4gt;2 in acetonitrile, Time= 4h, Ambient temperature Che, Chi-Ming; Leung, Wai-Ho; Li, Chi-Keung; Poon, Chung-Kwong; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 3; (1991); p. 379 - 384 View in Reaxys With sodium hypochlorite, ruthenium(IV) oxide in tetrachloromethane, water, T= 60 - 65 °C , Yield given Ogibin, Yu. N.; Ilovaiskii, A. I.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 40; nb. 1.1; (1991); p. 99 - 105; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1991); p. 115 - 121 View in Reaxys

97 % Turn- With air, Na5PV2Mo10O40 on activated carbon in toluene, Time= 22h, T= 100 °C , p= 760Torr ov. Neumann, Ronny; Levin, Michal; Journal of Organic Chemistry; vol. 56; nb. 19; (1991); p. 5707 - 5710 View in Reaxys With polybromochloride in dichloromethane, Time= 18h, T= 30 °C , polybromochloride was anodically generated, Yield given Konno, Akinori; Fukui, Kouta; Fuchigami, Toshio; Nonaka, Tsutomu; Tetrahedron; vol. 47; nb. 4/5; (1991); p. 887 - 894 View in Reaxys With 2,6-dimethylpyridine, sodium perchlorate in acetonitrile, Time= 12h, preparative, potential-controlled electrolysis; graphite felt electrode coated with 4-amino-2,2,6,6-tetramethylpiperidinyl-1-oxyl (4-amino-TEMPO), Yield given Kashiwagi, Yoshitomo; Ohsawa, Akio; Osa, Tetsuo; Ma, Zhenkun; Bobbitt, James M.; Chemistry Letters; nb. 4; (1991); p. 581 - 584

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

108/438

2018-03-11 22:07:32


View in Reaxys 60 % Spectr.

With ammonium persulfate, sulfuric acid, sodium dodecyl-sulfate, cerium(IV) ammonium sulphate, silver nitrate in cyclohexane, water, Time= 5h, T= 50 °C , two phases Skarzewski, Jacek; Tetrahedron; vol. 40; nb. 23; (1984); p. 4997 - 5000 View in Reaxys With hydrogenchloride, oxygen, sodium L-ascorbate, 5,10,15,20-tetraphenyl-21 H,23- H-porphine manganese(III)chloride in benzene, pH=8.5, pO2 = 1 atm Fontecave, Marc; Mansuy, Daniel; Tetrahedron; vol. 40; nb. 21; (1984); p. 4297 - 4312 View in Reaxys With potassium hydroxide, 3-methyl-10-ethyl-5-deazaisoalloxazine in water, N,N-dimethyl-formamide, Time= 1h, T= 90 °C Yoneda, Fumio; Mori, Kenya; Matsuo, Sawako; Kadokawa, Yoko; Sakuma, Yoshiharu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 1836 - 1839 View in Reaxys With sodium chromate(VI), sulfuric acid in water Thyrion, F. C.; Bulletin des Societes Chimiques Belges; vol. 93; nb. 4; (1984); p. 281 - 290 View in Reaxys With sodium dichromate in water, 1,2-dichloro-ethane Thyrion, F. C.; Bulletin des Societes Chimiques Belges; vol. 93; nb. 4; (1984); p. 281 - 290 View in Reaxys

91 % Chromat.

With tert.-butylhydroperoxide, zirconyl acetate in tetrachloromethane, Time= 1h, Heating Kaneda, Kiyotomi; Kawanishi, Yasuyuki; Teranishi, Shiichiro; Chemistry Letters; (1984); p. 1481 - 1482 View in Reaxys

61 % Chromat.

With manganese(IV) oxide in acetonitrile, Time= 8h, T= 17 °C Kimura, Takahide; Fujita, Mitsue; Ando, Takashi; Chemistry Letters; nb. 8; (1988); p. 1387 - 1388 View in Reaxys

100 % Chromat.

With 1-oxo-4-methoxy-2,2,6,6-tetramethylpiperidinium chloride in dichloromethane, Time= 0.0166667h, T= 25 °C Miyazawa, Takeo; Endo, Takeshi; Shiihashi, Shigeo; Okawara, Makoto; Journal of Organic Chemistry; vol. 50; nb. 8; (1985); p. 1332 - 1334 View in Reaxys With ruthenium(IV) oxide, lt;NBu4gt;4lt;W10O32gt; in acetonitrile, Time= 3h, Irradiation, Yield given Yamase, Toshihiro; Usami, Takashi; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1988); p. 183 - 190 View in Reaxys

100 % Chromat.

With copper diacetate, oxygen, lt;NBu4gt;lt;Os(N)(CH2SiMe3)2(CrO4)gt; in acetonitrile, Time= 72h, T= 70 °C Zhang, Naijie; Mann, Charles M.; Shapley, Patricia A.; Journal of the American Chemical Society; vol. 110; nb. 19; (1988); p. 6591 - 6592 View in Reaxys

95 % Turn- With sodium carbonate in dichloromethane, acetonitrile, T= 15 °C , electrolysis ov. Brinkhaus, Karl-Heinz Grosse; Steckham, Eberhard; Schmidt, Werner; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 37; nb. 6; (1983); p. 499 - 508 View in Reaxys With tripropylammonium fluorochromate (VI) in nitrobenzene, acetonitrile, T= 44.9 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

109/438

2018-03-11 22:07:32


Bhattacharjee; Chaudhuri; Dasgupta; Bulletin of the Chemical Society of Japan; vol. 57; nb. 1; (1984); p. 258 260 View in Reaxys 96 % Chromat.

With lt;MoO(O2)2C5H4N(O)COOgt;Bu4N in 1,2-dichloro-ethane, Time= 5h, T= 50 °C Bortolini, O.; Campestrini, S.; Furia, F. Di; Modena, G.; Valle, G.; Journal of Organic Chemistry; vol. 52; nb. 24; (1987); p. 5467 - 5469 View in Reaxys With oxygen, dihydrogen hexachloroplatinate, copper dichloride in acetone, Time= 24h, Ambient temperature, Irradiation, Yield given Cameron, Randy E.; Bocarsly, Andrew B.; Journal of the American Chemical Society; vol. 107; nb. 21; (1985); p. 6116 - 6117 View in Reaxys With dihydrogen peroxide, lt;C5H5N(CH2)15CH3gt;4Klt;IMo6O24gt; in water, 1,2-dichloro-ethane, Time= 3h, T= 50 °C , Yield given Dengel, Andrew C.; El-Hendawy, Ahmed M.; Griffith, William P.; Mostafa, Sahar I.; Williams, David J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 24; (1992); p. 3489 - 3496 View in Reaxys

40 % Chromat.

With manganese(IV) oxide, bentonite, Time= 0.0166667h, T= 175 °C , Irradiation Martinez, Luis A.; Garcia, Olivia; Delgado, Francisco; Alvarez, Cecilio; Patino, Rocio; Tetrahedron Letters; vol. 34; nb. 33; (1993); p. 5293 - 5294 View in Reaxys With dihydrogen peroxide, iron(II) in acetonitrile, Yield given Sugimoto, Hiroshi; Sawyer, Donald T.; Journal of the American Chemical Society; vol. 106; nb. 15; (1984); p. 4283 - 4285 View in Reaxys

83 % Chromat.

With trichloromelamine in dichloromethane, Time= 20h, Ambient temperature Kondo, Shuji; Ohira, Mari; Kawasoe, Shinya; Kunisada, Hideo; Yuki, Yasuo; Journal of Organic Chemistry; vol. 58; nb. 18; (1993); p. 5003 - 5004 View in Reaxys

100 % Chromat.

With lt;RuIV(terpy)(dcbipy)Ogt;lt;ClO4gt;2 in acetonitrile, Time= 4h, Ambient temperature Che, Chi-Ming; Ho, Clare; Lau, Tai-Chu; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 8; (1991); p. 1901 - 1908 View in Reaxys With lt;Bu4Ngt;4lt;Pt2(P2O5H2)4gt; in neat (no solvent), Time= 7h, Irradiation, Yield given Che, Chi-Ming; Lee, Wai-Man; Cho, Kar-Cheong; Harvey, Pierre D.; Gray, Harry B.; Journal of Physical Chemistry; vol. 93; nb. 8; (1989); p. 3095 - 3099 View in Reaxys With perchloric acid, mercury(II) diacetate, N-bromoacetamide in water, acetic acid, Time= 12h, Yield given Negi, Suresh C.; Bhatia, Indu; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 11; (1981); p. 3966 - 3980 View in Reaxys

40 % Spectr.

With dihydrogen peroxide, lt;N(C6H13)4gt;3lt;PO4lt;WO(O2)2gt;4gt; in benzene, Time= 3h, Ambient temperature Dengel, Andrew C.; Griffith, William P.; Parkin, Bernardeta C.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 18; (1993); p. 2683 - 2688 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

110/438

2018-03-11 22:07:32


With L-ascorbic acid sodium salt, oxygen, Aliquat 336, 5,10,15,20-tetraphenyl-21 H,23- H-porphine manganese(III)chloride, T= 20 °C , p= 760Torr , pH 8.5 (tris buffer), Yield given Mansuy, Daniel; Fontecave, Marc; Bartoli, Jean-Francois; Journal of the Chemical Society, Chemical Communications; nb. 6; (1983); p. 253 - 254 View in Reaxys With lithium perchlorate, N,N,N',N'-tetrakis(phenyl)-1,4-benzenediamine cation radical in acetonitrile, Irradiation, electrolysis Moutet, Jean-Claude; Reverdy, Gilbert; Journal of the Chemical Society, Chemical Communications; nb. 12; (1982); p. 654 - 655 View in Reaxys 82 % Chromat.

With oxygen, 2-ethoxycarbonyl-1-cyclopentanone, cobalt(II) [bis(salicylidene-N-(methyl-3-hydroxypropionate))] in acetonitrile, T= 60 - 70 °C Punniyamurthy; Iqbal, Javed; Tetrahedron Letters; vol. 35; nb. 23; (1994); p. 4007 - 4010 View in Reaxys

83 % Chromat.

With tetrabutylammonium perchlorate, bromide in dichloromethane, Ambient temperature, indirect electrooxidation Takiguchi, Tsuyoshi; Nonaka, Tsutomu; Bulletin of the Chemical Society of Japan; vol. 60; nb. 9; (1987); p. 3137 3142 View in Reaxys

84 % Spectr.

With lt;Ph4Asgt;2lt;OsVI(CN)4(O)2gt; in acetonitrile, Time= 4.5h, T= 25 °C , Irradiation Wing-Wah Yam, Vivian; Che, Chi-Ming; Tang, Wai-Tong; Journal of the Chemical Society, Chemical Communications; nb. 2; (1988); p. 100 - 102 View in Reaxys

100 % Chromat.

With silver tetrafluoroborate, bis(quinuclidine)bromine(I) tetrafluoroborate in dichloromethane, Time= 0.116667h Blair, Larry K.; Parris, Kevin D.; Lee, On Fai Daniel; Jenkins, Karen F.; Feese, Robin Chaney; et al.; Journal of Organic Chemistry; vol. 51; nb. 26; (1986); p. 5454 - 5456 View in Reaxys With N-Bromosuccinimide, tetra-(n-butyl)ammonium iodide, 1.) acetone, Et2O, freezer, overnight, 2.) CH3CN, irradiated, 1 h, Yield given. Multistep reaction Beebe, Thomas R.; Boyd, Leslie; Fonkeng, Steve B.; Horn, Jamie; Mooney, Teresa M.; et al.; Journal of Organic Chemistry; vol. 60; nb. 20; (1995); p. 6602 - 6603 View in Reaxys With 2,4,6-trimethylphenyl bromide, triphenylphosphine in water, N,N-dimethyl-formamide, acetone, Time= 7h, T= 120 °C , Yield given Wilson, Noel S.; Keay, Brian A.; Journal of Organic Chemistry; vol. 61; nb. 9; (1996); p. 2918 - 2919 View in Reaxys

86 % Chromat.

With dihydrogen peroxide, (cetylpyridinium)8CeW10O36 in chloroform, Time= 6h, T= 61 °C Shiozaki; Kominami; Kera; Synthetic Communications; vol. 26; nb. 9; (1996); p. 1663 - 1668 View in Reaxys

99 % Chromat.

With N-chloro-succinimide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, tetrabutyl-ammonium chloride, sodium hydrogencarbonate, potassium carbonate in dichloromethane, Time= 2h, Ambient temperature, pH 8.6 Einhorn, Jacques; Einhorn, Cathy; Ratajczak, Fabien; Pierre, Jean-Louis; Journal of Organic Chemistry; vol. 61; nb. 21; (1996); p. 7452 - 7454 View in Reaxys With N-hydroxy-o-benzenedisulphonimide in acetonitrile, Time= 5h, T= 60 °C , Yield given Barbero, Margherita; Degani, Lacopo; Fochi, Rita; Perracino, Paolo; Journal of Organic Chemistry; vol. 61; nb. 25; (1996); p. 8762 - 8764

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

111/438

2018-03-11 22:07:32


View in Reaxys 67 % Chromat.

With acetyl nitrate on montmorillonite K10, Time= 2h, Ambient temperature De Oliveira Filho; Moreira; Moran, Paulo J. S.; Rodrigues, J. Augusto R.; Tetrahedron Letters; vol. 37; nb. 29; (1996); p. 5029 - 5032 View in Reaxys With tert.-butylhydroperoxide, Mn2O3(N,N',N''-trimethyl-1,4,7-triazacyclononane)2 in acetone, Time= 2.5h, Ambient temperature, Yield given Zondervan, Charon; Hage, Ronald; Feringa, Ben L.; Chemical Communications; nb. 5; (1997); p. 419 - 420 View in Reaxys

89 % Chromat.

With bis(2-methoxycarbonylphenyl) diselenide, N-chloro-p-chlorobenzenesulfonamide sodium salt in 1,2-dichloroethane, Time= 15h, T= 80 °C Onami, Tetsuo; Ikeda, Masanori; Woodard, Scott S.; Bulletin of the Chemical Society of Japan; vol. 69; nb. 12; (1996); p. 3601 - 3605 View in Reaxys With polymer supported perruthenate in dichloromethane Hinzen, Berthold; Ley, Steven V.; Journal of the Chemical Society - Perkin Transactions 1; nb. 1; (1998); p. 1 - 2 View in Reaxys

90 % Chromat.

With palladium diacetate, oxygen in dimethyl sulfoxide, Time= 48h, T= 80 °C Peterson, Karl P.; Larock, Richard C.; Journal of Organic Chemistry; vol. 63; nb. 10; (1998); p. 3185 - 3189 View in Reaxys With silica gel, ferric nitrate in hexane, Time= 4h, Heating Khadilkar, Bhushan; Borkar, Shobha; Synthetic Communications; vol. 28; nb. 2; (1998); p. 207 - 212 View in Reaxys With oxygen, polymer supported perruthenate in toluene, Time= 0.5h, T= 75 °C , Yield given Hinzen, Berthold; Lenz, Roman; Ley, Steven V.; Synthesis; nb. 7; (1998); p. 977 - 979 View in Reaxys With pyridine, oxygen, palladium diacetate in toluene, Time= 2h, T= 80 °C , Yield given Nishimura, Takahiro; Onoue, Tomoaki; Ohe, Kouichi; Uemura, Sakae; Tetrahedron Letters; vol. 39; nb. 33; (1998); p. 6011 - 6014 View in Reaxys With tert.-butylhydroperoxide, tetrabutylammomium bromide, copper dichloride in dichloromethane, water, T= 25 °C , Yield given Rothenberg, Gadi; Feldberg, Liron; Wiener, Harold; Sasson, Yoel; Journal of the Chemical Society. Perkin Transactions 2; nb. 11; (1998); p. 2429 - 2434 View in Reaxys bei der elektrolytischen Oxydation Koidzumi; Memoirs of the College of Science, Kyoto Imperial University; vol. <A> 11; p. 383; Chem. Zentralbl.; vol. 99; nb. II; (1928); p. 2331 View in Reaxys beim Leiten ueber eine gluehende Platinspirale Trillat; Bulletin de la Societe Chimique de France; vol. <3> 29; (1903); p. 43 View in Reaxys

100 % Chromat.

With lt;RuV(N4O)Ogt;(ClO4)2 in acetonitrile, Time= 0.5h, T= 25 °C , var. substrates, Product distribution

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

112/438

2018-03-11 22:07:32


Che, Chi-Ming; Yam, Vivian Wing-Wah; Mak, Thomas C. W.; Journal of the American Chemical Society; vol. 112; nb. 6; (1990); p. 2284 - 2291 View in Reaxys With diperiodatonickelate(IV) ion, sodium perchlorate in sodium hydroxide, T= 26.9 °C , Mechanism Khan, Jaffar Ali; Chandraiah, U.; Kumar, B. Kishore; Kandlikar, Sushama; Indian Journal of Chemistry, Section A: Inorganic, Bio-inorganic, Physical, Theoretical & Analytical Chemistry; vol. 29; nb. 3; (1990); p. 241 - 244 View in Reaxys With diperiodatonickelate(IV) ion, sodium perchlorate in sodium hydroxide, T= 21.9 - 41.9 °C , ΔH(excit.), ΔG(excit.), ΔS(excit.), ΔH, ΔG, ΔS, Rate constant, Equilibrium constant, Thermodynamic data Khan, Jaffar Ali; Chandraiah, U.; Kumar, B. Kishore; Kandlikar, Sushama; Indian Journal of Chemistry, Section A: Inorganic, Bio-inorganic, Physical, Theoretical & Analytical Chemistry; vol. 29; nb. 3; (1990); p. 241 - 244 View in Reaxys With {Ru(2,2':6',2''-terpyridine)(N,N,N',N'tetramethylethylenediamine)O}(ClO4)2, T= 25 °C Ho, Clare; Che, Chi-Ming; Lau, Tai-Chu; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 3; (1990); p. 967 - 970 View in Reaxys With flavin 1, flavin 2, effect of metal concentration discussed, Rate constant Shinkai, Seiji; Nakao, Hideki; Ueda, Kaori; Manabe, Osamu; Tetrahedron Letters; vol. 25; nb. 46; (1984); p. 5295 - 5298 View in Reaxys 39 % Chromat.

With potassium carbonate, 10-methyl-2H,3H,4H,10H-pyrimido[4,5-b]quinoline-2,4-di-one, Time= 1h, T= 90 °C , other time, aerobic condition, other 10-alkyl-5-deazaflavin, Product distribution Kuroda, Kazunori; Nagamatus, Tomohisa; Sakuma, Yoshiharu; Yoneda, Fumio; Journal of Heterocyclic Chemistry; vol. 19; (1982); p. 929 - 931 View in Reaxys With poly(vinylpyridiniumdichromate) in cyclohexane, Time= 18h, T= 70 °C , other solvent, times; var. primary and secondary alcohols, Product distribution Frechet, Jean M.J.; Darling, Pauline; Farrall, M. Jean; Journal of Organic Chemistry; vol. 46; nb. 8; (1981); p. 1728 - 1730 View in Reaxys With Clay-Supported Iron(III) Nitrate in pentane, Time= 4h, Heating, other oxidizing agent, conversion to benzaldehyde Cornelis, Andre; Laszlo, Pierre; Synthesis; nb. 10; (1980); p. 849 - 850 View in Reaxys With N-Bromosuccinimide, perchloric acid in acetic acid, T= 40 °C , other equiv of oxidant, other equiv of substrate, with or without Hg(OAc)2, HgCl2, succinimide, Mechanism, Rate constant Gopalakrishnan, G.; Pai, B. R.; Venkatasubramanian, N.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 19; nb. 4; (1980); p. 293 - 296 View in Reaxys With sodium hypochlorite, 1,4-diaza-bicyclo[2.2.2]octane, N-benzyl-N,N,N-triethylammonium chloride in dichloromethane, water, Time= 3h, T= 38 - 40 °C , Mechanism Mathur, S. N.; Rao, S. Nagabushan; Bhalerao, U. T.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 27; nb. 1-12; (1988); p. 666 View in Reaxys With Me2Se*NCS, 1,8-diazabicyclo[5.4.0]undec-7-ene in toluene, Time= 4h, Ambient temperature, other reagents, other solvents, other bases; various prim. and sec. alcohols, Product distribution Takaki, Ken; Yasumura, Masateru; Negoro, Kenji; Journal of Organic Chemistry; vol. 48; nb. 1; (1983); p. 54 - 57

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

113/438

2018-03-11 22:07:32


View in Reaxys With lt;RuVL(O)gt;2+-complex lt;HL = lt;2-hydroxy-2-(2-pyridyl)ethylgt;bislt;2-(2-pyridyl)ethylgt;aminegt; in perchloric acid, T= 24.9 °C , ΔH(excit.), ΔS(excit.), Mechanism, Rate constant Che, Chi-Ming; Ho, Clare; Lau, Tai-Chu; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 5; (1991); p. 1259 - 1263 View in Reaxys With lt;Ru(VI)(dmbipy)2O2gt;lt;ClO4gt;2 in acetonitrile, Time= 4h, T= 298 °C , activation enthalpy, activation entropy; other temperature, kinetic isotope effect, Kinetics, Thermodynamic data Che, Chi-Ming; Leung, Wai-Ho; Li, Chi-Keung; Poon, Chung-Kwong; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 3; (1991); p. 379 - 384 View in Reaxys With oxygen, TMP-BDPox in dichloromethane, water, Time= 8h, Ambient temperature, Irradiation, other alcohols; var. catalyst; effect of pH and irradiation, Product distribution, Kinetics Suzuki, Toshiaki; Iizuka, Kenzo; Nabeshima, Tatsuya; Yano, Yumihiko; Chemistry Letters; nb. 9; (1990); p. 1497 - 1500 View in Reaxys 97 % Turn- With air, Na5PV2Mo10O40 on activated carbon in toluene, Time= 22h, T= 100 °C , p= 760Torr ov. Neumann, Ronny; Levin, Michal; Journal of Organic Chemistry; vol. 56; nb. 19; (1991); p. 5707 - 5710 View in Reaxys With quinolinium dichromate(VI) in N,N-dimethyl-formamide, T= 29.9 - 49.9 °C , dependence on concentration of reactants, also addition of aq. HCl; ΔH(excit.), ΔG(excit.), ΔS(excit.), Kinetics, Thermodynamic data Dey, Doyamoy; Mahanti, Mahendra K.; Journal of Organic Chemistry; vol. 55; nb. 23; (1990); p. 5848 - 5850 View in Reaxys With polybromochloride in dichloromethane, Time= 18h, T= 30 °C , polybromochloride was anodically generated from Bu4ClO4 and Bu4NBr (ex-cell precisely-controlled electrooxidation), Product distribution Konno, Akinori; Fukui, Kouta; Fuchigami, Toshio; Nonaka, Tsutomu; Tetrahedron; vol. 47; nb. 4/5; (1991); p. 887 - 894 View in Reaxys With 2,6-dimethylpyridine, sodium perchlorate in acetonitrile, electrocatalytic oxidation on graphite felt electrode coated with 4-amino-2,2,6,6-tetramethylpiperidinyl-1-oxyl (4-amino-TEMPO), current efficiency, turnover number, Mechanism, Product distribution Kashiwagi, Yoshitomo; Ohsawa, Akio; Osa, Tetsuo; Ma, Zhenkun; Bobbitt, James M.; Chemistry Letters; nb. 4; (1991); p. 581 - 584 View in Reaxys With potassium bromate in hydrogenchloride, acetic acid, ΔH(excit), ΔS(excit), effect of hydrochloric acid and acetic acid concentration, influence of temperature, Kinetics, Mechanism, Thermodynamic data Gupta, Kalyan Kali Sen; Kumar, Saroj Chandra; Sen, Pratik Kumar; Banerjee, Amalendu; Tetrahedron; vol. 44; nb. 8; (1988); p. 2225 - 2232 View in Reaxys 40.8 % Chromat.

With peracetic acid, cobalt(II) acetate in acetic acid, Time= 2h, T= 80 °C , other reagent, temperature and time, Product distribution Morimoto, Takashi; Hirano, Masao; Wachi, Michinori; Murakami, Tadashi; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1984); p. 1949 - 1952 View in Reaxys With 2,4-dimethylpyrido[5,6-h](10-methyl)-isoalloxazine, oxygen, Zr(4+)-flavin in acetonitrile, T= 30 °C , Rate constant Shinkai, Seiji; Ishikawa, Yu-ichi; Manabe, Osamu; Chemistry Letters; (1982); p. 809 - 812

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

114/438

2018-03-11 22:07:32


View in Reaxys With perchloric acid, potassium hexacyanoferrate(III) in water, acetic acid, T= 55 °C , Rate constant, Mechanism Bhattacharjee, A. K.; Mahanti, M. K.; Bulletin de la Societe Chimique de France; vol. 1; nb. 11-12; (1983); p. 270 272 View in Reaxys With chloramine-B, effect of temp., in H2O/D2O (kinetic isotope effect), Rate constant Mukherjee, Jogeshwar; Banerji, Kalyan K.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 676 - 678 View in Reaxys With chloramine-B in water, acetic acid, ΔH(excit.), ΔG(excit.), ΔS(excit.), Rate constant, Thermodynamic data Mukherjee, Jogeshwar; Banerji, Kalyan K.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 676 - 678 View in Reaxys 84 % Chromat.

With potassium tert-butylate, 3-hydroxy-N-methylacridinium iodide, Time= 8h, T= 80 °C , var.: oxidant: none, Ac(1+), in the dark, Product distribution, Mechanism Shinkai, Seiji; Hamada, Hisatake; Kuroda, Hideo; Manabe, Osamu; Chemistry Letters; (1980); p. 1235 - 1238 View in Reaxys

141 %

With air, 3-methyl-5-deaza-10-oxaflavin, Time= 10h, T= 90 °C , oxidation by various 5-deaza-10-oxaflavins, Product distribution Yoneda, Fumio; Hirayama, Ryoichi; Yamashita, Machiko; Chemistry Letters; (1980); p. 1157 - 1160 View in Reaxys With potassium dichromate, perchloric acid, sodium perchlorate, manganese(II) in water, T= 35 °C , ΔH(excit.), ΔS(excit.), Kinetics, Mechanism, Thermodynamic data Sengupta, Kalyan Kali; Samanta, Tapashi; Basu, Samarendra Nath; Tetrahedron; vol. 42; nb. 2; (1986); p. 681 686 View in Reaxys With tris(2,2'-bipyridine)nickel(III)(3+) in perchloric acid, water, ΔH (excite); ΔS (excite), Kinetics, Mechanism, Thermodynamic data Fox, David; Wells, Cecil F.; Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases; vol. 78; (1982); p. 1525 - 1532 View in Reaxys

100 % Chromat.

With potassium carbonate, 8-fluoro-3,10-dimethyl-5-deazaflavin, Time= 10h, T= 90 °C , time dependence, various 5deazaflavins; dehydrogenation of alcohols by 5-deazaflavins as autorecycling oxidizing agents, Product distribution Yoneda, Fumio; Mori, Kenya; Matsuo, Sawako; Kadokawa, Yoko; Sakuma, Yoshiharu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 1836 - 1839 View in Reaxys

100 % Chromat.

With sodium nitrite in water, trifluoroacetic acid, T= 20 °C , prototype reaction, oth. alcohols, oth. reagent, Mechanism Rodkin, M. A.; Shtern, M. M.; Cheprakov, A. V.; Makhon'kov, D. I.; Merdaleishvili, R. E.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 3; (1988); p. 434 - 440; Zhurnal Organicheskoi Khimii; vol. 24; nb. 3; (1988); p. 488 - 495 View in Reaxys With tripropylammonium fluorochromate (VI) in dimethyl sulfoxide, T= 24.9 °C , ΔH(excit.), ΔS(excit.); mechanism; effect of substrate concentrations; other solvents; var. benzyl alcohols; kinetic isotope effect, Rate constant, Thermodynamic data, Kinetics Banerji, Kalyan K.; Journal of Organic Chemistry; vol. 53; nb. 10; (1988); p. 2154 - 2159 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

115/438

2018-03-11 22:07:32


With sodium dichromate, sulfuric acid in water, T= 18.6 - 42.2 °C , Kinetics, Mechanism Thyrion, F. C.; Bulletin des Societes Chimiques Belges; vol. 93; nb. 4; (1984); p. 281 - 290 View in Reaxys With sodium dichromate, sulfuric acid in water, 1,2-dichloro-ethane, T= 18.6 - 42.2 °C , Kinetics, Mechanism Thyrion, F. C.; Bulletin des Societes Chimiques Belges; vol. 93; nb. 4; (1984); p. 281 - 290 View in Reaxys With ditellurato cuprate(III), ruthenium trichloride, T= 31.9 °C , in alkaline medium, Kinetics, Rate constant Bal Reddy, K.; Sethuram, B.; Navaneeth Rao, T.; Bulletin des Societes Chimiques Belges; vol. 90; nb. 10; (1981); p. 1017 - 1022 View in Reaxys 100 % Spectr.

in benzene, Time= 2h, T= 70 °C , Comparison of reaction efficiencies of silica gel supported KMnO4, Product distribution Al Jazzaa, Abdulaziz; Clark, H. James; Robertson, Malcolm; Chemistry Letters; (1982); p. 405 - 408 View in Reaxys With hydroxocobalt(III) Schiff base in 1,2-dichloro-ethane, Time= 24h, T= 50 °C , Rate constant Nishinaga, Akira; Kondo, Toshiyuki; Matsuura, Teruo; Chemistry Letters; (1985); p. 1319 - 1322 View in Reaxys With perchloric acid, bromamine B in acetic acid, T= 24.9 - 44.9 °C , ΔH(excit.), ΔS(excit.), ΔG(excit.); effect of the concentration of perchloric acid (0.1-1.0 M), sodium N-bromobenzenesulfonamide (0.002-0.0125 M), benzenesulfonamide (0-0.01 M), acetic acid (0-70percent) on rate constant; kinetic isotope effect, Rate constant, Thermodynamic data Kothari, Seema; Banerji, Kalyan Kumar; Canadian Journal of Chemistry; vol. 63; (1985); p. 2726 - 2729 View in Reaxys

13 mmol

With lt;lt;(bpy)2Co(OH)gt;(ClO4)gt;, oxygen in acetonitrile, Time= 1h, T= 25 °C , p= 760Torr , var. time, temp., cobalt complex conc., and bases in <(bpy)2CoII(base)>2+ complexes; n-hexanol, Product distribution Sobkowiak, Andrzej; Sawyer, Donald T.; Journal of the American Chemical Society; vol. 113; nb. 25; (1991); p. 9520 - 9523 View in Reaxys With perchloric acid, oxochromium(IV), lithium perchlorate in water, T= 25 °C , Rate constant Scott, Susannah L.; Bakac, Andreja; Espenson, James H.; Journal of the American Chemical Society; vol. 114; nb. 11; (1992); p. 4205 - 4213 View in Reaxys With trans-lt;Ru(VI)L2O2gt;2+ in acetonitrile, T= 24.9 °C , other solvent, other catalysts; ΔH(excit.), ΔS(excit.), kinetic isotope effect, Mechanism, Rate constant, Thermodynamic data Che, Chi-Ming; Tang, Wai-Tong; Lee, Wai-On; Wong, Kwok-Yin; Lau, Tai-Chu; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 9; (1992); p. 1551 - 1556 View in Reaxys With lt;RuIV(terpy)(dcbipy)Ogt;lt;ClO4gt;2 in perchloric acid, T= 24.9 °C , ΔH(excit.), ΔS(excit.), Rate constant, Thermodynamic data Che, Chi-Ming; Ho, Clare; Lau, Tai-Chu; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 8; (1991); p. 1901 - 1908 View in Reaxys With cis-lt;RuVL1(Cl)Ogt;2+gt; in trifluoroacetic acid, various ruthenium oxo complexes, Rate constant Li, Chi-Keung; Tang, Wai-Tong; Che, Chi-Ming; Wong, Kwok-Yin; Wang, Ru-Ji; Mak, Thomas C. W.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 8; (1991); p. 1909 - 1914

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

116/438

2018-03-11 22:07:32


View in Reaxys With air, 2,4,6,8-tetraoxodipyrimidines, Time= 25h, T= 90 °C , various catalysts, Product distribution, Mechanism Nagamatsu, Tomohisa; Yamato, Hirotake; Ono, Masami; Takarada, Shigeki; Yoneda, Fumio; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 16; (1992); p. 2101 2110 View in Reaxys With cis-nitrous acid in sulfuric acid, T= 25 °C , acidity dependence, Rate constant Moodie, Roy B.; Richards, Stuart N.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1986); p. 1833 - 1838 View in Reaxys With {Ru(IV)O(2,2`-bipyridine)(PPh3)}(ClO4)2 in water, T= 25 °C , oxidation; other catalysts and solvents, Rate constant Marmion, Mary E.; Takeuchi, Kenneth J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1988); p. 2385 - 2392 View in Reaxys With pyridine, lead(IV) acetate, T= 29.9 - 44.9 °C , mechanism in the absence of pyridine, Mechanism Banerjee, S. K.; Shanker, R.; Zeitschrift fuer Physikalische Chemie (Leipzig); vol. 268; nb. 2; (1987); p. 409 - 412 View in Reaxys With potassium hydroxide, potassium metaperiodate, KNiIO6, T= 27.4 °C , ΔE(activ.), Rate constant, Thermodynamic data, Kinetics Murthy, C. P.; Sethuram, B.; Rao, T. Navaneeth; Zeitschrift fuer Physikalische Chemie (Leipzig); vol. 267; nb. 6; (1986); p. 1212 - 1218 View in Reaxys 0.2 %

With 1-benzyl-3-morpholinocarbonylpyridinium bromide, phenylmagnesium bromide, multistep, 1.) THF, 3h, room temperature, 2.) +DMF, 22 h, 25 deg C, Product distribution Shinkai, Seiji; Era, Hiroyuki; Tsuno, Takaharu; Manabe, Osamu; Bulletin of the Chemical Society of Japan; vol. 57; nb. 5; (1984); p. 1435 - 1436 View in Reaxys With tripropylammonium fluorochromate (VI) in nitrobenzene, acetonitrile, T= 29.9 °C , var. temp., var. solvent composition, var. ratio of reaction partners, Kinetics, Mechanism, Thermodynamic data Bhattacharjee; Chaudhuri; Dasgupta; Bulletin of the Chemical Society of Japan; vol. 57; nb. 1; (1984); p. 258 260 View in Reaxys With oxygen, dihydrogen hexachloroplatinate, copper dichloride in acetone, Time= 24h, Ambient temperature, Irradiation, various alcohols, various times, Mechanism, Quantum yield Cameron, Randy E.; Bocarsly, Andrew B.; Journal of the American Chemical Society; vol. 107; nb. 21; (1985); p. 6116 - 6117 View in Reaxys With {Ru(IV)(2,2'-bipyridine)2(pyridine)O}(2+) in water, acetone, T= 25 °C , var. solv.: 0.1M HClO4 or 10percent aq. MeOH, CH3CN; ΔH and -ΔS, Rate constant, Product distribution Roecker, Lee; Meyer, Thomas J.; Journal of the American Chemical Society; vol. 109; nb. 3; (1987); p. 746 - 754 View in Reaxys With trans-lt;RuIII(NO2)(PMe3)2(trpy)gt;(2+) in water, T= 5 °C , pH=6.8; ΔHexcit, ΔSexcit; further solvent: o-dichlorobenzene; further temperature: 22 deg C, Rate constant, Thermodynamic data Leising, Randolph A.; Takeuchi, Kenneth J.; Journal of the American Chemical Society; vol. 110; nb. 12; (1988); p. 4079 - 4080

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

117/438

2018-03-11 22:07:32


View in Reaxys With dihydrogen peroxide, tetrakis(acetonitrile)iron(II) perchlorate in acetonitrile, Time= 0.166667h, T= 5 °C , various peroxides Sugimoto, Hiroshi; Sawyer, Donald T.; Journal of the American Chemical Society; vol. 107; nb. 20; (1985); p. 5712 - 5716 View in Reaxys With ammonium cerium(IV) nitrate, trifluoroacetic acid in water, effect of oxidizing agent, Product distribution Rodkin, M. A.; Beletskaya, I. P.; Makhon'kov, D. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 34; nb. 1; (1985); p. 206 - 207; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1985); p. 218 - 220 View in Reaxys With perchloric acid, sodium N-chloromethylcarbamate in water, T= 29.9 °C , further temperatures, further objects of study: ΔH(activ.), ΔS(activ.), ΔG(activ.), Kinetics, Thermodynamic data, Mechanism Negi, S. C.; Mathur, Abha; Banerji, Kalyan K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 5; (1987); p. 399 - 401 View in Reaxys With ditelluratocuprate(III), hydroxide, T= 14.9 °C , other alkanols and aryl alcohols and oxidants, var. temp.; ΔH(excit.), ΔS(excit.), Rate constant, Mechanism, Thermodynamic data Gupta, Kalyan Kali Sen; Nandy, Bijay Kumar; Gupta, Shipra Sen; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 4; (1993); p. 767 - 772 View in Reaxys With ditelluratoargentate(III), hydroxide, T= 44.9 °C , ΔH(excit.), ΔS(excit.), Thermodynamic data, Rate constant Gupta, Kalyan Kali Sen; Nandy, Bijay Kumar; Gupta, Shipra Sen; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 4; (1993); p. 767 - 772 View in Reaxys With 2,4,7-trimethylquinolt;8,7-ggt;pteridine-9,11(7H,10H)-dione, copper dichloride in acetonitrile, T= 30 °C , var. metal salts, Rate constant Shinkai; Ishikawa; Manabe; Bulletin of the Chemical Society of Japan; vol. 56; nb. 6; (1983); p. 1694 - 1699 View in Reaxys With potassium permanganate, perchloric acid in water, acetic acid, Time= 12h, T= 24.9 - 44.9 °C , ΔH(excit.), ΔS(excit.), ΔG(excit.) at 298K, Thermodynamic data, Kinetics, Rate constant Mathur, Sandhya; Gupta, Anita; Banerji, Kalyan K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 27; nb. 7; (1988); p. 581 - 583 View in Reaxys With diperiodatoargentate(III), T= 34.9 °C , E(activ.), ΔS(excit.), other temperatures, Kinetics, Mechanism, Thermodynamic data Rao, P. Jaya Prakash; Sethuram, B.; Navaneeth Rao, T.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 20; nb. 7; (1981); p. 733 - 734 View in Reaxys With perchloric acid, mercury(II) diacetate, N-bromoacetamide in water, acetic acid, T= 29.9 °C , other temperatures; without Hg(OAc)2; kinetic and solvent isotope effects; ΔH(excit.), ΔS(excit.), ΔG(excit.), Kinetics, Mechanism, Thermodynamic data Negi, Suresh C.; Bhatia, Indu; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 11; (1981); p. 3966 - 3980 View in Reaxys With 3.67E-2M Ag(II) in phosphoric acid, T= 288 °C , E(activ.), ΔS(excit.), Kinetics, Thermodynamic data

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

118/438

2018-03-11 22:07:32


Jaya Prakash Rao, P.; Sethuram, B.; Navaneeth Rao, T.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 21; nb. 6; (1982); p. 612 - 614 View in Reaxys With potassium hexacyanoferrate(III), ruthenium trichloride, Rate constant Nath, Narendra; Singh, L. P.; Singh, R. P.; Journal of the Indian Chemical Society; vol. 58; (1981); p. 1204 - 1205 View in Reaxys With potassium bromate, sulfuric acid, mercury(II) diacetate in water, acetic acid, T= 30 - 45 °C , var. concn. of H2SO4; ΔE(excit.), ΔH(excit.), Kinetics, Thermodynamic data Vijayalakshmi; Sundaram, E. V.; Journal of the Indian Chemical Society; vol. 57; nb. 8; (1980); p. 800 - 803 View in Reaxys With perchloric acid, N-Chlorourethan in acetic acid, Time= 12h, T= 24.9 °C , ΔH(excit.), ΔS(excit.), ΔG(excit.), further temperature, in the dark, Kinetics, Rate constant, Mechanism Jain, Suman; Banerji, Kalyan K.; Bulletin of the Chemical Society of Japan; vol. 61; (1988); p. 1767 - 1772 View in Reaxys With potassium hydroxide, bis(dihydrogentellurato)-cuprate(III) in tert-butyl alcohol, T= 24.9 °C , also with argentate(III) oxidant; other temperatures; activation enthalpy and entropy, Rate constant, Kinetics, Thermodynamic data Gupta, Kalyan Kali Sen; Nandy, Bijay Kumar; Gupta, Shipra Sen; Journal of Organic Chemistry; vol. 59; nb. 4; (1994); p. 858 - 863 View in Reaxys With perchloric acid, oxygen, pteridine-2,4-(1H,3H)-dione in acetonitrile, T= 24.9 °C , Irradiation, other catalysts, Quantum yield Fukuzumi, Shunichi; Tanii, Kumiko; Tanaka, Toshio; Journal of the Chemical Society, Chemical Communications; nb. 13; (1989); p. 816 - 818 View in Reaxys With potassium hydroxide, osmium(VIII) oxide in water, T= 31.9 °C , ΔG(excit.), Thermodynamic data, Rate constant, Mechanism Somaiah, P. Veera; Reddy, K. Bal; Sethuram, B.; Rao, T. Navaneeth; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 27; nb. 10; (1988); p. 876 - 879 View in Reaxys With copper(I) complex of 1,4,7-triisopropyl-1,4,7-triazacyclononane, nitrogen(II) oxide, Ambient temperature, other Cu(I) complexes Mahapatra, Samiran; Halfen, Jason A.; Tolman, William B.; Journal of the Chemical Society, Chemical Communications; nb. 14; (1994); p. 1625 - 1626 View in Reaxys With dicopper(II) pyrazole in acetonitrile, T= 30 °C , Rate constant, Equilibrium constant Martens; Klein Gebbink; Feiters; Nolte; Journal of the American Chemical Society; vol. 116; nb. 13; (1994); p. 5667 - 5670 View in Reaxys With potassium permanganate, perchloric acid, acetic acid, Time= 2h, T= 30 °C , var. of conc., time, temp., pH, without HOAc, ΔH(excit.), ΔS(excit.), Rate constant, Thermodynamic data, Mechanism Sen, Pratik K.; Sanyal, Ankan; Gupta, Kalyan K. Sen; International Journal of Chemical Kinetics; vol. 27; nb. 4; (1995); p. 379 - 390 View in Reaxys With sodium bis(2-ethyl-2-hydroxybutanoato(2-))oxochromate(V), 2-ethyl-2-hydroxybutyric acid in perchloric acid, acetic acid, T= 29.9 °C , other temp., ΔH(excit.), ΔG(excit.), ΔS(excit.), Kinetics, Thermodynamic data, Mechanism Sreelatha, G.; Rao, M. Prasada; Sethuram, B.; Rao, T. Navaneeth; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 27; nb. 12; (1988); p. 1031 - 1034

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

119/438

2018-03-11 22:07:32


View in Reaxys With copper(III) periodate, rhodium (III) hydroxide in water, T= 34.9 °C , without catalyst, other temp., Rate constant, Kinetics, Mechanism Reddy, K. Bal; Sethuram, B.; Rao, T. Navaneeth; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 27; nb. 8; (1988); p. 730 - 731 View in Reaxys With cethyltrimethylammonium permanganate in chloroform, T= 30 °C , var. temp., Ea, ΔH(excit.), ΔS(excit.), ΔG(excit.), Rate constant, Thermodynamic data Dash, Sukalyan; Mishra, Bijay K.; International Journal of Chemical Kinetics; vol. 27; nb. 7; (1995); p. 627 - 636 View in Reaxys 100 % Turnov.

With oxygen, 10-methylacridinium cation in [D3]acetonitrile, T= 24.9 °C , Irradiation, Kinetics, Quantum yield, Mechanism Fukuzumi, Shunichi; Kuroda, Sadaki; Tanaka, Toshio; Journal of the Chemical Society, Chemical Communications; nb. 2; (1987); p. 120 - 122 View in Reaxys With lead(IV) acetate, acetic acid in benzene, T= 29.9 °C , ΔH of activation, ΔS of activation, ΔG of activation; presence of pyridine; kinetic isotope effect; other temperatures, Rate constant, Mechanism, Thermodynamic data Bhatia, Indu; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 4; (1982); p. 1076 - 1092 View in Reaxys With oxygen, Cu-Na-ZSM-5, T= 399.9 °C , p= 760Torr , var. temp., other cat. system, Product distribution Hayashibara, Hirofumi; Nishiyama, Satoru; Tsuruya, Shigeru; Masai, Mitsuo; Journal of Catalysis; vol. 153; nb. 2; (1995); p. 254 - 264 View in Reaxys With pyridinium hydrobromide perbromide in water, acetic acid, Time= 12h, T= 24.9 °C , other monosubstituted benzyl alcohols, var. temp., polarity of solvents, and conc. of PHPB, Rate constant, Mechanism, Thermodynamic data Suri, Deepa; Banerji, Kalyan K.; Kothari, Seema; Journal of Chemical Research, Miniprint; nb. 7; (1995); p. 1734 1758 View in Reaxys

94 % Spectr.

With manganese(IV) oxide in dichloromethane, Time= 12h, Ambient temperature, add of CH3OH, Product distribution Endo, Katsuya; Takahashi, Hiroyasu; Aihara, Minako; Heterocycles; vol. 42; nb. 2; (1996); p. 589 - 615 View in Reaxys With N-Bromosuccinimide, tetra-(n-butyl)ammonium iodide in acetonitrile, Irradiation, various benzyl alcohols, 1,2diols, and α-hydroxy carboxylic acids, selective oxidation, Product distribution Beebe, Thomas R.; Boyd, Leslie; Fonkeng, Steve B.; Horn, Jamie; Mooney, Teresa M.; et al.; Journal of Organic Chemistry; vol. 60; nb. 20; (1995); p. 6602 - 6603 View in Reaxys With lt;trislt;(2-pyridyl)methylgt;aminegt;2Fe2O(μ-OAc)(3+) in water, other alcohols, var. solvents, var. iron complexes (biomimetics of methane monooxygenase active sites), Mechanism Rabion, Alain; Chen, Shan; Wang, Jianping; Buchanan, Robert M.; Seris, Jean-Louis; Fish, Richard H.; Journal of the American Chemical Society; vol. 117; nb. 49; (1995); p. 12356 - 12357 View in Reaxys With pyridinium bromochromate in dimethyl sulfoxide, Time= 15h, T= 24.9 °C , energy data: ΔH(excit.), ΔS(excit.), ΔG(excit.); other substituted benzyl alkohols; var. temp., var. solvents, Rate constant, Kinetics, Mechanism Pareek, Arun; Kothari, Seema; Banerji, Kalyan K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 34; nb. 11; (1995); p. 968 - 974

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

120/438

2018-03-11 22:07:32


View in Reaxys With cis-lt;Ru(VI)(N,N,N',N'-tetramethyl-3,6-diazaoctane-1,8-diamine)O2gt;(2+) in acetonitrile, T= 24.9 °C , other temperatures; also in the presence of H2O; ΔH(excit.); ΔS(excit.), Kinetics, Thermodynamic data Cheng, Wing-Chi; Yu, Wing-Yiu; Li, Chi-Kueng; Che, Chi-Ming; Journal of Organic Chemistry; vol. 60; nb. 21; (1995); p. 6840 - 6846 View in Reaxys With perchloric acid, ammonium cerium(IV) nitrate in water, acetonitrile, T= 20 - 28 °C , Ea, var. concentration of reagents, Rate constant, Kinetics, Thermodynamic data Lin, Hong-Ping; Leu, Jeng Rong; Jwo, Jing-Jer; Journal of the Chinese Chemical Society (Taipei, Taiwan); vol. 41; nb. 5; (1994); p. 519 - 526 View in Reaxys With uranium(VI) perchlorate, oxygen in water, T= 24 °C , Irradiation, Rate constant, Quantum yield Mao, Yun; Bakac, Andreja; Journal of Physical Chemistry; vol. 100; nb. 10; (1996); p. 4219 - 4223 View in Reaxys With perchloric acid, riboflavin 2',3',4',5'-tetra-acetate in acetonitrile, Irradiation, electrochemical oxidation; also in the presence of duroquinone, Product distribution Ishikawa, Masashi; Okimoto, Hiroyuki; Morita, Masayuki; Matsuda, Yoshiharu; Chemistry Letters; nb. 11; (1996); p. 953 - 954 View in Reaxys With bis(2,2'-bipyridyl) copper(II) permanganate in acetic acid, T= 9.9 - 29.9 °C , Kinetics, Mechanism Vyas; Kothari; Banerji; International Journal of Chemical Kinetics; vol. 29; nb. 1; (1997); p. 9 - 16 View in Reaxys With potassium dichromate, sodium carbonate, tetrabutylammomium bromide in toluene, Time= 4h, T= 100 °C , also without catalyst, Rate constant Yadav; Haldavanekar; Journal of Physical Chemistry A; vol. 101; nb. 1; (1997); p. 36 - 48 View in Reaxys With NbCl5, phosphoric acid monophenyl ester, tetra(n-butyl)ammonium hydroxide, dihydrogen peroxide in 1,2-dichloro-ethane, Time= 5h, T= 40 °C , var. reagents ratios; var. reagents, Product distribution Batista, Celia Maria de Souza; Melo, Simone Coriolano de Souza; Gelbard, Georges; Lachter, Elizabeth Roditi; Journal of Chemical Research, Synopses; nb. 3; (1997); p. 92 - 93 View in Reaxys With lt;Ru(IV)(tpp)(NTs)gt; in dichloromethane, T= 24.9 °C , also kinetic isotope effect, Rate constant Au, Sze-Man; Fung, Wai-Hong; Cheng, Ming-Chuan; Che, Chi-Ming; Peng, Shie-Ming; Chemical Communications; nb. 17; (1997); p. 1655 - 1656 View in Reaxys With toluene-4-sulfonic acid, quinolinium chlorochromate(VI) in dimethyl sulfoxide, Time= 24h, T= 24.9 °C , ΔH(excit.), ΔS(excit.), ΔG(excit.); var. temp.; also in the mixture solvents; kinetic isotope effect, Rate constant, Kinetics, Thermodynamic data Oezguen, Beytiye; Degirmenbas, Nebahat; Journal of Chemical Research, Miniprint; nb. 1; (1997); p. 220 - 227 View in Reaxys With potassium permanganate, Tris(3,6-dioxaheptyl)amine in dichloromethane, Rate constant Rankin, Kathryn N.; Liu, Qing; Hendry, Jennifer; Yee, Henry; Noureldin, Nazih A.; Lee, Donald G.; Tetrahedron Letters; vol. 39; nb. 10; (1998); p. 1095 - 1098 View in Reaxys 92 % Chromat.

With bis(1H-benzimidazolinium) dichromate in tetrachloromethane, Time= 0.0166667h, Heating, other benzylic and allylic alcohols, other solvent: acetone

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

121/438

2018-03-11 22:07:32


Meng, Qing-Hua; Feng, Jun-Cai; Bian, Ning-Sheng; Liu, Bin; Li, Chang-Chuan; Synthetic Communications; vol. 28; nb. 6; (1998); p. 1097 - 1102 View in Reaxys With perchloric acid, tetraaquapalladium(II), T= 55 °C , kinetic of oxidation of aliphatic C1-C4 alcohols and benzyl alcohol with palladium(II) tetraaqua complex in perchloric acid; proposed oxidation routes, Rate constant Ukraintsev; Potekhin; Russian Journal of General Chemistry; vol. 67; nb. 10; (1997); p. 1509 - 1512 View in Reaxys With K(2) added Cu(57)-NaY zeolite, T= 299.9 - 329.9 °C , effect of alkali metals added to Cu-NaY zeolite on the yield of reaction; other additives, Product distribution Xu, Jian; Ekblad, Mikael; Nishiyama, Satoru; Tsuruya, Shigeru; Masai, Mitsuo; Journal of the Chemical Society - Faraday Transactions; vol. 94; nb. 3; (1998); p. 473 - 479 View in Reaxys 95 % Chromat.

With oxygen, Mg6Al2Ru0.5(OH)16CO3 in toluene, Time= 8h, T= 60 °C , other allylic and benzylic alcohols, Mechanism Kaneda, Kiyotomi; Yamashita, Toyokazu; Matsushita, Tsuyoshi; Ebitani, Kohki; Journal of Organic Chemistry; vol. 63; nb. 6; (1998); p. 1750 - 1751 View in Reaxys

90.30 % Chromat.

With CrO3*tetramisole in 1,2-dichloro-ethane, Time= 6h, T= 80 °C , other temperatures, solvent, different substrate:reagent ratios, Product distribution Nijasure; Joshi; Sawant; Synthetic Communications; vol. 28; nb. 21; (1998); p. 4025 - 4033 View in Reaxys With perchloric acid, tetraaquapalladium(II) perchlorate, T= 38 °C , Oxidation, Kinetics, Further Variations: Temperatures, gas medium Ukraintsev; Potekhin; Avetikyan; Russian Journal of General Chemistry; vol. 66; nb. 5; (1996); p. 697 - 700 View in Reaxys

80 % Turn- With potassium carbonate, hydroquinone, tris(triphenylphosphine)ruthenium(II) chloride in various solvent(s), Time= ov. 20h, T= 60 °C Hanyu, Atsushi; Takezawa, Eiichiro; Sakaguchi, Satoshi; Ishii, Yasutaka; Tetrahedron Letters; vol. 39; nb. 31; (1998); p. 5557 - 5560 View in Reaxys With BIBC in dichloromethane, Time= 6h, Heating, Yield given Oezguen, B.; Degirmenbasi, N.; Synthetic Communications; vol. 29; nb. 5; (1999); p. 763 - 766 View in Reaxys With polymer-supported phenyliodine(III) diacetate in dichloromethane, Ambient temperature, Yield given Ley, Steven V.; Thomas, Andrew W.; Finch, Harry; Journal of the Chemical Society - Perkin Transactions 1; nb. 6; (1999); p. 669 - 671 View in Reaxys 96 % Chromat.

With oxygen, Ru-Co-Al-CO3 HT in toluene, Time= 1h, T= 60 °C Matsushita, Tsuyoshi; Ebitani, Kohki; Kaneda, Kiyotomi; Chemical Communications; nb. 3; (1999); p. 265 - 266 View in Reaxys With dihydrogen peroxide, methyltrioxorhenium(VII), sodium bromide in water, T= 25 °C , Kinetics, Rate constant Espenson; Zhu; Zauche; Journal of Organic Chemistry; vol. 64; nb. 4; (1999); p. 1191 - 1196 View in Reaxys With N,N,N-trimethylbenzenemethanaminium dichloroiodate, acetic acid, zinc(II) chloride, Time= 15h, T= 24.85 °C , Energy data: ΔH(excit.), ΔS(excit.); effect of reagents concentration, effect of benzyltrimethylammonium chloride and acrylonitrile, Rate constant, Kinetics, Mechanism

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

122/438

2018-03-11 22:07:32


Rao, P. Surya Chandra; Suri, Deepa; Kothari, Soona; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 9; (1998); p. 2251 - 2272 View in Reaxys With K10-montmorillonite clay-supported tetrabutylammonium periodate in 2,2,4-trimethylpentane, Time= 1.5h, Heating, Yield given Venkatachalapathy; Rajarajan; Shayira Banu; Pitchumani; Tetrahedron; vol. 55; nb. 13; (1999); p. 4071 - 4076 View in Reaxys 87 % Chromat.

With aluminum oxide, quinolinium monofluorochromate(VI) in dichloromethane, Time= 3h, Ambient temperature, other solvents, reaction times, other reagent, Product distribution Rajkumar, G. Abraham; Arabindoo, Banumathi; Murugesan; Synthetic Communications; vol. 29; nb. 12; (1999); p. 2105 - 2114 View in Reaxys With dihydrogen peroxide, cobalt(II) acetate, Time= 2h, T= 70 °C , also oxidation of toluene; var. time Puzari; Nath; Baruah, Jubaraj B.; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 37; nb. 8; (1998); p. 723 - 725 View in Reaxys With 2,6-dimethylpyridine, sodium perchlorate, (+/-)-4-benzyloxy-2,2,8a-trimethyldecahydroquinolinyl-N-oxyl in acetonitrile, Time= 10h, T= 20 °C , Electrochemical reaction, 0.8 V vs. Ag/Ag(1+), Oxidation Kurashima, Futoshi; Kashiwagi, Yoshitomo; Kikuchi, Chikara; Anzai, Jun-Ichi; Osa, Tetsuo; Heterocycles; vol. 50; nb. 1; (1999); p. 79 - 82 View in Reaxys With 2,6-dimethylpyridine, (+/-)-cis,cis-4-benzoyloxy-2,2,8a-trimethyldecahydroquino.., Time= 10h, T= 20 °C , Electrolysis, Oxidation Kashiwagi, Yoshitomo; Kurashima, Futoshi; Anzai, Jun-Ichi; Osa, Tesuo; Heterocycles; vol. 51; nb. 8; (1999); p. 1945 - 1948 View in Reaxys

99 % Chromat.

With chromium(VI) oxide, Time= 0.00833333h, microwave irradiation, Oxidation Heravi, Majid M.; Ajami, Dariush; Tabar-Hydar, Kourosh; Ghassemzadeh, Mitra; Journal of Chemical Research - Part S; nb. 5; (1999); p. 334 - 335 View in Reaxys

81 % Spectr.

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, hydrogen bromide, methyltrioxorhenium(VII) in acetic acid, Time= 2h, Oxidation, Product distribution Herrmann, Wolfgang A.; Zoller, Jochen P.; Fischer, Richard W.; Journal of Organometallic Chemistry; vol. 579; nb. 1-2; (1999); p. 404 - 407 View in Reaxys

99 % Chromat.

With chromium(VI) oxide, Time= 0.00833333h, microwave irradiation, Oxidation, Product distribution, Further Variations: other alcohols Heravi, Majid M.; Ajami, Dariush; Tabar-Hydar, Kourosh; Ghassemzadeh, Mitra; Journal of Chemical Research - Part S; nb. 5; (1999); p. 334 - 335 View in Reaxys With poly(2-vinylpyridine) supported chromium peroxide in toluene, Heating, Oxidation, Product distribution, Further Variations: Catalysts Lakouraj, M. Mansour; Keyvan; Journal of Chemical Research - Part S; nb. 3; (1999); p. 206 - 207 View in Reaxys With TEMPOL in acetonitrile, T= 24.85 °C , Oxidation, Kinetics Zauche, Timothy H.; Espenson, James H.; International Journal of Chemical Kinetics; vol. 31; nb. 5; (1999); p. 381 - 385

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

123/438

2018-03-11 22:07:32


View in Reaxys With pyridine, oxygen, palladium diacetate in toluene, Time= 2h, T= 80 °C , Oxidation, Product distribution, Further Variations: Reagents, Solvents Nishimura, Takahiro; Onoue, Tomoaki; Ohe, Kouichi; Uemura, Sakae; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6750 - 6755 View in Reaxys With benzyltrimethylammonium tribromide, acetic acid in water, Oxidation, Kinetics, Activation energy, Further Variations: Reaction partners, Temperatures, Solvents, effect of benzyltrimethylammonium chloride and bromide ion Anjana; Kothari, Seema; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 8; (1999); p. 2118 2135 View in Reaxys With [Cu(II)2(ArO(.))2](PF6)2 in acetonitrile, T= 25 °C , Oxidation, Kinetics, Further Variations: Catalysts Itoh, Shinobu; Taki, Masayasu; Takayama, Shigehisa; Nagatomo, Shigenori; Kitagawa, Teizo; Sakurada, Norio; Arakawa, Ryuichi; Fukuzumi, Shunichi; Angewandte Chemie - International Edition; vol. 38; nb. 18; (1999); p. 2774 - 2776 View in Reaxys With oxygen, nitric acid, sodium nitrite in perchloric acid, Time= 0.416667h, T= 61.85 °C , p= 750.06Torr , Electrochemical reaction, Oxidation, Activation energy, Equilibrium constant, Further Variations: Temperatures Dorfman; Aleshkova; Russian Journal of Organic Chemistry; vol. 35; nb. 7; (1999); p. 987 - 994 View in Reaxys With sodium hexachloroiridate in acetate buffer, tert-butyl alcohol, T= 44.85 °C , pH= 4.45, Oxidation, Kinetics, Thermodynamic data Sen Gupta, Kalyan K.; Bhattacharjee, Nandini; Journal of Physical Organic Chemistry; vol. 13; nb. 3; (2000); p. 157 - 161 View in Reaxys 98 % Chromat.

With 4 A molecular sieve, oxygen, p-Toluic acid, bis(acetylacetonato)dioxidomolybdenum(VI), copper(II) nitrate in toluene, T= 100 °C , Oxidation Lorber, Christian Y.; Smidt, Sebastian P.; Osborn, John A.; European Journal of Inorganic Chemistry; nb. 4; (2000); p. 655 - 658 View in Reaxys

98 % Chromat.

With N-tert-butyl benzenesulfinimidoyl chloride, 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane, Time= 0.5h, T= -78 °C Mukaiyama, Teruaki; Matsuo, Jun-Ichi; Yanagisawa, Manabu; Chemistry Letters; nb. 9; (2000); p. 1072 - 1073 View in Reaxys With dihydrogen peroxide, tetrahexylammonium chloride, [La(III)W10O36](9-) in water, Time= 3h, Heating, Oxidation, Product distribution, Further Variations: Catalysts, Reagents Griffith, William P.; Morley-Smith, Neil; Nogueira, Helena I.S.; Shoair, Abdel G.F.; Suriaatmaja, Maria; White, Andrew J.P.; Williams, David J.; Journal of Organometallic Chemistry; vol. 607; nb. 1-2; (2000); p. 146 - 155 View in Reaxys With acetobacter sp. ALEG in 2,2,4-trimethylpentane, water, Time= 24h Gandolfi, Raffaella; Ferrara, Nicola; Molinari, Francesco; Tetrahedron Letters; vol. 42; nb. 3; (2001); p. 513 - 514 View in Reaxys

94 % Chromat.

With aluminum oxide, potassium ferrate(VI), tetrabutylammomium bromide in pentane, Time= 2h, Product distribution, Further Variations: Reagents, Solvents, time Caddick; Murtagh; Weaving; Tetrahedron; vol. 56; nb. 47; (2000); p. 9365 - 9373 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

124/438

2018-03-11 22:07:32


With sodium hydroxide, sodium perchlorate, potassium hexacyanoferrate(III), (2,2':6',2''-terpyridine)trichlororuthenium(III) in water, T= 25 °C , Kinetics Kelson, Eric P.; Phengsy, Proma P.; International Journal of Chemical Kinetics; vol. 32; nb. 12; (2000); p. 760 - 770 View in Reaxys With 3,3-dimethyldioxirane in acetone, T= 24.5 °C , Oxidation, Kinetics, Further Variations: Temperatures Grabovskii; Suvorkina; Kabal'nova; Khursan; Shereshovets; Russian Chemical Bulletin; vol. 49; nb. 8; (2000); p. 1332 - 1337 View in Reaxys With iodine(I) azide in acetonitrile, Heating Viuf, Christel; Bols, Mikael; Angewandte Chemie - International Edition; vol. 40; nb. 3; (2001); p. 623 - 625 View in Reaxys With dipyridinium dichromate, perchloric acid, acetic acid, T= 35 °C , Oxidation, Kinetics, Further Variations: Reagents, concentration dependence Karunakaran, Chockalingam; Suresh, Sadasivam; Journal of Chemical Research - Part S; nb. 3; (2000); p. 114 115 View in Reaxys With Hexadecane, oxygen, copper(l) chloride, polymer immobilised TEMPO in N,N-dimethyl-formamide, Time= 1.5h, T= 25 °C Dijksman; Arends; Sheldon; Synlett; nb. 1; (2001); p. 102 - 104 View in Reaxys With [PSb(V)(O)Mo11O39] tetra(n-butylammonium) in benzonitrile, Time= 20h, T= 135 °C Khenkin, Alexander M.; Shimon, Linda J. W.; Neumann, Ronny; European Journal of Inorganic Chemistry; nb. 3; (2001); p. 789 - 794 View in Reaxys With chloroauric acid in acetate buffer, T= 24.85 °C , pH= 4.05, Kinetics, Further Variations: pH-values, Solvents, Reagents, Temperatures, chloride concentration Pal, Biswajit; Sen, Pratik K.; Sen Gupta, Kalyan K.; Journal of Physical Organic Chemistry; vol. 14; nb. 5; (2001); p. 284 - 294 View in Reaxys With trimethyltrimethoxysilane, oxygen, tetramethylorthosilicate in toluene, Time= 0.75h, T= 75 °C , Product distribution Pagliaro, Mario; Ciriminna, Rosaria; Tetrahedron Letters; vol. 42; nb. 27; (2001); p. 4511 - 4514 View in Reaxys With 9-phenyl-cyclohepta[b]pyrimido[5,4-d]furan-8,10(9H)-dione, Time= 120h, T= 90 °C Takayasu, Tohru; Mizuta, Yutaka; Nitta, Makoto; Heterocycles; vol. 54; nb. 2; (2001); p. 601 - 606 View in Reaxys With 3,3-dimethyldioxirane in acetone, T= 0 °C , Kinetics Angelis, Yiannis S.; Hatzakis, Nikos S.; Smonou, Ioulia; Orfanopoulos, Michael; Tetrahedron Letters; vol. 42; nb. 22; (2001); p. 3753 - 3756 View in Reaxys 100 % Chromat.

With pyridine, oxygen, Pd(II)-hydrotalcite in toluene, Time= 2h, T= 80 °C Uemura; Kakiuchi; Nishimura; Inoue; Bulletin of the Chemical Society of Japan; vol. 74; nb. 1; (2001); p. 165 172 View in Reaxys With oxygen, Pd561(phen)60(OAc)180 in isopropyl alcohol, T= 60 °C , Kinetics

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

125/438

2018-03-11 22:07:32


Gladyi; Starchevsky; Pazdersky; Vargaftik; Moiseev; Russian Chemical Bulletin; vol. 50; nb. 5; (2001); p. 921 922 View in Reaxys With pyridinium chlorochromate, Time= 0.25h, T= 20 °C Salehi; Firouzabadi; Farrokhi; Gholizadeh; Synthesis; nb. 15; (2001); p. 2273 - 2276 View in Reaxys 92 % Chromat.

With 1,4-diaza-bicyclo[2.2.2]octane, oxygen, K2lt;OsO2(OH)4gt; in water, tert-butyl alcohol, Time= 16h, T= 50 °C , p= 750.06Torr , pH= 10.4 Doebler, Christian; Mehltretter, Gerald M; Sundermeier, Uta; Eckert, Markus; Militzer, Hans-Christian; Beller, Matthias; Tetrahedron Letters; vol. 42; nb. 48; (2001); p. 8447 - 8449 View in Reaxys

98 % Chromat.

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, oxygen, manganese(II) nitrate, cobalt(II) nitrate in acetic acid, Time= 10h, T= 20 °C Cecchetto, Andrea; Fontana, Francesca; Minisci, Francesco; Recupero, Francesco; Tetrahedron Letters; vol. 42; nb. 38; (2001); p. 6651 - 6653 View in Reaxys With cetyltrimethylammonium cerium(IV) nitrate in benzene, Time= 3h, Heating Mishra; Kuanar; Sharma; Nayak; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 40; nb. 8; (2001); p. 724 - 726 View in Reaxys With Mn(N,N'-ethylenebis(salicylaldiminato))O in acetonitrile, Time= 12h, T= 24.85 °C , Kinetics Kumbhat, Vinita; Sharma, Pradeep K.; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; (2001); p. 562 - 585 View in Reaxys With ammonium peroxydisulfate, Montmorillonite, silver nitrate in hexane, Time= 2.5h, T= 60 °C , Product distribution, Further Variations: Reagents Hirano; Kojima; Yakabe; Morimoto; Journal of Chemical Research - Part S; nb. 7; (2001); p. 274 - 276 View in Reaxys With benzyltrimethylammonium chlorobromate, acetic acid, T= 34.85 °C , Kinetics, Further Variations: Temperatures, Reagents Sita Rama Raju; Sharma; Banerji; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 39; nb. 12; (2000); p. 1258 - 1263 View in Reaxys With perchloric acid, oxygen, palladium in water, T= -218.15 °C , Kinetics, Activation energy, Further Variations: Temperatures Matsura; Potekhin; Ukraintsev; Russian Journal of General Chemistry; vol. 72; nb. 1; (2002); p. 105 - 109 View in Reaxys

98 % Chromat.

With N-(tert-butyl)benzenesulfinimidoyl chloride, 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane, Time= 0.5h, T= -78 °C Matsuo, Jun-Ichi; Iida, Daisuke; Tatani, Kazuya; Mukaiyama, Teruaki; Bulletin of the Chemical Society of Japan; vol. 75; nb. 2; (2002); p. 223 - 234 View in Reaxys With quinolinium monofluorochromate(VI) in dimethyl sulfoxide, T= 34.85 °C , Kinetics, Further Variations: Temperatures, Solvents Dave, Itishri; Sharma, Vinita; Banerji, Kalyan K.; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 41; nb. 3; (2002); p. 493 - 499 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

126/438

2018-03-11 22:07:32


With sodium hypochlorite, N-butyl-N,N-dimethyl-(α-phenyl)ethylammonium bromide in dichloromethane, Time= 1.16667h, Heating Reddy, Ch. Venkateshwar; Mahesh; Raju; Reddy, V.V. Narayana; Synthetic Communications; vol. 32; nb. 18; (2002); p. 2797 - 2802 View in Reaxys With tris(triphenylphosphine)ruthenium(II) chloride, tetramethyl ammoniumhydroxide, oxygen, Time= 5h, T= 80 °C , p= 760Torr Wolfson, Adi; Wuyts, Stijn; De Vos, Dirk E.; Vankelecom, Ivo F.J.; Jacobs, Pierre A.; Tetrahedron Letters; vol. 43; nb. 45; (2002); p. 8107 - 8110 View in Reaxys With tetra-N-butylammonium tribromide, potassium bromide in water, acetic acid, Time= 12h, T= 14.85 °C , Kinetics, Activation energy, Further Variations: Temperatures, Reaction partners, Solvents Kumar, Ashok; Sharma, Pradeep K.; Banerji, Kalyan K.; Journal of Physical Organic Chemistry; vol. 15; nb. 10; (2002); p. 721 - 727 View in Reaxys With sodium hydroxide, sodium ruthenate(VI), potassium hexacyanoferrate(III) in tert-butyl alcohol, T= 30 °C , Kinetics Mucientes; Santiago; Almena; Poblete; Rodriguez-Cervantes; International Journal of Chemical Kinetics; vol. 34; nb. 7; (2002); p. 421 - 429 View in Reaxys 98 % Turn- With polymer-supported iodoxybenzoic acid in dichloromethane, Time= 5h, T= 25 °C ov. Lei; Denecker; Jegasothy; Sherrington; Slater; Sutherland; Tetrahedron Letters; vol. 44; nb. 8; (2003); p. 1635 1637 View in Reaxys 70 % Chromat.

With sodium hypochlorite, sodium hydrogencarbonate, potassium bromide, polymer-immobilized TEMPO radical in dichloromethane, water, Time= 1h, T= 0 °C , pH= 9.1, Anelli oxidation Tanyeli, Cihangir; Guemues, Ayseguel; Tetrahedron Letters; vol. 44; nb. 8; (2003); p. 1639 - 1642 View in Reaxys With ferric nitrate, phosphotungstic acid in hexane, Time= 0.25h, T= 20 °C , Product distribution, Further Variations: Catalysts, Solvents Firouzabadi, Habib; Iranpoor, Nasser; Amani, Kamal; Synthesis; nb. 3; (2003); p. 408 - 412 View in Reaxys With oxygen, triethylamine, palladium diacetate in 1,2-dichloro-ethane, Time= 12h, T= 25 °C Schultz, Mitchell J.; Park, Candice C.; Sigman, Matthew S.; Chemical Communications; nb. 24; (2002); p. 3034 3035 View in Reaxys With tetra-O-acetyl riboflavin, oxygen, sodium dodecyl-sulfate in water, UV-irradiation, Quantum yield Yasuda, Masahide; Nakai, Takuya; Kawahito, Yasumasa; Shiragami, Tsutomu; Bulletin of the Chemical Society of Japan; vol. 76; nb. 3; (2003); p. 601 - 605 View in Reaxys With oxygen, (-)-sparteine in 1,2-dichloro-ethane, T= 50 °C , Kinetics Mueller, Jaime A.; Sigman, Matthew S.; Journal of the American Chemical Society; vol. 125; nb. 23; (2003); p. 7005 - 7013 View in Reaxys With 2,2,6,6-tetramethyl-piperidine-N-oxyl, sodium hypochlorite, potassium bromide in acetonitrile, Time= 1h, T= 5 20 °C , pH= 8.0 - 10.0

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

127/438

2018-03-11 22:07:32


Zanka, Atsuhiko; Chemical and Pharmaceutical Bulletin; vol. 51; nb. 7; (2003); p. 888 - 889 View in Reaxys With polystyrene supported 2-iodyl benzamide in dichloromethane, Time= 1h, T= 25 °C Chung, Woo-Jae; Kim, Duk-Ki; Lee, Yoon-Sik; Tetrahedron Letters; vol. 44; nb. 52; (2003); p. 9251 - 9254 View in Reaxys 100 % Chromat.

With potassium sulfate, potassium hydrogensulfate, potassium peroxomonosulfate, tetrabutylammomium bromide, mer-tris[(2-oxazolinyl)phenolato]manganese(III) in dichloromethane, water, Time= 0.0333333h, T= 20 °C Bagherzadeh, Mojtaba; Tetrahedron Letters; vol. 44; nb. 50; (2003); p. 8943 - 8945 View in Reaxys With quinaldinium chlorochromate on neutral Al2O3 in hexane, Time= 2h, T= 20 °C , Product distribution, Further Variations: Solvents, Reagents Degirmenbasi, Nebahat; Oezguen, Beytiye; Monatshefte fur Chemie; vol. 134; nb. 12; (2003); p. 1565 - 1569 View in Reaxys With air, uracil-annulated heteroazulene cation tetrafluoroborate salt, potassium carbonate in acetonitrile, Time= 16h, Irradiation Naya, Shin-Ichi; Nitta, Makoto; Tetrahedron; vol. 59; nb. 37; (2003); p. 7291 - 7299 View in Reaxys

84 % Chromat.

With N-(phenylthio)-N-(tert-butyl)amine, chloroamine-T in toluene, Time= 6h, T= 0 - 20 °C , Product distribution, Further Variations: Solvents, Reagents Kitagawa, Hideo; Mukaiyama, Teruaki; Chemical and pharmaceutical bulletin; vol. 50; nb. 9; (2002); p. 1276 1279 View in Reaxys With quinaldinium fluorochromate in dichloromethane, Time= 3h, T= 20 °C Degirmenbasi, Nebahat; Oezguen, Beytiye; Monatshefte fur Chemie; vol. 135; nb. 4; (2004); p. 407 - 410 View in Reaxys With 2-iodoxybenzoic acid methyl ester, boron trifluoride diethyl etherate, potassium bromide in chloroform, T= 50 °C Zhdankin, Viktor V.; Litvinov, Dmitry N.; Koposov, Alexey Y.; Luu, Thanh; Ferguson, Michael J.; McDonald, Robert; Tykwinski, Rik R.; Chemical Communications; nb. 1; (2004); p. 106 - 107 View in Reaxys With N -hydroxyphthalimide, cobalt(II) acetate, 3-chloro-benzenecarboperoxoic acid in acetonitrile, T= 25 °C , Kinetics Minisci, Francesco; Recupero, Francesco; Cecchetto, Andrea; Gambarotti, Cristian; Punta, Carlo; Faletti, Roberta; Paganelli, Roberto; Pedulli, Gian Franco; European Journal of Organic Chemistry; nb. 1; (2004); p. 109 - 119 View in Reaxys With toluene-4-sulfonic acid, quinoxalinium dichromate in dimethyl sulfoxide, Time= 24h, T= 24.85 °C , Kinetics, Thermodynamic data, Further Variations: Temperatures, Solvents, acidity Oezguen, Beytiye; Degirmenbasi, Nebahat; Monatshefte fuer Chemie; vol. 135; nb. 5; (2004); p. 483 - 492 View in Reaxys

74 % Chromat.

With air, sodium acetate, 3-[1-(2,3,4,5-tetraphenylphenyl)]pyridine, palladium diacetate in toluene, Time= 48h, T= 80 °C , Product distribution, Further Variations: Reagents Iwasawa, Tetsuo; Tokunaga, Makoto; Obora, Yasushi; Tsuji, Yasushi; Journal of the American Chemical Society; vol. 126; nb. 21; (2004); p. 6554 - 6555 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

128/438

2018-03-11 22:07:32


98 % Spectr.

With pyridine, palladium diacetate, oxygen in toluene, Time= 4h, T= 80 °C , p= 250Torr , Kinetics, Further Variations: Pressures Steinhoff, Bradley A.; Guzei, Ilia A.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 126; nb. 36; (2004); p. 11268 - 11278 View in Reaxys With potassium dichromate, sulfuric acid, tetrabutylammomium bromide, T= 34.85 °C , Kinetics, Further Variations: Reagents, Temperatures Bijudas; Nair, T. D. Radhakrishnan; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 43; nb. 6; (2004); p. 1216 - 1218 View in Reaxys With thermophilic alcohol dehydrogenase in phosphate buffer, T= 4.85 °C , pH= 7.0, Enzyme kinetics, Further Variations: Reagents, Temperatures Liang, Zhao-Xun; Tsigos, Iason; Bouriotis, Vassilis; Klinman, Judith P.; Journal of the American Chemical Society; vol. 126; nb. 31; (2004); p. 9500 - 9501 View in Reaxys With Pd[1,3-bis(2,6-di-iPrC6H3)imidazol-2-ylidene](OAc)2(H2O), oxygen, acetic acid, 3 A molecular sieve in benzene, T= 42.55 °C , Kinetics, Further Variations: Temperatures, Solvents Mueller, Jaime A.; Goller, Christopher P.; Sigman, Matthew S.; Journal of the American Chemical Society; vol. 126; nb. 31; (2004); p. 9724 - 9734 View in Reaxys With quinolinium bromochromate in dimethyl sulfoxide, T= 34.85 °C , Kinetics, Further Variations: Solvents, Temperatures Prakash, Om; Sharma, Pradeep K.; Journal of the Indian Chemical Society; vol. 81; nb. 6; (2004); p. 467 - 473 View in Reaxys With perchloric acid, bis-[(trifluoroacetoxy)iodo]benzene in water, acetic acid, T= 34.85 °C , Kinetics, Further Variations: Temperatures Kansara, Alpna; Sharma, Pradeep K.; Banerji, Kalyan K.; Journal of Chemical Research; nb. 9; (2004); p. 581 584 View in Reaxys

79 % Spectr.

With tetracoordinate 1,2-iodoxetane 1-oxide in [D3]acetonitrile, Time= 2h, T= 60 °C Kano, Naokazu; Ohashi, Masaki; Hoshiba, Kazuhisa; Kawashima, Takayuki; Tetrahedron Letters; vol. 45; nb. 44; (2004); p. 8173 - 8175 View in Reaxys With C30H26N3OP, potassium carbonate, copper(l) chloride, 1-methyl-pyrrolidin-2-one, Time= 60h, T= 110 °C Tsai, Weiwen; Liu, Yi-Hung; Peng, Shie-Ming; Liu, Shiuh-Tzung; Journal of Organometallic Chemistry; vol. 690; nb. 2; (2005); p. 415 - 421 View in Reaxys

100 % Chromat.

With sodium hypochlorite, poly(ethylene glycol)-supported 4-hydroxy-TEMPO-derivative, sodium bromide in dichloromethane, sodium hydrogencarbonate, Time= 0.0833333h, T= 0 °C , pH= 9, Product distribution, Further Variations: Reagents Ferreira, Pedro; Phillips, Emyr; Rippon, David; Shik, Chi Tsang; Hayes, Wayne; Journal of Organic Chemistry; vol. 69; nb. 20; (2004); p. 6851 - 6859 View in Reaxys With β‐cyclodextrin in water, Time= 1h, T= 50 °C , Product distribution, Further Variations: Reagents, Temperatures Ji, Hong-Bing; Shi, Dong-Po; Shao, Ming; Li, Zhong; Wang, Le-Fu; Tetrahedron Letters; vol. 46; nb. 14; (2005); p. 2517 - 2520 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

129/438

2018-03-11 22:07:32


100 % Turnov.

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, oxygen in acetonitrile, Time= 15h, T= 65 °C Wu, Xue-E.; Ma, Li; Ding, Meng-Xian; Gao, Lian-Xun; Chemistry Letters; vol. 34; nb. 3; (2005); p. 312 - 313 View in Reaxys With supercritical CO2, water, 1-butyl-3-methylimidazolium Tetrafluoroborate, T= 45.05 °C , p= 66005.3Torr , Electrochemical reaction, Product distribution, Further Variations: Reagents, Pressures Zhao, Guoying; Jiang, Tao; Wu, Weize; Han, Buxing; Liu, Zhimin; Gao, Haixiang; Journal of Physical Chemistry B; vol. 108; nb. 34; (2004); p. 13052 - 13057 View in Reaxys

92 % Spectr.

With trimethylamine-N-oxide, CHDFe-(CO)3 in benzene, Time= 10h, T= 20 °C Pearson, Anthony J.; Kwak, Yoonhyun; Tetrahedron Letters; vol. 46; nb. 32; (2005); p. 5417 - 5419 View in Reaxys With [2,2]bipyridinyl, oxygen, 4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical, copper in water, acetonitrile, T= 25 °C , pH= 12.5 - 13.5, Kinetics, Further Variations: conc. of TEMPO; immobilization Geisslmeir, David; Jary, Walther G.; Falk, Heinz; Monatshefte fur Chemie; vol. 136; nb. 9; (2005); p. 1591 - 1599 View in Reaxys With oxygen, palladium/alumina, Time= 4h, T= 100 °C , Product distribution, Kinetics, Further Variations: Catalysts, Temperatures Wu, Hongli; Zhang, Qinghong; Wang, Ye; Advanced Synthesis and Catalysis; vol. 347; nb. 10; (2005); p. 1356 1360 View in Reaxys With air, benzocycloheptatriene cation derivative in acetonitrile, Time= 16h, UV-irradiation, Product distribution, Further Variations: Reagents Naya, Shin-Ichi; Tokunaka, Takeshi; Nitta, Makoto; Journal of Organic Chemistry; vol. 68; nb. 24; (2003); p. 9317 - 9321 View in Reaxys

93 % Chromat.

With 4 A molecular sieve, oxirane-based polymer-micelle incarcerated ruthenium, 4-methylmorpholine N-oxide in hexane, acetone, Time= 2.5h, T= 20 °C , Product distribution, Further Variations: Reagents Miyamura, Hiroyuki; Akiyama, Ryo; Ishida, Tasuku; Matsubara, Ryosuke; Takeuchi, Masahiro; Kobayashi, Shu; Tetrahedron; vol. 61; nb. 51; (2005); p. 12177 - 12185 View in Reaxys With polymer-bound chromium(VI) oxide, T= 55 °C , Kinetics, Further Variations: Temperatures Jawanjal; Hilage; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 44; nb. 9; (2005); p. 1827 - 1830 View in Reaxys With iron(III) porphyrin derivative, 3-chloro-benzenecarboperoxoic acid in various solvent(s), T= -100 °C , Kinetics, Further Variations: Reagents, Temperatures Na, Young Oh; Suh, Yumi; Mi, Joo Park; Mi, Sook Seo; Kim, Jinheung; Nam, Wonwoo; Angewandte Chemie International Edition; vol. 44; nb. 27; (2005); p. 4235 - 4239 View in Reaxys With Methylobacterium extorquens IMI 369321 alcohol dehydrogenase, sodium .beta.-nicotinamide adenine dinucleotide phosphate in various solvent(s), pH= 6.0, Enzyme kinetics, Further Variations: Reagents Koutsompogeras, Panagiotis; Kyriacou, Adamantini; Zabetakis, Ioannis; Journal of Agricultural and Food Chemistry; vol. 54; nb. 1; (2006); p. 235 - 242 View in Reaxys With [bis(acetoxy)iodo]benzene, ruthenium trichloride in water, acetonitrile, Time= 1h, T= 20 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

130/438

2018-03-11 22:07:32


Yusubov, Mekhman S.; Chi, Ki-Whan; Park, Joo Yeon; Karimov, Rashad; Zhdankin, Viktor V.; Tetrahedron Letters; vol. 47; nb. 35; (2006); p. 6305 - 6308 View in Reaxys With [RuCl2(PPh3)2(NA)], Time= 3h, T= 20 °C , Product distribution, Further Variations: Reagents Mahalingam; Karvembu; Chinnusamy; Natarajan; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 64; nb. 4; (2006); p. 886 - 890 View in Reaxys With N-benzyl-N-(2-iodylphenyl)pivalamide in acetonitrile, Time= 0.333333h, Heating, Product distribution, Further Variations: Reagents Ladziata, Uladzimir; Koposov, Alexey Y.; Lo, Ka Y.; Willging, Jeff; Nemykin, Victor N.; Zhdankin, Viktor V.; Angewandte Chemie - International Edition; vol. 44; nb. 43; (2005); p. 7127 - 7131 View in Reaxys With tetramethylammonium monofluorochromate(VI), toluene-4-sulfonic acid in acetonitrile, Time= 10h, T= 25 °C , Kinetics, Further Variations: Temperatures Gharib; Zare; Ghammami; Ebrahimi; Russian Chemical Bulletin; vol. 54; nb. 2; (2005); p. 462 - 465 View in Reaxys With phosphate buffer, β-CD-A,D-diuronic acid dihydroxyacetone cyclic ester, dihydrogen peroxide, T= 25 °C , pH= 7, Enzyme kinetics, Further Variations: Reagents, Temperatures Marinescu, Lavinia G.; Bols, Mikael; Angewandte Chemie - International Edition; vol. 45; nb. 28; (2006); p. 4590 4593 View in Reaxys With 2,2,6,6-tetramethyl-piperidine-N-oxyl, sodium hydroxide, dinuclear copper(II) in water, acetonitrile, T= 20 °C , Kinetics Striegler, Susanne; Tetrahedron; vol. 62; nb. 39; (2006); p. 9109 - 9114 View in Reaxys 53 % Turn- With 3 Angstroem MS, oxygen, [PPh4][Ru(N)Me2(μ2-O)2Pd((-)-sparteine)] in chlorobenzene, Time= 20h, T= 95 ov. 100 °C Kuiper, Jesse L.; Shapley, Patricia A.; Journal of Organometallic Chemistry; vol. 692; nb. 8; (2007); p. 1653 - 1660 View in Reaxys With oxygen, palladium/alumina in various solvent(s), Time= 15.2333h, T= 80 °C , p= 105008Torr , Product distribution, Further Variations: Pressures Caravati, Matteo; Grunwaldt, Jan-Dierk; Baiker, Alfons; Physical Chemistry Chemical Physics; vol. 7; nb. 2; (2005); p. 278 - 285 View in Reaxys With 3-ethoxyprop-1-ene, oxygen, quinuclidinetetraoxo-osmium(VIII), oxotrimesityliridium(V) in tetrahydrofuran, Time= 72h, atmospheric pressure Fortner, Kevin C.; Laitar, David S.; Muldoon, John; Pu, Lihung; Braun-Sand, Sonja B.; Wiest, Olaf; Brown, Seth N.; Journal of the American Chemical Society; vol. 129; nb. 3; (2007); p. 588 - 600 View in Reaxys With 1,3,5-trichloro-2,4,6-triazine, dimethyl sulfoxide, triethylamine in tetrahydrofuran, Time= 1.5h, T= -30 - 20 °C De Luca; Giacomelli; Porcheddu; Journal of Organic Chemistry; vol. 66; nb. 23; (2001); p. 7907 - 7909 View in Reaxys 86 % Chromat.

With tert.-butylhydroperoxide, [(Me3tacn)Ru(CF3CO2)2(H2O)]CF3CO2-SiO2 in hexane, Time= 14h, T= 45 °C Cheung, Wai-Hung; Yu, Wing-Yiu; Yip, Wing-Ping; Zhu, Nian-Yong; Che, Chi-Ming; Journal of Organic Chemistry; vol. 67; nb. 22; (2002); p. 7716 - 7723 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

131/438

2018-03-11 22:07:32


100 % Chromat.

With pyridine, oxygen, Pd(II)-supported hydrotalcite in toluene, Time= 2h, T= 80 °C , Oxidation Nishimura, Takahiro; Kakiuchi, Nobuyuki; Inoue, Masashi; Uemura, Sakae; Chemical Communications; nb. 14; (2000); p. 1245 - 1246 View in Reaxys

84 % Chromat.

With oxygen, chloranil, decalin, Na5PV2Mo10O40, Time= 18h, T= 90 °C , Oxidation, Oxidative dehydrogenation Neumann, Ronny; Khenkin, Alexander M.; Vigdergauz, Inga; Chemistry - A European Journal; vol. 6; nb. 5; (2000); p. 875 - 882 View in Reaxys

98 % Chromat.

With pyridine, air, Pd(II)-hydrotalcite in toluene, Time= 3h, T= 65 °C , p= 760.051Torr , Product distribution, Further Variations: Catalysts, Temperatures Kakiuchi; Maeda; Nishimura; Uemura; Journal of Organic Chemistry; vol. 66; nb. 20; (2001); p. 6620 - 6625 View in Reaxys With sodium carbonate, methyl vinyl ketone, bis(1,5-cyclooctadiene)diiridium(I) dichloride in toluene, Time= 12h, T= 100 °C Farnworth, Marc V.; Cross, Michael J.; Louie, Janis; Tetrahedron Letters; vol. 45; nb. 40; (2004); p. 7441 - 7443 View in Reaxys With sodium hypochlorite, polyamine immobilised piperidinyl oxyl, potassium hydrogencarbonate in water, Time= 0.5h, T= 0 °C , pH= 9.1, Oxidation Dijksman, Arne; Arends, Isabel W.C.E.; Sheldon, Roger A.; Chemical Communications; nb. 4; (2000); p. 271 272 View in Reaxys With dipyridinium dichromate, trichloroacetic acid in acetonitrile, T= 19.99 °C , Kinetics, Thermodynamic data, Further Variations: Temperatures Kabilan; Girija; Reis, Joao Carlos R.; Segurado, Manuel A.P.; De Oliveira, Jaime D. Gomes; Journal of the Chemical Society. Perkin Transactions 2; nb. 6; (2002); p. 1151 - 1157 View in Reaxys

100 % Chromat.

With [bis(acetoxy)iodo]benzene, fluorous-tagged TEMPO radical in dichloromethane, Time= 2h, T= 20 °C Pozzi, Gianluca; Cavazzini, Marco; Holczknecht, Orsolya; Quici, Silvio; Shepperson, Ian; Tetrahedron Letters; vol. 45; nb. 22; (2004); p. 4249 - 4251 View in Reaxys With oxygen, sol-gel entrapped nPr4-ammonium perruthenate ormosil (B-Me3) in carbon dioxide, Time= 4h, T= 75 °C , p= 165017Torr , Product distribution, Further Variations: Catalysts Ciriminna, Rosaria; Campestrini, Sandro; Pagliaro, Mario; Advanced Synthesis and Catalysis; vol. 345; nb. 11; (2003); p. 1261 - 1267 View in Reaxys With sodium hypochlorite, tetra(n-butyl)ammonium hydrogensulfate in dichloromethane, Time= 2h, T= 20 °C , pH= 9 Grigoropoulou; Clark; Hall; Scott; Chemical Communications; nb. 6; (2001); p. 547 - 548 View in Reaxys With 2,2,6,6-tetramethyl-piperidine-N-oxyl, H5PV2Mo10O40, oxygen in acetone, Time= 6h, T= 100 °C , p= 1520.1Torr Ben-Daniel; Alsters; Neumann; Journal of Organic Chemistry; vol. 66; nb. 25; (2001); p. 8650 - 8653 View in Reaxys With 2,2,6,6-tetramethyl-piperidine-N-oxyl, H5PV2Mo10O40, oxygen in acetone, T= 25 °C , p= 1520.1Torr , Kinetics, Activation energy, Thermodynamic data, Further Variations: Reagents, Pressures Ben-Daniel; Alsters; Neumann; Journal of Organic Chemistry; vol. 66; nb. 25; (2001); p. 8650 - 8653 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

132/438

2018-03-11 22:07:32


With oxygen, sodium acetate, (neocuproine)Pd(OAc)2 in water, dimethyl sulfoxide, Time= 1h, T= 70 °C , p= 22502.3Torr Ten Brink, Gerd-Jan; Arends, Isabel W. C. E.; Hoogenraad, Marcel; Verspui, Goeran; Sheldon, Roger A.; Advanced Synthesis and Catalysis; vol. 345; nb. 4; (2003); p. 497 - 505 View in Reaxys With [2,2]bipyridinyl, air, copper(ll) bromide, 2,2,6,6-tetramethyl-piperidine-N-oxyl, potassium tert-butylate in water, acetonitrile, Time= 2.5h, T= 25 °C Gamez, Patrick; Arends, Isabel W. C. E.; Reedijk, Jan; Sheldon, Roger A.; Chemical Communications; nb. 19; (2003); p. 2414 - 2415 View in Reaxys With air, RuO2-FAU zeolite in toluene, Time= 1.5h, T= 80 °C Zhan, Bi-Zeng; White, Mary Anne; Sham, Tsun-Kong; Pincock, James A.; Doucet, Rene J.; Rao, K.V. Ramana; Robertson, Katherine N.; Cameron, T. Stanley; Journal of the American Chemical Society; vol. 125; nb. 8; (2003); p. 2195 - 2199 View in Reaxys With oxygen, [silica sol-gel (10percent 3,3,3-F3-propylated)]-[NPr4][RuO4] in carbon dioxide, T= 75 °C , p= 165017Torr , Kinetics, Further Variations: Catalysts Ciriminna, Rosaria; Campestrini, Sandro; Pagliaro, Mario; Advanced Synthesis and Catalysis; vol. 346; nb. 2-3; (2004); p. 231 - 236 View in Reaxys With air, cis-{NBu(n)4}{Os(N)(CH2SiMe3)2(CrO4)}, methoxybenzene in toluene, T= 40 °C , Catalytic oxidation, Kinetics, Further Variations: Solvents, Catalysts, Temperatures, Reaction partners Shapley, Patricia A.; Zhang, Najie; Allen, Jana L.; Pool, Douglas H.; Liang, Hong-Chang; Journal of the American Chemical Society; vol. 122; nb. 6; (2000); p. 1079 - 1091 View in Reaxys With air, 1percent Au/SiO2, T= 279.84 °C Biella, Serena; Rossi, Michele; Chemical Communications; nb. 3; (2003); p. 378 - 379 View in Reaxys With 2-iodoxybenzenesulfamide of (R)-1-phenylethylamine in chloroform, Time= 17h, T= 50 °C Koposov, Alexey Y.; Litvinov, Dmitry N.; Zhdankin, Viktor V.; Tetrahedron Letters; vol. 45; nb. 13; (2004); p. 2719 - 2721 View in Reaxys With oxygen, Pd on ordered mesoporous carbon in various solvent(s), Time= 13h, T= 100 °C Lu, An-Hui; Li, Wen-Cui; Hou, Zhenshan; Schueth, Ferdi; Chemical Communications; nb. 10; (2007); p. 1038 1040 View in Reaxys 94 % Chromat.

With pyridine-3-carbaldehyde-bis(CF3(CF2)7CH2CH2O-) acetal, 3 A molecular sieve, octadecafluorodecahydronaphthalene (cis+trans), palladium diacetate, oxygen in toluene, Time= 5h, T= 80 °C Nishimura, Takahiro; Maeda, Yasunari; Kakiuchi, Nobuyuki; Uemura, Sakae; Journal of the Chemical Society, Perkin Transactions 1; nb. 24; (2000); p. 4301 - 4305 View in Reaxys

100 % Chromat.

With oxygen, H5PV2Mo10O40 in various solvent(s), Time= 16h, T= 100 °C , p= 1520.1Torr Haimov, Adina; Neumann, Ronny; Chemical Communications; nb. 8; (2002); p. 876 - 877 View in Reaxys With pyridine, oxygen, palladium diacetate in toluene, T= 80 °C , p= 200Torr , Kinetics, Further Variations: Pressures

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

133/438

2018-03-11 22:07:32


Steinhoff, Bradley A.; Stahl, Shannon S.; Organic Letters; vol. 4; nb. 23; (2002); p. 4179 - 4181 View in Reaxys 100 % Chromat.

With pyridine, oxygen, palladium diacetate in toluene, Time= 2h, T= 80 °C Choi, Kwang-Min; Akita, Tomoki; Mizugaki, Tomoo; Ebitani, Kohki; Kaneda, Kiyotomi; New Journal of Chemistry; vol. 27; nb. 2; (2003); p. 324 - 328 View in Reaxys With sodium hydroxide, 1,10-Phenanthroline, oxygen, iron(III)-acetylacetonate in toluene, Time= 6h, T= 80 °C , Product distribution, Further Variations: Reagents Xiong, Yonglian; Xiao, Dehai; Li, Jing; Xie, Xiaofan; Yang, Xiangguang; Wu, Yue; Zeitschrift fur Physikalische Chemie; vol. 219; nb. 8; (2005); p. 1121 - 1131 View in Reaxys With tetramethylammonium monofluorochromate(VI) in acetic acid, Kinetics Sadeghy; Ghammami; Russian Journal of General Chemistry; vol. 75; nb. 12; (2005); p. 1886 - 1888 View in Reaxys With oxygen, palladium/alumina in carbon dioxide, T= 80 °C , p= 108761Torr , Product distribution, Further Variations: Pressures Grunwaldt, Jan-Dierk; Baiker, Alfons; Physical Chemistry Chemical Physics; vol. 7; nb. 20; (2005); p. 3526 - 3539 View in Reaxys

99 % Spectr.

With N,N,N',N'-tetramethylguanidine in chloroform-d1, Time= 1.5h, T= 20 °C , Product distribution, Further Variations: Reagents Matano, Yoshihiro; Suzuki, Takeshi; Shinokura, Tomonori; Imahori, Hiroshi; Tetrahedron Letters; vol. 48; nb. 16; (2007); p. 2885 - 2888 View in Reaxys With cetyl-trimethylammonium dichromate, acetic acid in dichloromethane, T= 26.84 °C , Kinetics, Further Variations: Solvents, Reagents, Temperatures Patel, Sabita; Mishra; International Journal of Chemical Kinetics; vol. 38; nb. 11; (2006); p. 651 - 656 View in Reaxys With N-methyl-2-indolinone, Ru(II) complex with tridentate O,N,S-donor ligand in chloroform, Time= 3h, T= 20 °C Balasubramanian; Karvembu; Prabhakaran; Chinnusamy; Natarajan; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 68; nb. 1; (2007); p. 50 - 54 View in Reaxys

96 % Chromat.

With dihydrogen peroxide, [MoO(O2)2(TEDA)2] in water, Time= 6h, T= 80 °C , Product distribution, Further Variations: Catalysts, Solvents Luan, Yi; Wang, Ge; Luck, Rudy L.; Yang, Mu; Han, Xiao; Chemistry Letters; vol. 36; nb. 10; (2007); p. 1236 1237 View in Reaxys Reaction Steps: 2 1: pyridine / diethyl ether / 5 h / 25 - 30 °C 2: 76 percent / Pd(OAc)2 / acetonitrile / 1 h / 80 °C / Heating With pyridine, palladium diacetate in diethyl ether, acetonitrile Minami, Ichiro; Tsuji, Jiro; Tetrahedron; vol. 43; nb. 17; (1987); p. 3903 - 3916 View in Reaxys Comparative Example 2 The ruthenium-carrying alumina prepared in Comparative Example 1 (0.044 g) was added to and suspended in trifluorotoluene (1.5 ml) and stirred at room temperature for 5 minutes. To the suspension, benzyl alcohol (0.108 g) was added, and oxidized by flowing oxygen through the suspension at 83° C. for 24 hours while stirring. The reaction mixture was analyzed. The conversion of benzyl alcohol was 23percent, and the selectivity to benzaldehyde was more than 99percent.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

134/438

2018-03-11 22:07:32


With oxygen in 2,3,4-trifluorotoluene, Time= 24h, T= 20 - 83 °C , Conversion of starting material Patent; Mizuno, Noritaka; Yamaguchi, Kazuya; Ishida, Hajime; US2004/204597; (2004); (A1) English View in Reaxys 3; 4; 5 : Example 3 The ruthenium-carrying alumina prepared in Example 1 (0.044 g) was added to and suspended in trifluorotoluene (1.5 ml) and stirred at room temperature for 5 minutes. To the suspension, benzyl alcohol (0.108 g) was added, and oxidized by flowing oxygen through the suspension at 83° C. for 24 hours while stirring. The reaction mixture was analyzed. The conversion of benzyl alcohol was 84percent, and the selectivity to benzaldehyde was more than 99percent.The ruthenium-carrying alumina prepared in Example 1 (0.11 g) was added to and suspended in trifluorotoluene (1.5 ml) and stirred at room temperature for 5 minutes. To the suspension, benzyl alcohol (0.108 g) was added, and oxidized by flowing oxygen through the suspension at 83° C. for 1 hour while stirring. The reaction mixture was analyzed. The conversion of benzyl alcohol was 99percent, and the selectivity to benzaldehyde was more than 99percent With oxygen in 2,3,4-trifluorotoluene, Time= 1 - 24h, T= 20 - 83 °C , Conversion of starting material Patent; Mizuno, Noritaka; Yamaguchi, Kazuya; Ishida, Hajime; US2004/204597; (2004); (A1) English View in Reaxys 24 : Example 24 The ruthenium-carrying alumina prepared in Example 2 (0.11 g) was added to and suspended in trifluorotoluene (1.5 ml) and stirred at room temperature for 5 minutes. To the suspension, benzyl alcohol (0.108 g) was added, and oxidized by flowing oxygen through the suspension at 83° C. for 1 hour while stirring. The reaction mixture was analyzed. The conversion of benzyl alcohol was 99percent, and the selectivity to benzaldehyde was more than 99percent. With oxygen in 2,3,4-trifluorotoluene, Time= 1h, T= 20 - 83 °C , Conversion of starting material Patent; Mizuno, Noritaka; Yamaguchi, Kazuya; Ishida, Hajime; US2004/204597; (2004); (A1) English View in Reaxys 1 :An operation was conducted in the same manner as in Example 8 except that 2 ml of acetic acid was replaced by 2 ml of propylene carbonate and there were used 0.2 g (1.35 mmol) of sodium bromate and 0.31 g (4.6 mmol) of 25percent aqueous ammonia. In the reaction mixture, 98.7percent (in terms of areal ratio of gas chromatography) of benzaldehyde used as a raw material remained, and formation of intended benzonitrile did not proceed substantially. With 1,2-propylene cyclic carbonate, sodium bromate, ammonia in water, Time= 15h, T= 90 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1555257; (2005); (A1) English View in Reaxys 2 :An operation was conducted in the same manner as in Example 8 except that sodium bromate was replaced by 0.14 g (1.35 mmol) of sodium chlorate and there was used 0.31 g (4.6 mmol) of 25percent aqueous ammonia. In the reaction mixture, 100percent (in terms of areal ratio of gas chromatography) of benzaldehyde used as a raw material remained, and there was no formation of intended benzonitrile. With sodium chlorate, ammonia, acetic acid in water, Time= 15h, T= 90 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1555257; (2005); (A1) English View in Reaxys IX :EXAMPLE IX; 170 mg of Fe (NO3) 3 9H2O (0.416mmol), 66mg 2,2'-bipyridyl (0. 416mmol), 85mg TEMPO (0.536mmol) and 80mg N-bromosuccinimide (0.45mmol) are dissolved in glacial acetic acid (7 cc) and the solution transferred into a jacketed glass reactor. The dissolution and thermostating of the catalyst solution is done as in Example III. When the temperature reached 45°C, 8250 mg of benzyl alcohol (76.6mmol) are injected through the septum adapter using a gas tight syringe. The recorded oxygen uptake rate was 0.587mmol 02/min and the GC analysis after 70min reaction time showed 100. 0percent conversion of the starting alcohol and 100.0percent selectivity to the desired benzylaldehyde. With oxygen, [2,2]bipyridinyl, N-Bromosuccinimide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, ferric nitrate in acetic acid, Time= 1.16667h, T= 45 °C , Product distribution / selectivity

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

135/438

2018-03-11 22:07:32


Patent; THE NUTRASWEET COMPANY; WO2005/82825; (2005); (A1) English View in Reaxys X :The Example Represents the Oxidation of Benzyl Alcohol0.1045 g AA-TEMPO (0.48 mmol), 0.124 g of Mg(NO3)2*6H2O (0.48 mmol) and 0.098 g N-bromosuccinimide (0.55 mmol) were dissolved in 4 ml of glacial acetic acid and the resulting solution was charged into the reaction flask. The amount of benzyl alcohol, the temperature, the pressure and the stirring rate were the same as for Example V. The recorded oxygen uptake rate was 0.631 mmol O2/min and the GC analysis after 60 min reaction time showed 100percent conversion of the starting alcohol and 93percent selectivity to benzyl aldehyde. With oxygen, T= 46 °C , p= 750.075Torr Patent; Degussa AG; US7030279; (2006); (B1) English View in Reaxys 92.6 8 :In the same manner as in Example 3, the operation was conducted, except that 0.43 g (4 mmols) of benzyl alco%Chromat. hol was used in place of m-methoxybenzyl alcohol and 1 ml (17.4 mmols) of acetic acid was used in place of 2 ml of acetic acid, and also 2 ml of dimethyl formamide and 0.2 g (1.35 mmols) of sodium bromate were used. With respect to the components in the reaction solution, the intended benzaldehyde was produced in an area ratio, as determined by gas chromatography, of 92.6percent.Example 3 (An embodiment of the invention described in the above embodiment [1]): Production of m-methoxybenzaldehyde In a 15 ml test tube type reaction vessel equipped with a magnetic stirrer and a reflux condenser, 0.55 g (4 mmols) of m-methoxybenzyl alcohol, 0.18 g (1.2 mmols) of sodium bromate and 2 ml (34.8 mmols) of acetic acid were charged, and then the resultant mixture was stirred at 90°C for 1.5 hours. Along with the progress of the reaction, a small amount of bromine was produced. After the completion of the reaction, bromine completely disappeared. With sodium bromate, acetic acid, N,N-dimethyl-formamide, Time= 1.5h, T= 90 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1661877; (2006); (A1) English View in Reaxys 1.3 1 :In the same manner as in Example 4, the operation was conducted, except that 0.43 g (4 mmols) of benzyl alco%Chromat. hol was used in place of m-methoxybenzyl alcohol and 2 ml of dimethyl formamide in place of 2 ml of acetic acid and 0.2 g (1.35 mmols) of sodium bromate were used. With respect to the components in the reaction solution, an area ratio as determined by gas chromatography of the intended benzaldehyde was 1.3percent and that of a raw material benzyl alcohol was 98.7percent. Example 4 (An embodiment of the invention described in the above embodiment [1]): Production of benzaldehyde In the same manner as in Example 3, the operation was conducted, except that 0.43 g (4 mmols) of benzyl alcohol was used in place of m-methoxybenzyl alcohol and 0.39 g (2 mmols) of sodium bromite trihydrate was used in place of sodium bromate, and also the mixture was stirred at 50°C for 4 hours. With respect to the components in the reaction solution, the intended benzaldehyde was produced in an area ratio, as determined by gas chromatography, of 93.5percent.Example 3 (An embodiment of the invention described in the above embodiment [1]): Production of mmethoxybenzaldehyde In a 15 ml test tube type reaction vessel equipped with a magnetic stirrer and a reflux condenser, 0.55 g (4 mmols) of m-methoxybenzyl alcohol, 0.18 g (1.2 mmols) of sodium bromate and 2 ml (34.8 mmols) of acetic acid were charged, and then the resultant mixture was stirred at 90°C for 1.5 hours. Along with the progress of the reaction, a small amount of bromine was produced. After the completion of the reaction, bromine completely disappeared. With sodium bromate, N,N-dimethyl-formamide, Time= 4h, T= 50 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1661877; (2006); (A1) English View in Reaxys 93.4 9 :In the same manner as in Example 8, the operation was conducted, except that 2 ml of propylene carbonate was %Chromat. used in place of 2 ml of dimethyl formamide. With respect to the components in the reaction solution, the intended benzaldehyde was produced in an area ratio, as determined by gas chromatography, of 93.4percent.Example 8 (An embodiment of the invention described in the above embodiment [1]): Production of benzaldehyde In the same manner as in Example 3, the operation was conducted, except that 0.43 g (4 mmols) of benzyl alcohol was used in place of m-methoxybenzyl alcohol and 1 ml (17.4 mmols) of acetic acid was used in place of 2 ml of acetic acid, and also 2 ml of dimethyl formamide and 0.2 g (1.35 mmols) of sodium bromate were used. With respect to the components in the reaction solution, the intended benzaldehyde was produced in an area ratio, as determined by gas chromatography, of 92.6percent.Example 3 (An embodiment of the invention described in the above embodiment [1]): Production of m-methoxybenzaldehyde In a 15 ml test tube type reaction vessel equipped with a magnetic stirrer and a reflux condenser, 0.55 g (4 mmols) of m-methoxybenzyl alcohol, 0.18 g (1.2 mmols) of sodium bromate and 2 ml (34.8

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

136/438

2018-03-11 22:07:32


mmols) of acetic acid were charged, and then the resultant mixture was stirred at 90°C for 1.5 hours. Along with the progress of the reaction, a small amount of bromine was produced. After the completion of the reaction, bromine completely disappeared. With 1,2-propylene cyclic carbonate, sodium bromate, acetic acid, Time= 1.5h, T= 90 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1661877; (2006); (A1) English View in Reaxys 93.5 4 :In the same manner as in Example 3, the operation was conducted, except that 0.43 g (4 mmols) of benzyl alco%Chromat. hol was used in place of m-methoxybenzyl alcohol and 0.39 g (2 mmols) of sodium bromite trihydrate was used in place of sodium bromate, and also the mixture was stirred at 50°C for 4 hours. With respect to the components in the reaction solution, the intended benzaldehyde was produced in an area ratio, as determined by gas chromatography, of 93.5percent.Example 3 (An embodiment of the invention described in the above embodiment [1]): Production of m-methoxybenzaldehyde In a 15 ml test tube type reaction vessel equipped with a magnetic stirrer and a reflux condenser, 0.55 g (4 mmols) of m-methoxybenzyl alcohol, 0.18 g (1.2 mmols) of sodium bromate and 2 ml (34.8 mmols) of acetic acid were charged, and then the resultant mixture was stirred at 90°C for 1.5 hours. Along with the progress of the reaction, a small amount of bromine was produced. After the completion of the reaction, bromine completely disappeared. With sodium bromite, acetic acid, Time= 4h, T= 50 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1661877; (2006); (A1) English View in Reaxys 2.2 2 :In the same manner as in Example 4, the operation was conducted, except that 0.43 g (4 mmols) of benzyl alco%Chromat. hol was used in place of m-methoxybenzyl alcohol and 1.8 ml of toluene and 0.2 ml (3.5 mmols) of acetic acid were used in place of 2 ml of acetic acid, and also 0.2 g (1.35 mmols) of sodium bromate was used. With respect to the components in the reaction solution, an area ratio as determined by gas chromatography of the intended benzaldehyde was 2.2percent and that of a raw material benzyl alcohol was 96.5percent. Example 4 (An embodiment of the invention described in the above embodiment [1]): Production of benzaldehyde In the same manner as in Example 3, the operation was conducted, except that 0.43 g (4 mmols) of benzyl alcohol was used in place of m-methoxybenzyl alcohol and 0.39 g (2 mmols) of sodium bromite trihydrate was used in place of sodium bromate, and also the mixture was stirred at 50°C for 4 hours. With respect to the components in the reaction solution, the intended benzaldehyde was produced in an area ratio, as determined by gas chromatography, of 93.5percent.Example 3 (An embodiment of the invention described in the above embodiment [1]): Production of mmethoxybenzaldehyde In a 15 ml test tube type reaction vessel equipped with a magnetic stirrer and a reflux condenser, 0.55 g (4 mmols) of m-methoxybenzyl alcohol, 0.18 g (1.2 mmols) of sodium bromate and 2 ml (34.8 mmols) of acetic acid were charged, and then the resultant mixture was stirred at 90°C for 1.5 hours. Along with the progress of the reaction, a small amount of bromine was produced. After the completion of the reaction, bromine completely disappeared. With sodium bromate, acetic acid in toluene, Time= 4h, T= 50 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1661877; (2006); (A1) English View in Reaxys 87.6 1 :Into a 50 ml three-necked flask equipped with a magnetic stirrer, a reflux condenser and a thermometer, 4.32 g %Chromat. (40 mmols) of benzyl alcohol, 2.0 g (13.5 mmols) of sodium bromate, 10 ml (174 mmols) of acetic acid and 10 ml of water were charged, and then the resultant mixture was stirred at room temperature for 24 hours. Along with the progress of the reaction, a small amount of bromine was produced and the temperature of the reaction solution was raised to 30°C. After the completion of the reaction, bromine completely disappeared. With respect to the components in the reaction solution, an area ratio as determined by gas chromatography of benzaldehyde was 91.7percent and that of benzyl alcohol was 5.1percent. Using n-tridecane as an internal standard substance, quantitative analysis was conducted by gas chromatography (GC). As a result, yield of benzaldehyde as the intended product of this reaction was 87.6percent. With sodium bromate, acetic acid in water, Time= 24h, T= 20 - 30 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1661877; (2006); (A1) English View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

137/438

2018-03-11 22:07:32


90 %Chromat.

5 :In the same manner as in Example 3, the operation was conducted, except that 0.43 g (4 mmols) of benzyl alcohol was used in place of m-methoxybenzyl alcohol and 2 ml (26.8 mmols) of propionic acid was used in place of acetic acid, and also the mixture was stirred at 80°C for 2.5 hours. With respect to the components in the reaction solution, the intended benzaldehyde was produced in an area ratio, as determined by gas chromatography, of 90.0percent.Example 3 (An embodiment of the invention described in the above embodiment [1]): Production of mmethoxybenzaldehyde In a 15 ml test tube type reaction vessel equipped with a magnetic stirrer and a reflux condenser, 0.55 g (4 mmols) of m-methoxybenzyl alcohol, 0.18 g (1.2 mmols) of sodium bromate and 2 ml (34.8 mmols) of acetic acid were charged, and then the resultant mixture was stirred at 90°C for 1.5 hours. Along with the progress of the reaction, a small amount of bromine was produced. After the completion of the reaction, bromine completely disappeared. With sodium bromate, propionic acid, Time= 2.5h, T= 80 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1661877; (2006); (A1) English View in Reaxys

1.4 3 :In the same manner as in Example 4, the operation was conducted, except that 0.43 g (4 mmols) of benzyl alco%Chromat. hol was used in place of m-methoxybenzyl alcohol and 2 ml of water in place of 2 ml of acetic acid and 0.2 g (1.35 mmols) of sodium bromate were used. With respect to the components in the reaction solution, an area ratio as determined by gas chromatography of the intended benzaldehyde was 1.4percent and that of a raw material benzyl alcohol was 97.9percent. Example 4 (An embodiment of the invention described in the above embodiment [1]): Production of benzaldehyde In the same manner as in Example 3, the operation was conducted, except that 0.43 g (4 mmols) of benzyl alcohol was used in place of m-methoxybenzyl alcohol and 0.39 g (2 mmols) of sodium bromite trihydrate was used in place of sodium bromate, and also the mixture was stirred at 50°C for 4 hours. With respect to the components in the reaction solution, the intended benzaldehyde was produced in an area ratio, as determined by gas chromatography, of 93.5percent.Example 3 (An embodiment of the invention described in the above embodiment [1]): Production of mmethoxybenzaldehyde In a 15 ml test tube type reaction vessel equipped with a magnetic stirrer and a reflux condenser, 0.55 g (4 mmols) of m-methoxybenzyl alcohol, 0.18 g (1.2 mmols) of sodium bromate and 2 ml (34.8 mmols) of acetic acid were charged, and then the resultant mixture was stirred at 90°C for 1.5 hours. Along with the progress of the reaction, a small amount of bromine was produced. After the completion of the reaction, bromine completely disappeared. With sodium bromate in water, Time= 4h, T= 50 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1661877; (2006); (A1) English View in Reaxys 90 %Chromat.

14 :In the same manner as in Example 3, the operation was conducted, except that 0.43 g (4 mmols) of benzyl alcohol was used in place of m-methoxybenzyl alcohol and 0.23 g (1.35 mmols) of potassium bromate was used in place of sodium bromate. With respect to the components in the reaction solution, the intended benzaldehyde was produced in an area ratio, as determined by gas chromatography, of 90.0percent.Example 3 (An embodiment of the invention described in the above embodiment [1]): Production of m-methoxybenzaldehyde In a 15 ml test tube type reaction vessel equipped with a magnetic stirrer and a reflux condenser, 0.55 g (4 mmols) of m-methoxybenzyl alcohol, 0.18 g (1.2 mmols) of sodium bromate and 2 ml (34.8 mmols) of acetic acid were charged, and then the resultant mixture was stirred at 90°C for 1.5 hours. Along with the progress of the reaction, a small amount of bromine was produced. After the completion of the reaction, bromine completely disappeared. With potassium bromate, acetic acid, Time= 1.5h, T= 90 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1661877; (2006); (A1) English View in Reaxys X :0.1045 g AA-TEMPO (0.48 mmol), 0.124 g of Mg(NO3)2*6H2O (0.48 mmol) and 0.098 g N-bromosuccinimide (0.55 mmol) were dissolved in 4 ml of glacial acetic acid and the resulting solution was charged into the reaction flask. The amount of benzyl alcohol, the temperature, the pressure and the stirring rate were the same as for Example V. The recorded oxygen uptake rate was 0.631 mmol O2/min and the GC analysis after 60 min reaction time showed 100 percent conversion of the starting alcohol and 93 percent selectivity to benzyl aldehyde. With oxygen, magnesium(II) nitrate, N-Bromosuccinimide, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy, acetic acid, Time= 1h, T= 46 °C , p= 750.075Torr , Product distribution / selectivity Patent; DEGUSSA AG; EP1674440; (2006); (A1) English

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

138/438

2018-03-11 22:07:32


View in Reaxys 2 :Example 2; A packed bed reactor was loaded with 5 cubic centimeters (cc) of magnesium carbonate pellets, having an average particle size of 1000 micrometers to 1400 micrometers. This catalyst was calcined in-situ for 16 to 22 hours at 390° C. at a rate of 0.2 to 5° C./min under 0.06 to 0.24 (10) g of nitrogen/hr/g of catalyst. The reaction was performed under atmospheric pressure. After calcination, the temperature was increased from 390° C. to 475° C. within two hours under nitrogen atmosphere. Once the reaction temperature was reached the nitrogen was turned off and the nitrogen was flushed out of the reactor. After 15 minutes of attaining this temperature, benzyl alcohol was introduced at 0.12 cc/min. The oxidation reaction was carried out under isothermal condition for a period of 16 hours. The constitution of the reaction mixture was monitored by gas chromatography/mass spectrometry. The results at the end of 16 hours are shown in Table 1. TABLE 1 Products Yield Benzaldehyde 36.67 Benzyl alcohol 62.94 Other 0.38 This example illustrates that essentially the only product produced by the reaction is benzaldehyde. The other products constituted only 1percent of the products, resulting in a 99percent selectivity for benzaldehyde. With magnesium carbonate calcinated at 390 C, Time= 16h, T= 390 - 475 °C , Gas phase, Product distribution / selectivity Patent; Ingelbrecht, Hugo; Kumar, Arun; Menon, Ashok Ramakrishnan; Nadkarni, Pradeep; Pawar, Rupesh; US2007/49767; (2007); (A1) English View in Reaxys 50 % Chromat.

With (ScScRaSa)-[Ru(terpy)(phbox-iPr)(OH2)](BF4)2 in phosphate buffer, pH= 7, Electrochemical reaction, Product distribution, Further Variations: pH-values Sala, Xavier; Santana, Naiara; Serrano, Isabel; Plantalech, Elena; Romero, Isabel; Rodriguez, Montserrat; Llobet, Antoni; Jansat, Susanna; Gomez, Montserrat; Fontrodona, Xavier; European Journal of Inorganic Chemistry; nb. 33; (2007); p. 5207 - 5214 View in Reaxys With oxygen, palladium/alumina in cyclohexane, T= 50 °C , Product distribution, Further Variations: Catalysts Mondelli, Cecilia; Ferri, Davide; Grunwaldt, Jan-Dierk; Krumeich, Frank; Mangold, Stefan; Psaro, Rinaldo; Baiker, Alfons; Journal of Catalysis; vol. 252; nb. 1; (2007); p. 77 - 87 View in Reaxys With tetra(n-butyl)ammonium hydroxide, oxygen, tetra-n-propylammonium perruthenate-methyltrimethoxysilane in carbon dioxide, T= 75 °C , p= 165017Torr , Kinetics, Further Variations: Catalysts, Reagents Campestrini, Sandro; Carraro, Massimo; Franco, Lorenzo; Ciriminna, Rosaria; Pagliaro, Mario; Tetrahedron Letters; vol. 49; nb. 3; (2008); p. 419 - 423 View in Reaxys With oxygen in toluene, Time= 24h, T= 79.84 °C , p= 760.051Torr Wang, Feng; Ueda, Wataru; Chemistry Letters; vol. 37; nb. 2; (2008); p. 184 - 185 View in Reaxys With air, Pd/meso-Al2O3 in toluene, Time= 24h, T= 60 °C Hackett, Simon F. J.; Brydson, Rik M.; Gass, Mhairi H.; Harvey, Ian; Newman, Andrew D.; Wilson, Karen; Lee, Adam F.; Angewandte Chemie - International Edition; vol. 46; nb. 45; (2007); p. 8593 - 8596 View in Reaxys With 3,3-dimethyldioxirane, Kinetics Jones, Janet W.; Vasquez, Pedro C.; Baumstark; Heterocyclic Communications; vol. 14; nb. 1-2; (2008); p. 11 14 View in Reaxys With sodium hydroxide, chloroamine-T, T= 29.84 °C , Kinetics, Further Variations: Reagents, Temperatures Prabhu; Journal of the Indian Chemical Society; vol. 84; nb. 11; (2007); p. 1135 - 1139 View in Reaxys With 3-chloro-benzenecarboperoxoic acid, iron(IV)-oxo meso-tetramesitylporphyrin π-cation radical in dichloromethane, acetonitrile, T= -40 °C , Kinetics, Further Variations: Temperatures

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

139/438

2018-03-11 22:07:32


Han, Ah-Rim; Jin Jeong, Yu; Kang, Yaeun; Yoon Lee, Jung; Sook Seo, Mi; Nam, Wonwoo; Chemical Communications; nb. 9; (2008); p. 1076 - 1078 View in Reaxys 93 %Chromat.

With α,α,α-trifluorotoluene, oxygen in water, Time= 5h, T= 20 °C Miyamura, Hiroyuki; Matsubara, Ryosuke; Kobayashi, Shu; Chemical Communications; nb. 17; (2008); p. 2031 2033 View in Reaxys With (TMP)+.FeIV(O)(ClO4) in acetonitrile, T= 23 °C , Kinetics, Temperature, Reagent/catalyst Pan, Zhengzheng; Horner, John H.; Newcomb, Martin; Journal of the American Chemical Society; vol. 130; nb. 25; (2008); p. 7776 - 7777 View in Reaxys With morpholinium chlorochromate in dimethyl sulfoxide, T= 24.84 °C , Kinetics, Solvent, Temperature Soni, Neelam; Tiwari, Vandana; Sharma, Vinita; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 47; nb. 5; (2008); p. 669 - 676 View in Reaxys

90 %Chromat.

With sodium tungstate (VI) dihydrate, sodium phosphate dibasic dodecahydrate, dihydrogen peroxide in DMA, Time= 1h, T= 90 °C Hida, Takemasa; Nogusa, Hideo; Tetrahedron; vol. 65; nb. 1; (2009); p. 270 - 274 View in Reaxys With Sulfolobus acidocaldarius cytochrome P450 119, dihydrogen peroxide, T= 22 °C , pH= 7.4, aq. phosphate buffer, Enzymatic reaction, Kinetics Sheng, Xin; Horner, John H.; Newcomb, Martin; Journal of the American Chemical Society; vol. 130; nb. 40; (2008); p. 13310 - 13320 View in Reaxys

76 %Chromat.

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], oxygen, triethylamine in toluene, Time= 12h, T= 80 °C , p= 1520.28Torr , Kinetics, Mechanism Jiang, Bi; Feng, Yuee; Ison, Elon A.; Journal of the American Chemical Society; vol. 130; nb. 44; (2008); p. 14462 - 14464 View in Reaxys With dihydrogen peroxide in N,N-dimethyl acetamide, water, Time= 0.5h, T= 80 °C Weng, Zhihuan; Wang, Jinyan; Zhang, Shouhai; Jian, Xigao; Bulletin of the Chemical Society of Japan; vol. 81; nb. 4; (2008); p. 525 - 529 View in Reaxys With oxygen in N,N-dimethyl-formamide, Time= 1.2h, T= 139.84 °C , p= 15001.5Torr Mertens; Vandezande; Ye; Poelman; De Vos; Vankelecom; Advanced Synthesis and Catalysis; vol. 350; nb. 9; (2008); p. 1241 - 1247 View in Reaxys

94 %Spectr.

With solid phase supported CuO/Cu composite, Time= 5h, T= 140 - 150 °C , Neat (no solvent) Pande, Surojit; Saha, Arindam; Jana, Subhra; Sarkar, Sougata; Basu, Mrinmoyee; Pradhan, Mukul; Sinha, Arun Kumar; Saha, Sandip; Pal, Anjali; Pal, Tarasankar; Organic Letters; vol. 10; nb. 22; (2008); p. 5179 - 5181 View in Reaxys With oxygen in carbon dioxide, Time= 12h, T= 60 °C , p= 135014Torr , Supercritical conditions Hou, Zhenshan; Theyssen, Nils; Brinkmann, Axel; Klementiev, Konstantin V.; Gruenert, Wolfgang; Buehl, Michael; Schmidt, Wolfgang; Spliethoff, Bernd; Tesche, Bernd; Weidenthaler, Claudia; Leitner, Walter; Journal of Catalysis; vol. 258; nb. 2; (2008); p. 315 - 323 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

140/438

2018-03-11 22:07:32


With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, alizarin red S, titanium(IV) oxide in benzotrifluoride, Time= 18h, p= 750.075Torr , visible-light irradiation Zhang, Miao; Chen, Chuncheng; Ma, Wanhong; Zhao, Jincai; Angewandte Chemie - International Edition; vol. 47; nb. 50; (2008); p. 9730 - 9733 View in Reaxys With toluene-4-sulfonic acid, 2,2'-bipyridinium chlorochromate in dimethyl sulfoxide, T= 24.84 °C , Kinetics, Mechanism, Solvent, Temperature, Reagent/catalyst Yajurvedi, Deeksha; Baghmar, Manju; Sharma, Pradeep K.; Journal of the Indian Chemical Society; vol. 85; nb. 5; (2008); p. 496 - 501 View in Reaxys With 2,2'-bipyridinium chlorochromate in dimethyl sulfoxide, Time= 15h, T= 24.84 °C , Darkness Yajurvedi, Deeksha; Baghmar, Manju; Sharma, Pradeep K.; Journal of the Indian Chemical Society; vol. 85; nb. 5; (2008); p. 496 - 501 View in Reaxys With hydrotalcite supported Cu nanoparticles in para-xylene, Time= 9h, T= 130 °C , Inert atmosphere Mitsudome, Takato; Mikami, Yusuke; Ebata, Kaori; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Chemical Communications; nb. 39; (2008); p. 4804 - 4806 View in Reaxys With tert.-butylhydroperoxide, diphenyl diselenide, sodium sulfate in PFTE, toluene, T= 80 °C Van Der Toorn, John C.; Kemperman, Gerjan; Sheldon, Roger A.; Arends, Isabel W.C.E.; Journal of Organic Chemistry; vol. 74; nb. 8; (2009); p. 3085 - 3089 View in Reaxys 98 %Chromat.

With 2,2'-azobis(isobutyronitrile), oxygen in acetonitrile, Time= 12h, T= 100 °C , p= 2584.17Torr , Autoclave Bordoloi, Ankur; Sahoo, Suman; Lefebvre; Halligudi; Journal of Catalysis; vol. 259; nb. 2; (2008); p. 232 - 239 View in Reaxys

99 %Spectr.

With 1-Phenylethanol, Ru(PPh3)(OH)-salen, oxygen in chloroform, T= 20 °C , chemoselective reaction Mizoguchi, Hirotaka; Uchida, Tatsuya; Ishida, Kohichi; Katsuki, Tsutomu; Tetrahedron Letters; vol. 50; nb. 26; (2009); p. 3432 - 3435 View in Reaxys With tetra-O-acetyl riboflavin, air in dimethylsulfoxide-d6, water-d2, Time= 0.416667h, T= 20 °C , Irradiation, Reactivity, Reagent/catalyst, Time, Solvent Schmaderer, Harald; Hilgers, Petra; Lechner, Robert; Koenig, Burkhard; Advanced Synthesis and Catalysis; vol. 351; nb. 1-2; (2009); p. 163 - 174 View in Reaxys With Pt/MOF-177, Time= 24h, T= 20 °C , in air Proch, Sebastian; Herrmannsdoerfer, Justus; Kempe, Rhett; Kern, Christoph; Jess, Andreas; Seyfarth, Lena; Senker, Juergen; Chemistry - A European Journal; vol. 14; nb. 27; (2008); p. 8204 - 8212 View in Reaxys With Ru(III)/titanate nanotubes Bavykin, Dmitry V.; Walsh, Frank C.; European Journal of Inorganic Chemistry; nb. 8; (2009); p. 977 - 997 View in Reaxys With 2-iodyl-N-methyl-N-butylaniline oxide, trifluoroacetic acid in acetone, Time= 3h, T= 20 °C Zhdankin, Viktor V.; Nemykin, Victor N.; Karimov, Rashad R.; Kazhkenov, Zeinul-Gabiden; Chemical Communications; nb. 46; (2008); p. 6131 - 6133 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

141/438

2018-03-11 22:07:32


26 %Chromat.

With oxygen, potassium carbonate in methanol, Time= 23h, T= 80 °C , p= 3750.38Torr Ishida, Tamao; Nagaoka, Megumi; Akita, Tomoki; Haruta, Masatake; Chemistry - A European Journal; vol. 14; nb. 28; (2008); p. 8456 - 8460 View in Reaxys With dihydrogen peroxide, cetyltrimethylammonim bromide in water, 1,2-dichloro-ethane, Molecular sieve, chemoselective reaction Yadav, Ganapati D.; Manyar, Haresh G.; Advanced Synthesis and Catalysis; vol. 350; nb. 14-15; (2008); p. 2286 2294 View in Reaxys

100 %Spectr.

With bis(2,4,6-triisopropylphenyl) tellurone in hexane, Time= 1h, Reflux Oba, Makoto; Okada, Yasunori; Nishiyama, Kozaburo; Shimada, Shigeru; Ando, Wataru; Chemical Communications; nb. 42; (2008); p. 5378 - 5380 View in Reaxys With dihydrogen peroxide in water, Time= 12h, T= 75 °C , chemoselective reaction Zhang, Yugen; Riduan, Siti Nurhanna; Ying, Jackie Y.; Chemistry - A European Journal; vol. 15; nb. 5; (2009); p. 1077 - 1081 View in Reaxys

99 %Chromat.

With oxygen in toluene, Time= 0.5h, T= 89.84 °C , chemoselective reaction Venkatesan; Senthil Kumar; Lee, Jyh-Fu; Chan, Ting-Shan; Zen, Jyh-Myng; Chemical Communications; nb. 14; (2009); p. 1912 - 1914 View in Reaxys With iron(III) orthophosphate tetrahydrate, dihydrogen peroxide in water, Time= 12h, T= 75 °C Shi, Feng; Tse, Man Kin; Li, Zuopeng; Beller, Matthias; Chemistry - A European Journal; vol. 14; nb. 29; (2008); p. 8793 - 8797 View in Reaxys

94 %Chromat.

With N-Bromosuccinimide in polyethylene glycol 400, Time= 1h, T= 60 °C Fan, Ji-Cai; Shang, Zhi-Cai; Liang, Jun; Liu, Xiu-Hong; Liu, Yang; Journal of Physical Organic Chemistry; vol. 21; nb. 11; (2008); p. 945 - 953 View in Reaxys

92 %Chromat.

With oxygen in water, 1,2-dichloro-ethane, T= 50 °C Wang, Naiwei; Matsumoto, Tsutomu; Ueno, Masaharu; Miyamura, Hiroyuki; Kobayashi, Shu; Angewandte Chemie, International Edition; vol. 48; (2009); p. 4744 - 4746; Angewandte Chemie; vol. 121; (2009); p. 4838 - 4840 View in Reaxys

50 %Spectr.

With Cp*Ir(Cl)2(nBu2Im), caesium carbonate in toluene, Time= 24h, T= 110 °C Prades, Amparo; Corberan, Rosa; Poyatos, Macarena; Peris, Eduardo; Chemistry - A European Journal; vol. 14; nb. 36; (2008); p. 11474 - 11479 View in Reaxys With RuO2*5.2H2O/CNT in toluene, Time= 0.5h, T= 80 °C , p= 750.075Torr , Air Yu, Hao; Fu, Xiaobo; Zhou, Chunmei; Peng, Feng; Wang, Hongjuan; Yang, Jian; Chemical Communications; nb. 17; (2009); p. 2408 - 2410 View in Reaxys With oxidized cytochrome P450 119 in glycerol, T= -50 °C , aq. phosphate buffer, UV-irradiation, Kinetics Wang, Qin; Sheng, Xin; Horner, John H.; Newcomb, Martin; Journal of the American Chemical Society; vol. 131; nb. 30; (2009); p. 10629 - 10636 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

142/438

2018-03-11 22:07:32


96 %Chromat.

With pyridine, 1-chloro-1λ3 -benzo[d][1,2]iodaoxol-3(1H)-one, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in ethyl acetate, Time= 0.5h, T= 20 °C Li, Xiao-Qiang; Zhang, Chi; Synthesis; nb. 7; (2009); p. 1163 - 1169; Art.No: F20408SS View in Reaxys With oxygen, titanium(IV) oxide in benzotrifluoride, Time= 8h, p= 750.075Torr , Irradiation Zhang, Miao; Wang, Qi; Chen, Chuncheng; Ma, Wanhong; Zhao, Jincai; Zang, Ling; Angewandte Chemie, International Edition; vol. 48; nb. 33; (2009); p. 6081 - 6084; Angewandte Chemie; vol. 121; nb. 33; (2009); p. 6197 6200 View in Reaxys With 6A,6D-di-O-(prop-2-one-1,3-dienyl)-α-cyclodextrin, dihydrogen peroxide, Time= 5h, T= 25 °C , pH= 7, aq. phosphate buffer Fenger, Thomas Hauch; Marinescu, Lavinia G.; Bols, Mikael; Organic and Biomolecular Chemistry; vol. 7; nb. 5; (2009); p. 933 - 943 View in Reaxys

82 %Chromat.

With γ-alumina-supported silver cluster in toluene, Time= 24h, T= 99.84 °C , Kinetics, Concentration Shimizu, Ken-Ichi; Sugino, Kenji; Sawabe, Kyoichi; Satsuma, Atsushi; Chemistry - A European Journal; vol. 15; nb. 10; (2009); p. 2341 - 2351 View in Reaxys With N-(2-iodylphenyl)-N,4-dimethylbenzenesulfonamide in acetonitrile, Time= 5h, Reflux, Inert atmosphere Mailyan, Artur K.; Geraskin, Ivan M.; Nemykin, Victor N.; Zhdankin, Viktor V.; Journal of Organic Chemistry; vol. 74; nb. 21; (2009); p. 8444 - 8447 View in Reaxys 29; 30; 31; 32; 33; 34 : Example 29 This example further illustrates the process of this invention for the oxidation of benzyl alcohol to benzaldehyde using a hydrotalcite-like catalyst, containing MoO42- anions at concentration 1.3 mmol.g-1, derived from a hydrotalcitelike material having chemical formula same as that in Example-1 except that the divalent cation was Ni2+ instead of Mg2+. [0151] The hydrotalcite-like material was prepared by the method similar to that described in Example-1 except that 0.9 mol nickel nitrate was used instead of 0.9 mol magnesium nitrate. [0152] The hydrotalcite-like catalyst was prepared from the hydrotalcite-like material by the method similar to that described in Example-1 except that 0.04 mol Na2 MoO4 was used instead of 0.12 mol KMnO4. The concentration of MoO42- anions in the catalyst was 1.3 mmol.g-1. The XRD data of both the hydrotalcite-like material and the hydrotalcite-like catalyst were similar to that of the hydrotalcite material prepared in Example-1. [0153] The catalytic oxidation of benzyl alcohol over the hydrotalcite-like catalyst was carried out by the method and reaction conditions same as that used in Example-1 except that the reaction was carried out under reflux at 204°C. and oxygen gas was bubbled continuously through the reaction mixture at a flow rate of 6 ml per min at atmospheric pressure, 1.0 atm. The conversion and product selectivity were as follows. [TABLE-US-00016] Conversion of benzyl alcohol 25.9percent Selectivity for benzaldehyde 89.2percent.EXAMPLE 30 [0154] This example further illustrates the process of this invention for the oxidation of benzyl alcohol to benzaldehyde using a hydrotalcite-like catalyst, containing WO42- anions at concentration 1.1 mmol.g-1, derived from a hydrotalcite-like material having chemical formula same as that in Example-1. [0155] The hydrotalcite-like material, with x=0.09, was prepared by the method similar to that described in Example-1. [0156] The hydrotalcite-like catalyst was prepared from the hydrotalcite-like material by the method similar to that described in Example-1 except that 0.05 mol Na2 WO4 was used instead of 0.12 mol KMnO4. The concentration of WO42- anions in the catalyst was 1.1 mmol.g-1. The XRD data of the hydrotalcite-like catalyst is similar to that of the hydrotalcite material prepared in Example-1. [0157] The catalytic oxidation of benzyl alcohol over the hydrotalcite-like catalyst was carried out by the method and reaction conditions same as that used in Example-29 except that the reaction period was 5 h. The conversion and product selectivity were as follows. [TABLE-US-00017] Conversion of benzyl alcohol 25.2percent Selectivity for benzaldehyde 93.7percent EXAMPLES 31 to 34 [0158] These examples further illustrate the process of the invention for the oxidation benzyl alcohol using CrO42- and Cr2 O72- anions containing hydrotalcite-like catalysts prepared in Examples 26 and 27, respectively. [0159] The process was carried by the method similar to that described in Example-30 except that the catalyst pretreatment and reaction conditions were different, as given in Table-6. The results of the oxidation are given in Table-6. With oxygen, hydrotalcite like catalyst, Time= 5 - 15h, T= 105 - 204 °C , p= 760.051Torr , Heating / reflux, Conversion of starting material

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

143/438

2018-03-11 22:07:32


Patent; Council of Scientific and Industrial Research; US2004/192972; (2004); (A1) English View in Reaxys With 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Singh, Pradhumn; Singh, Monika; Singh, Ajai K.; Journal of Organometallic Chemistry; vol. 694; nb. 24; (2009); p. 3872 - 3880 View in Reaxys With 2,2,6,6-tetramethyl-piperidine-N-oxyl, oxygen, potassium carbonate, copper(II) sulfate in water, Time= 2h, T= 80 °C , p= 760.051Torr , chemoselective reaction Figiel, Pawel J.; Sibaouih, Ahlam; Ahmad, Jahir Uddin; Nieger, Martin; Raeisaenen, Minna T.; Leskelae, Markku; Repo, Timo; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2625 - 2632 View in Reaxys 97 %Chromat.

With sodium tetrachloroaurate dihydrate, oxygen, caesium carbonate in toluene, Time= 2h, T= 30 °C , p= 760.051Torr Karimi, Babak; Kabiri Esfahani, Farhad; Chemical Communications; nb. 37; (2009); p. 5555 - 5557 View in Reaxys With N,N'-diacetyl-6(A),6(D)-diamino-6(A),6(D)-dideoxy-N,N'-(2-oxopropa-1,3-dienyl)-β-cyclodextrin, dihydrogen peroxide in water, Time= 5h, T= 20 °C , pH= 7, aq. phosphate buffer, Kinetics, Reagent/catalyst, chemoselective reaction Marinescu, Lavinia G.; Doyagueez, Elisa G.; Petrillo, Marta; Fernandez-Mayoralas, Alfonso; Bols, Mikael; European Journal of Organic Chemistry; nb. 1; (2010); p. 157 - 167 View in Reaxys

41 %Chromat.

With C77H60Cl2N4O4PRu2, 4-methylmorpholine N-oxide in dichloromethane, Time= 8h, Reflux Venkatachalam; Raja; Pandiarajan; Ramesh; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 71; nb. 3; (2008); p. 884 - 891 View in Reaxys

97 %Chromat.

With 1-methyl-3-(2-oxo-2-(2,2,6,6-tetramethyl-1-ylooxy-4-piperidoxyl)ethyl)imidazolium chloride, carbon dioxide, water, oxygen, sodium nitrite, Time= 8h, T= 99.84 °C , p= 82508.3Torr , Autoclave Miao, Cheng-Xia; He, Liang-Nian; Wang, Jing-Lun; Wu, Fang; Journal of Organic Chemistry; vol. 75; nb. 1; (2010); p. 257 - 260 View in Reaxys

95 %Chromat.

With sodium hypochlorite, potassium bromide in dichloromethane, Cyclooctan, water, Time= 0.08h, pH= 9.1, Flow microreactor, Cooling with ice Bogdan, Andrew; McQuade, D. Tyler; Beilstein Journal of Organic Chemistry; vol. 5; (2009); Art.No: A17 View in Reaxys

98 %Chromat.

With oxygen, potassium carbonate in α,α,α-trifluorotoluene, Time= 1.5h, T= 80 °C , p= 760.051Torr Karimi, Babak; Zamani, Asghar; Abedi, Sedigheh; Clark, James H.; Green Chemistry; vol. 11; nb. 1; (2009); p. 109 - 119 View in Reaxys

54 %Chromat.

With oxygen in toluene, Time= 1h, T= 99.84 °C Yang, Jie; Guan, Yejun; Verhoeven, Tiny; Van Santen, Rutger; Li, Can; Hensen, Emiel J. M.; Green Chemistry; vol. 11; nb. 3; (2009); p. 322 - 325 View in Reaxys With oxygen, titanium(IV) oxide in water, T= 26.84 °C , UV-irradiation, Kinetics, chemoselective reaction Yurdakal, Sedat; Palmisano, Giovanni; Loddo, Vittorio; Alagoez, Ouzhan; Augugliaro, Vincenzo; Palmisano, Leonardo; Green Chemistry; vol. 11; nb. 4; (2009); p. 510 - 516 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

144/438

2018-03-11 22:07:32


With oxygen in water, Time= 336h, T= 20 °C , p= 760.051Torr , pH= 6.5 - 7 Tonucci, Lucia; Nicastro, Marco; D'Alessandro, Nicola; Bressan, Mario; D'Ambrosio, Primiano; Morvillo, Antonino; Green Chemistry; vol. 11; nb. 6; (2009); p. 816 - 820 View in Reaxys 8 %Chromat.

With oxygen in carbon dioxide, Time= 12h, T= 100 °C , Autoclave Wang, Jin-Quan; He, Liang-Nian; Miao, Cheng-Xia; Green Chemistry; vol. 11; nb. 7; (2009); p. 1013 - 1017 View in Reaxys With Oxone, tetrabutylammomium bromide in water, Time= 1h, T= 20 °C , Irradiation Wu, Shang; Ma, Hengchang; Yan, Penghua; Wang, Jianqiang; Ding, Juanjuan; Lei, Ziqiang; Letters in Organic Chemistry; vol. 6; nb. 5; (2009); p. 424 - 427 View in Reaxys With oxygen in α,α,α-trifluorotoluene, T= 110 °C , p= 1500.15Torr Barats, Delina; Neumann, Ronny; Advanced Synthesis and Catalysis; vol. 352; nb. 2-3; (2010); p. 293 - 298 View in Reaxys

99 %Chromat.

With styrene, Cu/La2O3 in 1,3,5-trimethyl-benzene, Time= 3h, T= 149.84 °C , Inert atmosphere, Autoclave Shi, Ruijuan; Wang, Fei; Tana; Li, Yong; Huang, Xiumin; Shen, Wenjie; Green Chemistry; vol. 12; nb. 1; (2010); p. 108 - 113 View in Reaxys With oxygen, potassium carbonate in toluene, Time= 6h, T= 100 °C , p= 4560.31Torr Oliveira, Rafael L.; Kiyohara, Pedro K.; Rossi, Liane M.; Green Chemistry; vol. 12; nb. 1; (2010); p. 144 - 149 View in Reaxys With Au/Al2O3, potassium carbonate in toluene, Time= 1.5h, T= 79.84 °C , p= 760.051Torr Quintanilla; Butselaar-Orthlieb; Kwakernaak; Sloof; Kreutzer; Kapteijn; Journal of Catalysis; vol. 271; nb. 1; (2010); p. 104 - 114 View in Reaxys With manganese(IV) oxide in chloroform, Time= 2h, Reflux Phillips, David J.; Graham, Andrew E.; Synlett; nb. 5; (2010); p. 769 - 773; Art.No: D30409ST View in Reaxys With [RuCl(P(C6H5)3)C6H4(CHNC6H4CO2)2], oxygen in dichloromethane, Time= 3h, T= 20 °C Arunachalam; Padma Priya; Jayabalakrishnan; Chinnusamy; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 74; nb. 2; (2009); p. 591 - 596 View in Reaxys With 1,4-diaza-bicyclo[2.2.2]octane, chloroamine-T, silica gel in 1,4-dioxane, water, T= 20 °C Yadav, Lal Dhar Singh; Srivastava, Vishnu Prabhakar; Patel, Rajesh; Synlett; nb. 7; (2010); p. 1047 - 1050 View in Reaxys With C41H34ClN3O2PRu, oxygen in dichloromethane, Time= 4h, T= 20 °C Priya, N. Padma; Arunachalam; Manimaran; Muthupriya; Jayabalakrishnan; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 72; nb. 3; (2009); p. 670 - 676 View in Reaxys With [Cu2(5-bpyT)2Br4](CH3CN)2, potassium tert-butylate, oxygen in water, acetonitrile, Time= 10h, T= 50 °C Lu, Zhengliang; Ladrak, Tim; Roubeau, Olivier; Van Der Toorn, John; Teat, Simon J.; Massera, Chiara; Gamez, Patrick; Reedijk, Jan; Dalton Transactions; nb. 18; (2009); p. 3559 - 3570 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

145/438

2018-03-11 22:07:32


With [(Cp*Ir)2(μ-NTs)2], potassium tert-butylate in (2)H8-toluene, T= 100 °C , Inert atmosphere Zhu, Mingwen; Fujita, Ken-Ichi; Yamaguchi, Ryohei; Organic Letters; vol. 12; nb. 6; (2010); p. 1336 - 1339 View in Reaxys With oxygen in methanol, toluene, T= 35 °C , p= 760.051Torr , Kinetics, Reagent/catalyst, Solvent Dhavamani; Parameswaran; Journal of the Indian Chemical Society; vol. 86; nb. 4; (2009); p. 383 - 387 View in Reaxys 98 %Chromat.

2-4 :A mixture of 1 mmol of benzyl alcohol, 5 mL of toluene, and 0.1 g of the catalyst prepared from Example 2-0 and including Ag particles immobilized on a hydrotalcite surface was stirred at 110° C. in an argon atmosphere for 24 hours and thereby yielded a corresponding carbonyl compound (benzaldehyde) in a yield equivalent to a gas chromatographic (GC) yield of 98percent, with a selectivity for benzaldehyde of 99percent or more. With Ag/HT in water, Time= 24h, T= 110 °C , Inert atmosphere, Product distribution / selectivity Patent; Kaneda, Kiyotomi; Yamasaki, Noritsugu; US2010/130758; (2010); (A1) English View in Reaxys With [ruthenium(II)chloride(.eta.6-p-cymene)(1-(4-methoxyphenyltelluromethyl)-1H-benzotriazole)](hexaflourophosphate), 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Das, Dipanwita; Singh, Pradhumn; Singh, Ajai K.; Journal of Organometallic Chemistry; vol. 695; nb. 7; (2010); p. 955 - 962 View in Reaxys

90 %Chromat.

With NiZn-Pd(0.02) nanocomposite catalyst in α,α,α-trifluorotoluene, Time= 2h, T= 79.84 °C , p= 760.051Torr , Kinetics, Reagent/catalyst, Solvent, Temperature, Time Hara, Takayoshi; Ishikawa, Masakazu; Sawada, Junya; Ichikuni, Nobuyuki; Shimazu, Shogo; Green Chemistry; vol. 11; nb. 12; (2009); p. 2034 - 2040 View in Reaxys

100 With sodium hypochlorite, sodium hydrogencarbonate, potassium bromide in dichloromethane, water, Time= 3h, T= %Chromat. 20 °C , pH= 9.1 Roeben, Caren; Studer, Armido; Hemme, Wilhelm L.; Eckert, Hellmut; Synlett; nb. 7; (2010); p. 1110 - 1114 View in Reaxys With oxygen in water, Time= 5h, p= 37503.8Torr Izarova, Natalya V.; Biboum, Rosa Ngo; Keita, Bineta; Mifsud, Maria; Arends, Isabel W. C. E.; Jameson, Geoffrey B.; Kortz, Ulrich; Dalton Transactions; nb. 43; (2009); p. 9385 - 9387 View in Reaxys 99 %Chromat.

With C56H42As2Cl2O3Ru, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux, Molecular sieve Muthukumar; Viswanathamurthi; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 74; nb. 2; (2009); p. 454 - 462 View in Reaxys With trimethyloctadecylammonium chloride in water, acetonitrile, Time= 6h, T= 24.84 °C , Darkness, Irradiation, chemoselective reaction Naya, Shin-Ichi; Tada, Hiroaki; Inoue, Aimi; Journal of the American Chemical Society; vol. 132; nb. 18; (2010); p. 6292 - 6293 View in Reaxys With dimethylsulfoxide-d6, iodopentafluorobenzene bis(trifluoroacetate), T= 20 °C , Inert atmosphere Schaefer, Sascha; Wirth, Thomas; Angewandte Chemie - International Edition; vol. 49; nb. 15; (2010); p. 2786 2789 View in Reaxys With oxovanadium(IV) sulfate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 2h, T= 80 °C , p= 3000.3Torr , Autoclave

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

146/438

2018-03-11 22:07:32


Du, Zhongtian; Ma, Jiping; Ma, Hong; Wang, Min; Huang, Yizheng; Xu, Jie; Catalysis Communications; vol. 11; nb. 8; (2010); p. 732 - 735 View in Reaxys With γ-Fe2O3-mesoporous silica, oxygen in PEG200, Time= 24h, T= 130 °C Lang, Leiming; Li, Baojun; Liu, Wei; Li, Xun; Xu, Zheng; Chemistry Letters; vol. 38; nb. 8; (2009); p. 806 - 807 View in Reaxys 62 %Chromat.

With (VO)4(3-hydrocypicolinate(2-))4, oxygen in acetonitrile, Time= 3h, T= 120 °C , p= 7500.75Torr , Autoclave Kodama, Shintaro; Ueta, Yukihiro; Yoshida, Jun; Nomoto, Akihiro; Yano, Shigenobu; Ueshima, Michio; Ogawa, Akiya; Dalton Transactions; nb. 44; (2009); p. 9708 - 9711 View in Reaxys

> 99 With Au/hydrotalcite in para-xylene, Time= 9h, T= 120 °C , Inert atmosphere %Chromat. Fang, Wenhao; Zhang, Qinghong; Chen, Jing; Deng, Weiping; Wang, Ye; Chemical Communications; vol. 46; nb. 9; (2010); p. 1547 - 1549 View in Reaxys With dihydrogen peroxide in water, Time= 6h, T= 89.84 °C Zhao, Wei; Zhang, Yingshuai; Ma, Baochun; Ding, Yong; Qiu, Wenyuan; Catalysis Communications; vol. 11; nb. 6; (2010); p. 527 - 531 View in Reaxys With oxygen, T= 250 °C , p= 760.051Torr Rao; Venkateswara Rao; Sai Prasad; Lingaiah; Catalysis Communications; vol. 11; nb. 6; (2010); p. 547 - 550 View in Reaxys With NBu4[O2V(O2CC2H2Ph)2], oxygen in acetonitrile, Time= 1h, T= 80 °C , Inert atmosphere, Molecular sieve Ohde, Christian; Limberg, Christian; Chemistry - A European Journal; vol. 16; nb. 23; (2010); p. 6892 - 6899 View in Reaxys With C31H29ClNO4PRu, oxygen in dichloromethane, Time= 6h, T= 32 °C Sathya; Raja; Padma Priya; Jayabalakrishnan; Applied Organometallic Chemistry; vol. 24; nb. 5; (2010); p. 366 373 View in Reaxys With oxygen in water, toluene, Time= 3h, T= 85 °C , p= 750.075Torr Yang, Xiaomin; Wang, Xiuna; Qiu, Jieshan; Applied Catalysis A: General; vol. 382; nb. 1; (2010); p. 131 - 137 View in Reaxys With dihydrogen peroxide in water, Time= 20h, T= 75 °C Bansal, Vipin Kumar; Thankachan, Pompozhi Protasis; Prasad, Rajendra; Applied Catalysis A: General; vol. 381; nb. 1-2; (2010); p. 8 - 17 View in Reaxys With oxygen, potassium carbonate in toluene, Time= 10h, T= 90 °C , p= 760.051Torr Yang, Hengquan; Ma, Zhancheng; Qing, Yong; Xie, Guangyong; Gao, Jie; zhang, Li; Gao, Jinhua; du, Lin; Applied Catalysis A: General; vol. 382; nb. 2; (2010); p. 312 - 321 View in Reaxys 84 %Chromat.

With dihydrogen peroxide in water, Time= 7h, T= 69.84 °C Ma, Baochun; Zhang, Yingshuai; Ding, Yong; Zhao, Wei; Catalysis Communications; vol. 11; nb. 9; (2010); p. 853 - 857 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, H4VPO7, oxygen in water, Time= 4h, T= 80 °C , p= 3000.3Torr , Autoclave

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

147/438

2018-03-11 22:07:32


Du, Zhongtian; Ma, Jiping; Ma, Hong; Gao, Jin; Xu, Jie; Green Chemistry; vol. 12; nb. 4; (2010); p. 590 - 592 View in Reaxys With oxygen, potassium carbonate in toluene, Time= 8h, T= 80 °C , p= 760.051Torr , chemoselective reaction Yang, Hengquan; Han, Xiaojing; Ma, Zhancheng; Wang, Runqin; Liu, Jing; Ji, Xiangfei; Green Chemistry; vol. 12; nb. 3; (2010); p. 441 - 451 View in Reaxys 95 %Chromat.

With acetaldehyde, Time= 24h, T= 30 °C , pH= 7.5, aq. phosphate buffer, Microbiological reaction, Combinatorial reaction / High throughput screening (HTS), Oppenauer oxidation, chemoselective reaction Orbegozo, Thomas; De Vries, Johannes G.; Kroutil, Wolfgang; European Journal of Organic Chemistry; nb. 18; (2010); p. 3445 - 3448 View in Reaxys

100 With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [Cu(AcO)2(py)]2-silica, oxygen in carbon dioxide, Time= 12h, %Chromat. T= 80 °C , p= 113636Torr , Supercritical conditions Herbert, Matthew; Montilla, Francisco; Galindo, Agustin; Dalton Transactions; vol. 39; nb. 3; (2010); p. 900 - 907 View in Reaxys With (+/-)-2-ethyl-2-(2-iodoxyphenyl)acetic acid methyl ester, trifluoroacetic acid in dichloromethane, Time= 8h, Reflux Altermann, Sabine M.; Schaefer, Sascha; Wirth, Thomas; Tetrahedron; vol. 66; nb. 31; (2010); p. 5902 - 5907 View in Reaxys With 10 palladium on carbon, oxygen in 2,3,4-trifluorotoluene, T= 90 °C , p= 3750.38Torr , Autoclave Ruiz, Violeta R.; Corma, Avelino; Sabater, Maria J.; Tetrahedron; vol. 66; nb. 3; (2010); p. 730 - 735 View in Reaxys 46 %Chromat.

With (TBA)2[SeO4{WO(O2)2}2], dihydrogen peroxide in water, acetonitrile, Time= 26.6667h, T= 49.84 °C , chemoselective reaction Kamata, Keigo; Lshimoto, Ryo; Hirano, Tomohisa; Kuzuya, Shinjiro; Uehara, Kazuhiro; Mizuno, Noritaka; Inorganic Chemistry; vol. 49; nb. 5; (2010); p. 2471 - 2478 View in Reaxys With ruthenium trichloride, iodobenzene, potassium peroxymonosulfate in water, acetonitrile, Time= 1.5h, T= 20 °C , Inert atmosphere Yusubov, Mekhman S.; Nemykin, Victor N.; Zhdankin, Viktor V.; Tetrahedron; vol. 66; nb. 31; (2010); p. 5745 5752 View in Reaxys

99 %Chromat.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [Cu2(H2O)2(.mu.-O-2-O2N-4-C6H3NN=C(COMe)COMe)2], potassium carbonate in water, Time= 22h, T= 49.84 °C , p= 760.051Torr Mahmudov, Kamran T.; Kopylovich, Maximilian N.; Silva, M. Fatima C. Guedes da; Figiel, Pawel J.; Karabach, Yauhen Yu.; Pombeiro, Armando J.L.; Journal of Molecular Catalysis A: Chemical; vol. 318; nb. 1-2; (2010); p. 44 - 50 View in Reaxys

100 With oxygen in o-xylene, Time= 0.75h, T= 90 °C , Flow conditions %Chromat. Yasu-eda, Takashi; Kitamura, Susumu; Ikenaga, Na-oki; Miyake, Takanori; Suzuki, Toshimitsu; Journal of Molecular Catalysis A: Chemical; vol. 323; nb. 1-2; (2010); p. 7 - 15 View in Reaxys With (TSPP)Rh(III)(H2O)2, oxygen, sodium hydroxide in water, Time= 7h, T= 80 °C , p= 760.051Torr , pH= 13.2 Liu, Lianghui; Yu, Mengmeng; Wayland, Bradford B.; Fu, Xuefeng; Chemical Communications; vol. 46; nb. 34; (2010); p. 6353 - 6355 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

148/438

2018-03-11 22:07:32


With trimethylamine-N-oxide, C18H26O4RuSi2 in water, acetone, Time= 18h, Reflux, Inert atmosphere, Oppenauerlike oxidation Moyer, Sara A.; Funk, Timothy W.; Tetrahedron Letters; vol. 51; nb. 41; (2010); p. 5430 - 5433 View in Reaxys With TEMPOL, N,N′-{1,3-bis[(pyridine-2-ylmethyl)amino]propan-2-al}atodicopper(II)(μ-acetato)diperchlorate, oxygen, sodium hydroxide in water, acetonitrile, T= 20 °C , Kinetics, Temperature, Reagent/catalyst, Concentration Striegler, Susanne; Dunaway, Natasha A.; Gichinga, Moses G.; Milton, Lisa K.; Tetrahedron; vol. 66; nb. 40; (2010); p. 7927 - 7932 View in Reaxys 92.6 With C12H10N3NiO(1+)*C18H15P*Cl(1-), periodic acid in acetonitrile, Time= 0.5h, T= 70 °C %Chromat. Ramakrishna, Dileep; Bhat, Badekai Ramachandra; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 40; nb. 8; (2010); p. 516 - 520 View in Reaxys 98 %Chromat.

With poly(4-methylvinylpyridinium permanganate)(63.47percent)/SBA-15 (P4MVPMnO4(63.47percent)/SBA-15), Time= 0.0833333h, T= 80 °C , Neat (no solvent), chemoselective reaction Kalbasi, Roozbeh Javad; Kolahdoozan, Majid; Shahabian, Keinaz; Zamani, Farzad; Catalysis Communications; vol. 11; nb. 14; (2010); p. 1109 - 1115 View in Reaxys With oxygen in cyclohexane, T= 80 °C , p= 1520.1Torr Villa, Alberto; Wang, Di; Dimitratos, Nikolaos; Su, Dangsheng; Trevisan, Valentina; Prati, Laura; Catalysis Today; vol. 150; nb. 1-2; (2010); p. 8 - 15 View in Reaxys With C50H39ClN2O2P2Ru, oxygen in dichloromethane, Time= 6h, T= 20 °C , p= 760.051Torr Arunachalam; Priya, N. Padma; Boopathi; Jayabalakrishnan; Chinnusamy; Applied Organometallic Chemistry; vol. 24; nb. 7; (2010); p. 491 - 498 View in Reaxys With oxygen, titanium(IV) oxide in acetonitrile, p= 760.051Torr , UV-irradiation, Kinetics, Quantum yield, Wavelength Higashimoto, Shinya; Suetsugu, Nobuaki; Azuma, Masashi; Ohue, Hiroyoshi; Sakata, Yoshihisa; Journal of Catalysis; vol. 274; nb. 1; (2010); p. 76 - 83 View in Reaxys With palladium on carbon, gold on carbon, oxygen in water, T= 60 °C , p= 1140.08Torr , Autoclave Wang, Di; Villa, Alberto; Spontoni, Paolo; Su, Dang Sheng; Prati, Laura; Chemistry - A European Journal; vol. 16; nb. 33; (2010); p. 10007 - 10013 View in Reaxys With sodium hypochlorite, CoCl(P(C6H5)3)(C13H11N2O), 1-ethyl-3-methyl-1H-imidazol-3-ium chloride, Time= 0.25h, T= 20 °C Ramakrishna, Dileep; Ramachandra Bhat, Badekai; Inorganic Chemistry Communications; vol. 13; nb. 1; (2010); p. 195 - 198 View in Reaxys

90 %Chromat.

With Au/Pd, oxygen in poly(ethylene glycol)-600, Time= 9h, T= 80 °C , p= 52505.3Torr , CO2 He, Jinling; Wu, Tianbin; Hu, Baoji; Cheng, Yan; Wu, Suxiang; Jiang, Tao; Han, Buxing; Science China Chemistry; vol. 53; nb. 7; (2010); p. 1592 - 1597 View in Reaxys With graphene oxide, Time= 144h, T= 100 °C , Neat (no solvent)

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

149/438

2018-03-11 22:07:32


Dreyer, Daniel R.; Jia, Hong-Peng; Bielawski, Christopher W.; Angewandte Chemie - International Edition; vol. 49; nb. 38; (2010); p. 6813 - 6816 View in Reaxys 90.6 With sodium hypochlorite solution, 1-ethyl-3-methyl imidazolium, Time= 0.25h, T= 20 °C %Chromat. Ramakrishna, Dileep; Bhat, Badekai Ramachandra; Karvembu, Ramasamy; Catalysis Communications; vol. 11; nb. 5; (2010); p. 498 - 501 View in Reaxys 99 %Chromat.

With C55H48As2N3O3RuS, 4-methylmorpholine N-oxide in dichloromethane, Time= 0.166667h, Molecular sieve, Reflux Muthukumar, Manisekar; Viswanathamurthi, Periasamy; Central European Journal of Chemistry; vol. 8; nb. 1; (2010); p. 229 - 240 View in Reaxys

89 %Chromat.

With dihydrogen peroxide in water, acetone, Time= 2h, T= 56 °C Kikukawa, Yuji; Yamaguchi, Kazuya; Mizuno, Noritaka; Inorganic Chemistry; vol. 49; nb. 18; (2010); p. 8194 8196 View in Reaxys With oxygen, potassium carbonate in water, Time= 8h, T= 80 °C , p= 760.051Torr Feng, Bo; Hou, Zhenshan; Yang, Hanmin; Wang, Xiangrui; Hu, Yu; Li, Huan; Qiao, Yunxiang; Zhao, Xiuge; Huang, Qingfa; Langmuir; vol. 26; nb. 4; (2010); p. 2505 - 2513 View in Reaxys With C40H34BrN3PRuS2, oxygen in dichloromethane, Time= 6h, T= 20 °C Arunachalam; Priya, N. Padma; Saravanakumar; Jayabalakrishnan; Chinnusamy; Journal of Coordination Chemistry; vol. 63; nb. 10; (2010); p. 1795 - 1806 View in Reaxys With C22H23NRuSSe(2+)*2F6P(1-), 4-methylmorpholine N-oxide in dichloromethane, Time= 2h, Reflux Singh, Pradhumn; Das, Dipanwita; Singh, Monika; Singh, Ajai K.; Inorganic Chemistry Communications; vol. 13; nb. 2; (2010); p. 223 - 226 View in Reaxys With 1-methylimidazole hydrogen sulfate, sodium nitrate, T= 80 °C Garima; Srivastava, Vishnu P.; Yadav, Lal Dhar S.; Tetrahedron Letters; vol. 51; nb. 49; (2010); p. 6436 - 6438 View in Reaxys

91 %Chromat.

With dihydrogen peroxide in water, Time= 7h, T= 70 °C Parghi, Kalpesh D.; Jayaram, Radha V.; Catalysis Communications; vol. 11; nb. 15; (2010); p. 1205 - 1210 View in Reaxys

80.1 With C49H41ClFeNOP2S, dihydrogen peroxide in acetonitrile, Time= 1.5h, T= 80 °C %Chromat. Rani, Sandya; Bhat, Badekai Ramachandra; Tetrahedron Letters; vol. 51; nb. 49; (2010); p. 6403 - 6405 View in Reaxys With oxygen in water, Time= 8h, T= 25 °C Ma, Zhancheng; Yang, Hengquan; Qin, Yong; Hao, Yajuan; Li, Guang; Journal of Molecular Catalysis A: Chemical; vol. 331; nb. 1-2; (2010); p. 78 - 85 View in Reaxys With C52H43N3O4P2RuS, 4-methylmorpholine N-oxide in dichloromethane, Time= 8h, Reflux Ulaganatha Raja; Gowri; Ramesh; Polyhedron; vol. 29; nb. 3; (2010); p. 1175 - 1181 View in Reaxys With 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux, Molecular sieve

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

150/438

2018-03-11 22:07:32


Muthukumar; Viswanathamurthi; Karvembu; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 185; nb. 11; (2010); p. 2201 - 2211 View in Reaxys With hydrogenchloride, oxygen, 4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical in water, 1,2-dichloro-ethane, Time= 16h, T= 40 °C Tao, Jianwei; Lu, Qiongqiong; Chu, Changhu; Liu, Renhua; Liang, Xinmiao; Synthesis; nb. 23; (2010); p. 3974 3976; Art.No: F14110SS View in Reaxys 99 %Chromat.

With oxygen in toluene, Time= 12h, T= 100 °C Nagashima, Kohji; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Green Chemistry; vol. 12; nb. 12; (2010); p. 2142 - 2144 View in Reaxys With Ru/Al2O3, oxygen in toluene, Time= 0.75h, T= 90 °C , p= 3750.38Torr , chemoselective reaction Zotova, Natalia; Hellgardt, Klaus; Kelsall, Geoffrey H.; Jessiman, Alan S.; Hii, King Kuok Mimi; Green Chemistry; vol. 12; nb. 12; (2010); p. 2157 - 2163 View in Reaxys With potassium nitrososulfonate, sodium chloride, sodium hydroxide in water, T= 25 °C , Inert atmosphere, Kinetics, Mechanism, Concentration De, Piyali; Kumar, Dhurjati Prasad; Mondal, Amit Kumar; Mandal, Pulak Chandra; Mukhopadhyay, Subrata; Banerjee, Rupendranath; Polyhedron; vol. 29; nb. 4; (2010); p. 1358 - 1362 View in Reaxys With oxygen in dichloromethane, Time= 12h, Irradiation Mizoshita, Norihiro; Yamanaka, Ken-Ichi; Shimada, Toyoshi; Tani, Takao; Inagaki, Shinji; Chemical Communications; vol. 46; nb. 48; (2010); p. 9235 - 9237 View in Reaxys

100 With oxygen in α,α,α-trifluorotoluene, water, Time= 9h, T= 20 °C , p= 760.051Torr %Chromat. Kaizuka, Kosuke; Miyamura, Hiroyuki; Kobayashi, Shu; Journal of the American Chemical Society; vol. 132; nb. 43; (2010); p. 15096 - 15098 View in Reaxys 80 %Chromat.

With 2CF3O3S(1-)*C12H32Cu2N4O2 (2+) in acetone, T= -30.16 °C Kang, Peng; Bobyr, Elena; Dustman, John; Hodgson, Keith O.; Hedman, Britt; Solomon, Edward I.; Stack, T. Daniel P.; Inorganic Chemistry; vol. 49; nb. 23; (2010); p. 11030 - 11038 View in Reaxys With oxygen in acetonitrile, Time= 3h, T= 100 °C , p= 6000.6Torr , UV-irradiation, Autoclave Su, Fangzheng; Mathew, Smitha C.; Lipner, Grzegorz; Fu, Xianzhi; Antonietti, Markus; Blechert, Siegfried; Wang, Xinchen; Journal of the American Chemical Society; vol. 132; nb. 46; (2010); p. 16299 - 16301 View in Reaxys With titanium-containing mesoporous silica, hydrogen fluoride, oxygen in benzotrifluoride, T= 20 °C , UV-irradiation Wang, Qi; Zhang, Miao; Chen, Chuncheng; Ma, Wanhong; Zhao, Jincai; Angewandte Chemie - International Edition; vol. 49; nb. 43; (2010); p. 7976 - 7979 View in Reaxys With Oxone, C26H20N2O3V, tetrabutylammomium bromide in dichloromethane, water, Time= 0.0833333h, T= 20 °C Bagherzadeh, Mojtaba; Amini, Mojtaba; Journal of Coordination Chemistry; vol. 63; nb. 21; (2010); p. 3849 - 3858 View in Reaxys

99 %Chromat.

With C48H35AsBrCl2O4Ru, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Molecular sieve, Reflux

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

151/438

2018-03-11 22:07:32


Muthukumar; Viswanathamurthi; Prabhakaran; Natarajan; Journal of Coordination Chemistry; vol. 63; nb. 21; (2010); p. 3833 - 3848 View in Reaxys With tert.-butylhydroperoxide in water, acetonitrile, Time= 5h, T= 60 °C Chattopadhyay, Tanmay; Kogiso, Masaki; Asakawa, Masumi; Shimizu, Toshimi; Aoyagi, Masaru; Catalysis Communications; vol. 12; nb. 1; (2010); p. 9 - 13 View in Reaxys 86 %Chromat.

With C48H45As2Cl2N2ORuS, 4-methylmorpholine N-oxide in dichloromethane, Time= 12h, T= 27 °C Gunasekaran; Karvembu; Inorganic Chemistry Communications; vol. 13; nb. 8; (2010); p. 952 - 955 View in Reaxys With oxygen in acetonitrile, p= 760.051Torr , Visible light irradiation, Kinetics, Quantum yield, chemoselective reaction Samiolo; Valigi; Gazzoli; Amadelli; Electrochimica Acta; vol. 55; nb. 26; (2010); p. 7788 - 7795 View in Reaxys

86.1 With chloro(N-(2-mercaptophenyl)salicylideneimine)bis(triphenylphosphine)iron(III), periodic acid in acetonitrile, %Chromat. Time= 1.5h, T= 70 °C Rani, Sandya; Ramachandra Bhat, Badekai; Inorganic Chemistry Communications; vol. 13; nb. 11; (2010); p. 1289 - 1292 View in Reaxys 49 %Chromat.

With tert.-butylhydroperoxide, [Co(4-nbz)2(py)2] in water, acetonitrile, Time= 18h, T= 27 °C Chakravorty, Stutee; Das, Birinchi K.; Polyhedron; vol. 29; nb. 8; (2010); p. 2006 - 2013 View in Reaxys

78 %Chromat.

With hydrotalcite-supported gold nanoparticles (Au/HT), air in toluene, Time= 24h, T= 40 °C , p= 760.051Torr Mitsudome, Takato; Noujima, Akifumi; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Advanced Synthesis and Catalysis; vol. 351; nb. 11-12; (2009); p. 1890 - 1896 View in Reaxys With N-(2-iodylphenyl)glutarylamide supported on amonomethylpolystyrene resin in 1,2-dichloro-ethane, Time= 1h, T= 85 °C Yusubov, Mekhman S.; Zhdankin, Viktor V.; Mendeleev Communications; vol. 20; nb. 4; (2010); p. 185 - 191 View in Reaxys With oxygen in cyclohexane, T= 80 °C , p= 1520.1Torr Chan-Thaw, Carine E.; Villa, Alberto; Prati, Laura; Thomas, Arne; Chemistry - A European Journal; vol. 17; nb. 3; (2011); p. 1052 - 1057 View in Reaxys With oxygen, T= 220 °C , Gas phase Zhao, Guofeng; Hu, Huanyun; Deng, Miaomiao; Ling, Min; Lu, Yong; Green Chemistry; vol. 13; nb. 1; (2011); p. 55 - 58 View in Reaxys With [2,2]bipyridinyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, sodium methylate, copper(ll) bromide in water, acetonitrile, Time= 2h, T= 30 °C Mase, Nobuyuki; Mizumori, Tomoya; Tatemoto, Yuji; Chemical Communications; vol. 47; nb. 7; (2011); p. 2086 2088 View in Reaxys With Oxone, catena{[nitrato-μ3-2,4,6-tris(2-pyridyl)-1,3,5-triazinesilver(I)][dinitrato-μ2-2,4,6-tris(2-pyridyl)-1,3,5-triazinesilver(I)]}, tetrabutylammomium bromide in dichloromethane, water, Time= 2h, T= 20 °C , Air atmosphere

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

152/438

2018-03-11 22:07:32


Najafpour, Mohammad Mahdi; Holynska, Malgorzata; Amini, Mojtaba; Kazemi, Sayed Habib; Lis, Tadeusz; Bagherzadeh, Mojtaba; Polyhedron; vol. 29; nb. 14; (2010); p. 2837 - 2843 View in Reaxys With Zn4(2-methylimidazole(-1H))MoO4*2(N,N-dimethylformamide), dihydrogen peroxide in acetonitrile, T= 80 °C Wang, Fei; Liu, Zi-Sheng; Yang, Hui; Tan, Yan-Xi; Zhang, Jian; Angewandte Chemie - International Edition; vol. 50; nb. 2; (2011); p. 450 - 453 View in Reaxys With dihydrogen peroxide in water, Time= 6h, T= 80 °C , Inert atmosphere, chemoselective reaction Stolle, Achim; Ondruschka, Bernd; Morgenthal, Ingrid; Andersen, Olaf; Bonrath, Werner; Journal of Molecular Catalysis A: Chemical; vol. 335; nb. 1-2; (2011); p. 228 - 235 View in Reaxys 92.1 With sodium hypochlorite solution, C48H40N3OP2Ru(1+)*Cl(1-), Time= 0.5h, T= 20 °C , Ionic liquid %Chromat. Ramakrishna, Dileep; Bhat, Badekai Ramachandra; Inorganic Chemistry Communications; vol. 14; nb. 1; (2011); p. 155 - 158 View in Reaxys With tetraethylammonium bromochromate in dimethyl sulfoxide, T= 24.84 °C , Kinetics, Mechanism, Temperature, Solvent Mansoor, S. Sheik; Shafi, S. Syed; Zeitschrift fur Physikalische Chemie; vol. 225; nb. 2; (2011); p. 249 - 263 View in Reaxys With hydrotalcite-supported gold nanoparticles in para-xylene, T= 119.84 °C , Inert atmosphere, Kinetics Fang, Wenhao; Chen, Jiashu; Zhang, Qinghong; Deng, Weiping; Wang, Ye; Chemistry - A European Journal; vol. 17; nb. 4; (2011); p. 1247 - 1256 View in Reaxys With tert.-butylhydroperoxide in acetonitrile, Time= 8h, T= 90 °C , Kinetics, Temperature Mahdavi, Vahid; Hasheminasab, Hamid Reza; Abdollahi, Sohrab; Journal of the Chinese Chemical Society; vol. 57; nb. 2; (2010); p. 189 - 198 View in Reaxys Typical procedure of oxidation of alcohols with PS-DCIB 2 in CH3CN-H2O: To a solution of benzyl alcohol 13a (0.021 g, 0.2 mmol) and pyridine (0.052 mL, 0.6mmol) in CH3CN-H2O (2 mL, v/v =1:1) was added PS-DICB 2 (0.223 g, 0.3 mmol) and TEMPO (0.003 g, 0.02 mmol) at room temperature, and the mixture was warmed up to 50 °C and magnetically stirred until the alcohol was consumed (monitored by TLC). The mixture was filtered, and the PS-IB resin was washed with CH3CN (3 x 1 mL) and collected for reuse. To the filtrate was added 2 mL of a standard solution of 2,4-dinitrophenylhydrazine (prepared from 3 g 2,4-DNP, 15 mL concd H2SO4, 70 mL EtOH,and 20 mL H2O). The precipitate was filtered, washed with water and 95percent ethanol, dried in vacuum to give 2,4-dinitrophenyl-hydrazone 14a (0.053 g, 92percent) With pyridine, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in water, acetonitrile, Time= 3h, T= 50 °C Chen, Jiang-Min; Zeng, Xiao-Mei; Middleton, Kyle; Zhdankin, Viktor V.; Tetrahedron Letters; vol. 52; nb. 16; (2011); p. 1952 - 1955 View in Reaxys 99 %Chromat.

With water, oxygen, sodium nitrite, Time= 1.5h, T= 30 °C , p= 1500.15Torr , Ionic liquid, Autoclave Miao, Cheng-Xia; Wang, Jin-Quan; Yu, Bing; Cheng, Wei-Guo; Sun, Jian; Chanfreau, Sebastien; He, LiangNian; Zhang, Suo-Jiang; Chemical Communications; vol. 47; nb. 9; (2011); p. 2697 - 2699 View in Reaxys

> 99 With oxygen, titanium(IV) oxide in acetonitrile, Time= 4h, T= 24.84 °C , Visible light irradiation, Kinetics %Chromat. Higashimoto, Shinya; Kitao, Naoya; Yoshida, Norio; Sakura, Teruki; Azuma, Masashi; Ohue, Hiroyoshi; Sakata, Yoshihisa; Journal of Catalysis; vol. 266; nb. 2; (2009); p. 279 - 285 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

153/438

2018-03-11 22:07:32


95 %Spectr.

With [RuCl2(p-cymene)(1,4-dibutyl-3-methyl-1,2,3-triazolylidene)] in toluene, Time= 16h, T= 70 °C Prades, Amparo; Peris, Eduardo; Albrecht, Martin; Organometallics; vol. 30; nb. 5; (2011); p. 1162 - 1167 View in Reaxys With iron(III) chloride, chloroamine-T in dichloromethane, T= 20 °C , Inert atmosphere Srivastava, Vishnu P.; Patel, Rajesh; Yadav, Lal Dhar S.; Advanced Synthesis and Catalysis; vol. 353; nb. 5; (2011); p. 695 - 700 View in Reaxys With 5,10,15,20-tetramesitylporphyrin in dichloromethane, acetonitrile, Time= 72h, p= 760.051Torr , Irradiation Hajimohammadi, Mahdi; Safari, Nasser; Mofakham, Hamid; Deyhimi, Farzad; Green Chemistry; vol. 13; nb. 4; (2011); p. 991 - 997 View in Reaxys

92.2 With [CuCl(P(C6H5)3)(C6H4(O)CHNNHC5H4N)], periodic acid in acetonitrile, Time= 0.5h, T= 20 °C %Chromat. Ramakrishna, Dileep; Bhat, Badekai Ramachandra; Inorganic Chemistry Communications; vol. 14; nb. 5; (2011); p. 690 - 693 View in Reaxys With [ruthenium(II)chloride(.eta.6-benzene)(N-[2-(phenylseleno)ethyl]morpholine)](hexafluorophosphate), 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Singh, Pradhumn; Singh, Ajai K.; European Journal of Inorganic Chemistry; nb. 26; (2010); p. 4187 - 4195 View in Reaxys 99 %Chromat.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [Cu(H2O)(O-2-O2N-4-C6H3NN=CCOCH2C(Me)2CH2CO)], potassium carbonate in water, Time= 22h, T= 50 °C , p= 760.051Torr Kopylovich, Maximilian N.; Mahmudov, Kamran T.; Da Silva, M. Fatima C. Guedes; Figiel, Pawel J.; Karabach, Yauhen Yu.; Kuznetsov, Maxim L.; Luzyanin, Konstantin V.; Pombeiro, Armando J.L.; Inorganic Chemistry; vol. 50; nb. 3; (2011); p. 918 - 931 View in Reaxys With oxygen in toluene, Time= 0.25h, T= 80 °C , p= 750.075Torr Zhang, Yanjie; Wang, Junhu; Zhang, Tao; Chemical Communications; vol. 47; nb. 18; (2011); p. 5307 - 5309 View in Reaxys With silica gel, palladium, Time= 24h, T= 90 °C , chemoselective reaction Lee, Adam F.; Ellis, Christine V.; Naughton, James N.; Newton, Mark A.; Parlett, Christopher M. A.; Wilson, Karen; Journal of the American Chemical Society; vol. 133; nb. 15; (2011); p. 5724 - 5727 View in Reaxys

90 %Chromat.

With C16H13ClIrNO(1-), sodium methylate in toluene, Time= 20h, Reflux, Inert atmosphere Fujita, Ken-Ichi; Yoshida, Tetsuya; Imori, Yoichiro; Yamaguchi, Ryohei; Organic Letters; vol. 13; nb. 9; (2011); p. 2278 - 2281 View in Reaxys With [Co(NH3)5Cl]Cl2, [(2,2':6',2''-terpyridine)Ru(2,3,5,6-tetrakis(2-pyridyl)pyrazine)Ru(2,2'-bipyridine)(H2O)] (+4)*4CF3SO3(-1), Time= 24h, T= 20 °C , pH= 6.8, Irradiation, aq. phosphate buffer Chen, Weizhong; Rein, Francisca N.; Scott, Brian L.; Rocha, Reginaldo C.; Chemistry - A European Journal; vol. 17; nb. 20; (2011); p. 5595 - 5604 View in Reaxys With dihydrogen peroxide in acetonitrile, Time= 6h, T= 20 °C , chemoselective reaction Islam; Roy, Anupam Singha; Mondal, Paramita; Mubarak, Manir; Mondal, Sanchita; Hossain, Dildar; Banerjee, Satabdi; Santra; Journal of Molecular Catalysis A: Chemical; vol. 336; nb. 1-2; (2011); p. 106 - 114 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

154/438

2018-03-11 22:07:32


84 %Chromat.

With oxygen, palladium diacetate, potassium carbonate, catacxium A in toluene, T= 80 °C , p= 750.075Torr , chemoselective reaction Gowrisankar, Saravanan; Neumann, Helfried; Beller, Matthias; Angewandte Chemie - International Edition; vol. 50; nb. 22; (2011); p. 5139 - 5143 View in Reaxys

> 99 With tert.-butylnitrite, oxygen in acetic acid, Time= 3.3h, T= 40 °C , p= 760.051Torr , chemoselective reaction %Chromat. Karimi, Babak; Badreh, Ebrahim; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4194 - 4198 View in Reaxys With oxygen in toluene, Time= 1h, T= 80 °C , p= 760.051Torr Yamaguchi, Kazuya; Kim, Jung Won; He, Jinling; Mizuno, Noritaka; Journal of Catalysis; vol. 268; nb. 2; (2009); p. 343 - 349 View in Reaxys With porous silica beads supported 2,2,6,6-tetramethylpiperdine 1-oxyl and adsorbed NOx (PSB-TEMPO/NOx), air in dichloromethane, Time= 4h, T= 20 °C Di, Lei; Hua, Zhang; Advanced Synthesis and Catalysis; vol. 353; nb. 8; (2011); p. 1253 - 1259 View in Reaxys With dihydrogen peroxide in water, Time= 5h, T= 25 °C Chattopadhyay, Tanmay; Kogiso, Masaki; Aoyagi, Masaru; Yui, Hiroharu; Asakawa, Masumi; Shimizu, Toshimi; Green Chemistry; vol. 13; nb. 5; (2011); p. 1138 - 1140 View in Reaxys 100 With tert.-butylnitrite, oxygen in water, Time= 4h, T= 50 °C , p= 760.051Torr %Chromat. Karimi, Babak; Farhangi, Elham; Chemistry - A European Journal; vol. 17; nb. 22; (2011); p. 6056 - 6060 View in Reaxys With palladium on carbon, [emim][NTf2], oxygen, Time= 1h, T= 160 °C , Ionic liquid Chen, Yuanting; Bai, Linlu; Zhou, Chunmei; Lee, Jong-Min; Yang, Yanhui; Chemical Communications; vol. 47; nb. 22; (2011); p. 6452 - 6454 View in Reaxys With 2-iodyl-3-propoxypyridine in acetonitrile, Time= 2h, Reflux, Inert atmosphere, chemoselective reaction Yoshimura, Akira; Banek, Christopher T.; Yusubov, Mekhman S.; Nemykin, Victor N.; Zhdankin, Viktor V.; Journal of Organic Chemistry; vol. 76; nb. 10; (2011); p. 3812 - 3819 View in Reaxys Stage 1: With potassium hydride in acetonitrile Stage 2: With 4-acetylamino-2,2,6,6-tetramethyl-piperidine-1-oxoam-monium perchlorate in acetonitrile, Time= 3h, T= 20 °C Zhu, Xiao-Qing; Chen, Xi; Mei, Lian-Rui; Organic Letters; vol. 13; nb. 9; (2011); p. 2456 - 2459 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, butane-2,3-dione dioxime, cobalt(II) nitrate in dichloromethane, Time= 2h, T= 70 °C , p= 3000.3Torr , Autoclave Jing, Yuanyuan; Jiang, Jun; Yan, Bo; Lu, Shuai; Jiao, Jiemin; Xue, Huazhen; Yang, Guanyu; Zheng, Gengxiu; Advanced Synthesis and Catalysis; vol. 353; nb. 7; (2011); p. 1146 - 1152 View in Reaxys With C28H32Co3N19O5 (1+)*NO3 (1-), 3-chloro-benzenecarboperoxoic acid in acetonitrile, Time= 0.166667h, T= 20 °C Shin, Jong Won; Rowthu, Sankara Rao; Hyun, Min Young; Song, Young Joo; Kim, Cheal; Kim, Bong Gon; Min, Kil Sik; Dalton Transactions; vol. 40; nb. 21; (2011); p. 5762 - 5773 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

155/438

2018-03-11 22:07:32


With oxygen in toluene, T= 99.84 °C , chemoselective reaction Tang, Qinghu; Gong, Xiaonan; Zhao, Peizheng; Chen, Yuanting; Yang, Yanhui; Applied Catalysis A: General; vol. 389; nb. 1-2; (2010); p. 101 - 107 View in Reaxys With boron trifluoride diethyl etherate in dichloromethane, Time= 12h Chen, Jiang-Min; Zeng, Xiao-Mei; Middleton, Kyle; Yusubov, Mekhman S.; Zhdankin, Viktor V.; Synlett; nb. 11; (2011); p. 1613 - 1617 View in Reaxys 0.26 g

With dihydrogen peroxide in water, Time= 7h, T= 20 °C Patil, Rajendra D.; Adimurthy, Subbarayappa; Synthetic Communications; vol. 41; nb. 18; (2011); p. 2712 - 2718 View in Reaxys General procedure for the one-pot conversion of alcohols to benzimidazoles: In a typical experiment, the primary alcohol (0.5-0.6 mmol) and IBX (1.1 equiv) were stirred in DMSO at ca. 20 °C. Once the oxidation of alcohol to aldehyde was complete, as judged from TLC analysis, o-phenylenediamine (1.1 equiv) was introduced into the reaction mixture and the reaction mixture was allowed to stir at room temperature until the aldehyde disappeared. At the end of the reaction, DMSO was removed under high vacuum, and the residue was treated with 1.0 M NaHCO3 solution until the pH was 8-9. The organic matter was extracted with ethyl acetate. Regular work-up followed by silica-gel column chromatography led to pure benzimidazoles, which were characterized spectroscopically. With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide, T= 20 °C Moorthy, Jarugu Narasimha; Neogi, Ishita; Tetrahedron Letters; vol. 52; nb. 30; (2011); p. 3868 - 3871 View in Reaxys With 1-octly-3-methylimidazolium persulfate, Time= 1h, T= 80 °C , neat (no solvent) Shi, Shenyi; Kong, Aiguo; Zhao, Xinhua; Zhang, Qiying; Shan, Yongkui; European Journal of Inorganic Chemistry; nb. 15; (2010); p. 2283 - 2289 View in Reaxys With tert.-butylhydroperoxide, bis(p-chlorophenyl) diselenide, Time= 6h, T= 80 °C Van Der Toorn, John C.; Kemperman, Gerjan; Sheldon, Roger A.; Arends, Isabel W. C. E.; European Journal of Organic Chemistry; nb. 23; (2011); p. 4345 - 4352 View in Reaxys

92 %Chromat.

With potassium tert-butylate, oxygen, copper dichloride, 4-methyl-2-((pyridin-2-ylmethylene)amino)phenol in water, acetonitrile, Time= 8h, T= 20 °C Uma Maheswari, Palanisamy; Hartl, Frantisek; Quesada, Manuel; Buda, Francesco; Lutz, Martin; Spek, Anthony L.; Gamez, Patrick; Reedijk, Jan; Inorganica Chimica Acta; vol. 374; nb. 1; (2011); p. 406 - 414 View in Reaxys

23.1 With ruthenium trichloride, potassium carbonate, Time= 48h %Chromat. Liu, Chuanzhi; Liao, Shiheng; Li, Qiang; Feng, Sunlin; Sun, Qing; Yu, Xiaochun; Xu, Qing; Journal of Organic Chemistry; vol. 76; nb. 14; (2011); p. 5759 - 5773 View in Reaxys 2.4. Catalytic oxidation experiments General procedure: The reactions were carried out in a stainless steel reactor equipped with a magnetic stirrer. In a typical run, a mixture of the substrate (1.0 mmol), toluene (5 mL), and the catalyst (0.02-0.2 g; ca. 0.45-4.5 wt.percent; Ru: 0.28-2.80 molpercent) was transferred in the reactor. The reactor was pressurized with oxygen to the total pressure of 10 atm and placed in an oil bath; then, the solution was intensively stirred at 80-120 °C for the reported time. The reactions were followed by gas chromatography (GC) (Shimadzu 17 instrument, Carbowax 20 M capillary column). To take the aliquots for the GC analysis at appropriate time intervals, stirring was stopped and the catalyst was quickly settled by the application of an external permanent magnet. The structures of the products were confirmed by GC/MS (Shimadzu QP2010-PLUS instrument, 70 eV).

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

156/438

2018-03-11 22:07:32


With oxygen in toluene, Time= 5h, T= 80 °C , p= 7600.51Torr , chemoselective reaction Costa, Vinicius V.; Jacinto, Marcos J.; Rossi, Liane M.; Landers, Richard; Gusevskaya, Elena V.; Journal of Catalysis; vol. 282; nb. 1; (2011); p. 209 - 214 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in N,N-dimethyl-formamide, Time= 18h, T= 100 °C , p= 1520.1Torr Maayan, Galia; Christou, George; Inorganic Chemistry; vol. 50; nb. 15; (2011); p. 7015 - 7021 View in Reaxys With 1-methyl-2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl, oxygen, nitric acid, sodium nitrite in water, Time= 4h, T= 40 °C Kuang, Yongbo; Nabae, Yuta; Hayakawa, Teruaki; Kakimoto, Masa-Aki; Green Chemistry; vol. 13; nb. 7; (2011); p. 1659 - 1663 View in Reaxys 91 %Chromat.

With 1H-imidazole, dihydrogen peroxide in water, acetonitrile, Time= 4h, T= 20 °C , chemoselective reaction Masoudian, Shahla; Yahyaei, Hooriye; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 50; nb. 7; (2011); p. 1002 - 1005 View in Reaxys With tris(2,2'-bipyridyl)ruthenium dichloride, pentaaminechlorocobalt(III) dichloride, [Ru(tpy)(bpy)(H2O)](ClO4)2, Time= 5h, T= 20 °C , pH= 6.8, Inert atmosphere, aq. phosphate buffer, Irradiation Li, Fei; Yu, Miao; Jiang, Yi; Huang, Fang; Li, Yanqing; Zhang, Biaobiao; Sun, Licheng; Chemical Communications; vol. 47; nb. 31; (2011); p. 8949 - 8951 View in Reaxys

41.3 %Spectr.

With tert.-butylhydroperoxide in hexane, acetonitrile, Time= 24h, T= 70 °C Hong, Haiyan; Hu, Lei; Li, Min; Zheng, Junwei; Sun, Xuhui; Lu, Xinhua; Cao, Xueqin; Lu, Jianmei; Gu, Hongwei; Chemistry - A European Journal; vol. 17; nb. 31; (2011); p. 8726 - 8730 View in Reaxys With oxygen, T= 280 °C Zhao, Guofeng; Hu, Huanyun; Deng, Miaomiao; Lu, Yong; Chemical Communications; vol. 47; nb. 34; (2011); p. 9642 - 9644 View in Reaxys With dihydrogen peroxide in water, Time= 1h, T= 90 °C Xie, Ting; Lu, Min; Zhang, Wenwen; Li, Jun; Journal of Chemical Research; vol. 35; nb. 7; (2011); p. 397 - 399 View in Reaxys

81.5 With dihydrogen peroxide in water, Time= 5.5h, Reflux %Chromat. Tan, Huaqiao; Chen, Weilin; Liu, Ding; Feng, Xiaojia; Li, Yangguang; Yan, Aixue; Wang, Enbo; Dalton Transactions; vol. 40; nb. 33; (2011); p. 8414 - 8418 View in Reaxys With (4-pyridyl)pentamethyldisiloxane, oxygen, palladium diacetate in toluene, Time= 18h, T= 79.84 °C Missaghi, Michael N.; Galloway, John. M.; Kung, Harold H.; Applied Catalysis A: General; vol. 391; nb. 1-2; (2011); p. 297 - 304 View in Reaxys With tripropylammonium fluorochromate in dimethyl sulfoxide, Time= 24h, T= 24.84 °C , Darkness, Kinetics, Temperature, Solvent Mansoor, S. Sheik; Shafi, S. Syed; Journal of Molecular Liquids; vol. 155; nb. 2-3; (2010); p. 85 - 90 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

157/438

2018-03-11 22:07:32


With potassium phosphate, recombinant rat brain aldo-keto reductase R1B10, nicotinamide adenine dinucleotide phosphate in methanol, Enzymatic reaction, Kinetics Endo, Satoshi; Matsunaga, Toshiyuki; Kuragano, Tsukasa; Ohno, Satoshi; Kitade, Yukio; Tajima, Kazuo; ElKabbani, Ossama; Hara, Akira; Archives of Biochemistry and Biophysics; vol. 503; nb. 2; (2010); p. 230 - 237 View in Reaxys With water, oxygen, Time= 6h, T= 24.84 °C , p= 760.051Torr , Sonication, Irradiation Tsukamoto, Daijiro; Ikeda, Makoto; Shiraishi, Yasuhiro; Hara, Takayoshi; Ichikuni, Nobuyuki; Tanaka, Shunsuke; Hirai, Takayuki; Chemistry - A European Journal; vol. 17; nb. 35; (2011); p. 9816 - 9824 View in Reaxys With 2,2'-azinobis(3-ethylbenzthiazolinesulfonate), copper(ll) sulfate pentahydrate, oxygen, horseradish peroxidase, Time= 20h, T= 20 °C , p= 3000.3Torr , pH= 7, Microbiological reaction, aq. phosphate buffer, Enzymatic reaction Fuchs, Michael; Schober, Markus; Pfeffer, Jan; Kroutil, Wolfgang; Birner-Gruenberger, Ruth; Faber, Kurt; Advanced Synthesis and Catalysis; vol. 353; nb. 13; (2011); p. 2354 - 2358 View in Reaxys 86 %Chromat.

With 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl, potassium tert-butylate, palladium diacetate, triethylamine, Time= 72h, Air, neat (no solvent) Jiang, Lan; Jin, Luolu; Tian, Haiwen; Yuan, Xueqin; Yu, Xiaochun; Xu, Qing; Chemical Communications; vol. 47; nb. 38; (2011); p. 10833 - 10835 View in Reaxys

93 %Chromat.

With periodic acid in water, Time= 7h, T= 27 °C , chemoselective reaction Babu, S. Ganesh; Priyadarsini, P. Aruna; Karvembu; Applied Catalysis A: General; vol. 392; nb. 1-2; (2011); p. 218 - 224 View in Reaxys With oxygen in water, Time= 2h, T= 80 °C , p= 760.051Torr , chemoselective reaction Wang, Shuai; Li, Wen-Cui; Hao, Guang-Ping; Hao, Yan; Sun, Qiang; Zhang, Xiang-Qian; Lu, An-Hui; Journal of the American Chemical Society; vol. 133; nb. 39; (2011); p. 15304 - 15307 View in Reaxys

100 With Oxone, [Mn(2,4,6-tri-(2-pyridyl)-1,3,5-triazine)Cl2(H2O)]*H2O, tetrabutylammomium bromide in dichlorome%Chromat. thane, water, Time= 0.0833333h, T= 20 °C Najafpour, Mohammad Mahdi; Amini, Mojtaba; Bagherzadeh, Mojtaba; Boghaei, Davar M.; McKee, Vickie; Transition Metal Chemistry; vol. 35; nb. 3; (2010); p. 297 - 303 View in Reaxys 76 %Chromat.

With oxygen in toluene, Time= 0.5h, T= 99.84 °C Liu, Peng; Guan, Yejun; Santen, Rutger A. Van; Li, Can; Hensen, Emiel J. M.; Chemical Communications; vol. 47; nb. 41; (2011); p. 11540 - 11542 View in Reaxys 2.3. Catalytic activity General procedure: The solvent-free aerobic oxidation of benzyl alcohol using molecular O2 was carried out in a batch-type reactor operated under atmospheric conditions. Experiments were conducted using a three-necked glass flask (capacity 25 mL) precharged with 5.4 g of benzyl alcohol and 20 mg of catalyst. The mixture was stirred using a magnetic stirrer and heated in a silicon oil bath. The system was equipped with a thermocouple to control the temperature and a reflux condenser. In each reaction run, the mixture was heated to 160 °C under vigorous stirring (stirring rate 1000 rpm). Oxygen was bubbled into the mixture at a constant flow rate of 20 mL/min using a mass flow controller to initiate the reaction. After the allowed reaction time, the catalyst powder was filtered off and the liquid organic products were analyzed using an Agilent 6890 gas chromatograph equipped with an HP-5 capillary column (30 m long and 0.32 mm in diameter, packed with silica-based Supel-cosil). With Pd/1Mn3Ce-C, oxygen, Time= 1h, T= 160 °C , chemoselective reaction

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

158/438

2018-03-11 22:07:32


Chen, Yuanting; Zheng, Huijian; Guo, Zhen; Zhou, Chunmei; Wang, Chuan; Borgna, Armando; Yang, Yanhui; Journal of Catalysis; vol. 283; nb. 1; (2011); p. 34 - 44 View in Reaxys 2 %Spectr. With sodium hydroxide, copper(ll) bromide in para-xylene, Time= 24h, T= 135 °C , Inert atmosphere Miura, Takashi; Kose, Osamu; Li, Feng; Kai, Sun; Saito, Susumu; Chemistry - A European Journal; vol. 17; nb. 40; (2011); p. 11146 - 11151 View in Reaxys With 2C24H20P(1+)*C56H80O8S2V2 (2-), oxygen in acetonitrile, Time= 1h, T= 80 °C , Molecular sieve Werncke, C. Gunnar; Limberg, Christian; Knispel, Christina; Mebs, Stefan; Chemistry - A European Journal; vol. 17; nb. 43; (2011); p. 12129 - 12135 View in Reaxys With cerium dioxide, oxygen, gold in water, Irradiation Tanaka, Atsuhiro; Hashimoto, Keiji; Kominami, Hiroshi; Chemical Communications; vol. 47; nb. 37; (2011); p. 10446 - 10448 View in Reaxys 65 %Spectr.

With C29H39Cl2IrN2, caesium carbonate in toluene, Time= 15h, Reflux Segarra, Candela; Mas-Marza, Elena; Mata, Jose A.; Peris, Eduardo; Advanced Synthesis and Catalysis; vol. 353; nb. 11-12; (2011); p. 2078 - 2084 View in Reaxys

97 %Chromat.

With sodium periodate, C30H22N2O8*2H2O*2Mn in acetonitrile, T= 60 °C Xie, Ming-Hua; Yang, Xiu-Li; Wu, Chuan-De; Chemistry - A European Journal; vol. 17; nb. 41; (2011); p. 11424 11427 View in Reaxys

89.5 With (tetraphenylporphyrin)copper(II), oxygen, isobutyraldehyde in o-xylene, Time= 37h, T= 60 °C %Chromat. Rahimi, Rahmatolah; Gholamrezapor, Ensieh; Naimi-Jamal, Mohammad Reza; Inorganic Chemistry Communications; vol. 14; nb. 10; (2011); p. 1561 - 1568 View in Reaxys > 99 With oxygen, potassium carbonate in α,α,α-trifluorotoluene, Time= 3h, T= 95 °C %Chromat. Karimi, Babak; Elhamifar, Dawood; Clark, James H.; Hunt, Andrew J.; Organic and Biomolecular Chemistry; vol. 9; nb. 21; (2011); p. 7420 - 7426 View in Reaxys With dihydrogen peroxide in water, Time= 2h, T= 90 °C Wang, Liang; Yi, Wen-Bin; Cai, Chun; ChemSusChem; vol. 3; nb. 11; (2010); p. 1280 - 1284 View in Reaxys 94 %Chromat.

With C51H51ClN2O2P2RuS, 4-methylmorpholine N-oxide in acetonitrile, Time= 12h, T= 27 °C Gunasekaran; Remya; Radhakrishnan; Karvembu; Journal of Coordination Chemistry; vol. 64; nb. 3; (2011); p. 491 - 501 View in Reaxys With Au/Al2O3, oxygen in toluene, Time= 2h, T= 80 °C , chemoselective reaction Zhao, Guofeng; Ling, Min; Hu, Huanyun; Deng, Miaomiao; Xue, Qingsong; Lu, Yong; Green Chemistry; vol. 13; nb. 11; (2011); p. 3088 - 3092 View in Reaxys

98 %Chromat.

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, C13H19ClCuN4O7S, potassium carbonate in water, Time= 6h, T= 80 °C , p= 760.051Torr

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

159/438

2018-03-11 22:07:32


Kopylovich, Maximilian N.; Mahmudov, Kamran T.; Haukka, Matti; Figiel, Pawel J.; Mizar, Archana; Da Silva, Jose A. L.; Pombeiro, Armando J. L.; European Journal of Inorganic Chemistry; nb. 27; (2011); p. 4175 - 4181 View in Reaxys With tert.-butylhydroperoxide in water, acetonitrile, Time= 8h, T= 60 °C Islam; Mondal, Paramita; Tuhina, Kazi; Roy, Anupam Singha; Hossain, Dilder; Mondal, Sanchita; Transition Metal Chemistry; vol. 35; nb. 7; (2010); p. 891 - 901 View in Reaxys With tert.-butylhydroperoxide in acetonitrile, Time= 4h, T= 60 °C Jaeger, Benjamin; Stolle, Achim; Scholz, Peter; Mueller, Matthias; Ondruschka, Bernd; Applied Catalysis A: General; vol. 403; nb. 1-2; (2011); p. 152 - 160 View in Reaxys With C13H11N3O2S, oxygen in dichloromethane, Time= 6h, T= 20 °C Raja; Sathya; Jayabalakrishnan; Journal of Coordination Chemistry; vol. 64; nb. 5; (2011); p. 817 - 831 View in Reaxys With oxygen, T= 59.84 °C , Neat (no solvent), UV-irradiation Feng, Wei; Wu, Guangjun; Li, Landong; Guan, Naijia; Green Chemistry; vol. 13; nb. 11; (2011); p. 3265 - 3272 View in Reaxys With oxygen in toluene, Time= 1h, T= 100 °C Tang, Qinghu; Wu, Chengming; Qiao, Ran; Chen, Yuanting; Yang, Yanhui; Applied Catalysis A: General; vol. 403; nb. 1-2; (2011); p. 136 - 141 View in Reaxys 76 %Chromat.

With 6-(N-phenylbenzimidazoyl)-2-pyridinecarboxylic acid, dihydrogen peroxide, sodium carbonate, iron(II) chloride in dichloromethane, Time= 0.5h, T= 20 °C , chemoselective reaction Join, Benoit; Moeller, Konstanze; Ziebart, Carolin; Schroeder, Kristin; Goerdes, Dirk; Thurow, Kerstin; Spannenberg, Anke; Junge, Kathrin; Beller, Matthias; Advanced Synthesis and Catalysis; vol. 353; nb. 16; (2011); p. 3023 - 3030 View in Reaxys With N,N'-dibromo-N,N'-1,2-ethanediylbis-(benzenesulfonamide), Time= 0.0333333h, T= 20 °C , neat (no solvent) Mahboubifar; Khazaei; Rostami; Asian Journal of Chemistry; vol. 23; nb. 2; (2011); p. 829 - 831 View in Reaxys With tert.-butylnitrite, oxygen, 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,2-dichloro-ethane, Time= 5h, T= 80 °C , p= 1500.15Torr , Autoclave Shen, Zhenlu; Dai, Jialiang; Xiong, Jie; He, Xijun; Mo, Weimin; Hu, Baoxiang; Sun, Nan; Hu, Xinquan; Advanced Synthesis and Catalysis; vol. 353; nb. 16; (2011); p. 3031 - 3038 View in Reaxys With oxygen, titanium(IV) oxide in water, T= 60 °C , UV-irradiation Camera-Roda; Santarelli; Augugliaro; Loddo; Palmisano; Yurdakal; Catalysis Today; vol. 161; nb. 1; (2011); p. 209 - 213 View in Reaxys

5.4 %Spectr.

With benzenesulfonamide, manganese(IV) oxide, potassium carbonate, Time= 24h, T= 120 °C Yu, Xiaochun; Liu, Chuanzhi; Jiang, Lan; Xu, Qing; Organic Letters; vol. 13; nb. 23; (2011); p. 6184 - 6187 View in Reaxys

82 %Spectr.

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, silver nitrate in water, Time= 2h, UV-irradiation Jeena, Vineet; Robinson, Ross S.; Chemical Communications; vol. 48; nb. 2; (2012); p. 299 - 301 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

160/438

2018-03-11 22:07:32


With cucurbit[8]uril, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in water, Time= 0.333333h, T= 95 °C Wang, Yong-Huan; Cong, Hang; Zhao, Fang-Fang; Xue, Sai-Feng; Tao, Zhu; Zhu, Qian-Jiang; Wei, Gang; Catalysis Communications; vol. 12; nb. 12; (2011); p. 1127 - 1130 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, 2Br(1-)*C24H36CuN4O2 (2+), oxygen in water, acetonitrile, Time= 2h, T= 80 °C , p= 1500.15Torr Wang, Qiufen; Zhang, Ying; Zheng, Gengxiu; Tian, Zhongzhen; Yang, Guanyu; Catalysis Communications; vol. 14; nb. 1; (2011); p. 92 - 95 View in Reaxys With 1,2-dihydroxy-9,10-anthracenedione, titanium(IV) oxide, nitrobenzene in tetrachloromethane, Time= 18h, T= 30 °C , Inert atmosphere, Irradiation Chen, Shifu; Zhang, Huaye; Yu, Xiaoling; Liu, Wei; Chinese Journal of Chemistry; vol. 29; nb. 3; (2011); p. 399 404 View in Reaxys 7 :Example 7 - Oxidation of Alcohols; [00228] Various alcohols may be oxidized to ketones or aldehydes using a graphene or graphit oxide catalyst. Specific examples are described below.[00229] Neat benzyl alcohol (PhCH2OH) was heated to 100 °C in the presence of 20 wtpercent graphene oxide or graphite oxide for 14 hours under ambient conditions. The general reaction scheme is shown in FIGURE 7. As FIGURE 8 indicates, acceptable variations in weight percentage graphene oxide or graphite oxide are between 5-200 wtpercent. Acceptable variations in reaction temperature are between 25-100°C. Acceptable variations in reaction time are between 3 -144 hours.[00230] Subsequent filtering of the reaction product afforded a mixture of benzylaldehyde (PhCHO):PhCH2OH in a 1 :3 molar ratio, as determined by 1H NMR spectroscopy. No over- oxidation to benzoic acid (PhC02H) or other by-products was detected under these conditions. NMR analysis and titrimetry of the reaction product mixture showed that water was released during the reaction.[00231] Atomic absorption and inductively coupled plasma mass spectrometry showed that the graphene oxide or graphite oxide catalyst used contained trace or no amounts of metals, indicating that the graphene oxide or graphite oxide and not a metal functioned as a catalyst. The catalytic activity of graphene oxide or graphite oxide was further confirmed by the inability of corresponding flake graphite to catalyze the alcohol oxidation reaction under identical conditions.[00232] The graphene oxide or graphite oxide used in the oxidation reaction was separated from the reaction mixture and filtered. The filtered material was characterized using FT-IR (KBr) and showed an attenuated signal relative to other peaks in the spectrum at υ = 3150 cm" l, corresponding to the O-H stretch as well as no diagnostic signals at 1685 cm"1,corresponding to the C=0 stretch and 1280 cm"1 or 1140 cm"1, corresponding to epoxide absorbances. C=0 and epoxide absorbance signals were seen in the unused catalyst. The FT- IR spectrum also showed signals at 1650 cm"1 and 1500 cm"1, corresponding to the presence of aromatic and olefin species. These signals were not seen in the unused catalyst. Power conductivity in the used graphene oxide or graphite oxide was also measured to be 15 S/m, which was a significant increase from the 2.2 x 10"5 S/m measured in the unused catalyst. Collectively, these results suggest that the graphene oxide or graphite oxide catalyst undergoes a partial reduction during the alcohol oxidation reaction. The used graphene oxide or graphite oxide is similar to r-graphene oxides or graphenes that have been synthesized by other methods.[00233] The catalytic function of the graphene oxide or graphite oxide, as opposed to direct oxidation of the alcohol by the graphene oxide or graphite oxide, was also confirmed. Under ambient conditions, when the graphene oxide or graphite oxide reacts with the alcohol as a catalyst, ambient oxygen is the terminal oxidant. In particular, the PhCH2OH to PhCHO reaction with a graphene oxide or graphite oxide was performed under a nitrogen atmosphere. After 24 hours of reaction time at 100 °C, an aliquot removed from the reaction mixture contained less than 5 molpercent PhCHO, indicating that the alcohol oxidation reaction was not able to proceed in the absence of oxygen. In contrast, if the graphene oxide or graphite oxide directly oxidized the alcohol, oxygen would not be needed and a higher PhCHO yield would be expected.[00234] The reaction was allowed to continue for another 24 hours at 100 °C and another aliquot was tested, showing only 23 molpercent conversion of the alcohol to PhCHO, further confirming the catalytic action of the graphene oxide or graphite oxide.[00235] Furthermore, when the graphene oxide or graphite oxide was separated from the reaction mixture by filtration, it was found to retain its oxidative properties and could be reused for multiple reaction cycles.[00236] The low yield under a nitrogen atmosphere also indicates that, in situations where it is desirable to diminish the oxidative capacity of the catalyst, an atmosphere lacking oxygen or other final oxidants may be used. [00237] To determine the role of radical species in the oxidation process, neat PhCH2OH was treated with 20 wtpercent graphene oxide or graphite oxide and 20 wtpercent butylatedhydroxytolulene (BHT). BHT affects the formation of radical species by forming a more stable, non-reactive radical that arrests the oxidation reaction or by inhibiting or preventing the formation of radicals. After 24 hours reaction time at 100 °C, less than 5 molpercent conversion of the alcohol to PhCHO was observed. However, when a 1 :1 : 1 mass ratio of graphene oxide or graphite ox-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

161/438

2018-03-11 22:07:32


ide:PhCH2OH:BHT was heated for 14 hours at 100 °C, a 26 molpercent conversion of the alcohol to PhCHO was observed. This indicates that BHT likely does not inhibit the graphene oxide or graphite oxide's ability to oxidize the alcohol, but rather impedes the oxidation of the reduced catalyst. This assessment was further confirmed by heating graphene oxide or graphite oxide in the presence of cyclopropylcarbinol, which reacts in a very specific manner, evidenced by the formation of olefinic species, in the present of radicals. These olefinic species may be readily identified spectroscopically. This resulted in the formation of number of products including olefinic species, but no aldehydes. Similar results are obtained in chromic-acid mediated oxidation of the same substrate, which is known to proceed using radical species. Accordingly, the graphene or graphite catalysis of alcohol oxidation likely proceeds via radical species.[00238] The oxidation properties of graphene oxide or graphite oxide were studied under various conditions. In particular, in the oxidation of neat benzyl alcohol to benzylaldehyde or benzoic acid, catalyst loading was varied between 5-200 wtpercent, temperature was varied between 25-150 °C, and reaction time was varied between 3-144 hours.[00239] Selected reaction parameters and results are presented in Table 5. All reactions in Table 5 were allowed to proceed for 24 hours. Loading (wtpercent) refers to the amount of graphene oxide or graphite oxide (GO) prepared by the Hummers method added to he reaction mixture, graphene oxide or graphite oxide was prepared by the Staudenmaier method. Graphite was natural flake graphite (Bay Carbon, Inc. or Alfa Aesar). PhCHO (percent) refers to the conversion of benzyl alcohol to benzylaldehyde. PhC02H (percent) refers to the conversion of benzyl alcohol to benzoic acid. TON refers to the turnover number, which was calculated as the ratio of the moles of oxidized product to mass of graphene oxide or graphite oxide.Table 5. Oxidation of benzyl alcohol to benzaldehyde and benzoic acid under various conditions. o 2 12 0 .00so 5 100 2 0 0:22G .sect. 150 0 0 11GO m 12 0 2:-SfGO m 100 24 2 1.1GO oo ifi 2? 2 1.2GO m ?:3/4 20 2 2.12GO 122 21 0:1 1.1SO m im. 22 12 1 ,2 O 200 00 22 0.22GO 200 100 22. 1 2:42GO 200 1 40 01 0:22[00240] At temperatures less than or equal to 75 °C, alcohol conversion peaked at 73 molpercent even with reaction times as long as 144 hours and catalyst loading as high as 200 wtpercent. At temperatures above 100 °C, conversion rates as high as 85 molpercent were observed with loading above 50 wtpercent. Conversion appeared to plateau at 6 hours under these conditions, indicating decomposition of the catalyst. At temperatures above or equal to 100 °C, an appreciable amount of PhC02H, which may not be desirable, was observed and the content of this acid increased with temperature, catalyst loading, and reaction time. Use of 200 wtpercent catalyst for a reaction time of 24 hours at 100 °C afforded a high conversion rate of 99percent with an aldehyde: acid ratio of 92:7.[00241] The turnover numbers in Table 5 remained relatively constant at 10" mol/g regardless of the reaction conditions, indicating that the catalyst consistently reached maximal activity.[00242] The scope and reactivity of the graphene oxide catalyst was confirmed using the reaction conditions of 200 wtpercent and 100 °C for 24 hours. A variety of primary and secondary benzylic and aliphatic alcohols were tested. The results of these tests are summarized in Table 6. For alcohol number 2 in the table, 2 molpercent benzaldehyde was also found. For alcohol number 3, a mixture of products was observed after 24 hours at 100 °C with 200 wtpercent graphene oxide or graphite oxide. The reported results are for a reaction for 24 hours at 75°C in 50 wtpercent graphene oxide or graphite oxide.Table 6. Oxidation of various alcohols.[00243] Overall, benzylic alcohols afforded the highest conversion, particularly dibenzylic alcohols such as benzhydrol (number 1 in Table 6). Cyclohexanol (number 4 in Table 6) showed conversion rates similar to benzyl alcohol. 2-thiophenemethanol (number 5 on Table 6) showed modest conversion rates with no sulfur oxidation, confirming the alcohol selectivity of the catalyst and its tolerance of functional groups. With oxygen, graphite oxide, Time= 24h, T= 75 °C , Product distribution / selectivity Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; BIELAWSKI, Christopher W.; DREYER, Daniel R.; JIA, Hong-Peng; WO2011/150329; (2011); (A2) English View in Reaxys With oxygen, nitric acid, sodium nitrite in 1,4-dioxane, T= 60 °C , p= 760.051Torr Aellig, Christof; Girard, Christophe; Hermans, Ive; Angewandte Chemie - International Edition; vol. 50; nb. 51; (2011); p. 12355 - 12360 View in Reaxys With coniferyl alcohol dehydrogenase isosyme I from cell free extract of Stretomyces sp. NL15-2K, nicotinamide adenine dinucleotide, pH= 9.5, Glycine-NaOH buffer, Enzymatic reaction, Kinetics, Concentration, pH-value, Reagent/ catalyst Nishimura, Motohiro; Kohno, Kunie; Nishimura, Yoshio; Inagaki, Masanori; Davies, Julian; Bioscience, Biotechnology and Biochemistry; vol. 75; nb. 9; (2011); p. 1770 - 1777 View in Reaxys With oxygen in toluene, Time= 8h, T= 20 °C , chemoselective reaction Singha, Sudarshan; Sahoo, Mitarani; Parida; Dalton Transactions; vol. 40; nb. 44; (2011); p. 11838 - 11844

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

162/438

2018-03-11 22:07:32


View in Reaxys With copper(ll) sulfate pentahydrate, dihydrogen peroxide in water, T= 100 °C , Kinetics, Concentration Ahmad, Jahir Uddin; Raeisaenen, Minna T.; Leskelae, Markku; Repo, Timo; Applied Catalysis A: General; vol. 411-412; (2012); p. 180 - 187 View in Reaxys 21 %Chromat.

With potassium permanganate, ammonia, water, oxygen in 1,4-dioxane, Time= 1h, T= 130 °C , p= 2280.15Torr , Autoclave Yamaguchi, Kazuya; Kobayashi, Hiroaki; Oishi, Takamichi; Mizuno, Noritaka; Angewandte Chemie - International Edition; vol. 51; nb. 2; (2012); p. 544 - 547 View in Reaxys

60 %Chromat.

With 2CH4O*C26H36N4O12V2, dihydrogen peroxide in water, acetonitrile, T= 80 °C , p= 760.051Torr Asghari Lalami, Nasim; Hosseini Monfared, Hassan; Noei, Hashem; Mayer, Peter; Transition Metal Chemistry; vol. 36; nb. 6; (2011); p. 669 - 677 View in Reaxys

51 %Chromat.

With tert.-butylhydroperoxide, [Co(III)(N-(dibenzylcarbamothioyl)benzamide(-H))3] in acetonitrile, Time= 24h, T= 80 °C Gunasekaran; Jerome; Ng, Seik Weng; Tiekink, Edward R.T.; Karvembu; Journal of Molecular Catalysis A: Chemical; vol. 353-354; (2012); p. 156 - 162 View in Reaxys With sodium chlorite, cis-[Ru(2,9-dimethyl-1,10-phenanthroline)2(OH2)2]2+, T= 22.84 °C , pH= 6.8, aq. phosphate buffer Hu, Zongmin; Du, Hongxia; Man, Wai-Lun; Leung, Chi-Fai; Liang, Haojun; Lau, Tai-Chu; Chemical Communications; vol. 48; nb. 8; (2012); p. 1102 - 1104 View in Reaxys

95 %Chromat.

With C28H37ClOOsP2, oxygen in toluene, Time= 48h, T= 120 °C , p= 760.051Torr , Mechanism, Reagent/catalyst, Solvent, Temperature, Time Esteruelas, Miguel A.; Garcia-Obregon, Tania; Herrero, Juana; Olivan, Montserrat; Organometallics; vol. 30; nb. 23; (2011); p. 6402 - 6407 View in Reaxys With [bis(acetoxy)iodo]benzene, sulfuric acid in water, tert-butyl alcohol, Time= 24h, T= 29.84 °C , Darkness, Kinetics, Concentration, Temperature Girija; Aruna; E-Journal of Chemistry; vol. 8; nb. 1; (2011); p. 264 - 268 View in Reaxys With 4‐(acetylamino)‐2,2,6,6‐tetramethyl‐1‐oxopiperidinium tetrafluoroborate in dichloromethane, T= 20 °C , Kinetics Qiu, Joseph C.; Pradhan, Priya P.; Blanck, Nyle B.; Bobbitt, James M.; Bailey, William F.; Organic Letters; vol. 14; nb. 1; (2012); p. 350 - 353 View in Reaxys With ethene, oxygen, sodium carbonate, Time= 1h, T= 60 °C , pH= 9 - 10 Qian, Kun; Zhai, Peng; Xian, Junyang; Hua, Qing; Chen, Kai; Huang, Weixin; Catalysis Communications; vol. 15; nb. 1; (2011); p. 56 - 59 View in Reaxys 2.6. Catalytic oxidation General procedure: Catalytic oxidation of primary alcohols to the corresponding aldehydes and secondary alcohols to ketones by ruthenium(II) carbonyl complexes was studied in the presence of NMO as co-oxidant. A typical reaction using the complex [Ru(η6-p-cymene)(AsPh3)(L4)] (4) as a catalyst and primary or secondary alcohol as substrates at a 1:100 M ratio is described as follows. A solution of ruthenium complex (4) (0.01 mmol) in 20 cm3 CH2Cl2 was added to the solution of substrate (1 mmol) and NMO (3 mmol). The solution mixture was refluxed for 3-10 h

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

163/438

2018-03-11 22:07:32


and the solvent was then evaporated from the mother liquor under reduced pressure. The residue was then extracted with diethyl ether (20 cm3) and was analyzed by GC and 1H NMR. The oxidized products were determined by GC and 1H NMR by comparison with authentic samples and no internal standards were used. With Ru[(.eta.6-p-cumene)(AsPh3)(C5H4NC(S)NC6H2(CH3)3)]BPh4, 4-methylmorpholine N-oxide in dichloromethane, Time= 10h, T= 40 °C Raja, M. Ulaganatha; Ramesh; Journal of Organometallic Chemistry; vol. 699; (2012); p. 5 - 11 View in Reaxys With dihydrogen peroxide, sodium bromide in ethanol, Time= 8h, T= 70 °C Qi, Lin; Qi, Xingyi; Wang, Jing; Zheng, Liwei; Catalysis Communications; vol. 16; nb. 1; (2011); p. 225 - 228 View in Reaxys With N-Bromosuccinimide, 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea in dichloromethane, Time= 90h, T= 10 °C , Inert atmosphere Tripathi, Chandra Bhushan; Mukherjee, Santanu; Journal of Organic Chemistry; vol. 77; nb. 3; (2012); p. 1592 1598 View in Reaxys 97 %Chromat.

2.5. Catalytic oxidation of alcohols General procedure: To a solution of alcohol (1 mmol) in dichloromethane (20 mL),ruthenium(II) complex (1 molpercent) and NMO (351 mg; 3 mmol) were added. The mixture was stirred at 27 °C for 12 h. Then the solution was concentrated and the alcohol and aldehyde/ketone were obtained by passing the solution through a short silica gel column (hexane/ethyl acetate). The extract was then analyzed by GC. With [Ru(S(C6H4)NCH(C6H4)O(Br))(CO)(PPh3)2], 4-methylmorpholine N-oxide in dichloromethane, Time= 12h, T= 27 °C Muthu Tamizh; Mereiter; Kirchner; Karvembu; Journal of Organometallic Chemistry; vol. 700; (2012); p. 194 201 View in Reaxys With tert.-butylhydroperoxide in decane, Time= 4h, T= 93.84 °C , Inert atmosphere Perez, Yolanda; Ballesteros, Ruth; Fajardo, Mariano; Sierra, Isabel; Del Hierro, Isabel; Journal of Molecular Catalysis A: Chemical; vol. 352; (2012); p. 45 - 56 View in Reaxys

96 %Chromat.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [Cu{NH=C(OMe)NC(OMe)=NH}2], oxygen, potassium carbonate in water, T= 50 °C , p= 760.051Torr Kopylovich, Maximilian N.; Karabach, Yauhen Yu.; Guedes Da Silva, M. Fatima C.; Figiel, Pawel J.; Lasri, Jamal; Pombeiro, Armando J. L.; Chemistry - A European Journal; vol. 18; nb. 3; (2012); p. 899 - 914 View in Reaxys With C8H20N(1+)*C30H15Br8O6PRe(1-), Time= 15h, T= 25 °C , p= 760.051Torr Lippert, Cameron A.; Riener, Korbinian; Soper, Jake D.; European Journal of Inorganic Chemistry; nb. 3; (2012); p. 554 - 561 View in Reaxys With tert.-butylhydroperoxide, C42H40ClN3OP2RuS2 in benzene, Time= 2h, T= 20 °C El-Hendawy, Ahmed M.; Fayed, Ahmed M.; Mostafa, Mohamed R.; Transition Metal Chemistry; vol. 36; nb. 4; (2011); p. 351 - 361 View in Reaxys Reaction Steps: 2 1: copper(II) nitrate trihydrate / 0.33 h / 20 °C / Neat (no solvent) 2: copper(II) nitrate trihydrate; water; silica gel; potassium bromide / 0.2 h / 90 °C / Neat (no solvent) With copper(II) nitrate trihydrate, water, silica gel, potassium bromide

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

164/438

2018-03-11 22:07:32


Shirini; Mashhadi-Nejad; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 187; nb. 3; (2012); p. 376 - 381 View in Reaxys 92 %Chromat.

With [Cp*Ir(6,6'-dihydroxy-2,2'-bipyridine)(H2O)](OTf)2 in water, Time= 20h, Inert atmosphere, Reflux Kawahara, Ryoko; Fujita, Ken-Ichi; Yamaguchi, Ryohei; Journal of the American Chemical Society; vol. 134; nb. 8; (2012); p. 3643 - 3646 View in Reaxys

81 %Chromat.

With oxone, tetrabutylammomium bromide in dichloromethane, water, Time= 0.5h, T= 20 °C Bagherzadeh, Mojtaba; Amini, Mojtaba; Boghaei, Davar M.; Najafpour, Mohammad Mahdi; McKee, Vickie; Applied Organometallic Chemistry; vol. 25; nb. 7; (2011); p. 559 - 563 View in Reaxys

35 %Chromat.

With Au/ZrO2 in toluene, Time= 22h, T= 110 °C Ishida, Tamao; Takamura, Rena; Takei, Takashi; Akita, Tomoki; Haruta, Masatake; Applied Catalysis A: General; vol. 413-414; (2012); p. 261 - 266 View in Reaxys With tert.-butylhydroperoxide, nitrobenzene, potassium hydoxide in chlorobenzene, Time= 24h, T= 140 °C Xiao, Fuhong; Liu, Yong; Tang, Chenglin; Deng, Guo-Jun; Organic Letters; vol. 14; nb. 4; (2012); p. 984 - 987 View in Reaxys

63 %Spectr.

With gold, 4-methylmorpholine N-oxide in d3-acetonitrile, Time= 48h, T= 85 °C , Sealed tube, Inert atmosphere Klobukowski, Erik R.; Angelici, Robert J.; Woo, L. Keith; Catalysis Letters; vol. 142; nb. 2; (2012); p. 161 - 167 View in Reaxys With dihydrogen peroxide in water, acetonitrile, Time= 6h, T= 60 °C , chemoselective reaction Islam, Manirul; Hossain, Dildar; Mondal, Paramita; Tuhina, Kazi; Roy, Anupam Singha; Mondal, Sanchita; Mobarak, Manir; Transition Metal Chemistry; vol. 36; nb. 2; (2011); p. 223 - 230 View in Reaxys With C33H32N7O7P2Ru, sodium acetate, T= 23 °C , pH= 5, Electrochemical reaction, Kinetics Vannucci, Aaron K.; Hull, Jonathan F.; Chen, Zuofeng; Binstead, Robert A.; Concepcion, Javier J.; Meyer, Thomas J.; Journal of the American Chemical Society; vol. 134; nb. 9; (2012); p. 3972 - 3975 View in Reaxys With dicarbonyl-(2,4-bis(trimethylsilyl)bicyclo[3.3.0]nona-1,4-dien-3-one)[acetonitrile]iron, acetone, Time= 18h, T= 90 °C , Inert atmosphere, Opppenauer oxidation Plank, Taylor N.; Drake, Jessica L.; Kim, Daniel K.; Funk, Timothy W.; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 597 - 601 View in Reaxys With 1H-imidazole, dihydrogen peroxide in water, acetonitrile, Time= 4h, T= 80 °C , p= 760.051Torr , chemoselective reaction Masoudian, Shahla; Hosseini Monfared, Hassan; Aghaei, Alireza; Transition Metal Chemistry; vol. 36; nb. 5; (2011); p. 521 - 530 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, silver nitrate, zinc(II) oxide in water, Time= 2h, Irradiation Jeena, Vineet; Robinson, Ross S.; Dalton Transactions; vol. 41; nb. 11; (2012); p. 3134 - 3137 View in Reaxys

87 %Chromat.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in tert-butyl alcohol, T= 25 °C , pH= 11.5, aq. sodium carbonate/bicarbonate buffer, Electrolysis

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

165/438

2018-03-11 22:07:32


Hill-Cousins, Joseph T.; Kuleshova, Jekaterina; Green, Robert A.; Birkin, Peter R.; Pletcher, Derek; Underwood, Toby J.; Leach, Stuart G.; Brown, Richard C. D.; ChemSusChem; vol. 5; nb. 2; (2012); p. 326 - 331 View in Reaxys With dihydrogen peroxide in water, Time= 6h, T= 50 °C Islam, Sk. Manirul; Roy, Anupam Singha; Mondal, Paramita; Salam, Noor; Journal of Molecular Catalysis A: Chemical; vol. 358; (2012); p. 38 - 48 View in Reaxys With oxygen, T= 160 °C , Activation energy, Kinetics, chemoselective reaction Chen, Yuanting; Wang, Houpeng; Liu, Chang-Jun; Zeng, Zhiyuan; Zhang, Hua; Zhou, Chunmei; Jia, Xinli; Yang, Yanhui; Journal of Catalysis; vol. 289; (2012); p. 105 - 117 View in Reaxys 85 %Spectr.

With oxygen in 1,4-dioxane, Time= 24h, T= 80 °C Asao, Naoki; Hatakeyama, Naoya; Menggenbateer; Minato, Taketoshi; Ito, Eisuke; Hara, Masahiko; Kim, Yousoo; Yamamoto, Yoshinori; Chen, Mingwei; Zhang, Wei; Inoue, Akihisa; Chemical Communications; vol. 48; nb. 38; (2012); p. 4540 - 4542 View in Reaxys With oxygen, Time= 5h, T= 120 °C , Neat (no solvent) Choudhary, Vasant R.; Dumbre, Deepa K.; Catalysis Communications; vol. 13; nb. 1; (2011); p. 82 - 86 View in Reaxys With air, cryptomelane-type KMn8O16*nH2O OMS in toluene, Time= 2h, T= 110 °C Dharmarathna, Saminda; King'ondu, Cecil K.; Pedrick, Wyatt; Pahalagedara, Lakshitha; Suib, Steven L.; Chemistry of Materials; vol. 24; nb. 4; (2012); p. 705 - 712 View in Reaxys

84 %Chromat.

With oxygen in water, Time= 4h, T= 60 °C , p= 760.051Torr Hossain, M. Jakir; Tsunoyama, Hironori; Yamauchi, Miho; Ichikuni, Nobuyuki; Tsukuda, Tatsuya; Catalysis Today; vol. 183; nb. 1; (2012); p. 101 - 107 View in Reaxys

82 %Spectr.

With ruthenium (III) chloride trihydrate, oxygen, N-cyclohexyl-cyclohexanamine in tetrahydrofuran, Time= 48h, T= 20 °C Yu, Kaihui; Ye, Dongnai; Shu, Lei; Zhang, Shiyong; Hu, Qiaosheng; Liu, Liangxian; Synthetic Communications; vol. 42; nb. 15; (2012); p. 2318 - 2326 View in Reaxys

99 %Chromat.

With C54H45As2ClO5Ru, 4-methylmorpholine N-oxide in dichloromethane, Time= 1h, Reflux, Molecular sieve Viswanathamurthi; Muthukumar; Journal of Chemical Sciences; vol. 123; nb. 5; (2011); p. 567 - 576 View in Reaxys With oxygen in water, Time= 8h, T= 50 °C , p= 760.051Torr , chemoselective reaction Liu, Jian; Yang, Heng Quan; Kleitz, Freddy; Chen, Zhi Gang; Yang, Tianyu; Strounina, Ekaterina; Lu, Gao Qing; Qiao, Shi Zhang; Advanced Functional Materials; vol. 22; nb. 3; (2012); p. 591 - 599 View in Reaxys With oxygen in toluene, Time= 24h, T= 89.84 °C , p= 760.051Torr , chemoselective reaction Premalatha; Raghavan; Viswanathan; Applied Catalysis A: General; vol. 419-420; (2012); p. 203 - 209 View in Reaxys

99 %Chromat.

With oxygen, caesium carbonate in toluene, Time= 1h, T= 20 °C Karimi, Babak; Esfahani, Farhad Kabiri; Advanced Synthesis and Catalysis; vol. 354; nb. 7; (2012); p. 1319 1326

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

166/438

2018-03-11 22:07:32


View in Reaxys With dihydrogen peroxide in water, Time= 0.0833333h, T= 90 °C , Microwave irradiation Garcia-Suarez, Eduardo J.; Balu, Alina Mariana; Tristany, Mar; Garcia, Ana Beatriz; Philippot, Karine; Luque, Rafael; Green Chemistry; vol. 14; nb. 5; (2012); p. 1434 - 1439 View in Reaxys 96 %Chromat.

With Iron(III) nitrate nonahydrate, sodium chloride in 1,2-dichloro-ethane, Time= 2h, T= 20 °C , p= 760.051Torr Tamura, Naoya; Aoyama, Tadashi; Takido, Toshio; Kodomari, Mitsuo; Synlett; vol. 23; nb. 9; (2012); p. 1397 1401 View in Reaxys

> 99 %Spectr.

With oxygen, potassium carbonate in dichloromethane, water, Time= 16h, T= 20 °C , p= 760.051Torr Zheng, Jie; Lin, Shengyue; Zhu, Xianhao; Jiang, Biwang; Yang, Zhen; Pan, Zhengying; Chemical Communications; vol. 48; nb. 50; (2012); p. 6235 - 6237 View in Reaxys With oxygen in toluene, Time= 20h, T= 26 °C , p= 760.051Torr Wang, Liang; Zhang, Jian; Meng, Xiangju; Zheng, Dafang; Xiao, Feng-Shou; Catalysis Today; vol. 175; nb. 1; (2011); p. 404 - 410 View in Reaxys With thermophilic alcohol dehydrogenase from Bacillus stearothermophilus, nicotinamide adenine dinucleotide, T= 30 °C , pH= 7, aq. phosphate buffer, Enzymatic reaction, Kinetics, Activation energy Nagel, Zachary D.; Dong, Ming; Bahnson, Brian J.; Klinman, Judith P.; Proceedings of the National Academy of Sciences of the United States of America; vol. 108; nb. 26; (2011); p. 10520 - 10525 View in Reaxys With microsomal alcohol oxidase from Aspergillus terreus, Time= 24h, T= 25 °C , pH= 7.5, aq. buffer Kakoti, Ankana; Kumar, Adepu Kiran; Goswami, Pranab; Journal of Molecular Catalysis B: Enzymatic; vol. 78; (2012); p. 98 - 104 View in Reaxys

> 99 With 13,17-bis(2-methoxycarbonylethyl)-2,7,12,18-tetramethylporphinatocobalt(II), oxygen, isovaleraldehyde in ace%Chromat. tonitrile, Time= 0.666667h, T= 60 °C Sun, Chengguo; Hu, Bingcheng; Liu, Zuliang; Heteroatom Chemistry; vol. 23; nb. 3; (2012); p. 295 - 303 View in Reaxys 95 %Chromat.

Representative procedure for the electrochemical selective oxidation of benzyl alcohol A solution of benzyl alcohol (Table 1, entry 1) {1.08 g 10 mmol} in 20 ml chloroform was taken in a beaker type undivided cell. To the above solution a 0.83percent sodium nitrate solution containing 2 ml of HCl (36.5percent solution) was added. The carbon anode (15 cm2) and stainless steel cathode (15 cm2) were placed in the upper aqueous phase. The organic phase alone was stirred with a magnetic stirrer at a rate of 50 rpm in such a way that the organic phase does not touch the electrodes. The electrolysis was conducted galvanostatically at a current density of 50 mA/cm2 until the quantity of charge indicated in Table 1 was passed. The electrolysis was monitored by HPLC (Shimadzu) using a shimpack ODS-18 column (250 mm .x. 4.6 mm) as the stationary phase. The eluent consisted of acetonitrile/water (80:20) at a flow rate of 1 ml/min. Samples including authentic samples were analyzed using UV detector at a wavelength of 254 nm. After completion of electrolysis, the organic phase was separated, washed with water (2 .x. 25 ml), dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to afford 1.13 g of crude benzaldehyde. The HPLC analysis of the residue showed 95percent purity. With hydrogenchloride, sodium nitrate in chloroform, water, Electrochemical reaction Christopher; Lawrence; Anbu Kulandainathan; Kulangiappar; Easu Raja; Xavier; Raja; Tetrahedron Letters; vol. 53; nb. 23; (2012); p. 2802 - 2804 View in Reaxys With pyridinum sulfonate fluorochromate, Time= 0.00416667h, Neat (no solvent), Microwave irradiation

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

167/438

2018-03-11 22:07:32


Bekhradnia, Ahmad R.; Arshadi, Sattar; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 42; nb. 5; (2012); p. 705 - 710 View in Reaxys 95.2 With periodic acid in acetonitrile, Time= 1.5h, T= 80 °C %Chromat. Rajarao, Ravindra; Kim; Bhat, Badekai Ramachandra; Journal of Coordination Chemistry; vol. 65; nb. 15; (2012); p. 2671 - 2682 View in Reaxys With sodium hydroxide in toluene, Time= 20h, T= 25 °C , sealed tube, UV-irradiation Zhang, Xingguang; Ke, Xuebin; Zhu, Huaiyong; Chemistry - A European Journal; vol. 18; nb. 26; (2012); p. 8048 - 8056 View in Reaxys With poly(L-lactide) based Pd(II) macrocomplex in toluene, Autoclave, aerobic condition Giachi, Guido; Frediani, Marco; Oberhauser, Werner; Passaglia, Elisa; Journal of Polymer Science, Part A: Polymer Chemistry; vol. 50; nb. 13; (2012); p. 2725 - 2731 View in Reaxys > 99 With oxygen, potassium carbonate in water, Time= 5h, T= 40 °C %Chromat. Karimi, Babak; Behzadnia, Hesam; Bostina, Mihnea; Vali, Hojatollah; Chemistry - A European Journal; vol. 18; nb. 28; (2012); p. 8634 - 8640 View in Reaxys 81 %Chromat.

With sodium hypochlorite, tetrabutylammomium bromide in ethyl acetate, Time= 1.95h, T= 20 °C Leduc, Andrew B.; Jamison, Timothy F.; Organic Process Research and Development; vol. 16; nb. 5; (2012); p. 1082 - 1089 View in Reaxys With dihydrogen peroxide in water, Time= 6h, T= 95 °C Zhang, Zhi-Ming; Yao, Shuang; Li, Yang-Guang; Han, Xin-Bao; Su, Zhong-Min; Wang, Zhi-Shu; Wang, En-Bo; Chemistry - A European Journal; vol. 18; nb. 30; (2012); p. 9184 - 9188 View in Reaxys With 3,5-dimethylpyrazolium chlorochromate, Time= 0.05h, T= 20 °C , Neat (no solvent) Canbulat, Melek; Oezguen, Beytiye; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 42; nb. 5; (2012); p. 634 - 637 View in Reaxys

90 %Spectr.

With [RuCl(ppy)(tpy)][PF6], oxygen, potassium carbonate in dichloromethane, Time= 8h, Reflux Taketoshi, Ayako; Beh, Xin Ning; Kuwabara, Junpei; Koizumi, Take-Aki; Kanbara, Takaki; Tetrahedron Letters; vol. 53; nb. 28; (2012); p. 3573 - 3576 View in Reaxys

80 %Chromat.

With dihydrogen peroxide, Time= 24h, T= 25 °C , Ionic liquid Karthikeyan, Parasuraman; Aswar, Sachin Arunrao; Muskawar, Prashant Narayan; Bhagat, Pundlik Rambhau; Kumar, S. Senthil; Catalysis Communications; vol. 26; (2012); p. 189 - 193 View in Reaxys

96 %Chromat.

With 3-(3-(1,2-dicarboxyethylamino)-3-oxopropyl)-1-methyl-1H-imidazol-3-ium bromide, dihydrogen peroxide, Time= 0.5h, T= 25 °C , Neat (no solvent) Karthikeyan, Parasuraman; Arunrao, Aswar Sachin; Narayan, Muskawar Prashant; Kumar, Sythana Suresh; Kumar, S. Senthil; Bhagat, Pundlik Rambhau; Journal of Molecular Liquids; vol. 173; (2012); p. 180 - 183 View in Reaxys With tetraethoxy orthosilicate, palladium diacetate, sodium carbonate in methanol, Time= 24h, T= 40 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

168/438

2018-03-11 22:07:32


Bai, Xing-Feng; Ye, Fei; Zheng, Long-Sheng; Lai, Guo-Qiao; Xia, Chun-Gu; Xu, Li-Wen; Chemical Communications; vol. 48; nb. 68; (2012); p. 8592 - 8594 View in Reaxys With oxygen in toluene, Time= 2h, T= 80 °C , chemoselective reaction Li, Wanjun; Wang, Aiqin; Liu, Xiaoyan; Zhang, Tao; Applied Catalysis A: General; vol. 433-434; (2012); p. 146 151 View in Reaxys With 9-phenylxanthylium tetrafluoroborate in acetonitrile, T= 60 °C , Kinetics, Temperature Liu, Qi; Zhao, Yu; Hammann, Blake; Eilers, James; Lu, Yun; Kohen, Amnon; Journal of Organic Chemistry; vol. 77; nb. 16; (2012); p. 6825 - 6833 View in Reaxys With dihydrogen peroxide, T= 70 °C , pH= 7.8, aq. Tris-HCl buffer, Kinetics, Temperature Wu, Yun; Yang, Ben-Hong; Li, Meng; Tian, Chang-An; Qiu, Ling-Guang; Asian Journal of Chemistry; vol. 24; nb. 9; (2012); p. 4044 - 4046 View in Reaxys 2.3. Catalytic oxidation experiments General procedure:The reactions were carried out in a stainless steel reactor equipped with a magnetic stirrer. In a typical run, a mixture of the substrate (0.4-1.2 mmol), solvent (if any) (2 mL), and the catalyst (10-40 mg; ca. 0.6-2.4 wt.percent; Au: 0.01-0.75 molpercent) was transferred in the reactor. The reactor was pressurized with oxygen to the total pressure of 10 atm and placed in an oil bath; then, the solution was intensively stirred at 80-130 °C for the reported time. The reactions were followed by gas chromatography (GC) (Shimadzu 17 instrument, Carbowax 20 M capillary column). At appropriate time intervals, stirring was stopped and after catalyst settling aliquots were taken and analyzed by GC. To ensure correct GC results in solvent-free reactions and in those with high initial substrate concentrations, the aliquots were diluted with methanol before the analysis. The structures of the products were confirmed by GC/MS (Shimadzu QP2010-PLUS instrument, 70 eV). With oxygen, Time= 4h, T= 120 °C , p= 7600.51Torr , Stainless steel reactor, chemoselective reaction Costa, Vinicius V.; Estrada, Miguel; Demidova, Yulia; Prosvirin, Igor; Kriventsov, Vladimir; Cotta, Rafaela F.; Fuentes, Sergio; Simakov, Andrey; Gusevskaya, Elena V.; Journal of Catalysis; vol. 292; (2012); p. 148 - 156 View in Reaxys With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] Hikawa, Hidemasa; Ino, Yukari; Suzuki, Hideharu; Yokoyama, Yuusaku; Journal of Organic Chemistry; vol. 77; nb. 16; (2012); p. 7046 - 7051 View in Reaxys Stage 1: With 1-butyl-3-methylimidazolium nitrate, Time= 2h, T= 20 °C Stage 2: With dihydrogen peroxide in water, T= 39.84 °C Zhou, Guojun; Zhang, Zhaorui; Feng, Xin; Dang, Bobo; Li, Xiaoyong; Sun, Yang; Catalysis Communications; vol. 25; (2012); p. 69 - 73 View in Reaxys Ca. 25 With N-(1-dodecyl)ferrocenylmethylimine-stabilized magnetite nanoparticles, dihydrogen peroxide in water, Time= %Chromat. 12h, T= 75 °C Kamonsatikul, Choavarit; Khamnaen, Tossapol; Phiriyawirut, Phairat; Charoenchaidet, Sumate; Somsook, Ekasith; Catalysis Communications; vol. 26; (2012); p. 1 - 5 View in Reaxys With dihydrogen peroxide in water, Time= 3h, T= 90 °C Hosseini-Monfared, Hassan; Naether, Christian; Winkler, Heiner; Janiak, Christoph; Inorganica Chimica Acta; vol. 391; (2012); p. 75 - 82 View in Reaxys 2.3. Catalytic tests

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

169/438

2018-03-11 22:07:32


Reactions were carried out in a 30 ml glass reactor equipped with a thermostat and an electronically controlled magnetic stirrer connected to a 5000 ml reservoir charged with oxygen (300 kPa). The oxygen uptake was followed by a mass-flow controller connected to a PC through an A/D board, plotting a flow time diagram.Glycerol oxidation: glycerol 0.3 M and the catalyst (substrate/total metal = 1000 mol/mol) were mixed in distilled water (total volume 10 ml) and 4 eq of NaOH. The reactor was pressurized at 300 kPa of oxygen and set to 50 °C. Once this temperature was reached, the gas supply was switched to oxygen and the monitoring of the reaction started. The reaction was initiated by stirring. Samples were removed periodically and analyzed by high-performance liquid chromatography (HPLC) using a column (Alltech OA- 10,308, 300 mm_7.8 mm) with UV and refractive index (RI) detection to analyze the mixture of the samples. Aqueous H3PO4 solution (0.1 wtpercent) was used as the eluent. Products were identified by comparison with the original samples.Benzyl alcohol oxidation: benzyl alcohol and the catalyst (alcohol/total metal = 5000 mol/mol) were mixed in cyclohexane (benzyl alcohol/cyclohexane 50/50 vol/vol; total volume, 10 ml). The reactor was pressurized at 200 kPa of oxygen and set to 80 °C. The reaction was initiated by stirring. Periodic removal of samples from the reactor was performed. Identification and analysis of the products were done by comparison with the authentic samples by GC using a HP 7820A gas chromatograph equipped with a capillary column (HP-5 30 m .x. 0.32 mm, 0.25 μm Film, made by Agilent Technologies) and TCD detector. Quantification of the reaction products was done by the external calibration method. With oxygen in cyclohexane, T= 80 °C , p= 1500.15Torr Villa, Alberto; Wang, Di; Veith, Gabriel M.; Prati, Laura; Journal of Catalysis; vol. 292; (2012); p. 73 - 80 View in Reaxys With iodosylbenzene in chloroform-d1, T= 19.84 °C , Kinetics Yokoyama, Atsutoshi; Ohkubo, Kei; Ishizuka, Tomoya; Kojima, Takahiko; Fukuzumi, Shunichi; Dalton Transactions; vol. 41; nb. 33; (2012); p. 10006 - 10013 View in Reaxys 72 %Chromat.

With oxygen in toluene, Time= 1h, T= 59.84 °C , p= 760.051Torr Liu, Peng; Li, Can; Hensen, Emiel J. M.; Chemistry - A European Journal; vol. 18; nb. 38; (2012); p. 12122 12129 View in Reaxys

96 %Chromat.

With tert.-butylhydroperoxide in acetonitrile, Time= 0.833333h, p= 760.051Torr , Reflux, Schiff Reaction Shojaei, Abdollah Fallah; Rafie, Mahboubeh Delavar; Loghmani, Mohammad Hassan; Bulletin of the Korean Chemical Society; vol. 33; nb. 8; (2012); p. 2748 - 2752 View in Reaxys Catalytic oxidation by TBHP General procedure: The liquid phase oxidation reactions were carried out in a two-necked round bottom flask fitted with a water condenser and placed in an oil bath at different temperatures under vigorous stirring for a certain period of time. Substrates (5 mmol) were taken in water (5 mL) for different sets of reactions together with catalyst in which 10 mmol of TBHP (70percent in aq.) was added. After the reaction, the organic products were separated from the reaction mixture by extraction with dichloromethane (5 mL×2). The combined organic portions were dried and concentrated. Product analysis was performed by Varian 3400 gas chromatograph equipped with a 30 m CP-SIL8CB capillary column and a Flame Ionization Detector using cyclohexanone as internal standard. All reaction products were identified by using Trace DSQ II GC-MS. With dihydrogen peroxide in water, Time= 6h, T= 50 °C Islam; Roy, Anupam Singha; Mondal, Paramita; Paul, Sumantra; Salam, Noor; Inorganic Chemistry Communications; vol. 24; (2012); p. 170 - 176 View in Reaxys With dihydrogen peroxide in water, Time= 2.08333h, T= 90 °C Leng, Yan; Wang, Jun; Jiang, Pingping; Catalysis Communications; vol. 27; (2012); p. 101 - 104 View in Reaxys

100 Typical procedure for the oxidation of alcohols %Chromat. General procedure: To a solution of alcohol (0.1 g) in2 mL of solvent was added the appropriate amount of GO (as indicated in Table2). The resulting mixture was irradiated in an ultrasonic bath or with an ultrasonic probe (methods A to G) for the time indicated in Table 2 prior to GC/MS analysis. The mixture was filtered through a sintered funnel and

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

170/438

2018-03-11 22:07:32


evaporated under reduced pressure. Purification was achieved by column chromatography using hexane as the eluent. The spectroscopic data of the obtained aldehydes were compared with authentic samples.16 Other products were also known compounds10–12 and were characterized by 1H NMR, mass spectrometry, and FT-IR spectroscopy. With Graphite oxide in acetonitrile, Time= 4h, Sonication Mirza-Aghayan, Maryam; Kashef-Azar, Elnaz; Boukherroub, Rabah; Tetrahedron Letters; vol. 53; nb. 37; (2012); p. 4962 - 4965 View in Reaxys > 99 With oxygen, Time= 4.5h, T= 70 °C , p= 760.051Torr %Chromat. Karimi, Babak; Elhamifar, Dawood; Yari, Omolbanin; Khorasani, Mojtaba; Vali, Hojatollah; Clark, James H.; Hunt, Andrew J.; Chemistry - A European Journal; vol. 18; nb. 42; (2012); p. 13520 - 13530 View in Reaxys Reaction Steps: 2 1: CuO*Fe3O4; sodium hydroxide / toluene / 72 h / 130 °C 2: hydrogenchloride; water / toluene; diethyl ether / 2 h / 20 °C / Inert atmosphere With hydrogenchloride, CuO*Fe3O4, water, sodium hydroxide in diethyl ether, toluene Perez, Juana M.; Cano, Rafael; Yus, Miguel; Ramon, Diego J.; European Journal of Organic Chemistry; nb. 24; (2012); p. 4548 - 4554 View in Reaxys Reaction Steps: 2 1: CuO*Fe3O4; sodium hydroxide / toluene / 96 h / 100 °C / Inert atmosphere 2: hydrogenchloride; water / toluene; diethyl ether / 2 h / 20 °C / Inert atmosphere With hydrogenchloride, CuO*Fe3O4, water, sodium hydroxide in diethyl ether, toluene Perez, Juana M.; Cano, Rafael; Yus, Miguel; Ramon, Diego J.; European Journal of Organic Chemistry; nb. 24; (2012); p. 4548 - 4554 View in Reaxys 86 %Chromat.

3.4 Procedure for catalytic oxidation of alcohols General procedure: Catalytic oxidation of primary alcohol to corresponding aldehyde and secondary alcohol to ketone by ruthenium(II) complexes were studied in the presence of NMO, H2O2 or ButOOH as co-oxidant. A typical reaction using the complex as a catalyst and primary or secondary alcohol, as substrate at 1:100 molar ratio was described as follows. A solution of [Ru(CO)2Cl2(α-NaiEt)] (1b) (0.01 mmol) in CH2Cl2 (20 ml) was added to the mixture containing PhCH2OH (1 mmol), NMO (3 mmol) and molecular sieves. The reaction mixture was refluxed for 1 h, and the solvent was then evaporated under reduced pressure. The residue was then extracted with diethyl ether (20 ml), concentrated to ≈1 ml and was analyzed by GC. The oxidation products were identified by GC co-injection with authentic samples. All other alcohols were oxidized following identical reaction protocol. With C17H14Cl2N4O2Ru, 4-methylmorpholine N-oxide in dichloromethane, Time= 1h, Molecular sieve, Reflux, Reagent/catalyst Sarkar, Shyamal Kumar; Jana, Mahendra Sekhar; Mondal, Tapan Kumar; Sinha, Chittaranjan; Journal of Organometallic Chemistry; vol. 716; (2012); p. 129 - 137 View in Reaxys

94.4 With [1,1′-(butane-1,4-diyl)-bis(3-methylimidazolium)]1.5 phosphotungstate, dihydrogen peroxide in water, acetoni%Chromat. trile, Time= 12h, T= 90 °C , Catalytic behavior, Time, Temperature, Solvent, Reagent/catalyst Leng, Yan; Zhao, Pingping; Zhang, Mingjue; Chen, Guojian; Wang, Jun; Science China Chemistry; vol. 55; nb. 9; (2012); p. 1796 - 1801 View in Reaxys With oxygen in toluene, Time= 1.5h, T= 80 °C , p= 760.051Torr View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

171/438

2018-03-11 22:07:32


44 %Chromat.

With palladium diacetate, potassium carbonate in neat (no solvent), Time= 2h, T= 120 °C , Sealed tube, Reagent/ catalyst, Temperature, Time View in Reaxys

97 %Chromat.

With [Fe(1,10-phenanthroline)2Cl2]NO3, dihydrogen peroxide in aq. buffer, Time= 0.5h, T= 55 °C , pH= 1, chemoselective reaction View in Reaxys With oxygen, Time= 12h, UV-irradiation, Catalytic behavior, Solvent View in Reaxys

99 %Chromat.

With Au/CeO2, oxygen in water, Time= 0.166667h, Irradiation, Kinetics, Catalytic behavior, Reagent/catalyst, chemoselective reaction Tanaka, Atsuhiro; Hashimoto, Keiji; Kominami, Hiroshi; Journal of the American Chemical Society; vol. 134; nb. 35; (2012); p. 14526 - 14533 View in Reaxys Catalytic oxidation General procedure: Catalytic oxidation of primary alcohols to corresponding aldehydes and secondary alcohols to ketones by ruthenium(II) complexes were studied in the presence of N-methyl morpholine N-oxide (NMO) as co-oxidant. In a typical reaction, ruthenium(II) complexes as a catalyst and primary or secondary alcohol, as substrates at 1:100 M ratios was described as follows. A solution of ruthenium complexes (0.01 mmol) in CH2Cl2 (20 cm3) was added to the mixture containing substrate (1 mmol), NMO (3 mmol) and molecular sieves. The solution mixture was refluxed for 2 h and the solvent was then evaporated from the mother liquor under reduced pressure. The solid residue was extracted with petroleum ether (60–80 °C) (20 cm3) concentrated to ∼1 ml and was analyzed by GC. The oxidation products were identified by GC co-injection with authentic samples. With C35H25ClN3O3PRu, 4-methylmorpholine N-oxide in dichloromethane, Time= 2h, Reflux, Reagent/catalyst Anitha; Manikandan; Endo; Hashimoto; Viswanathamurthi; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 99; (2012); p. 174 - 180 View in Reaxys With dinitrogen pentoxide, Heating, Inert atmosphere, Gas phase, Kinetics Harrison, Joel C.; Wells; International Journal of Chemical Kinetics; vol. 44; nb. 12; (2012); p. 778 - 788 View in Reaxys With dihydrogen peroxide in acetonitrile, Time= 4h, T= 90 °C , Reagent/catalyst, Time Reis, Michele C.; Barros, Suellen D.T.; Lachter, Elizabeth R.; San Gil, Rosane A.S.; Flores, Jhonny H.; Pais Da Silva, Maria I.; Onfroy, Thomas; Catalysis Today; vol. 192; nb. 1; (2012); p. 117 - 122 View in Reaxys

94 %Chromat.

With lithium hydroxide monohydrate, Pd/DNA in water, Time= 12h, T= 60 °C , Inert atmosphere Tang, Lin; Sun, Huayin; Li, Yunfeng; Zha, Zhenggen; Wang, Zhiyong; Green Chemistry; vol. 14; nb. 12; (2012); p. 3423 - 3428 View in Reaxys With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in acetonitrile, Time= 0.416667h, T= 80 °C , Inert atmosphere Gualtierotti, Jean-Baptiste; Schumacher, Xavier; Fontaine, Patrice; Masson, Géraldine; Wang, Qian; Zhu, Jieping; Chemistry - A European Journal; vol. 18; nb. 46; (2012); p. 14812 - 14819 View in Reaxys Kinetic study Fresh catalysts were used each time to acquire the kinetic data. The oxidation of BzOH was carried out in a magnetically stirred glass reactor (50 mL) by dispersing the catalysts in 17.1 mL aqueous medium composed of BzOH and H2O2. Temperature was controlled using a thermocouple located in the reactor. Samples (from the reactor) were taken periodically (with a syringe) and centrifuged to separate the catalyst from the mixture. The products were analyzed using a gas chromatography, equipped with flame ionization detector (FID, SE-30 capillary column) and identi-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

172/438

2018-03-11 22:07:32


fied by comparison with known standards. External calibration method was used for quantitative analysis of the concentrations of reactants and products generated. With dihydrogen peroxide in water, Kinetics, Temperature, Concentration Zhan, Guowu; Hong, Yingling; Lu, Fenfen; Ibrahim, Abdul-Rauf; Du, Mingming; Sun, Daohua; Huang, Jiale; Li, Qingbiao; Li, Jun; Journal of Molecular Catalysis A: Chemical; vol. 366; (2013); p. 215 - 221 View in Reaxys With O32W10 (4-)*4C9H14N(1+), dihydrogen peroxide in water, Time= 15h, T= 60 °C Liu, Dan; Gui, Jianzhou; Lu, Feng; Sun, Zhaolin; Park, Yong-Ki; Catalysis Letters; vol. 142; nb. 11; (2012); p. 1330 - 1335 View in Reaxys 2.3 Typical procedures for the aerobic oxidation of alcohols General procedure: Catalyst Pd1Au1/LDH (0.1 g) was placed into a 50 ml dry reaction flask with a reflux condenser. Water (3 ml) and 1-phenylethyl alcohol (0.12 ml, 1 mmol) was added via syringe under N2. After the addition, the resulting mixture was purged with oxygen three times and then stirred at desired temperature for a given time under a balloon of oxygen. After reaction, the reaction mixture was extracted with ethyl ether three times. The resulting organic layer was dried with Na2SO4 and then analyzed with GC and GC–MS with the use of n-octane as internal standard to determine the conversion and selectivity. Then the ethyl ether in catalytic aqueous phase was removed under vacuum at room temperature, and the aqueous phase was directly reused by the addition of fresh substrate for the next reaction cycle. With oxygen in water, Time= 1.5h, T= 79.84 °C , Green chemistry Shi, Yu; Yang, Hanmin; Zhao, Xiuge; Cao, Ting; Chen, Jizhong; Zhu, Wenwen; Yu, Yinyin; Hou, Zhenshan; Catalysis Communications; vol. 18; (2012); p. 142 - 146 View in Reaxys 92 %Chromat.

With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) in tert-butyl alcohol, Time= 20h, T= 130 °C , Reagent/catalyst, Solvent Kawahara, Ryoko; Fujita, Ken-Ichi; Yamaguchi, Ryohei; Angewandte Chemie - International Edition; vol. 51; nb. 51; (2012); p. 12790 - 12794; Angew. Chem.; (2012); p. 12962 - 12966 View in Reaxys With C21H22N2O2Pd, oxygen in toluene, Time= 12h, T= 100 °C , p= 3000.3Torr , Reagent/catalyst Melero, Cristobal; Shishilov, Oleg N.; Alvarez, Eleuterio; Palma, Pilar; Campora, Juan; Dalton Transactions; vol. 41; nb. 46; (2012); p. 14087 - 14100 View in Reaxys 3.6 Catalytic activity of the [LAphCuCl]2 complex for the oxidation of alcohols General procedure: The oxidation was carried out in an oxygen atmosphere at room temperature. In a typical experiment, alcohol (1 mmol), [LAphCuCl]2 (0.024 g, 5 molpercent) and Cs2CO3 (0.650 g, 2 mmol) in 5 ml of air (oxygen) saturated toluene were taken in a 15-ml two-necked round-bottom flask which was equipped with an air or oxygen balloon. The solution was magnetically stirred for some hours and the mixture was filtered through a plug of silica, then diluted with toluene (2 ml). The progress of the reaction was monitored by gas chromatography. In a separate blank test, a 15-ml two-necked round-bottom flask was charged with a solution of copper(II) chloride or the ligand in a mixed medium of Cs2CO3 (0.650 g, 2 mmol) in 5 ml of air (oxygen) saturated toluene. Then the flask was equipped with an oxygen balloon. The progress of the reaction was monitored by gas chromatography. With oxygen, caesium carbonate in toluene, Time= 8h, T= 20 °C , Catalytic behavior, Solvent, Reagent/catalyst Balaghi, S. Esmael; Safaei, Elham; Rafiee, Mohammad; Kowsari, Mohammad Hossein; Polyhedron; vol. 47; nb. 1; (2012); p. 94 - 103 View in Reaxys With tert.-butylhydroperoxide, cis-(2,2'-bipyridine-κ2-N,N)bis(perchlorate)manganese(II), tetrabutylammomium bromide in acetonitrile, Time= 4h, T= 80 °C , Concentration, Reagent/catalyst, Temperature, Solvent Kani, Ibrahim; Kurtca, Mehmet; Turkish Journal of Chemistry; vol. 36; nb. 6; (2012); p. 827 - 840 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

173/438

2018-03-11 22:07:32


With dihydrogen peroxide in acetonitrile, Time= 2h, T= 60 °C , Reagent/catalyst Sharma, Rajesh V.; Soni, Kapil K.; Dalai, Ajay K.; Catalysis Communications; vol. 29; (2012); p. 87 - 91 View in Reaxys 78 %Spectr.

With FeCl3(η1-2,2,6,6-tetramethylpiperidine-N-oxyl) in benzene-d6, Time= 0.5h, Inert atmosphere, Reagent/catalyst Scepaniak, Jeremiah J.; Wright, Ashley M.; Lewis, Richard A.; Wu, Guang; Hayton, Trevor W.; Journal of the American Chemical Society; vol. 134; nb. 47; (2012); p. 19350 - 19353 View in Reaxys 2.3 Catalytic test reactions A solution of 116 mg (0.23 mmol, 0.5 eq) [(Cu(OTf))2(μ-toluene)] with 0.9 mmol (2.0 eq) ligand in 0.5 mL pure MeCN was prepared. 0.5 g benzyl alcohol was mixed with 180 mg powdered NaOH. Both mixtures were combined and vigorously stirred at 298 K. Samples of the reaction mixtures were taken, mixed with CD2Cl2 upon which a greenbrown precipitate was formed. The remaining solution was isolated and submitted to NMR spectroscopic analysis. NMR spectra (300 MHz) were recorded and product yields were determined by integration of the aldehyde proton.

1H

With copper (I) trifluoromethane sulfonate toluene complex, H2(Me2salhexF4), oxygen, sodium hydroxide in acetonitrile, T= 24.84 °C Butsch, Katharina; Guenther, Thomas; Klein, Axel; Stirnat, Kathrin; Berkessel, Albrecht; Neudoerfl, Joerg; Inorganica Chimica Acta; vol. 394; (2013); p. 237 - 246 View in Reaxys 100 With C24H20N6O8PdS2, periodic acid in acetonitrile, Time= 2h, T= 70 °C , Schlenk technique, Catalytic behavior, Re%Chromat. agent/catalyst, Time Dayan, Serkan; Kalaycioglu, Nilgun Ozpozan; Applied Organometallic Chemistry; vol. 27; nb. 1; (2013); p. 52 - 58 View in Reaxys With oxygen in toluene, Time= 1.5h, T= 80 °C , p= 760.051Torr Chen, Gongzhou; Wu, Shijian; Liu, Hongli; Jiang, Huanfeng; Li, Yingwei; Green Chemistry; vol. 15; nb. 1; (2013); p. 230 - 235 View in Reaxys 60 %Chromat.

With Pd0003K0.03Ti1.47Sr1.02O4, oxygen in toluene, Time= 24h, T= 120 °C , p= 750.075Torr , chemoselective reaction Adilina, Indri Badria; Hara, Takayoshi; Ichikuni, Nobuyuki; Kumada, Nobuhiro; Shimazu, Shogo; Bulletin of the Chemical Society of Japan; vol. 86; nb. 1; (2013); p. 146 - 152 View in Reaxys

99 %Chromat.

With tetrakis(actonitrile)copper(I) hexafluorophosphate, C18H28N5O2, oxygen, 1,8-diazabicyclo[5.4.0]undec-7-ene in chlorobenzene, Time= 2h, T= 70 °C Liu, Xiaolong; Pan, Shanfei; Wu, Junshi; Wang, Yapei; Chen, Wanzhi; Organometallics; vol. 32; nb. 1; (2013); p. 209 - 217 View in Reaxys

96 %Chromat.

Experimental Procedures for oxidation of Various alcohols: General procedure: A CH3CN solution of alcohol (1 mmol), ZnBr2 (45 mg, 0.2 mmol), and chloramine-T (282 mg, 1 mmol) was placed in a three necked flask with a reflux condenser. After the mixture was stirred under reflux for 1.5-5 h. After cooling to room temperature, the solution was quenched by adding water and the resulting mixture was extracted with AcOEt. Removal of the solvent under reduced pressure gave the crude product, which was purified by column chromatography on silica gel to give the corresponding carbonyls. With chloroamine-T, zinc dibromide in acetonitrile, Time= 1.5h, Reflux Wang, Peng; Cai, Jin; Yang, Jiabin; Sun, Chunlong; Li, Lushen; Hu, Huayou; Ji, Min; Tetrahedron Letters; vol. 54; nb. 6; (2013); p. 533 - 535 View in Reaxys 2.2 Photocatalytic reaction

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

174/438

2018-03-11 22:07:32


General procedure: In acetonitrile (CH3CN) containing BnOH (50 μmol) in a test tube, Pt–TiO2 powder (50 mg) was suspended. The tube was sealed with a rubber septum and then photoirradiated by a UV light-emitting diode (UVLED, PJ-1505-2CA, CCS Inc., Kyoto, maximum energy at λ = 366 nm) under Ar with magnetic stirring at room temperature. After the reaction, the gas phase was analyzed by a gas chromatograph (Shimadzu, GC-8A equipped with MS-5A columns). After the suspension had been filtered to remove the particles, the amounts of BnOH remaining and product(s) were determined by high-performance liquid chromatography (Shimadzu, SPD-20A detector, LC-20AT pump, DGU-20A3 degasser, CTO-10ASvp oven, equipped with a Shim-pack FC-ODS column, eluent: ultra pure water/CH3CN = 50/50, flow rate: 0.5 cm3 min−1, oven: 313 K, λ: 220 nm). To obtain apparent quantum efficiency (AQE), a spectrum and light intensity of the UV–LED were determined using a spectroradiometer USR-45D (Ushio). With 1 wt platinum/titanium(IV) oxide in acetonitrile, Time= 1h, T= 20 °C , Inert atmosphere, Sealed tube, UV-irradiation, Green chemistry, Catalytic behavior, Solvent, Reagent/catalyst, Time, Concentration Imamura, Kazuya; Tsukahara, Hikaru; Hamamichi, Kenta; Seto, Naoko; Hashimoto, Keiji; Kominami, Hiroshi; Applied Catalysis A: General; vol. 450; (2013); p. 28 - 33 View in Reaxys With tris(2,2'-bipyridyl)ruthenium dichloride, chloropentamminecobalt(III)(2+), diaqua(tris(2-pyridylmethyl)amine)ruthenium(II)(2+) in water-d2, T= 24.84 °C , Irradiation Ohzu, Shingo; Ishizuka, Tomoya; Hirai, Yuichirou; Fukuzumi, Shunichi; Kojima, Takahiko; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1563 - 1567 View in Reaxys 78 %Chromat.

5 :The ruthenium complex 1 which has been produced in the Example 1 was added to a glass vessel in which boiling chips are added. Subsequently, benzyl alcohol and the solvent described the Table 2 below were added thereto. The mixture was then stirred with heating under the reaction condition described in the Table 2. The results are given in the following Table 2. [Table 2] With Ru-MACHO-BH in acetone, Time= 3h, T= 60 °C , Product distribution / selectivity Patent; TAKASAGO INTERNATIONAL CORPORATION; TOUGE, Taichiro; AOKI, Kunie; NARA, Hideki; KURIYAMA, Wataru; WO2012/144650; (2012); (A1) English View in Reaxys With [Cu(bapbpy)(H2O)]Cl2·H2O in methanol, acetonitrile, Catalytic behavior, Kinetics, Reagent/catalyst Gamba, Ilaria; Mutikainen, Ilpo; Bouwman, Elisabeth; Reedijk, Jan; Bonnet, Sylvestre; European Journal of Inorganic Chemistry; nb. 1; (2013); p. 115 - 123 View in Reaxys Stage 1: in acetonitrile, Time= 0.5h, T= 50 °C , Inert atmosphere Stage 2: With tert.-butylhydroperoxide in acetonitrile, Time= 8h, T= 90 °C , Inert atmosphere, Reagent/catalyst, Concentration, Solvent Mahdavi, Vahid; Mardani, Mahdieh; Journal of Chemical Sciences; vol. 124; nb. 5; (2012); p. 1107 - 1115 View in Reaxys Stage 1: in dichloromethane, Time= 0.05h, T= 10 °C , Sonication Stage 2: With sodium hypochlorite, sodium bromide in dichloromethane, water, Time= 0.0833333h, T= 10 °C , pH= 9.1 Zheng, Zhi; Wang, Jianli; Zhang, Miao; Xu, Lixin; Ji, Jianbing; ChemCatChem; vol. 5; nb. 1; (2013); p. 307 - 312 View in Reaxys With oxygen in N,N-dimethyl acetamide, Time= 1.5h, T= 120 °C , p= 760.051Torr Gao, Qingsheng; Giordano, Cristina; Antonietti, Markus; Angewandte Chemie - International Edition; vol. 51; nb. 47; (2012); p. 11740 - 11744; Angew. Chem.; vol. 124; nb. 47; (2012); p. 11910 - 11914,5 View in Reaxys

6 %Spectr. With [RuCl(η5-(3-phenyl)indenyl)(PPh3)2], potassium hexamethylsilazane in acetone, toluene, Time= 16h, T= 110 °C , Schlenk technique, Catalytic behavior

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

175/438

2018-03-11 22:07:32


Manzini, Simone; Urbina-Blanco, Cesar A.; Nolan, Steven P.; Organometallics; vol. 32; nb. 2; (2013); p. 660 664 View in Reaxys For the oxidation reaction, a 0,7 mL solid phase reactor was packed with 0.44 g SiliCat TEMPO7 (0.82 mmol/g) connected to the microchip output and to a product collector. Two 5 mL PTFE loops were connected to a 250 lL glass microreactor (chip) in a fluidic pathway (Fig. 4). The reactant mixtures, a 0.2 M solution of benzyl alcohol in DCM (solvent 1) and a 0.5 M aq NaOCl. buffered at pH 9 (solvent 2), were then premixed in the glass chip at room temperature prior to injection in the solid phase reactor. In detail, solvent 1 and 2 were pressurised to 1 bar and pumped at a flow rate ranging from 50 to 500 lL/min to achieve the desired residence time (from 3.2 to 0.3 min) in the solid phase reactor. At 50 lL/min flow rate (entry 1 in Table 3) pure benzaldehyde was the only product obtained with full conversion of the alcohol substrate With sodium hypochlorite solution in dichloromethane, water, Time= 0.0533333h, T= 20 °C , p= 750.075Torr , pH= 9, Flow reactor Pandarus, Valerica; Ciriminna, Rosaria; Beland, Francois; Gingras, Genevieve; Drobot, Maxime; Jina, Omar; Pagliaro, Mario; Tetrahedron Letters; vol. 54; nb. 9; (2013); p. 1129 - 1132 View in Reaxys With oxygen in toluene, Time= 3h, T= 120 °C Santra, Chiranjit; Rahman, Sumbul; Bojja, Sreedhar; James, Olusola O.; Sen, Debasis; Maity, Sudip; Mohanty, Ashok Kumar; Mazumder; Chowdhury, Biswajit; Catalysis Science and Technology; vol. 3; nb. 2; (2013); p. 360 - 370 View in Reaxys With Pd on CdS–TiO2 in water, Time= 4h, T= 24.84 °C , p= 760.051Torr , Inert atmosphere, Irradiation, Quantum yield, Catalytic behavior, Reagent/catalyst, Time Higashimoto, Shinya; Tanaka, Yoshimi; Ishikawa, Ryo; Hasegawa, Shoko; Azuma, Masashi; Ohue, Hiroyoshi; Sakata, Yoshihisa; Catalysis Science and Technology; vol. 3; nb. 2; (2013); p. 400 - 403 View in Reaxys With oxygen, Time= 6h, T= 100 °C , p= 750.075Torr , Green chemistry, Catalytic behavior, Reagent/catalyst Chen, Tao; Zhang, Fazhi; Zhu, Yue; Catalysis Letters; vol. 143; nb. 2; (2013); p. 206 - 218 View in Reaxys With oxygen in water, Time= 2h, T= 80 °C , Kinetics, Catalytic behavior, Reagent/catalyst, Time Chen, Hong; Tang, Qinghu; Chen, Yuanting; Yan, Yibo; Zhou, Chunmei; Guo, Zhen; Jia, Xinli; Yang, Yanhui; Catalysis Science and Technology; vol. 3; nb. 2; (2013); p. 328 - 338 View in Reaxys With 1-methyl-1H-imidazole, [2,2]bipyridinyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, copper(I) triflate in acetonitrile, T= 27 °C , p= 600Torr , Inert atmosphere Hoover, Jessica M.; Ryland, Bradford L.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 135; nb. 6; (2013); p. 2357 - 2367 View in Reaxys 8 %Chromat.

With 10 wt Co on TiO2 in o-xylene, Time= 24h, T= 80 °C Shimizu, Ken-Ichi; Kon, Kenichi; Seto, Mayumi; Shimura, Katsuya; Yamazaki, Hiroshi; Kondo, Junko N.; Green Chemistry; vol. 15; nb. 2; (2013); p. 418 - 424 View in Reaxys With oxygen, T= 240 °C , Gas phase, Catalytic behavior, Reagent/catalyst, Time Zhang, Yuxu; Xu, Liqiang; Tang, Bin; Li, Zhiwen; Catalysis Science and Technology; vol. 3; nb. 1; (2013); p. 222 229 View in Reaxys

88 %Chromat.

With oxygen in toluene, Time= 5.5h, T= 85 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

176/438

2018-03-11 22:07:32


Hossain, Shahin; Jin, Myung-Jong; Park, Ji-Hoon; Yingjie, Qian; Yang, Da-Ae; Catalysis Letters; vol. 143; nb. 1; (2013); p. 122 - 125 View in Reaxys With dihydrogen peroxide in water, acetonitrile, Time= 8h, T= 60 °C , Reagent/catalyst Islam, Sk. Manirul; Paul, Sumantra; Mobarok, Manir; Roy, Anupam Singha; Mondal, Paramita; Transition Metal Chemistry; vol. 38; nb. 1; (2013); p. 7 - 14 View in Reaxys 2.3 Catalytic tests General procedure: The liquid-phase oxidation of alcohols with O2 in the presence or absence of solvent was conducted at atmospheric pressure in a round-bottom flask (50 mL) equipped with a condenser under stirring conditions. The temperature was controlled with a water bath and kept at 70 or 80 °C. The reaction time was 5–20 h. The detailed reaction conditions for different batches are shown in the footnotes of tables and the captions of figures. The obtained products were analyzed on two GC-14B gas chromatographs equipped with flame ionization detectors and a 50-m OV-1 and a 30-m PEG capillary column, respectively. With copper(II) oxide-supported gold, oxygen in toluene, Time= 20h, T= 80 °C , p= 760.051Torr , Green chemistry, Catalytic behavior, Reagent/catalyst, Solvent, Time Wang, Hui; Fan, Weibin; He, Yue; Wang, Jianguo; Kondo, Junko N.; Tatsumi, Takashi; Journal of Catalysis; vol. 299; (2013); p. 10 - 19 View in Reaxys 99 %Chromat.

With oxygen in toluene, Time= 4h, T= 110 °C , Reagent/catalyst, Time, Temperature, Concentration Kamimura, Akio; Nozaki, Yuichiro; Nishiyama, Mai; Nakayama, Masaharu; RSC Advances; vol. 3; nb. 2; (2013); p. 468 - 472 View in Reaxys With [Cu2((E)-(N)-4-(hydroxybenzoic acid)-(5-bromo-2-hydroxybenzylidene)benzohydrazide)2(CH3OH)2](NO3)2, dihydrogen peroxide in acetonitrile, Time= 5h, T= 80 °C Hosseini-Monfared, Hassan; Pousaneh, Elaheh; Sadighian, Somayeh; Ng, Seik Weng; Tiekink, Edward R. T.; Zeitschrift fur Anorganische und Allgemeine Chemie; vol. 639; nb. 2; (2013); p. 435 - 442 View in Reaxys 4.7 Procedure for catalytic oxidation of alcohols General procedure: Catalytic oxidation of primary alcohol to corresponding aldehyde and secondary alcohol to ketone by ruthenium(II) complexes were studied in the presence of NMO as cooxidant. A typical reaction using the complex as a catalyst and primary or secondary alcohol, as substrate at 1:100 molar ratio was described as follows. A solution of [Ru(CO)2(L)Cl2] (1) (0.01 mmol) in CH2Cl2 (25 mL) was added to the mixture containing PhCH2OH (1 mmol), NMO (3 mmol) and molecular sieves. The reaction mixture was refluxed for 2 h, and the solvent was then evaporated under reduced pressure. The residue was then extracted with diethyl ether (20 mL), concentrated to ≈1 mL. Conversions were determined by GC instrument equipped with a flame ionization detector (FID) using a HP-5 column of 30 m length, 0.53 mm diameter and 5.00 μm film thickness. The column, injector and detector temperatures were 200, 250 and 250 °C, respectively. The carrier gas was N2 (UHP grade) at a flow rate of 30 mL/min. The injection volume of sample was 2 mL. The oxidation products were identified by GC co injection with authentic samples. All other alcohols were oxidized following identical reaction protocol. With C11H7I2N3O2RuS, 4-methylmorpholine N-oxide in dichloromethane, Time= 2h, T= 400 °C , Molecular sieve, Reagent/catalyst Kundu, Subhankar; Sarkar, Deblina; Jana, Mahendra Sekhar; Pramanik, Ajoy Kumar; Jana, Subrata; Mondal, Tapan Kumar; Journal of Molecular Structure; vol. 1035; (2013); p. 277 - 284 View in Reaxys With C40H64N16O14V6 (4-), oxygen in acetonitrile, Time= 12h, T= 130 °C , p= 1500.15Torr , Autoclave, Mechanism, Reagent/catalyst Chen, Baokuan; Huang, Xianqiang; Wang, Boe; Lin, Zhengguo; Hu, Jufang; Chi, Yingnan; Hu, Changwen; Chemistry - A European Journal; vol. 19; nb. 14; (2013); p. 4408 - 4413 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

177/438

2018-03-11 22:07:32


With oxygen in neat (no solvent), Time= 1h, T= 160 °C , p= 760.051Torr , chemoselective reaction Qi, Ben; Wang, Yanbing; Lou, Lan-Lan; Huang, Linyue; Yang, Ying; Liu, Shuangxi; Journal of Molecular Catalysis A: Chemical; vol. 370; (2013); p. 95 - 103 View in Reaxys 100 2.1. General procedure for oxidation of alcohols with tert-BuOOH catalyzed by [Mo(CO)5(at)APy-MWCNT] %Chromat. General procedure: In a 25 mL round bottom flask equipped with a magnetic stirrer bar and a condenser, alcohols (1 mmol),tert-BuOOH (2 mmol, 80percent solution in di-tert-butylperoxide), catalyst (90 mg, 0.015 mmol) and CCl4 (4 mL) were mixed and refluxed. The progress of the reaction was monitored by GLC. At the end of the reaction, the reaction mixture was diluted Et2O (20 mL) and filtered. The products were extracted with CH2Cl2 (2 10 mL) and were purified on silica-gel plates or a silica-gel column (CCl4-Et2O, 4:1). FT IR and 1H NMR spectral data was used to confirm the identities of the products. With tert.-butylhydroperoxide in tetrachloromethane, Time= 0.666667h, Reflux Araghi, Mehdi; Ghorbani, Azam; Yeganeh, Faten Eshrati; Comptes Rendus Chimie; vol. 16; nb. 2; (2013); p. 109 - 113 View in Reaxys 53 %Chromat.

With manganese(IV) oxide, oxygen in 1,4-dioxane, Time= 2h, T= 70 °C , p= 2280.15Torr , Green chemistry, Reagent/catalyst Yamaguchi, Kazuya; Kobayashi, Hiroaki; Wang, Ye; Oishi, Takamichi; Ogasawara, Yoshiyuki; Mizuno, Noritaka; Catalysis Science and Technology; vol. 3; nb. 2; (2013); p. 318 - 327 View in Reaxys With 4O(2-)*2Mo(6+)*C44H56N2O4 (4-)*2C2H6OS, dihydrogen peroxide in acetonitrile, Time= 6h, T= 60 °C , Catalytic behavior, Reagent/catalyst Riisioe, Antti; Lehtonen, Ari; Haenninen, Mikko M.; Sillanpaeae, Reijo; European Journal of Inorganic Chemistry; nb. 9; (2013); p. 1499 - 1508 View in Reaxys

86 %Chromat.

3.4. Procedure for catalytic oxidation General procedure: Catalytic oxidation of primary and secondary alcohols to the corresponding aldehydes and ketones respectively by ruthenium(II) and osmium(II) carbonyl iodide complexes were studied in the presence of NMO as a co-oxidant and the byproduct, water, was removed by using about 0.5 g of molecular sieves. Typical reactions were carried out using the ruthenium and osmium complexes as the catalyst and benzyl alcohol, 2-butanol, cyclopentanol and cyclohexanol as substrates in a 1:100 molar ratio. Solutions of the ruthenium and osmium complexes (0.01 mmol) in 20 cm3 CH2Cl2 were added to a solution of the substrate (1 mmol) and NMO (3 mmol). The solution mixture was refluxed for 2 h and the solvent was then evaporated from the mother liquor under reduced pressure. The residue was then extracted with petroleum ether (20 cm3) and was analyzed by GC using an Agilent 7890 series Gas chromatography instrument equipped with a flame ionization detector (FID) using a HP-5 column of 30 m length, 0.53 mm diameter and 5.00 lm film thickness. The ether extracts were evaporated to give the corresponding aldehydes/ketones, which were then isolated and quantified as their 2,4-dinitrophenylhydrazone derivatives. With trans-(Cl)-[Ru(CO)2Cl2(1-ethyl-2-(phenylazo)imidazole)], 4-methylmorpholine N-oxide in dichloromethane, Time= 2h, Reflux, Molecular sieve, Reagent/catalyst Sarkar, Shyamal Kumar; Jana, Mahendra Sekhar; Mondal, Tapan Kumar; Sinha, Chittaranjan; Polyhedron; vol. 50; nb. 1; (2013); p. 246 - 254 View in Reaxys General procedure for oxidation ethylbenzene, cyclohexene and benzyl alcohol General procedure: In this procedure the heterogeneous catalyst (5.0 mg), the substrate (9.0 mmol) and an oxidant (9.0 mmol, 80percent aqueous solution TBHP) were added in three necked round bottom flask equipped with a refluxed condenser. The mixture was stirred at desired temperature. After filtering and washing the used catalyst with solvent, the filtrate was monitored by GC analysis. The products were identified by GC–MS techniques. The conversion and selectivity were calculated with GC area normalization. Finally, comparative experiments were performed under different conditions. With tert.-butylhydroperoxide in neat (no solvent), Time= 24h, T= 100 °C , Temperature

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

178/438

2018-03-11 22:07:32


Habibi; Faraji; Arshadi; Fierro; Journal of Molecular Catalysis A: Chemical; vol. 372; (2013); p. 90 - 99 View in Reaxys 2.3 Reactivity tests General procedure: The gas-phase selective oxidation of alcohols on these catalysts with molecular oxygen was carried out on a fixed-bed quartz tube reactor (i.d., 16 mm) under atmospheric pressure as described previously [14,15,26,27]. Circular chips (16.1 mm diameter) of the microfibrous-structured Au/Ni-fiber catalysts were punched down from their large sheet sample and packed layer-up-layer into the tube reactor with total mass of 0.3 g. Note that the diameter of 0.1 mm larger than the i.d. of the tubular reactor was retained deliberately to avoid the appearance of the gap between the reactor wall and the edges of the catalyst chips thereby preventing the gas bypassing. Alcohols were fed continuously using a high-performance liquid pump, in parallel with O2 (oxidant) and N2 (diluted gas) feeding using the calibrated mass flow controllers, into the reactor heated to the desired reaction temperature. The organic phase of the liquid effluent was collected for analyzing by an HP 5890 gas chromatography–flame ionization detector (GC–FID) with a 60-m HP-5 ms capillary column. The gas-phase products such as H2, COx, and C1– C3 hydrocarbons were analyzed by an HP-5890 GC with thermal conductivity detector (TCD) and a 30-m AT-plot 300 capillary column. Reaction temperature, WHSV, and alcoholic hydroxyl (O2/ol) were varied in range from 220 to 380 °C, 10 to 70 h−1, and 0.4 to 1.2, respectively. Prior to the reaction testing, as-prepared catalysts were all activated by performing the benzyl alcohol oxidation at a high temperature of 380 °C for 1 h, using molar ratio of O2 to O2/ ol = 0.6 and WHSV = 20 h−1. With oxygen, T= 380 °C , p= 760.051Torr , Temperature Zhao, Guofeng; Deng, Miaomiao; Jiang, Yifeng; Hu, Huanyun; Huang, Jun; Lu, Yong; Journal of Catalysis; vol. 301; (2013); p. 46 - 53 View in Reaxys With 2,6-dimethylpyridine in acetonitrile, Electrochemical reaction Swiech, Olga; Bilewicz, Renata; Megiel, Elzbieta; RSC Advances; vol. 3; nb. 17; (2013); p. 5979 - 5986 View in Reaxys 2.3. Oxidation reaction of benzyl alcohol The oxidation of benzyl alcohol was carried out with O2 in a three-necked flask of 50 mL with a reflux condenser, and the flask was placed in a thermostatic bath with a magnetic stirrer. In a typical experiment, metal nanoparticle colloid (20 mL) was heated at the set temperature with an accuracy of ±0.1 K and bubbled with pure O2 for 60 min. Then, an appropriate amount of benzyl alcohol was added into the reaction mixture, and the oxidation reaction was started under vigorous magnetic stirring by bubbling O2. The reactions were monitored by sampling the reaction mixture (0.5 mL) at fixed intervals. The reaction mixture was immediately quenched with 2 M HCl aqueous solution (0.5 mL) and extracted three times with ethyl acetate (5 mL). The obtained organic layer was dried with Na2SO4 and analyzed by a CP-3800 gas chromatograph with an FID detector using the external standard method. With Au0.9Ag0.1, oxygen in water, T= 39.84 °C , p= 760.051Torr , pH= 7, Activation energy, Catalytic behavior, Reagent/catalyst, Temperature, Concentration Huang, Xuemin; Wang, Xueguang; Wang, Xiaoshu; Wang, Xinxing; Tan, Mingwu; Ding, Weizhong; Lu, Xionggang; Journal of Catalysis; vol. 301; (2013); p. 217 - 226 View in Reaxys Microwave assisted oxidation of benzyl alcohol and aromatic alkenes General procedure: The reaction was carried out in a CEM Discover microwave reactor equipped with a PC-controlled interface. The method was power controlled in which samples (vessel size 10 mL) were irradiated at 300 W (maximum power output) to achieve different temperatures. In a typical reaction, a mixture containing 2 mmol of substrate, 0.4 mL of H2O2 (50 wt.percent), 2 mL of water and 0.05 g of catalyst was microwaved in a CEM-DISCOVER reactor for different times of reaction (typically between 3 and 15 min) at 300 W, reaching a maximum temperature between 100 and 120 °C (average temperature 100 °C). Dodecane was added to the mixture as internal standard. The microwave method was power-controlled and reactions were carried out in closed vessel mode (pressure 120– 200 psi-8.3 to 13.4 bar-developed in the system). Upon reaction completion (in both cases), samples were collected, extracted with an organic solvent (typically toluene) and subsequently analysed by GC and GC/MS in an Agilent 6890N fitted with an HP-5 capillary column (30 m × 0.32 mm × 0.25 μm) and a flame ionization detector (FID). With dihydrogen peroxide in water, Time= 0.25h, T= 120 °C , p= 6205.94 - 10343.2Torr , Microwave irradiation, Sealed tube, Green chemistry

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

179/438

2018-03-11 22:07:32


Balu, Alina Mariana; Lin, Carol Sze Ki; Liu, Hongli; Li, Yingwei; Vargas, Carolina; Luque, Rafael; Applied Catalysis A: General; vol. 455; (2013); p. 261 - 266 View in Reaxys With oxygen in toluene, Time= 24h, T= 90 °C , Catalytic behavior Parlett, Christopher M. A.; Bruce, Duncan W.; Hondow, Nicole S.; Newton, Mark A.; Lee, Adam F.; Wilson, Karen; ChemCatChem; vol. 5; nb. 4; (2013); p. 939 - 950 View in Reaxys With C22H22N6O7V2 (2-)*2H(1+), dihydrogen peroxide in water, acetonitrile, Time= 5h, T= 80 °C Hosseini-Monfared, Hassan; Farrokhi, Afsaneh; Alavi, Sohaila; Mayer, Peter; Transition Metal Chemistry; vol. 38; nb. 3; (2013); p. 267 - 273 View in Reaxys With oxygen in toluene, Time= 6h, T= 14.84 - 24.84 °C , p= 760.051Torr , UV-irradiation Sugano, Yoshitsune; Shiraishi, Yasuhiro; Tsukamoto, Daijiro; Ichikawa, Satoshi; Tanaka, Shunsuke; Hirai, Takayuki; Angewandte Chemie - International Edition; vol. 52; nb. 20; (2013); p. 5295 - 5299; Angew. Chem.; vol. 125; nb. 20; (2013); p. 5403 - 5407,5 View in Reaxys Oxidation reactions were carried out in a round-bottomed flask, sealed with a septum. In a general procedure, 10 mL of the NP solution (in water or IL) was stirred and heated to 60 ◦C under a flow of oxygen for about 10 min for aqueous systems, and for about 1 h in IL systems to compensate for the higher viscosity of the IL. After this, 500 or 5000 equivalents (based on one equivalent of metal catalyst) of the alcohol substrate was injected into the flask. For aqueous work, at incremental times 1.0 mL of the reaction mixture was sampled and the products were then extracted by two, 0.5 mL aliquots of ethyl acetate, shaking in 1 min intervals for 5 min per extraction. For IL samples, after ∼12 h, the reaction vessel was removed from the constant temperature bath, and subjected to vacuum-stripping while being heated for extraction of the products and/or unreacted substrate. Conversion and selectivity were obtained from GC using a FID detector (Agilent Technologies 7890A) and a HP-Innowax capillary column. Two reactions were typically run for each sample. The neat organic liquids extracted were subsequently characterized by 1H NMR, 13C NMR, and GC-FID techniques. For GC-FID analysis, 25 L of a neat extract was mixed with 1 mL ethyl acetate in a GC-vial, and subjected to analysis. With trihexyl(tetradecyl)phosphonium chloride, Time= 12h, T= 60 °C , Reagent/catalyst, Solvent Maclennan, Aimee; Banerjee, Abhinandan; Scott, Robert W.J.; Catalysis Today; vol. 207; (2013); p. 170 - 179 View in Reaxys With TiO1.966N0.034, water, oxygen in acetonitrile, Time= 2h, Irradiation, Reagent/catalyst Zhang, Zizhong; Luo, Zhishan; Yang, Zhiping; Zhang, Shuying; Zhang, Yu; Zhou, Yangen; Wang, Xuxu; Fu, Xianzhi; RSC Advances; vol. 3; nb. 20; (2013); p. 7215 - 7218 View in Reaxys 72 %Chromat.

With sodium bromate, cis-[Ru(2,9-Me2phen)2(OH2)2](PF6)2 in water, Time= 10h, T= 23 °C Hu, Zongmin; Ma, Li; Xie, Jianhui; Du, Hongxia; Lam, William W. Y.; Lau, Tai-Chu; New Journal of Chemistry; vol. 37; nb. 6; (2013); p. 1707 - 1710 View in Reaxys With dihydrogen peroxide in water, Heating, Green chemistry Rajabi, Fatemeh; Pineda, Antonio; Naserian, Sareh; Balu, Alina Mariana; Luque, Rafael; Romero, Antonio A.; Green Chemistry; vol. 15; nb. 5; (2013); p. 1232 - 1237 View in Reaxys With tert.-butylhydroperoxide, Au0768Pd0232 in ethanol, water, Time= 6h, T= 50 °C , Irradiation Huang, Xiaoqing; Li, Yongjia; Chen, Yu; Zhou, Hailong; Duan, Xiangfeng; Huang, Yu; Angewandte Chemie International Edition; vol. 52; nb. 23; (2013); p. 6063 - 6067; Angew. Chem.; vol. 125; nb. 23; (2013); p. 6179 - 6183 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

180/438

2018-03-11 22:07:32


55 %Chromat.

With oxygen, T= 350 °C , Inert atmosphere, Gas phase, Catalytic behavior, Reagent/catalyst, Temperature Meng, Yongtao; Genuino, Homer C.; Kuo, Chung-Hao; Huang, Hui; Chen, Sheng-Yu; Zhang, Lichun; Rossi, Angelo; Suib, Steven L.; Journal of the American Chemical Society; vol. 135; nb. 23; (2013); p. 8594 - 8605 View in Reaxys

> 99 With dmap, palladium(II) pivalate, Trimethylacetic acid in toluene, Time= 24h, T= 100 °C , p= 760.051Torr , Time %Chromat. John, Lukas C.; Gunay, Ahmet; Wood, Andrew J.; Emmert, Marion H.; Tetrahedron; vol. 69; nb. 27-28; (2013); p. 5758 - 5764 View in Reaxys With C19H31Cl2N3Ru in toluene, T= 100 °C , Reagent/catalyst Canseco-Gonzalez, Daniel; Albrecht, Martin; Dalton Transactions; vol. 42; nb. 20; (2013); p. 7424 - 7432 View in Reaxys 91 %Chromat.

With copper(l) iodide, di-tert-butyl peroxide, (E)-N-((Z)-4-((2,6-dimethylphenyl)amino)pent-3-en-2-ylidene)-2,6-dimethylaniline in N,N-dimethyl-formamide, Time= 6h, T= 90 °C , Sealed tube, Inert atmosphere, Reagent/catalyst, Solvent Zhu, Yefeng; Wei, Yunyang; European Journal of Organic Chemistry; nb. 21; (2013); p. 4503 - 4508 View in Reaxys

99.4 Typical procedure for the oxidation of benzyl alcohol %Chromat. A mixture of FeCl3·6H2O (8 molpercent, 21.6 mg), SBA-15-TEMPO (2 molpercent, 95.2 mg) in toluene (2 mL) was stirred for 1 min at room temperature in a 25 mL flask. Benzyl alcohol (1 mmol, 108 mg) was then added to the mixture. After stirring for 2 min, NaNO2 (10 molpercent, 6.9 mg) was added to the mixture. The resulting mixture was transferred to an autoclave. After the autoclave was closed, dioxygen was charged to 0.1 MPa. The progress of the reaction was monitored by GC using n-nonane as an internal standard. With iron(III) chloride hexahydrate, oxygen, sodium nitrite in toluene, Time= 2h, T= 25 °C , p= 760.051Torr , Autoclave, Catalytic behavior, Reagent/catalyst, Time Wang, Lianyue; Li, Jun; Zhao, Xiaoping; Lv, Ying; Zhang, Hengyun; Gao, Shuang; Tetrahedron; vol. 69; nb. 30; (2013); p. 6041 - 6045 View in Reaxys 2. Material and methods General procedure: All chemicals were of analytic grade and directly used as received. The four spinel ferrites were synthesized through one-pot sol–gel method [16,18], the typical process was as following: 1mol/L M (II, Cu2+, Co2+, Ni2+, Zn2+) nitrate salt solution and 0.5mol/L Fe(NO3)3·9H2O solution with a M2+/Fe3+ ratio of 1.0/2.0 was mixed together and stirred for 3h at room temperature. After stirring, pre-calculated amount of citrate and EDTA were added into the former solution, respectively. The final pH value was adjusted ∼7 through the addition of ammonia solution. The resulted solution was stirred for another 1h and followed by the evaporation of water and then a dried gel was formed. The obtained gel was calcined to remove template and other organic compounds using a temperature programmed rising procedure initially at 450°C for 5h and further to 950°C for 10h in the air oven at a heat rate of 2°C/ min. The phase compositions of the resultant spinel ferrites were determined by powder X-ray diffraction (XRD) on Bruker D8 to record a data set in a continuous scan mode in the range of 10–85° with intervals of 0.05°. Transmission electron microscopy (TEM) was used to investigate structural features of the catalysts with a Hitachi HF-2000 instrument. Scanning electron microscopy and energy-dispersive X-ray analysis (EDX) was obtained with Japanese JSM-6360LV operating at an acceleration voltage of 10kV. (0003) Oxidation of benzyl alcohol was conducted in a round flask (25mL) equipped with reflux condenser and magnetic stirrer under argon environment. In a typical reaction procedure, acetonitrile solvent (2mL), benzyl alcohol (2.0mL) and 30percent H2O2 (1mL) were mixed together and then spinel ferrite catalyst (0.40g) was added into the solution at room temperature. The zero time was recorded when the reaction temperature reached the desired temperature of 70°C. The whole reaction procedure was under the stirring speed of 1000rpm. Reaction products were collected after the reaction time of 10h through centrifugation for 30min and analyzed by Agilent 6890 gas chromatography equipped with a DV-101 column (0.2mm×0.25μm×50m) and FID detector. With NiFe2O4, dihydrogen peroxide in acetonitrile, Time= 10h, T= 20 - 70 °C , Inert atmosphere, Reagent/catalyst, chemoselective reaction Yan, Kai; Wu, Xu; An, Xia; Xie, Xianmei; Journal of Alloys and Compounds; vol. 552; (2013); p. 405 - 408

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

181/438

2018-03-11 22:07:32


View in Reaxys II : Example II Benzyl Alcohol to Benzaldehyde (0019) This reaction was conducted similarly in apparatus as the examples of U.S. Pat. No. 7,618,546, as was Example I. The reactant organic substrate was 1 mM of benzyl alcohol. Micromolar iron(II) catalyst was used; amounts of ozone 0.1 mM was used. It only took a few seconds to react. NMR showed that when it was conducted in the presence of acetonitrile over 90percent of the benzyl alcohol is selectively oxidized to benzaldehyde rather than benzoic acid. From the above reactions it is expected that similar reaction kinetics will occur with other alcohols and ethers. With ozone in acetonitrile Patent; Iowa State University Research Foundation, Inc.; Bakac, Andreja; Pestovsky, Oleg; US8507730; (2013); (B1) English View in Reaxys 85.1 With 2,2,6,6-tetramethyl-piperidine-N-oxyl, Cu(9-(2'-hydroxy-3'-phenylthio-5'-tert-butylphenyl)-6-methylthio-3-ace%Chromat. tyl-5,7,8-triazanona-3,6,8-trien-2-one(2-)), potassium carbonate in water, acetonitrile, Time= 24h, T= 50 °C , p= 760.051Torr , Reagent/catalyst Arion, Vladimir B.; Platzer, Sonja; Rapta, Peter; Machata, Peter; Breza, Martin; Vegh, Daniel; Dunsch, Lothar; Telser, Joshua; Shova, Sergiu; Mac Leod, Tatiana C. O.; Pombeiro, Armando J. L.; Inorganic Chemistry; vol. 52; nb. 13; (2013); p. 7524 - 7540 View in Reaxys 2.Representative procedure for the tandem oxidative amidation of benzyl alcoholswith amine hydrochloride salts General procedure: Amixture of Fe(NO3)3.9H2O (20 mg, 0.05 mmol,5.0 mol percent), TEMPO (15.6 mg, 0.10 mmol, 10 mol percent) and benzyl alcohol (1.0 mmol,1 equiv) in acetonitrile (1.0 mL) was stirred under open air at roomtemperature (ca 23 oC) for 2 h. Amine hydrochloride salt (1.2 mmol,1.2 equiv), powdered CaCO3 (110 mg, 1.1 mmol, 1.1 equiv) and TBHP(70 wtpercent in H2O, 0.16 mL, 1.1 mmol, 1.1 equiv) were added sequentiallyto the mixture. The reaction vessel was capped and allowed to stir at 60 oCfor 16 h. After cooled to room temperature, the volatiles were removed under reducedpressure and the crude product was purified by flash chromatography on silicagel by gradient elution of ethyl acetate in petroleum ether to obtain the amideproduct. All amides were identified by full spectroscopic characterization andcomparison with literature or analogous literature data. With Iron(III) nitrate nonahydrate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in acetonitrile, Time= 2h, T= 20 °C , Inert atmosphere, Green chemistry, Time, Reagent/catalyst Ghosh, Subhash Chandra; Ngiam, Joyce S.Y.; Seayad, Abdul M.; Tuan, Dang Thanh; Johannes, Charles W.; Chen, Anqi; Tetrahedron Letters; vol. 54; nb. 36; (2013); p. 4922 - 4925 View in Reaxys > 99 Procedures for catalytic oxidation %Chromat. General procedure: The oxidation reaction was done in the following procedure:187 mg of the reduced 2 wtpercent Ir/TiO2 (Ir: 20 mol, 1.25 molpercent tosubstrates), the solvent (toluene or mesitylene, 1.5 mL), and thesubstrate (1.5 mmol) were charged into a glass vial (17 mL). Thereaction was started by stirring the reaction mixture at 353 K inalcohol oxidation or 423 K in xanthene oxidation under molecularoxygen at atmospheric pressure. The products were identified by comparison of the mass and NMR spectra with those of authenticsamples. The yields of the products were determined using GCanalyses with an internal standard technique. With oxygen in toluene, Time= 1h, T= 79.84 °C , p= 760.051Torr Yoshida, Akihiro; Mori, Yoshinori; Ikeda, Tsuyoshi; Azemoto, Kazuki; Naito, Shuichi; Catalysis Today; vol. 203; (2013); p. 153 - 157 View in Reaxys With oxygen in neat (no solvent), Time= 5h, T= 129.84 °C Wang, Feifei; Lu, Zhansheng; Yang, Lin; Zhang, Yanxing; Tang, Qinghu; Guo, Yuming; Ma, Xiaoming; Yang, Zongxian; Chemical Communications; vol. 49; nb. 59; (2013); p. 6626 - 6628 View in Reaxys With oxygen, potassium carbonate in toluene, Time= 8h, T= 80 °C , p= 3800.26Torr

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

182/438

2018-03-11 22:07:32


Yang, Huayan; Wang, Yu; Lei, Jing; Shi, Lei; Wu, Xiaohu; Maekinen, Ville; Lin, Shuichao; Tang, Zichao; He, Jian; Haekkinen, Hannu; Zheng, Lansun; Zheng, Nanfeng; Journal of the American Chemical Society; vol. 135; nb. 26; (2013); p. 9568 - 9571 View in Reaxys With oxygen, Time= 3h, T= 60 °C , p= 750.075Torr , Irradiation, Reagent/catalyst, Temperature, Time Chen, Yan; Zhang, Jinshui; Zhang, Mingwen; Wang, Xinchen; Chemical Science; vol. 4; nb. 8; (2013); p. 3244 3248 View in Reaxys 3.2. Oxidation versus disproportionation of benzyl alcohol underaerobic conditions From the data provided in Section 3.1 and from previous studies,further proof that disproportionation of benzyl alcohol reactionis the only reaction that is active under anaerobic conditions isprovided. When an oxidant is used in this reaction, instead of He alone, besides disproportionation, oxidative dehydrogenationof benzyl alcohol to benzaldehyde occurs and in fact becomesthe most favoured reaction. With the help of the new quantificationmethodology, it becomes easier to study the response ofthese two reactions separately to increases in temperature. Initially,the reactions were performed in a GSR at 80, 100 and 120 °Cand the TONO, TOND and TONTot values are presented in Fig. 2A.With increase of temperature there is an overall increase in TONTot,mostly because of the higher contribution from TOND as comparedto TONO. Besides toluene and benzaldehyde, other products includingbenzene, dibenzyl ether, benzoic acid and benzyl benzoate werealso detected, but at very low concentrations (<5percent molar selectivity).As the objective of this present work was to investigate thesereactions in a continuous mode, the reactions were carried out ina MPBR at 80, 100, 120, 140°C and the different turn-over numbers(TONO, TOND and TONTot) were calculated for all the runs. Apressure drop of 1.25 bar was also observed over the range of temperaturesstudied and did not vary significantly with the increaseof temperature. The effect of temperature on the different turnovernumbers is interesting as shown in Fig. 2B. Initially, an increase inoxidation was observed from 80 °C to 100 °C followed by a stabilisationat temperatures 120 °C and 140 °C. A substantial increasein the disproportionation reaction (TOND) was observed with anincrease in the reaction temperature. At reaction temperaturesabove 100 C, any increase in the overall reaction (TONTot) is exclusivelybecause of an increase in the disproportionation reactionand not the oxidation reaction. This suggests that raising the temperatureis not the correct approach to increase the yield of thedesired benzaldehyde product. This trend is more pronounced inMPBR when compared to GSR. At every temperature tested, TOND is higher in the MPBR compared to the GSR. Stoichiometrically,oxygen is not involved in the disproportionation reaction, but comparingthe TOND data between aerobic and anaerobic conditions atdifferent temperatures (Table 1), it is evident that oxygen has a substantialpromotional effect on the disproportionation reaction. Thisobservation in the MPBR is in agreement with the GSR With oxygen in neat (no solvent), T= 100 °C , p= 750.075Torr , Catalytic behavior, Reagent/catalyst, Temperature, Pressure Cao, Enhong; Sankar, Meenakshisundaram; Nowicka, Ewa; He, Qian; Morad, Moataz; Miedziak, Peter J.; Taylor, Stuart H.; Knight, David W.; Bethell, Donald; Kiely, Christopher J.; Gavriilidis, Asterios; Hutchings, Graham J.; Catalysis Today; vol. 203; (2013); p. 146 - 152 View in Reaxys With iodine, dimethyl sulfoxide, Time= 10h, T= 100 °C , Sealed tube, Reagent/catalyst, Solvent, Temperature Ge, Wenlei; Zhu, Xun; Wei, Yunyang; RSC Advances; vol. 3; nb. 27; (2013); p. 10817 - 10822 View in Reaxys With [ruthenium(II)(η6-benzene)(chloride)(S(CH2C5H4N)2)](hexafluorophosphate), 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux, Reagent/catalyst, Time Prakash, Om; Sharma, Kamal Nayan; Joshi, Hemant; Gupta, Pancham Lal; Singh, Ajai K.; Dalton Transactions; vol. 42; nb. 24; (2013); p. 8736 - 8747 View in Reaxys With sodium hypochlorite, sodium hydrogencarbonate, potassium bromide in dichloromethane, water, Time= 3h, T= 0 °C , pH= 9, Reagent/catalyst Zeng, Zhaoyang; Matuschek, David; Studer, Armido; Schwickert, Christian; Poettgen, Rainer; Eckert, Hellmut; Dalton Transactions; vol. 42; nb. 24; (2013); p. 8585 - 8596 View in Reaxys 2.3. Reactivity tests

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

183/438

2018-03-11 22:07:32


The gas-phase oxidation of alcohols was performed on a fixed-bed quartz tube reactor (700 mm length by 16 mm inner diameter)under atmospheric pressure as described previously [31,32]. Cata-lyst used in each test was 0.3 g (200–300 mesh). Alcohols were fedcontinuously via a high-performance liquid pump in parallel withO2(oxidant) and N2(diluted gas of 100 ml/min) feeding, which usedcalibrated mass flow controllers, into the reactor under steadystate temperature conditions. The weight hourly space velocity(WHSV) was calculated by dividing the mass flow rate of the alco-hol feedstock by the catalyst mass. The effluent was cooled usingan ice-salt bath (−15C) to condense the vapors for analysis usinga Shimadzu-2014 gas chromatography-flame ionization detector(GC-FID) with a 60 m HP-5ms capillary column. The gas-phaseproducts phaseproducts, such as H2, COx, and C1–C3 hydrocarbons, were ana-lyzed using an HP-5890 GC with a thermal conductivity detector(TCD) and a 30 m AT-plot 300 capillary column. The reproducibilityof the conversion and selectivity of the product was high and theerror range was ±0.2percent. A carbon mass balance close to 100percent was achieved. With oxygen, Time= 1h, T= 280 °C , Gas phase, Reagent/catalyst, Temperature Zhao, Guofeng; Hu, Huanyun; Jiang, Zheng; Zhang, Shuo; Lu, Yong; Applied Catalysis A: General; vol. 467; (2013); p. 171 - 177 View in Reaxys 92 %Spectr.

With (phthalocyaninato)iron(II), sodium t-butanolate in toluene, Time= 12h, T= 80 °C Bala, Manju; Verma, Praveen Kumar; Kumar, Neeraj; Sharma, Upendra; Singh, Bikram; Canadian Journal of Chemistry; vol. 91; nb. 8; (2013); p. 732 - 737 View in Reaxys With oxygen, T= 210 °C , p= 760.051Torr , Inert atmosphere, Reagent/catalyst, Temperature Wu, Yuen; Wang, Dingsheng; Chen, Xiaobin; Zhou, Gang; Yu, Rong; Li, Yadong; Journal of the American Chemical Society; vol. 135; nb. 33; (2013); p. 12220 - 12223 View in Reaxys

> 95 %Spectr.

With phosphoric acid in water, toluene, Time= 18h, T= 25 °C , p= 760.051Torr , pH= 3.4, Irradiation, Inert atmosphere, Sealed tube Liu, Zijun; Caner, Joaquim; Kudo, Akihiko; Naka, Hiroshi; Saito, Susumu; Chemistry - A European Journal; vol. 19; nb. 29; (2013); p. 9452 - 9456 View in Reaxys With C35H44ClCuN2O2, oxygen, caesium carbonate in toluene, Time= 4h, T= 24.84 °C , Catalytic behavior, Reagent/ catalyst, Solvent, Time, Temperature Balaghi, S. Esmael; Safaei, Elham; Chiang, Linus; Wong, Edwin W. Y.; Savard, Didier; Clarke, Ryan M.; Storr, Tim; Dalton Transactions; vol. 42; nb. 19; (2013); p. 6829 - 6839 View in Reaxys With nanoITO-RuII-OH2 2+ in aq. acetate buffer, pH= 5, Electrochemical reaction, Catalytic behavior Mendez, Manuel A.; Alibabaei, Leila; Concepcion, Javier J.; Meyer, Thomas J.; ACS Catalysis; vol. 3; nb. 8; (2013); p. 1850 - 1854 View in Reaxys With calcined PtCl42− supported Rb9Cu6(P2O7)4Cl2 framework in tert-butyl alcohol, Time= 4h, T= 130 °C , p= 15001.5Torr , Catalytic behavior, Kinetics, Temperature, Reagent/catalyst, Time Hinde, Christopher S.; Van Aswegen, Sivan; Collins, Gillian; Holmes, Justin D.; Hor, T. S. Andy; Raja, Robert; Dalton Transactions; vol. 42; nb. 35; (2013); p. 12600 - 12605 View in Reaxys With [Ru3(μ3-O)(CH3COO)6(H2O)3](CH3COO), oxygen in toluene, Time= 6h, T= 79.84 °C , p= 759.826Torr , Kinetics, Catalytic behavior, Reagent/catalyst, Time Muratsugu, Satoshi; Lim, Min Hwee; Itoh, Takahiro; Thumrongpatanaraks, Wipavee; Kondo, Mio; Masaoka, Shigeyuki; Andy Hor; Tada, Mizuki; Dalton Transactions; vol. 42; nb. 35; (2013); p. 12611 - 12619 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

184/438

2018-03-11 22:07:32


96 %Chromat.

With C23H35N3O3 (1+)*Br(1-), copper in chlorobenzene, Time= 15h, T= 80 °C Liu, Xiaolong; Xia, Qinqin; Zhang, Yuejiao; Chen, Congyan; Chen, Wanzhi; Journal of Organic Chemistry; vol. 78; nb. 17; (2013); p. 8531 - 8536 View in Reaxys

> 99 Catalytic Activity Measurements %Chromat. General procedure: Given amount of alcohols(benzyl alcohol or 1-phenylethanol, 2.00 g) and catalysts (20mg) were dissolved in toluene (20 mL) in 100 mL a roundbottom flask (Table 2). All reactions were carried out at 90°C at one atm pressure of O2 for given time. Yields are calculated by gas chromatography (Agilent 7890A). With oxygen in toluene, Time= 3h, T= 90 °C , p= 760.051Torr , Reagent/catalyst, Time, Concentration Kim, Sohee; Jung, Jong-Hwa; Kim, Dong-Hee; Woo, Dong Kyun; Park, Joon B; Choi, Myong Yong; Kwon, KiYoung; Bulletin of the Korean Chemical Society; vol. 34; nb. 1; (2013); p. 221 - 224 View in Reaxys 42 %Chromat.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in 1,4-dioxane, n-heptane, o-xylene, T= 140 °C , p= 18751.9Torr , Temperature, Pressure, Solvent, Reagent/catalyst, Concentration Obermayer, David; Balu, Alina M.; Romero, Antonio A.; Goessler, Walter; Luque, Rafael; Kappe, C. Oliver; Green Chemistry; vol. 15; nb. 6; (2013); p. 1530 - 1537 View in Reaxys With (phthalocyaninato)iron(II), sodium t-butanolate, Time= 12h, T= 100 °C Bala, Manju; Verma, Praveen Kumar; Sharma, Upendra; Kumar, Neeraj; Singh, Bikram; Green Chemistry; vol. 15; nb. 6; (2013); p. 1687 - 1693 View in Reaxys With oxygen, nitric acid in 1,2-dichloro-ethane, Time= 0.00833333h, T= 55 °C , p= 3750.38Torr , Flow reactor, Solvent, Temperature, Time Aellig, Christof; Scholz, David; Conrad, Sabrina; Hermans, Ive; Green Chemistry; vol. 15; nb. 7; (2013); p. 1975 - 1980 View in Reaxys

92 %Chromat.

With dihydrogen peroxide in water, acetonitrile, Time= 10h, T= 20 °C , Catalytic behavior, Reagent/catalyst Islam, Sk. Manirul; Paul, Sumantra; Roy, Anupam Singha; Banerjee, Satabdi; Ghosh, Kajari; Dey, Ram Chandra; Santra; Transition Metal Chemistry; vol. 38; nb. 6; (2013); p. 675 - 682 View in Reaxys With tert.-butylhydroperoxide in water, acetonitrile, T= 60 °C Shilpa; Gayathri; Transition Metal Chemistry; vol. 38; nb. 6; (2013); p. 705 - 713 View in Reaxys With oxygen in N,N-dimethyl-formamide, Time= 7h, T= 120 °C Nie, Renfeng; Shi, Juanjuan; Du, Weichen; Ning, Wensheng; Hou, Zhaoyin; Xiao, Feng-Shou; Journal of Materials Chemistry A; vol. 1; nb. 32; (2013); p. 9037 - 9045 View in Reaxys Reaction Steps: 2 1: sodium hydroxide; oxygen / water / 24 h / 40 °C / Green chemistry 2: sodium hydroxide; oxygen / water / 12 h / 40 °C With oxygen, sodium hydroxide in water Zhang, Leilei; Wang, Wentao; Wang, Aiqin; Cui, Yitao; Yang, Xiaofeng; Huang, Yanqiang; Liu, Xiaoyan; Liu, Wengang; Son, Jin-Young; Oji, Hiroshi; Zhang, Tao; Green Chemistry; vol. 15; nb. 10; (2013); p. 2680 - 2684 View in Reaxys Reaction Steps: 3 1: sodium hydroxide; oxygen / water / 2 h / 25 °C 2: sodium hydroxide; oxygen / water / 12 h / 40 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

185/438

2018-03-11 22:07:32


3: sodium hydroxide; oxygen / water / 12 h / 40 °C With oxygen, sodium hydroxide in water Zhang, Leilei; Wang, Wentao; Wang, Aiqin; Cui, Yitao; Yang, Xiaofeng; Huang, Yanqiang; Liu, Xiaoyan; Liu, Wengang; Son, Jin-Young; Oji, Hiroshi; Zhang, Tao; Green Chemistry; vol. 15; nb. 10; (2013); p. 2680 - 2684 View in Reaxys Reaction Steps: 3 1: sodium hydroxide; oxygen / water / 2 h / 25 °C 2: sodium hydroxide; oxygen / water / 12 h / 40 °C 3: sodium hydroxide; oxygen / water / 12 h / 40 °C With oxygen, sodium hydroxide in water Zhang, Leilei; Wang, Wentao; Wang, Aiqin; Cui, Yitao; Yang, Xiaofeng; Huang, Yanqiang; Liu, Xiaoyan; Liu, Wengang; Son, Jin-Young; Oji, Hiroshi; Zhang, Tao; Green Chemistry; vol. 15; nb. 10; (2013); p. 2680 - 2684 View in Reaxys With sodium phosphotungstate, dihydrogen peroxide, β‐cyclodextrin in n-heptane, water, Time= 24h, T= 40 °C , Schlenk technique, Inert atmosphere, Green chemistry Leclercq, Loïc; Company, Roberto; Mühlbauer, Andrea; Mouret, Adrien; Aubry, Jean-Marie; Nardello-Rataj, Véronique; ChemSusChem; vol. 6; nb. 8; (2013); p. 1533 - 1540 View in Reaxys 3.3. Experiments on the RMR to compare performance with STMR In order to compare the performance of the RMR with the STMR,two different sets of experiments were performed: (a) First set: in these the catalyst was removed from the STMR andthen it was inserted into the RMR. This ensured that exactlythe same form of catalyst and the same overall length of cat-alyst (18 monoliths, total catalytic bed length = 900 mm) wasused. As a reminder, the catalyst loading was about 2.7 wtpercent Pt,and this catalyst had already been in use for 160 h. This testwas also selected to ensure that by putting the catalyst into 3shorter tubes in the RMR (rather than one long tube in STMR),the overall performance in terms of conversion and selectivitywould not change.(b) Second set: in these, the old coated monoliths (1st batch) wereremoved, and 18 sections of Pt coated carbon monoliths (from afreshly prepared 2nd batch) were inserted into the RMR. The Ptloading for this 2nd batch of catalyst was measured to be about2.5 wtpercent Pt and this was slightly lower than that used in the firstset of experiments. However, the same number of monolithswas used as in the first set.Experiments were then performed over the following set of con-ditions:(a) Liquid flow rate = 1.0 dm3h−1; and total gas flowrate = 0.818 dm3min−1 STP.(b) The oxygen concentration was 70 vol percent (corresponding to 221percentexcess oxygen), and 100 vol percent (corresponding to 359percent excessoxygen).(c) The backpressure on the reactor was set at = 12 bar(g), and operating temperature = 110C.(d) After the reactor reached its operating temperature and pres-sure and the reactants were fed, a period of 2 h was allowed for the reactor to reach steady-state conditions before any sampleswere taken.The results of these experiments are presented in Table 3. Fromthe data it is clear that a good match was obtained when exactlythe same catalyst was used in the two different reaction sys-tems. This is very encouraging, as it shows that the way in whichthe single long catalytic tube in the STMR had been split into 3shorter tubes in the RMR had not affected the performance ofthe reactor – neither the conversion nor the selectivity had beenchanged.Next, the performance of the used and fresh batch of catalyst canbe compared and it is clear that there is a slight reduction in con-version, but also a small increase in selectivity. The slight reductionin conversion is not surprising as the catalyst loading was slightlylower (i.e. 2.5 versus 2.7 wtpercent Pt). This slight variation was not ofany concern. With oxygen, Time= 2h, T= 110 °C , p= 9000.9Torr , Flow reactor, Catalytic behavior, Time, Temperature, Pressure Al Badran; Awdry; Kolaczkowski; Catalysis Today; vol. 216; (2013); p. 229 - 239 View in Reaxys 62 %Chromat.

With [Cu(1,10-phenanthroline-5,6-dione)2(H2O)](ClO4)2, oxygen, tetrabutyl ammonium methoxide in methanol, acetonitrile, Time= 7h, T= 25 °C , Mechanism, Catalytic behavior, Reagent/catalyst, Solvent, Time, Concentration Das, Oindrila; Paine, Tapan Kanti; Dalton Transactions; vol. 41; nb. 37; (2012); p. 11476 - 11481 View in Reaxys With oxygen, Time= 4h, p= 750.075Torr , UV-irradiation, Catalytic behavior Shen, Lijuan; Liang, Shijing; Wu, Weiming; Liang, Ruowen; Wu, Ling; Dalton Transactions; vol. 42; nb. 37; (2013); p. 13649 - 13657 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

186/438

2018-03-11 22:07:32


96 %Chromat.

2.4. Procedure for catalytic oxidation of alcohols General procedure: Oxidation of primary alcohols to aldehydes and secondary ones to ketones with NMO were catalyzed in the presence of [RuCl(κ2-N,O-L-Cl)(CO)(PPh3)2] (1), [RuCl(κ2-N,O-L-Me)(CO)(PPh3)2] (2), or [RuCl(κ2-N,OL-NO2)(CO)(PPh3)2] (3). A typical reaction using 1, 2 or 3 as catalyst is as follows. A solution of 1, 2 or 3 (1 Mpercent) in 20 mL of CH2Cl2 was added to the mixture of substrate (1 mM) and NMO (2 mM). The mixture was stirred at room temperature for 9 h and the solvent was evaporated under reduced pressure with a rotary evaporator resulting in a solid mass. It was shaken with petroleum ether (30–40 °C)(20 mL). The oxidized product extracted into petroleum ether was analyzed by GC. With C50H40ClN2O4P2Ru*0.5C6H14, 4-methylmorpholine N-oxide in dichloromethane, Time= 12h, T= 20 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst, Time Yin, Xiao-Feng; Lin, Hui; Jia, Ai-Quan; Chen, Qun; Zhang, Qian-Feng; Journal of Coordination Chemistry; vol. 66; nb. 18; (2013); p. 3229 - 3240 View in Reaxys

94 %Chromat.

With dihydrogen peroxide in water, Time= 6h, T= 50 °C , Green chemistry Salam, Noor; Sinha, Arjyabaran; Mondal, Paramita; Roy, Anupam Singha; Jana, Nikhil R.; Islam, Sk. Manirul; RSC Advances; vol. 3; nb. 39; (2013); p. 18087 - 18098 View in Reaxys

95 %Chromat.

With dihydrogen peroxide in water, Time= 1.5h, T= 90 °C , Green chemistry, Temperature, Solvent, Time, Concentration, Reagent/catalyst Pourjavadi, Ali; Hosseini, Seyed Hassan; Matloubi Moghaddam, Firouz; Koushki Foroushani, Behzad; Bennett, Craig; Green Chemistry; vol. 15; nb. 10; (2013); p. 2913 - 2919 View in Reaxys Alcohol Oxidation by GO–IBX; General Procedure General procedure: The alcohol oxidation reaction was carried out in a cylinder typeglass reactor (Carousel 12 Plus Reaction Station, Radleys, U.K.)with a cross-shaped magnetic stirring bar. Primary or secondary alcoholsubstrates (1 μmol), GO–IBX amide (2 μmol of IBX), andH2O (2 mL) were added to the reactor and stirred for 24 h at 80 °C.To analyze the oxidation product, the final solution was diluted5× using acetone with internal standard (biphenyl) and analyzed byGC and GC–MS. With trifluoroacetic acid in water, N,N-dimethyl-formamide, Time= 12h, T= 50 °C , Green chemistry Kim, Yo-Han; Jang, Hyung-Seok; Kim, Young-O; Ahn, So-Dam; Yeo, Sewon; Lee, Sang-Myung; Lee, YoonSik; Synlett; vol. 24; nb. 17; (2013); p. 2282 - 2286; Art.No: ST-2013-U0564-L View in Reaxys

95 %Chromat.

With oxygen in toluene, Time= 4h, T= 80 °C , p= 760.051Torr , Reagent/catalyst Mori, Kohsuke; Yamaguchi, Takuya; Ikurumi, Shohei; Yamashita, Hiromi; Chemical Communications; vol. 49; nb. 89; (2013); p. 10468 - 10470 View in Reaxys With hexaammonium heptamolybdate tetrahydrate, dihydrogen peroxide, Flow reactor Buonomenna; Drioli; Organic Process Research and Development; vol. 12; nb. 5; (2008); p. 982 - 988 View in Reaxys

> 99 With 1-methyl-1H-imidazole, [2,2]bipyridinyl, 2,2,6,6-tetramethyl-piperidine-N-oxyl, tetrakis(acetonitrile)copper(I) tri%Chromat. fluoromethanesulfonate, oxygen in acetonitrile, Time= 0.0833333h, T= 100 °C , p= 26252.6Torr , Inert atmosphere, Flow reactor Greene, Jodie F.; Hoover, Jessica M.; Mannel, David S.; Root, Thatcher W.; Stahl, Shannon S.; Organic Process Research and Development; vol. 17; nb. 10; (2013); p. 1247 - 1251 View in Reaxys With dimethyl sulfoxide, N-ethyl-N,N-diisopropylamine, trifluoroacetic anhydride in dichloromethane, T= -20 °C , Flow reactor, Temperature

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

187/438

2018-03-11 22:07:32


Van Der Linden, Jacobus J. M.; Hilberink, Peter W.; Kronenburg, Claudia M. P.; Kemperman, Gerardus J.; Organic Process Research and Development; vol. 12; nb. 5; (2008); p. 911 - 920 View in Reaxys 94 %Chromat.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C49H74N4O34, copper(II) acetate monohydrate, sodium carbonate in water, Time= 10h, Reflux, Green chemistry Zhang, Guofu; Han, Xingwang; Luan, Yuxin; Wang, Yong; Wen, Xin; Xu, Li; Ding, Chengrong; Gao, Jianrong; RSC Advances; vol. 3; nb. 42; (2013); p. 19255 - 19258 View in Reaxys

<8 With [2,2]bipyridinyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper(l) chloride, T= 20 °C , Green chemistry %Chromat. Yu, Jiatao; Xu, Jian; Lu, Ming; Applied Organometallic Chemistry; vol. 27; nb. 10; (2013); p. 606 - 610 View in Reaxys With sulfur trioxide pyridine complex, dimethyl sulfoxide, triethylamine in methanol, dichloromethane, T= 0 °C Clavette, Christian; Vincent Rocan, Jean-Francois; Beauchemin, Andre M.; Angewandte Chemie - International Edition; vol. 52; nb. 48; (2013); p. 12705 - 12708; Angew. Chem.; vol. 125; nb. 48; (2013); p. 12937 - 12940,4 View in Reaxys With 1-methyl-1H-imidazole, tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate, 4,4'-Dimethoxy-2,2'-bipyridin, 9-azabicyclo[3.3.1]nonane N-oxyl, oxygen in acetonitrile, T= 27 °C , p= 600Torr , Kinetics, Reagent/catalyst Steves, Janelle E.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 135; nb. 42; (2013); p. 15742 - 15745 View in Reaxys 99 %Chromat.

With 9-azabicyclolt;3.3.1gt;nonane-N-oxyl, oxygen, acetic acid, sodium nitrite, Time= 3h, T= 20 °C , p= 760.051Torr , Reagent/catalyst, Solvent Lauber, Markus B.; Stahl, Shannon S.; ACS Catalysis; vol. 3; nb. 11; (2013); p. 2612 - 2616 View in Reaxys With air, methyl red-MIL-125(Ti) in acetonitrile, Irradiation, Reagent/catalyst Nasalevich, Maxim A.; Goesten, Maarten G.; Savenije, Tom J.; Kapteijn, Freek; Gascon, Jorge; Chemical Communications; vol. 49; nb. 90; (2013); p. 10575 - 10577 View in Reaxys Procedure for catalytic oxidation of alcohols General procedure: Catalytic oxidation of primary alcohols to corresponding aldehydes and secondary alcohols to ketones by ruthenium(II) complexes were studied in the presence of NMO as co-oxidant. A typical reaction using the complex as a catalyst and primary or secondary alcohol, as substrate at 1:100 M ratio was described as follows. A solution of complex 1 (0.01 mmol) in CH2Cl2 (25 mL) wasadded to the mixture containing PhCH2OH (1 mmol), NMO(3 mmol) and molecular sieves. The reaction mixture was refluxedand conversion of PhCH2OH to PhCHO was monitored taking the reaction mixture at 10 min time interval. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was then extracted with diethyl ether, concentrated to 1 mL. Conversions were determined by GC instrument equipped with a flame ionization detector (FID) using a HP-5 column of 30 mlength, 0.53 mm diameter and 5.00 lm film thickness. The column,injector and detector temperatures were 200, 250 and 250 C respectively. The carrier gas was N2 (UHP grade) at a flow rate of 30 mL/min. The injection volume of sample was 2 lL. The oxidation products were identified by GC co-injection with authentic samples. No significant conversion was observed after 50 min. Allother alcohols were oxidized by refluxing the reaction mixture for 1 h and conversions were monitored following the identical protocol. With C14H14I2N2O4RuS, 4-methylmorpholine N-oxide in dichloromethane, T= 40 °C , Molecular sieve, Reagent/catalyst Jana, Subrata; Jana, Mahendra Sekhar; Sarkar, Deblina; Paira, Mrinal Kanti; Mondal, Tapan Kumar; Journal of Molecular Structure; vol. 1054-1055; (2013); p. 83 - 88 View in Reaxys With [CoII(3,5-ditert-butylsemiquinonate)(hydrotris(3,5-dimethylpyrazolyl)borate)], oxygen in dichloromethane, acetonitrile, T= 31.84 °C , Kinetics

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

188/438

2018-03-11 22:07:32


Ikeda, Atsushi; Hoshino, Kazuya; Komatsuzaki, Hidehito; Satoh, Minoru; Nakazawa, Jun; Hikichi, Shiro; New Journal of Chemistry; vol. 37; nb. 8; (2013); p. 2377 - 2383 View in Reaxys 2.3. Catalytic reactions The catalytic oxidation of benzyl alcohol was carried out in abatch-type reactor equipped with a reflux condenser and magneticstirrer as the reported literature [21]. Before use, the catalysts werepretreated under argon at 450C for 3 h. Typically, 100 mg catalystwas added to a 50 ml glass flask pre-charged with 2 mmol benzylalcohol and 10 ml toluene at 100C. Reaction was started by bub-bling O2into the mixture at a flow rate of 12 ml/min under vigorousstirring. In order to avoid the effects of mass transfer effects for thereaction, the stirring speed was controlled strictly at a fixed value.The reaction products were analyzed on a gas chromatography (GC5890) equipped with a flame ionization detector (FID) with SE-54.After reaction, the catalyst was washed with ethanol and dried at60C overnight for further characterization. With oxygen in toluene, Time= 2h, T= 100 °C , Reagent/catalyst Yang, Ming; Ling, Qiang; Rao, Richuan; Yang, Hongxiao; Zhang, Qingyun; Liu, Huade; Zhang, Aimin; Journal of Molecular Catalysis A: Chemical; vol. 380; (2013); p. 61 - 69 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [bis(acetoxy)iodo]benzene in dichloromethane, T= 20 °C Khan, Imran A.; Saxena, Anil K.; Journal of Organic Chemistry; vol. 78; nb. 23; (2013); p. 11656 - 11669 View in Reaxys With oxygen in toluene, Time= 2h, T= 100 °C , Concentration, Temperature, Reagent/catalyst Alabbad, Saad; Adil; Alwarthan, Abdulrahman; Siddiqui, M. Rafiq H.; Asian Journal of Chemistry; vol. 25; nb. 16; (2013); p. 8927 - 8932 View in Reaxys 70 %Chromat.

With 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate in tert-butyl alcohol, pH= 11.5, pH-value Green, Robert A.; Hill-Cousins, Joseph T.; Brown, Richard C.D.; Pletcher, Derek; Leach, Stuart G.; Electrochimica Acta; vol. 113; (2013); p. 550 - 556 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in tert-butyl alcohol, pH= 11.5, Electrochemical reaction, Activation energy Green, Robert A.; Hill-Cousins, Joseph T.; Brown, Richard C.D.; Pletcher, Derek; Leach, Stuart G.; Electrochimica Acta; vol. 113; (2013); p. 550 - 556 View in Reaxys

85 %Chromat.

General procedure for solvent-free aerobic oxidation of alcohols In a typical reaction, benzyl alcohol (0.2mL, 2mmol) and magnetic catalyst (0.06g) were loaded in a two-neck round bottom flask. The mixture was then immersed in a 50°C oil bath and the oxygen flow was bubbled into the mixture to initiate the reaction. The reaction mixture was then stirred under solvent-free condition. The progress of reaction was monitored by thin layer chromatography (TLC). On completion of the reaction, the catalyst was removed by an external magnet and the liquid organic product was analyzed by an Agilent gas chromatograph 6890 equipped with a HP-5 capillary column. Dodecane was the internal standard to calculate benzyl alcohol conversion and benzaldehyde selectivity. With oxygen in neat (no solvent), Time= 1.5h, T= 50 °C , Solvent, Reagent/catalyst Zamani, Farzad; Hosseini, Seyed Mohsen; Catalysis Communications; vol. 43; (2014); p. 164 - 168 View in Reaxys With FeII(1,3-bis(2'-pyridylimino)isoindoline)(CH3CN)3(H2O)0.5(ClO4)2, dihydrogen peroxide in acetonitrile, T= 25 °C , Inert atmosphere, Kinetics Pap, Jozsef S.; Cranswick, Matthew A.; Balogh-Hergovich; Barath, Gabor; Giorgi, Michel; Rohde, Gregory T.; Kaizer, Jozsef; Speier, Gabor; Que Jr., Lawrence; European Journal of Inorganic Chemistry; nb. 22-23; (2013); p. 3858 - 3866 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

189/438

2018-03-11 22:07:32


With oxygen, Time= 2h, Irradiation Tang, Zi-Rong; Yin, Xia; Zhang, Yanhui; Xu, Yi-Jun; Inorganic Chemistry; vol. 52; nb. 20; (2013); p. 11758 - 11766 View in Reaxys With Ruthenium/carbon nanotubes-TiO2 catalyst in water, toluene, Time= 3h, T= 85 °C , Reagent/catalyst Yu, Chang; Fan, Liman; Yang, Juan; Shan, Yuanyuan; Qiu, Jieshan; Chemistry - A European Journal; vol. 19; nb. 48; (2013); p. 16192 - 16195 View in Reaxys With oxygen in toluene, Time= 3h, T= 90 °C , p= 750.075Torr , Catalytic behavior Hammond, Ceri; Schuemperli, Martin T.; Conrad, Sabrina; Hermans, Ive; ChemCatChem; vol. 5; nb. 10; (2013); p. 2983 - 2990 View in Reaxys With 1-methyl-1H-imidazole, [2,2]bipyridinyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, copper(I) triflate in acetonitrile, T= 27 °C , p= 600Torr , Kinetics, Reagent/catalyst, Solvent Hoover, Jessica M.; Ryland, Bradford L.; Stahl, Shannon S.; ACS Catalysis; vol. 3; nb. 11; (2013); p. 2599 2605 View in Reaxys 2.4 Allylic alcohol selox Catalyst screening was performed using a Radleys Starfish carousel batch reactor on a 10cm3 scale at 90°C under a bubbled O2 flow (3cm3min−1 at 1bar). Catalyst (50mg) was added to a reaction mixture of allylic alcohol (8.4mmol, Sigma-Aldrich purity of all >95percent), mesitylene (0.1cm3, Sigma-Aldrich 99percent) as an internal standard, and toluene (10cm3, Fisher Scientific 99.8percent). Control reactions in the absence of any solid phase, or presence of bare alumina supports, were conducted in parallel with tests on Pd/meso-Al2O3 and gave negligible conversion of any alcohols. Reactions were periodically sampled, with aliquot (0.25cm3) withdrawn, filtered, and diluted with toluene (1.75cm3, Fisher Scientific 99.8percent) for triplicate analysed on a Varian 3900GC with CP-8400 autosampler (CP-Sil5 CB column, 15m x 0.25mm x 0.25 μm). Initial rates were calculated from the initial linear region of the alcohol conversion profiles (typically 0.3–1h reaction), with selectivity and overall mass balances calculated using calibrated response factors for reactants and products. Conversion and selectivity values are reported within ±3 percent error, with mass balances in all cases ≥95 percent during the first hour and ≥90 percent over 24h. Catalyst recyclability was assessed by screening a spent quantity of catalysts from a scaled-up (by a factor of 2.5) to ensure significant catalyst recovery by hot filtration. Spent catalysts were stirred in 50ml toluene at 90°C for 10min (three times) before drying at 120°C for 2h and subsequent catalytic testing under identical conditions to those stated above. With oxygen in toluene, 1,3,5-trimethyl-benzene, Time= 1h, T= 90 °C , p= 750.075Torr , Catalytic behavior, Reagent/ catalyst Parlett, Christopher M.A.; Durndell, Lee J.; Wilson, Karen; Bruce, Duncan W.; Hondow, Nicole S.; Lee, Adam F.; Catalysis Communications; vol. 44; (2014); p. 40 - 45 View in Reaxys With oxygen in neat (no solvent), Time= 2.5h, T= 100 °C , p= 3000.3Torr , Autoclave, Pressure, Temperature Silva, Tiago A. G.; Landers, Richard; Rossi, Liane M.; Catalysis Science and Technology; vol. 3; nb. 11; (2013); p. 2993 - 2999 View in Reaxys With di-tert-butyl peroxide in acetonitrile, Time= 9h, T= 65 °C , Catalytic behavior Zou, Xiaoxin; Goswami, Anandarup; Asefa, Tewodros; Journal of the American Chemical Society; vol. 135; nb. 46; (2013); p. 17242 - 17245 View in Reaxys 98 %Chromat.

General procedure for the oxidation of alcohols General procedure: All oxidation experiments are performed in a 120mL autoclave equipped with the magnetic stirring and temperature control. A typical procedure for the oxidation of benzyl alcohol is as follows: 1.08g (10.0mmol) of benzyl alcohol, 0.0156g (0.1mmol) of TEMPO, 0.274g (0.5mmol) of CAN, 0.0690g (1.0mmol) of NaNO2, additive in suitable amount and 10mL of H2O were charged into the reactor, and the atmosphere inside is replaced with oxy-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

190/438

2018-03-11 22:07:32


gen after the reactor is sealed. Then, pure oxygen is charged to 0.3MPa at room temperature. In the following, the autoclave is heated to 80°C under stirring, and then kept for 2h. After reaction, the autoclave was cooled to room temperature and excess gas was purged. The mixture was transferred into a flask, in which the reactor was washed with CH2Cl2 for 3–5 times in order to transfer completely. Next, the products are extracted with 6mL CH2Cl2 three times. The obtained products were analyzed with internal standard technique by GC with a flame ionization detector (all products were determined on GC–MS with an Agilent 6890N GC/5973 MS detector). With ammonium cerium (IV) nitrate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, tetramethylammonium bromide, sodium nitrite in water, Time= 1.5h, T= 80 °C , p= 2250.23Torr , Autoclave, Sealed tube, Concentration, Reagent/catalyst, Time Yan, Yongtao; Tong, Xinli; Wang, Kaixuan; Bai, Xueqin; Catalysis Communications; vol. 43; (2014); p. 112 - 115 View in Reaxys 94 %Chromat.

With periodic acid in water, Time= 2h, T= 27 °C Ganesamoorthy; Muthu Tamizh; Shanmugasundaram; Karvembu; Tetrahedron Letters; vol. 54; nb. 51; (2013); p. 7035 - 7039 View in Reaxys With Au/CeO2, oxygen, caesium carbonate in chlorobenzene, Time= 8h, T= 90 °C , p= 760.051Torr , Catalytic behavior, Activation energy, Kinetics, Reagent/catalyst Wang, Min; Wang, Feng; Ma, Jiping; Li, Mingrun; Zhang, Zhe; Wang, Yehong; Zhang, Xiaochen; Xu, Jie; Chemical Communications; vol. 50; nb. 3; (2014); p. 292 - 294 View in Reaxys With oxygen, T= 240 °C , p= 456.031Torr , Flow reactor, Catalytic behavior, Reagent/catalyst, Time Guan, Yu; Zhao, Na; Tang, Bin; Jia, Qinqin; Xu, Xiaohong; Liu, Hong; Boughton, Robert I.; Chemical Communications; vol. 49; nb. 98; (2013); p. 11524 - 11526 View in Reaxys With dihydrogen peroxide, cetyltrimethylammonim bromide in water, 1,2-dichloro-ethane, Time= 1h, T= 60 °C , Inert atmosphere, Mechanism, Reagent/catalyst, Concentration Yadav, Ganapati D.; Sharma, Rajesh V.; Journal of Catalysis; vol. 311; (2014); p. 121 - 128 View in Reaxys With 1-tosyloxy-1-oxo-1H-1λ5-benzo[d][1,2]iodoxol-3-one in dichloromethane, Time= 0.05h, T= 20 °C Yusubov, Mekhman S.; Svitich, Dmitrii Yu.; Yoshimura, Akira; Nemykin, Victor N.; Zhdankin, Viktor V.; Chemical Communications; vol. 49; nb. 96; (2013); p. 11269 - 11271 View in Reaxys With tert.-butylhydroperoxide in acetonitrile, Time= 6h, Reflux Wang, Anqi; Jing, Huanwang; Dalton Transactions; vol. 43; nb. 3; (2014); p. 1011 - 1018 View in Reaxys With amphiphilic nonionic triblock copolymer P123-stabilized Pd nanoclusters, air in water, Time= 9h, T= 34.84 °C , pH= 3.5, pH-value, Time Dun, Ruirui; Wang, Xueguang; Tan, Mingwu; Huang, Zhen; Huang, Xuemin; Ding, Weizhong; Lu, Xionggang; ACS Catalysis; vol. 3; nb. 12; (2013); p. 3063 - 3066 View in Reaxys With bismuth(III) tungsten(VI) oxide, oxygen in water, Time= 10h, T= 20 °C , p= 750.075Torr , UV-irradiation, Green chemistry, Kinetics, chemoselective reaction Zhang, Yanhui; Xu, Yi-Jun; RSC Advances; vol. 4; nb. 6; (2014); p. 2904 - 2910 View in Reaxys 2.4. Oxidation of alcohols General procedure: In a typical procedure, a mixture of 0.2 g catalyst with the grain size of 200–230 mesh, 15 mL solvent (acetonitrile) and 30 mmol of alcohol (benzyl alcohol, cyclohexanol or n-hexanol) was stirred in a three-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

191/438

2018-03-11 22:07:32


necked flask under nitrogen atmosphere at 50 °C for 30 min. The stirring rate of the solution was set at 750 cycle/ min.Then 30 mmol of the oxidant (TBHP) was added. The mixture was refluxed at 90 °C for 8 h under nitrogen atmosphere (Table 2). After filtration, the solid was washed with CH2Cl2 and the reaction mixture was analyzed by GC. A GC–MS model Thermo Finnigan(60 m, RTX-1 column) was used for identification of products and a GC (PerkinElmer Model 1800) was used for product analysis. The GC was equipped with a flame ionization detector (FID) connected to a 3percent OV-17 column with length of 2.5 m and diameter of 1/8 in. With tert.-butylhydroperoxide in acetonitrile, Time= 8h, T= 90 °C , Inert atmosphere, Kinetics, Reagent/catalyst, Concentration, Solvent, Temperature Mahdavi, Vahid; Soleimani, Shima; Materials Research Bulletin; vol. 51; (2014); p. 153 - 160 View in Reaxys With tert.-butylhydroperoxide, cobalt ferrite in dimethyl sulfoxide, Time= 6.5h, T= 90 °C Burange, Anand S.; Kale, Sandip R.; Zboril, Radek; Gawande, Manoj B.; Jayaram, Radha V.; RSC Advances; vol. 4; nb. 13; (2014); p. 6597 - 6601 View in Reaxys General procedure for oxidation of ethylbenzene, cyclohexene and benzyl alcohol General procedure: In this procedure, the heterogeneous catalyst (5.0 mg), the substrate (9.0 mmol) and an oxidant (9.0 mmol, 80percent TBHP) were added in a three-necked round bottom flask equipped with a refluxed condenser.The mixture was stirred at the desired temperature.After filtering and washing with solvent, the filtrate was monitored by GC. The products were identified by GC-MS techniques.The conversion and selectivity were calculated with GC area normalization. Finally, comparative experiments were performed under different conditions. With tert.-butylhydroperoxide in neat (no solvent), Time= 12h, T= 60 °C , Temperature Habibi, Davood; Faraji, Ali Reza; Comptes Rendus Chimie; vol. 16; nb. 10; (2013); p. 888 - 896 View in Reaxys 79 %Chromat.

4.6 General procedure for Oppenauer oxidation General procedure: In a typical run, an oven-dried round bottom flask was charged with a known mole percent of catalyst, K2CO3 (1.7mmol), primary or secondary alcohol (1.0mmol) in acetone medium (8mL). The mixture was stirred at 40°C. After the specified time the reaction mixture was extracted with ether (4×10mL). The combined organic layer was washed with water (3×10mL), and dried over anhydrous Na2SO4. Solvent was removed under vacuum. The residue was dissolved in hexane and analyzed by GC–MS. With C49H42ClIrN2P2, potassium carbonate in acetone, Time= 6h, Oppenauer Oxidation, Reagent/catalyst Paul, Piyali; Richmond, Michael G.; Bhattacharya, Samaresh; Journal of Organometallic Chemistry; vol. 751; (2014); p. 760 - 768 View in Reaxys With oxygen in water, Time= 1.5h, T= 79.84 °C , p= 750.075Torr , Reagent/catalyst Chen, Chen; Yang, Hanmin; Chen, Jizhong; Zhang, Ran; Guo, Li; Gan, Huimei; Song, Baoning; Zhu, Wenwen; Hua, Li; Hou, Zhenshan; Catalysis Communications; vol. 47; (2014); p. 49 - 53 View in Reaxys

60 %Chromat.

With oxygen in neat (no solvent), Time= 4h, T= 45 °C , Solvent, Temperature Zamani, Farzad; Hosseini, Seyed Mohsen; Kianpour, Sahar; Dalton Transactions; vol. 43; nb. 9; (2014); p. 3618 - 3625 View in Reaxys With oxygen in neat (no solvent), Time= 4h, T= 120 °C , p= 1500.15Torr , Time, Reagent/catalyst Alhumaimess, Mosaed; Lin, Zhongjie; He, Qian; Lu, Li; Dimitratos, Nickolaos; Dummer, Nicholas F.; Conte, Marco; Taylor, Stuart H.; Bartley, Jonathan K.; Kiely, Christopher J.; Hutchings, Graham J.; Chemistry - A European Journal; vol. 20; nb. 6; (2014); p. 1701 - 1710 View in Reaxys With VO(H2O)(1-phenyl-3-methyl-4-touloyl-5-pyrazolone(1-))2, dihydrogen peroxide in acetonitrile, T= 90 °C , Catalytic behavior, Reagent/catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

192/438

2018-03-11 22:07:32


Parihar, Sanjay; Jadeja; Gupta, Vivek K.; RSC Advances; vol. 4; nb. 20; (2014); p. 10295 - 10302 View in Reaxys 91 %Chromat.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, Ir(4,4'-di-tert-butyl-2,2'-bipyridyl)(2-phenylpyridine)2(PF6), tetrabutyl-ammonium chloride, oxygen, sodium hydrogencarbonate in dichloromethane, water, Time= 48h, T= 20 °C , Irradiation, Green chemistry, Reagent/catalyst, Solvent, chemoselective reaction Liu, Dongwang; Zhou, Hongxia; Gu, Xiangyong; Shen, Xiaoqin; Li, Pixu; Chinese Journal of Chemistry; vol. 32; nb. 2; (2014); p. 117 - 122 View in Reaxys With HNb3O8, oxygen, Time= 4h, T= 24.84 °C , p= 750.075Torr , UV-irradiation, Reagent/catalyst, chemoselective reaction Liang, Shijing; Wen, Linrui; Lin, Sen; Bi, Jinhong; Feng, Pingyun; Fu, Xianzhi; Wu, Ling; Angewandte Chemie - International Edition; vol. 53; nb. 11; (2014); p. 2951 - 2955; Angew. Chem.; vol. 126; nb. 11; (2014); p. 2995 2999,5 View in Reaxys

> 95 %Spectr.

With C54H44N8Rh(1+)*Cl(1-), potassium tert-butylate in 1,2-dichloro-benzene, Time= 24h, T= 150 °C , Irradiation, Reagent/catalyst, Time Olguin, Juan; Mueller-Bunz, Helge; Albrecht, Martin; Chemical Communications; vol. 50; nb. 26; (2014); p. 3488 - 3490 View in Reaxys With 2,2,6,6-tetramethyl-piperidine-N-oxyl, potassium carbonate in water, Time= 22h, T= 70 °C , Catalytic behavior, Reagent/catalyst, Concentration, Temperature Ma, Zhen; Wei, Lijuan; Alegria, Elisabete C.B.A.; Martins, Luisa M.D.R.S.; Guedes Da Silva, M. Fatima C.; Pombeiro, Armando J.L.; Dalton Transactions; vol. 43; nb. 10; (2014); p. 4048 - 4058 View in Reaxys With dihydrogen peroxide in water, Time= 4h, T= 80 °C , Reagent/catalyst Wang, Liang; Sun, Jing; Meng, Xiangju; Zhang, Weiping; Zhang, Jian; Pan, Shuxiang; Shen, Zhe; Xiao, FengShou; Chemical Communications; vol. 50; nb. 16; (2014); p. 2012 - 2014 View in Reaxys

90 %Spectr.

With C29H45Cl2N3ORuSi, tetrabutyl ammonium fluoride in 1,2-dichloro-benzene, Time= 16h, T= 110 °C , Catalytic behavior, Kinetics, Solvent, Reagent/catalyst Delgado-Rebollo, Manuela; Canseco-Gonzalez, Daniel; Hollering, Manuela; Mueller-Bunz, Helge; Albrecht, Martin; Dalton Transactions; vol. 43; nb. 11; (2014); p. 4462 - 4473 View in Reaxys With copper(II) nitrate trihydrate, dihydrogen peroxide in water, Time= 6h, T= 80 °C , Catalytic behavior, Solvent, Temperature, Time Guan, Jingqi; Liu, Jing; Transition Metal Chemistry; vol. 39; nb. 2; (2014); p. 233 - 238 View in Reaxys 3.8. Catalytic oxidation of benzyl alcohol In a typical catalytic oxidation reaction, benzyl alcohol (5 mmol), H2O2 (5 mmol) as the oxidant were added with 0.5 g of the catalyst and the contents were heated at 80 °C in the presence of acetonitrile as the solvent for 8 h. The course of the reaction and the yield of the products formed were confirmed by gas chromatography (GC). With nickel aluminate, dihydrogen peroxide in acetonitrile, Time= 8h, T= 80 °C , Time Ragupathi; Vijaya, J. Judith; Surendhar; Kennedy, L. John; Polyhedron; vol. 72; (2014); p. 1 - 7 View in Reaxys Oxidation of other alcohols over Cr-13X General procedure: The catalytic oxidation of cyclohexanol (Scheme 1) was carriedout in a 25-mL single-necked round-bottom glass flask equipped with a cryogenic-liquid condenser under atmospheric pressure. In a typical run, 40.0 mmol of cyclohexanol, 10.0 mmol of TBHP,and 100 mg of the catalyst were added to the reactor, and the mix-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

193/438

2018-03-11 22:07:32


ture was stirred vigorously by a magnetic stirrer and heated in a preheated water bath. After the completion of the reaction, the liquid products were separated by centrifugation and analyzed by a gas chromatograph equipped with a capillary column (SE-30, 30 m × 0.25 mm × 0.25 m) and an FID detector, in which chlorobenzene was used as an internal standard to quantify all the components, and the solid catalyst was separated by filtration and washed thoroughly with acetone and ethanol, and dried at 373 K overnight for the next use. The cyclohexanol conversion, cyclohexanone selectivity, TBHP conversion and TBHP efficiency werecalculated by using Eqs. (1)-(4). With tert.-butylhydroperoxide in neat (no solvent), Time= 7h, T= 89.84 °C , p= 760.051Torr , Green chemistry Li, Kun; Zhou, Dan; Deng, Jiejie; Lu, Xinhuan; Xia, Qinghua; Journal of Molecular Catalysis A: Chemical; vol. 387; (2014); p. 31 - 37 View in Reaxys With oxygen in toluene, Time= 8h, T= 79.84 °C , p= 760.051Torr , chemoselective reaction Geng, Longlong; Zhang, Xiuyan; Zhang, Wenxiang; Jia, Mingjun; Liu, Gang; Chemical Communications; vol. 50; nb. 22; (2014); p. 2965 - 2967 View in Reaxys 99 %Spectr.

With C39H37N6OPRu(2+)*2F6P(1-)*CH2Cl2, potassium tert-butylate in toluene, Time= 0.5h, T= 100 °C , Reagent/catalyst, Time Naziruddin, Abbas Raja; Zhuang, Chun-Shiuan; Lin, Wan-Jung; Hwang, Wen-Shu; Dalton Transactions; vol. 43; nb. 14; (2014); p. 5335 - 5342 View in Reaxys With oxygen, T= 100 °C , p= 760.051Torr , Catalytic behavior Kang, Xinchen; Zhang, Jianling; Shang, Wenting; Wu, Tianbin; Zhang, Peng; Han, Buxing; Wu, Zhonghua; Mo, Guang; Xing, Xueqing; Journal of the American Chemical Society; vol. 136; nb. 10; (2014); p. 3768 - 3771 View in Reaxys With C24H29ClRhSe2 (1+)*F6P(1-), potassium carbonate, acetone in water, Time= 5h, T= 80 °C , Oppenauer Oxidation, Catalytic behavior, Reagent/catalyst Prakash, Om; Sharma, Kamal Nayan; Joshi, Hemant; Gupta, Pancham L.; Singh, Ajai K.; Organometallics; vol. 33; nb. 4; (2014); p. 983 - 993 View in Reaxys With [Ru(CO)(1-methyl-2-{(o-thiomethyl)phenylazo}imidazole)I2], 4-methylmorpholine N-oxide in dichloromethane, T= 40 °C , Molecular sieve, Reflux, Reagent/catalyst Jana, Subrata; Jana, Mahendra Sekhar; Biswas, Sujan; Sinha, Chittaranjan; Mondal, Tapan Kumar; Journal of Molecular Structure; vol. 1065-1066; nb. 1; (2014); p. 52 - 60 View in Reaxys

95 %Chromat.

General Procedure for the Hydrogen Transfer Oxidation of Benzylic Primary Alcohols Shown in Table 4 General procedure: Under an atmosphere of argon, catalyst 2e (2.0 molpercent), benzylic primary alcohol (1.0 mmol), isopropenyl acetate (1.0 mmol), and toluene (18 mL) were placed in a flask. The mixture was stirred at 80 °C for 10 h. The conversion of benzylic primary alcohol and the yield of benzaldehyde derivative were determined by GC analysis using biphenyl as an internal standard. With Isopropenyl acetate, C16H21ClIrNO in toluene, Time= 10h, T= 80 °C , Inert atmosphere Fujita, Ken-Ichi; Uejima, Takehisa; Yamaguchi, Ryohei; Chemistry Letters; vol. 42; nb. 12; (2013); p. 1496 - 1498 View in Reaxys

99 %Chromat.

Typical procedure for the oxidation process: General procedure: In a three-neck round bottom flask, KCC-1/TEMPO (0.05 g, about 0.02 mmol) was dispersed in acetonitrile (15 mL) and sonicated for 15 min followed by the addition of alcohol (2 mmol), NaNO2 (6.9 mg, 0.1 mmol). Oxygen was introduced to the flask with a rate of 0.004 m3/h and the flask was placed in an oil bath thermostated at 80 °C. The reaction was initiated by the addition of 10percent H2SO4 solution (0.1 mL). When the reaction was finished, the catalyst was recovered by filtration and used after drying without further treatment. After extraction with CH2Cl2 and drying over MgSO4, the crude product was analyzed by GC.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

194/438

2018-03-11 22:07:32


With sulfuric acid, oxygen, sodium nitrite in acetonitrile, Time= 3h, T= 80 °C , Catalytic behavior, Reagent/catalyst Zhu, Jie; Zhao, Xue-Jing; Wang, Peng-Cheng; Lu, Ming; Chemistry Letters; vol. 42; nb. 12; (2013); p. 1505 1507 View in Reaxys With 2PMo12O40 (3-)*2C10H9N3*Pd(2+)*2OV(2+)*14C2H6OS, oxygen in dimethyl sulfoxide, Time= 6h, T= 130 °C , p= 760.051Torr , Reagent/catalyst Huang, Xianqiang; Zhang, Xiaomei; Zhang, Dan; Yang, Song; Feng, Xiao; Li, Jikun; Lin, Zhengguo; Cao, Jie; Pan, Ran; Chi, Yingnan; Wang, Bo; Hu, Changwen; Chemistry - A European Journal; vol. 20; nb. 9; (2014); p. 2557 - 2564 View in Reaxys 2.4. Catalytic reaction General procedure: The selective oxidation of benzyl alcohol (as well as 4-methylbenzyl alcohol and 4-nitrobenzyl alcohol) was carried outin a bath-type reactor operated under atmospheric conditions.Alcohol (1 mmol), deionized water (50 ml), and catalyst (4 mg,0.001 mmol of Pt) were added into a three-necked glass flask,stirred continuously (1200 rpm) and heated to 75 C in an oil bath.The temperature was controlled by a thermocouple, and a reflux condenser was used to condense the vapor of products. Oxygenflow (25 ml/min) was bubbled into the mixture to initiatethe reaction. After the given reaction time, the catalyst powderwas filtered off and the reactant and product were extractedusing toluene (10 ml) for three times. The supernatant (mixture ofresidual reactant, product) was analyzed using an Agilent gas chromatograph6890 equipped with a HP-5 capillary column (30 m longand 0.32 mm in diameter, packed with silica-based supel cosil),and flame ionization detector (FID). Dodecane was the internalstandard. The turnover frequency (TOF) was defined as the numberof benzyl alcohol (BA) converted over one surface-active Pt atomper hour:TOF (h−1)= MBA ·XMPt ·D·twhere MBA and MPt are the amount of BA and Pt in feed (mol) respectively,X is the conversion of BA, D is the Pt dispersion calculatedusing electrochemical method, and t is the reaction time (h). With oxygen in water, Time= 1h, T= 75 °C , Catalytic behavior, Reagent/catalyst, Time Zhou, Chunmei; Chen, Hong; Yan, Yibo; Jia, Xinli; Liu, Chang-Jun; Yang, Yanhui; Catalysis Today; vol. 211; (2013); p. 104 - 108 View in Reaxys Catalytic aerobic benzyl alcohol oxidation The solvent-free aerobic oxidation of benzyl alcohol reaction was carried out over the ZrO2 supported Pd catalysts (Pd/ZrO2) as a model reaction using O2 as the oxidant. The reaction was carried out using a three-necked glass flask (capacity 50 ml) pre-charged with benzyl alcohol and catalyst in a ratio of 250/1 mmol/mg. The mixture was stirred using a magnetic stirrer and heated in a silicon oil bath. The system was equipped with a reflux condenser and a thermocouple to control the temperature. In the initial reaction run, the mixture was heated to 160 C under vigorous stirring and oxygen was bubbled through the mixture at a constant flow rate of 30 ml min−1 to initiate the reaction. After 1 h, oxygen flow was stopped. The reaction mixture was then analyzed using an Agilent 4890 gas chromatograph equipped with a Simplicity-wax capillarycolumn using a hydrogen flame ionization detector. Dodecane wasused as an internal standard to calculate benzyl alcohol conversion and benzaldehyde selectivity. After the sample analysis, the reactor was placed back to the oil bath, stirred vigorously and heated up tothe former temperature. Oxygen was introduced into the reactor again after the temperature of the reaction mixture was stabilized. The reaction was run for 8 h in total and the samples for GC analyses were collected every hour. The same reaction was conducted at 140 and 150 C as well in order to further study the influence of the reaction temperature. With oxygen in neat (no solvent), Time= 1h, T= 160 °C , Reflux, Kinetics, Temperature Guo, Qiuting; With, Patrick; Liu, Yuan; Glaeser, Roger; Liu, Chang-Jun; Catalysis Today; vol. 211; (2013); p. 156 - 161 View in Reaxys With molybdenum carbide in dimethyl sulfoxide, Time= 8h, T= 120 °C , Inert atmosphere, Reagent/catalyst Li, Zhongcheng; Chen, Chunhui; Zhan, Ensheng; Ta, Na; Li, Yong; Shen, Wenjie; Chemical Communications; vol. 50; nb. 34; (2014); p. 4469 - 4471 View in Reaxys With tert.-butylhydroperoxide in neat (no solvent), Time= 24h, T= 24.84 °C , Green chemistry, Catalytic behavior, Reagent/catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

195/438

2018-03-11 22:07:32


Pal, Nabanita; Cho, Eun-Bum; Kim, Dukjoon; RSC Advances; vol. 4; nb. 18; (2014); p. 9213 - 9222 View in Reaxys General Procedure for the Aerobic Oxidation General procedure: In a typical oxidation reaction, alcohol substrate (1 mmol), silica-supported4-OH-TEMPO=NOx (0.5 g), and methylene dichloride (6 mL) were placed in a 50 mL long-necked, round-bottom flask equipped with a ground-glass elbow to get in touch with the atmosphere. The resulting mixture was magnetically stirred at room temperature and ambient pressure. The reaction was monitored by TLC and GC with a HP-5 capillary column and an FID detector. When the reaction completed, the catalyst was separated from the reaction mixture by vacuum filteration, during which the catalyst was washed five times with dichloromethane (10 mL), dried in air, and then adsorbed NOx gas for reuse. The filtrate was separated and solvent removed under reduced pressure. The final product was examined by 1H and 13C NMR analysis. With silica supported 4-OH-TEMPO/NOx, air in dichloromethane, Time= 7h, T= 20 °C , chemoselective reaction Zhang, Hua; Fu, Luoling; Synthetic Communications; vol. 44; nb. 5; (2014); p. 610 - 619 View in Reaxys General procedure for aerobic oxidation reaction catalysed by PS-teta–VO General procedure: The aerobic oxidation reactions were carried out in a 50mL stainless steel autoclave at different temperatures under vigorous stirring for a certain period of time. We examined the catalytic activity of vanadium complex using alcohol as the substrate and molecular oxygen as the primary oxidant. The oxidation of alcohol (5mmol) was conducted under oxygen pressure (5.0bar) at 60°C for 5h in the presence of vanadium complex (5mg) in water (5mL). After the reaction, the organic products were separated from the reaction mixture by extraction with dichloromethane (5mL×2). The combined organic portions were dried and concentrated. Product analysis was performed by Varian 3400 gas chromatograph equipped with a 30m CP-SIL8CB capillary column. With oxygen in water, Time= 5h, T= 60 °C , p= 3750.38Torr , Autoclave, Green chemistry, Catalytic behavior, Temperature, Pressure, Solvent, Concentration Islam, Sk. Manirul; Molla, Rostam Ali; Roy, Anupam Singha; Ghosh, Kajari; Salam, Noor; Iqubal, Md. Asif; Tuhina; Journal of Organometallic Chemistry; vol. 761; (2014); p. 169 - 178 View in Reaxys General procedure for the oxidation of alcohols with QnFC/H5IO6 under solvent-free conditions General procedure: A mixture of the corresponding alcohol (1 mmol) and QnFC (3 mol percent) was ground in a mortar until it becamehomogeneous and H5 IO6 (1.1 mmol) was introduced slowly. The progress of the reaction was monitored usingTLC on silica gel (n-hexane-ethylacetate = 2:1). Upon completion of the reaction, work up with ether (3 15mL) and evaporation of the solvent gave the corresponding carbonyl compounds. With quinaldinium fluorochromate(VI), periodic acid in neat (no solvent), Time= 0.0333333h, T= 20 °C , Reagent/ catalyst, Solvent, Temperature Oezdemir, Melek Canbulat; Oezgun, Hatice Beytiye; Turkish Journal of Chemistry; vol. 38; nb. 1; (2014); p. 63 69 View in Reaxys With oxygen in toluene, Time= 16h, T= 70 °C Deiana, Luca; Jiang, Yan; Palo-Nieto, Carlos; Afewerki, Samson; Incerti-Pradillos, Celia A.; Verho, Oscar; Tai, Cheuk-Wai; Johnston, Eric V.; Cordova, Armando; Angewandte Chemie - International Edition; vol. 53; nb. 13; (2014); p. 3447 - 3451; Angew. Chem.; vol. 126; nb. 13; (2014); p. 3515 - 3519,5 View in Reaxys 37.3 μmol

With oxygen, Time= 1h, Irradiation, Time, Reagent/catalyst Higashimoto, Shinya; Shirai, Ryo; Osano, Yuta; Azuma, Masashi; Ohue, Hiroyoshi; Sakata, Yoshihisa; Kobayashi, Hisayoshi; Journal of Catalysis; vol. 311; (2014); p. 137 - 143 View in Reaxys

93 %Chromat.

Representative procedure for the Oxidation of Benzyl alcohols to Benzaldehyde(3b) [2] with DBDMH: General procedure: DBDMH (1 mmol) was added to a mixture of 1b (1 mmol) and dichloromethane (20ml). The reaction was kept at room temperature. After the mixture was stirred for0.5h, the mixture was washed with water (330 ml),dried with anhydrous MgSO4,filtered, and vacuum evaporated. The residue was purified by column chromatography (silica gel: petroleum ether/ethyl acetate, 30:1) to afford the product as light yellowsolid (93percent yield).

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

196/438

2018-03-11 22:07:32


With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione in dichloromethane, Time= 0.5h, T= 25 °C , chemoselective reaction Li, Zhongzhou; Zhu, Wei; Bao, Jinlong; Zou, Xinzhuo; Synthetic Communications; vol. 44; nb. 8; (2014); p. 1155 - 1164 View in Reaxys 98 %Chromat.

Typical oxidation of alcohols General procedure: Into a reaction vessel with a reflux condenser were placed Pd-pol (23.1 mg, Pdpercentw = 2.3), benzyl alcohol (108.1 mg, 1.0 mmol), K2CO3 (138.2 mg, 1.0 mmol) and water (5 mL). The resulting mixture was stirred at 100°C under 1 atm of air. After 6 h, the mixture was cooled down to room temperature and the organic product was extracted with ethyl acetate (3 mL). The water phase was washed with ethyl acetate (2×5 mL) and the organic layers were collected. GLC analysis of the ethyl acetate solution using biphenyl as an internal standard gave a 98percent yield of benzyl aldehyde with >99percent selectivity. With potassium carbonate in water, Time= 6h, T= 100 °C , p= 760.051Torr , Kinetics, Temperature, Reagent/catalyst, Time Dell'Anna, Maria Michela; Mali, Matilda; Mastrorilli, Piero; Cotugno, Pietro; Monopoli, Antonio; Journal of Molecular Catalysis A: Chemical; vol. 386; (2014); p. 114 - 119 View in Reaxys 2.3 Catalytic test General procedure: The dehydrogenation of alcohols was performed in a 10ml 2-neck flask equipped with a reflux condenser under N2 atmosphere. The fresh Mo2N nanobelts (60mg) were liquid-sealed by dimethyl sulfoxide under nitrogen flow and quickly transferred into the flask. 1mmol alcohol was added into the flask containing 4ml dimethyl sulfoxide and the catalyst. The reaction mixture was heated to 150°C and maintained at that temperature for a certain period. After reaction, the liquid product was collected by centrifugation and analyzed by an Agilent GC-7890 gas chromatography equipped with a HP-5 capillary column. For the recycle test, the catalyst was immersed in dimethyl sulfoxide to avoid its exposure to air. With Mo2N in dimethyl sulfoxide, Time= 28h, T= 150 °C , Inert atmosphere, Time, Temperature Li, Zhongcheng; Chen, Chunhui; Zhan, Ensheng; Ta, Na; Shen, Wenjie; Catalysis Communications; vol. 51; (2014); p. 58 - 62 View in Reaxys Catalytic Reaction General procedure: The oxidation reaction was carried out in a one-necked round bottom glass reactor equipped with a condenser. In a typical run, 1 mmol of benzyl alcohol, 3 cm3 of o-xylene and 0.020 g of catalyst (4.53 wtpercent Pd) were heated at 85 °C under open air at atmospheric pressure. The hydrogenation reaction was carried out under atmospheric pressure of hydrogen at room temperature. The reaction vessel was refilled with hydrogen three times. In a typical run,1 mmol of substrate, 2 cm3 of methanol and 0.010 g of catalyst (4.53 wtpercent Pd) were stirred at room temperature,and hydrogen at atmospheric pressure was introduced to the reaction vessel. After completion of the reaction, the catalyst was filtered off and the conversion was measured using a GC (Acme 6000, Younglin, Korea) fitted with a high performance HP-5 capillary column and a FID. A hot filtering experiment was carried out by separating the catalyst quickly from the reaction mixture after 8 hr eaction time, and the filtrate was then maintained at 85 Cfor an additional 6 h. With 4.5 wtpercent of Pd nanoparticles supported on the chromium terephthalate metal organic framework MIL-101, air in o-xylene, Time= 14h, T= 85 °C , p= 760.051Torr , Reagent/catalyst Bhattacharjee, Samiran; Kim, Jun; Ahn, Wha-Seung; Journal of Nanoscience and Nanotechnology; vol. 14; nb. 3; (2014); p. 2546 - 2552 View in Reaxys With Ti0.9V0.1O2, dihydrogen peroxide in methanol, Time= 2h, T= 20 °C , Reagent/catalyst Amini, Mojtaba; Naslhajian, Hadi; Farnia, S. Morteza F.; New Journal of Chemistry; vol. 38; nb. 4; (2014); p. 1581 - 1586 View in Reaxys 2.2. Electrochemical measurement of the PPy-TEMPO electrode

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

197/438

2018-03-11 22:07:32


CHI620B electrochemical workstation (CH Instrument Inc., USA)was used for voltammetric study. The electrochemical polymer-ization of the PPy-TEMPO electrode was performed on the smallPt sheet (0.08 cm2) in 0.1 M NaClO4CH3CN solution containing0.01 M Py-TEMPO by cyclic voltammetry between 0 and 1.1 V ata scan rate of 100 mV s −1. A big Pt sheet (3.0 cm2) was used as thecounter electrode and a silver/silver ion electrode (0.1 M AgNO3) asthe reference one.The electrocatalytic activity of the PPy-TEMPO electrode wasmeasured for the oxidation of benzyl alcohol in 0.1 M NaClO4-CH3CN solution containing 10 mM benzyl alcohol and 20 mM2,6-lutidine by cyclic voltammetry between 0 and 0.8 V at a scanrate of 50 mV s−1.Preparative electrolysis experiments were performed on EG & GModel 263A potentiostat/galvanostat in 0.1 M NaClO4-CH3CN solu-tion containing 4 mmol benzyl alcohol and 20 mM 2,6-lutidine. Theanode was the PPy-TEMPO electrode with the area 3 cm2, and thecathode was the platinum sheet electrode (3 cm2). The experimentswere carried out under a constant current 20 mA/cm2with mod-erate stirring. The concentrations of reactants and products wereanalyzed by gas chromatograph system equipped with a capillarycolumn by internal standard method. With 2,6-dimethylpyridine, sodium perchlorate in acetonitrile, Electrochemical reaction Lu, Jin-Jin; Ma, Jia-Qi; Yi, Jing-Miao; Shen, Zhen-Lu; Zhong, Yi-Jun; Ma, Chun-An; Li, Mei-Chao; Electrochimica Acta; vol. 130; (2014); p. 412 - 417 View in Reaxys 58 %Chromat.

With tert.-butylhydroperoxide, palladium diacetate in chlorobenzene, Time= 12h, T= 80 °C , Sealed tube, Inert atmosphere Tang, Hui; Qian, Cheng; Lin, Dongen; Jiang, Huanfeng; Zeng, Wei; Advanced Synthesis and Catalysis; vol. 356; nb. 2-3; (2014); p. 519 - 527 View in Reaxys With ZnO0.8N0.1F0.1/Pt/CdS nanostructures in water, Irradiation, Catalytic behavior Lingampalli; Rao; Journal of Materials Chemistry A; vol. 2; nb. 21; (2014); p. 7702 - 7705 View in Reaxys With dihydrogen peroxide in neat (no solvent), Time= 4h, T= 90 °C , Reagent/catalyst, Solvent Meng, Ling-Yan; Zhai, Shang-Ru; Li, Shi; Zhai, Bin; An, Qing-Da; Song, Xiao-Wei; European Journal of Inorganic Chemistry; nb. 14; (2014); p. 2337 - 2344 View in Reaxys With Raney nickel in 5,5-dimethyl-1,3-cyclohexadiene, Reflux Mehta, Astha; Thaker; Londhe; Nandan, Santosh R.; Applied Catalysis A: General; vol. 478; (2014); p. 241 - 251 View in Reaxys With 200 U laccase from Trametes versicolor, oxygen, benzotriazol-1-ol in aq. buffer, T= 45 °C , pH= 4.5, Green chemistry, Enzymatic reaction Heidary, Marjan; Khoobi, Mehdi; Ghasemi, Sabrieh; Habibi, Zohreh; Faramarzi, Mohammad Ali; Advanced Synthesis and Catalysis; vol. 356; nb. 8; (2014); p. 1789 - 1794 View in Reaxys With reduced graphene oxide-MnCoO nanocomposite in acetonitrile, Time= 2h, T= 140 °C , p= 15751.6Torr Jha, Ajay; Mhamane, Dattakumar; Suryawanshi, Anil; Joshi, Sameer M.; Shaikh, Parvez; Biradar, Narayan; Ogale, Satishchandra; Rode, Chandrashekhar V.; Catalysis Science and Technology; vol. 4; nb. 6; (2014); p. 1771 - 1778 View in Reaxys

94 %Spectr.

With tert.-butylnitrite, [Cu(4,7-bis(4-pyridyl)-1,1,3,3-tetramethylisoindolin-2-yloxyl)2(SiF6)], oxygen, Time= 24h, T= 80 °C , Sealed tube, Reagent/catalyst Li, Liangchun; Matsuda, Ryotaro; Tanaka, Iku; Sato, Hiroshi; Kanoo, Prakash; Jeon, Hyung Joon; Foo, Maw Lin; Wakamiya, Atsushi; Murata, Yasujiro; Kitagawa, Susumu; Journal of the American Chemical Society; vol. 136; nb. 21; (2014); p. 7543 - 7546 View in Reaxys General procedure for oxidation of aromatic alcohols

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

198/438

2018-03-11 22:07:32


All oxidation experiments are performed in a 120 mL autoclave equipped with the magnetic stirring and automatic temperature control. A typical procedure for the oxidation of 1 is as follows: a CH2Cl2 (10 mL) solution of 1 (1.0 g, 9.2 mmol), NBS (3.0 molpercent), DDQ (7.0 molpercent), and NaNO2 (10.0 molpercent) is charged into the reactor, and the atmosphere inside is replaced with the pure oxygen after the reactor is sealed. Under stirring, oxygen is charged to 0.3 MPa at room temperature and the autoclave is preheated to 90 °C, and then kept for 2 h. After reaction, the autoclave was cooled and the mixture is analyzed by GC and GC–MS after the excess gas (unreacted oxygen and little nitrogen oxide) is purged. With N-Bromosuccinimide, oxygen, 2,3-dicyano-5,6-dichloro-p-benzoquinone, sodium nitrite in dichloromethane, Time= 2h, T= 90 °C , p= 2250.23Torr , Autoclave, Catalytic behavior, Solvent, Reagent/catalyst Tong, Xinli; Sun, Yongfa; Yan, Yongtao; Luo, Xuan; Liu, Jinbiao; Wu, Zhidong; Journal of Molecular Catalysis A: Chemical; vol. 391; nb. 1; (2014); p. 1 - 6 View in Reaxys 99 %Chromat.

With hydrogenchloride, sodium bromate, N-(1-oxo-2,2,6,6-tetramethylpiperidin-4-yl)-benzoylamide in dichloromethane, water, Time= 1h, T= 20 °C Shen, Jiaxuan; Sun, Jiangkai; Qin, Shuangshuang; Chu, Changhu; Liu, Renhua; Chinese Journal of Chemistry; vol. 32; nb. 5; (2014); p. 405 - 409 View in Reaxys With reduced graphene oxide–TiO2 (5percentRGO–TiO2) in water, Time= 4h, Irradiation, Catalytic behavior, Reagent/catalyst Yuan, Lan; Yu, Qianqian; Zhang, Yanhui; Xu, Yi-Jun; RSC Advances; vol. 4; nb. 29; (2014); p. 15264 - 15270 View in Reaxys

92 %Chromat.

Typical procedure for oxidation of alcohols by H2O2 General procedure: In a 25 mL round-bottomed flask equipped with a reflux condenser, a mixture of 1 g PWM/ SiO2(M = Cr, Mn, Fe, Co, Ni, and Cu)catalyst containing 0.03 mmol POM, 3 mL acetonitrile and 1 mmol of alcohol was added. Then 1 mL of H2O2 30percent was added and the mixture was refluxed for 2 h with stirring. The progress of the reaction was monitored by GC equipped with a flame ionization detector and a silica pack column. At the end of reaction, the catalyst was filtered out and 10 mL NaHCO3 10percent was added. The organic phase extracted with chloroform and dried. Flash chromatography on a short column of silica gel with ethyl acetate:n-hexane as eluent gave pure products. With dihydrogen peroxide in water, acetonitrile, Time= 4h, Reflux, Catalytic behavior, Reagent/catalyst, Solvent Farsani, Mostafa Riahi; Yadollahi, Bahram; Journal of Molecular Catalysis A: Chemical; vol. 392; (2014); p. 8 - 15 View in Reaxys

100 With 1-methyl-1H-imidazole, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 24h, T= %Chromat. 20 °C , Reagent/catalyst Joglekar, Madhura; Pylypenko, Svitlana; Otting, Megan M.; Valenstein, Justin S.; Trewyn, Brian G.; Chemistry of Materials; vol. 26; nb. 9; (2014); p. 2873 - 2882 View in Reaxys With oxygen in toluene, Time= 3h, T= 70 °C , Sealed tube Anderson, Mattias; Afewerki, Samson; Berglund, Per; Cordova, Armando; Advanced Synthesis and Catalysis; vol. 356; nb. 9; (2014); p. 2113 - 2118 View in Reaxys 98 %Chromat.

With copper(II) tetrasulfophthalocyanine supported on three-dimensional nitrogendopedgraphene-based frameworks, air in water, Time= 8h, T= 20 °C , p= 760.051Torr , Reagent/catalyst Mahyari, Mojtaba; Laeini, Mohammad Sadegh; Shaabani, Ahmad; Chemical Communications; vol. 50; nb. 58; (2014); p. 7855 - 7857 View in Reaxys

99 %Chromat.

With H3PW4O12, dihydrogen peroxide, cetyltrimethylammonim bromide in water, Time= 3h, T= 80 °C , Green chemistry, Reagent/catalyst, Temperature

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

199/438

2018-03-11 22:07:32


Zhu, Jie; Shen, Meng-Nan; Zhao, Xue-Jing; Wang, Peng-Cheng; Lu, Ming; ChemPlusChem; vol. 79; nb. 6; (2014); p. 872 - 878 View in Reaxys With 1,4-diaza-bicyclo[2.2.2]octane, C6Cl4O6Ru2 in toluene, Time= 12h, Inert atmosphere, Reflux Khalafi-Nezhad, Ali; Panahi, Farhad; ACS Catalysis; vol. 4; nb. 6; (2014); p. 1686 - 1692 View in Reaxys With oxygen in toluene, Time= 4h, T= 80 °C Wang, Jiang; Lang, Xianjun; Zhaorigetu, Bao; Jia, Meilin; Wang, Jun; Guo, Xiaofang; Zhao, Jincai; ChemCatChem; vol. 6; nb. 6; (2014); p. 1737 - 1747 View in Reaxys Stage 1: in dichloromethane, Time= 0.00833333h, Sonication, Micellar solution Stage 2: With sodium hypochlorite, sodium bromide in dichloromethane, Time= 0.05h, T= 10 °C , pH= Ca. 9.1, Micellar solution, Catalytic behavior, Reagent/catalyst Zheng, Zhi; Wang, Jianli; Chen, Hualiang; Feng, Linbin; Jing, Ren; Lu, Meizhen; Hu, Bao; Ji, Jianbing; ChemCatChem; vol. 6; nb. 6; (2014); p. 1626 - 1634 View in Reaxys 99 %Chromat.

Typical Experiment for the Oxidation of 2-Octanol (1) General procedure: NaOCl·5H2O crystals (2.0 g, 12.2 mmol) were added in oneportion to a mixture of Bu4NHSO4 (0.17 g, 0.50 mmol),TEMPO (21 mg, 0.13 mmol), and 1 (1.30 g, 10.0 mmol) inCH2Cl2 (10 mL) at 5 °C. After 15 min, GC monitoringshowed that 1 had been consumed. The reaction was stoppedafter 0.5 h by quenching with aq sat. Na2SO3 solution (20mL). The organic layer was separated, and the aqueous layerwas extracted with CH2Cl2 (30 mL). The combined organiclayers were washed with H2O (30 mL), dried over Na2SO4,and concentrated to give 2 as colorless oil (1.27 g, crudeyield of 99.2percent, GC analysis showed the product to be 96.8percentpure). A 0.42 g portion of the crude 2 was purified by bulbto-bulb distillation (6 kPa, 120–130 °C) to afford pure 2(0.40 g, 95percent). GC–MS analysis gave identical results tothose of an authentic sample. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium hypochlorite pentahydrate, tetra(n-butyl)ammonium hydrogensulfate in dichloromethane, Time= 1h, T= 5 °C Okada, Tomohide; Asawa, Tomotake; Sugiyama, Yukihiro; Kirihara, Masayuki; Iwai, Toshiaki; Kimura, Yoshikazu; Synlett; vol. 25; nb. 4; (2014); p. 596 - 598; Art.No: ST-2013-U1017-L View in Reaxys

96 %Chromat.

With sodium carbonate, silver nitrate in toluene, Time= 6h, Reflux, Reagent/catalyst, Time, chemoselective reaction Wang, Jiayi; Li, Yuan; Peng, Yanqing; Song, Gonghua; Journal of the Chinese Chemical Society; vol. 61; nb. 5; (2014); p. 517 - 520 View in Reaxys With dmap, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper(II) sulfate in water, N,N-dimethyl-formamide, T= 20 °C , Reagent/catalyst Mugemana, Clement; Chen, Ba-Tian; Bukhryakov, Konstantin V.; Rodionov, Valentin; Chemical Communications; vol. 50; nb. 58; (2014); p. 7862 - 7865 View in Reaxys Catalytic oxidations with t-BuOOH or H2O2 The oxidation of benzyl alcohol by [MoO2(dhsm)(EtOH)] (1b) is typical. To the alcohol (2.5 mmol), complex (1b) (0.01 mmol) and 70 percent in water t-BuOOH (5 mmol) were added. The reaction mixture was stirred at 70 °C for 3 h, extracted with CH2Cl2 (3 x 10 mL). The extracts were combined, dried over anhydrous Na2SO4, evaporated to dryness and aldehyde product was quantified as its 2,4-dinitrophenylhydrazone derivative [8,9] (equivalent to 1 mmol of benzaldehyde product was obtained). The absence of benzoic product was detected by TLC techniques. The same experiment were carried out using 30 percent H2O2 (5 mmol) instead of 70 percent t-BuOOH where 0.25 mmol benzaldehyde was produced. With tert.-butylhydroperoxide, cis-[MoO2(dhsm)(ethanol)] in water, Time= 3h, T= 70 °C , Catalytic behavior, Reagent/catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

200/438

2018-03-11 22:07:32


Fayed, Ahmed M.; Elsayed, Shadia A.; El-Hendawy, Ahmed M.; Mostafa, Mohamed R.; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 129; (2014); p. 293 - 302 View in Reaxys 100 Typical procedure for catalyticoxidation of benzyl alcohol %Chromat. General procedure: The catalytic reactions were performed in a 10 mL round bottom flask equipped with a magnetic stirring bar, and a reflux condenser. The oxidation ofbenzyl alcohol was carried out as follow: catalyst (0.01mmol), CH3CN (3 mL), substrate (1 mmol), and H2O2 (30percent, 1 mL) were charged in the reaction flask. The reaction was carried out at 80 °C and the progress of reaction was detected by TLC accompanied with GC by the internal standard method. Assignments of products were made by comparison with authentic samples. With 2O34PW9 (9-)*4Zn(2+)*10C16H36N(1+), dihydrogen peroxide in acetonitrile, Time= 0.75h, T= 80 °C , Reagent/catalyst, Time Farsani, Mostafa Riahi; Jalilian, Fariba; Yadollahi, Bahram; Rudbari, Hadi Amiri; Polyhedron; vol. 76; (2014); p. 102 - 107 View in Reaxys With dihydrogen peroxide in water, Time= 6h, T= 100 °C , Reagent/catalyst, Temperature Liu, Kun; Chen, Tingting; Hou, Zhiqiang; Wang, Yuanyuan; Dai, Liyi; Catalysis Letters; vol. 144; nb. 2; (2014); p. 314 - 319 View in Reaxys 2.1. Catalysis part Aerobic AcH oxidation experiments were carried out in a quartztube containing different amount of FeCl3in CH3CN (5 mL) in air at room temperature. The AcH and products concentrations were calculatedfrom the results of GC-FID analysis, and then calculated thesubstrate conversion and the selectivity toward AcH (benzene wasused as an external standard). GC-TCD was employed for determinationof the gas-phase products. The conditions for benzyl alcoholoxidation were similar to the above AcH oxidation process, exceptthat benzyl alcohol (0.02 M) was added into the solution containingdifferent amount of AcH, FeCl3 in CH3CN (5 mL). The substrateconversion and the selectivity toward benzaldehyde (toluene wasused as an external standard) were calculated from the results ofGC-FID and GC-TCD analysis. With iron(III) chloride, acetic acid in acetonitrile, Time= 3h, T= 25 °C , Catalytic behavior, Kinetics Li, Renhong; Kobayashi, Hisayoshi; Yan, Xiaoqing; Fan, Jie; Catalysis Today; vol. 233; (2014); p. 140 - 146 View in Reaxys With oxygen in neat (no solvent), T= 230 °C , Gas phase, Green chemistry Mao, Junjie; Zhao, Guofeng; Wang, Dingsheng; Li, Yadong; RSC Advances; vol. 4; nb. 48; (2014); p. 25384 25388 View in Reaxys With dye sensitized photoelectrosynthesis cell in aq. acetate buffer, T= 20 °C , pH= 4.5, Irradiation Song, Wenjing; Vannucci, Aaron K.; Farnum, Byron H.; Lapides, Alexander M.; Brennaman, M. Kyle; Kalanyan, Berç; Alibabaei, Leila; Concepcion, Javier J.; Losego, Mark D.; Parsons, Gregory N.; Meyer, Thomas J.; Journal of the American Chemical Society; vol. 136; nb. 27; (2014); p. 9773 - 9779 View in Reaxys With oxygen, p-benzoquinone in acetonitrile, T= 25 - 35 °C , p= 760.051Torr , Irradiation Abedi, Sedigheh; Morsali, Ali; ACS Catalysis; vol. 4; nb. 5; (2014); p. 1398 - 1403 View in Reaxys General Procedure for Oxidation of Alcohols General procedure: Chemicals and reagents were purchased fromAldrich or Fisher and used without further purification unless noted. The required amount of H5IO6(see Table 2) and CrO2 (0.042 g, 0.5 mmol) were ground together in amortar to produce a uniform gray-black mixture, which was then transferred to a50 mL round-bottomed flask along with a magnetic stir bar. Water (5.0 mL) was added, and the mixture wasstirred for 5-10 minutes to dissolve the H5IO6. Then 20.0 mL acetonitrile (ACN) was added andthe mixture was stirred vigorously to disperse the black CrO2solid. At this point the solution phasewas dark yellow. The alcohol reactant(5.0 mmol, weighed if solid, via pipette if liquid) was added in one portionwith vigorous stirring, and within one minute the solution phase became muchlighter (although it gradually darkened during the reaction period).

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

201/438

2018-03-11 22:07:32


With chromium (VI) oxide, periodic acid in acetonitrile, Time= 0.25h, T= 20 °C , Reagent/catalyst, Solvent Few, Chip S.; Williams, Kathryn R.; Wagener, Kenneth B.; Tetrahedron Letters; vol. 55; nb. 32; (2014); p. 4452 4454 View in Reaxys 100 With caesium carbonate in toluene, Time= 12h, T= 100 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst %Chromat. Sabater, Sara; Mata, Jose A.; Peris, Eduardo; ACS Catalysis; vol. 4; nb. 6; (2014); p. 2038 - 2047 View in Reaxys 2.3 Gas-phase oxidative dehydrogenation of benzyl alcohol Gas-phase oxidative dehydrogenation of benzyl alcohol was carried out over K6As2W18−xMoxO62 (x=0–3) catalysts. 0.5g of HPA was charged into the tubular glass reactor. Vaporized benzyl alcohol (1.15mmol/h) was fed into the reactor together with a mixed stream of oxygen (10ml/min) and nitrogen (20ml/min). Catalytic reaction was performed at 300°C for 5h. Reaction products were periodically sampled and analyzed using a gas chromatograph (YL6100 GC, Younglin) equipped with a flame ionization detector. DB-5 (Agilent, 60m×0.32mm) capillary column was used for product separation. With α-K6As2W18O62, oxygen in neat (no solvent, solid phase), Time= 5h, T= 300 °C , Reagent/catalyst Choi, Jung Ho; Kang, Tae Hun; Bang, Yongju; Song, Ji Hwan; Song, In Kyu; Catalysis Communications; vol. 55; (2014); p. 29 - 33 View in Reaxys Further the synthesized complexes were subjected for catalytic study. The catalytic activity study toward the oxidation of benzyl alcohol was carried out in a 50 mL two necked RB flask fitted with a water cooled condenser. In a typical reaction, benzyl alcohol (3.11 mL, 30 mmol) and 30percent H2O2 (4.8mL, 45 mmol) were mixed and the reaction mixture was heated in an oil bath with continuous stirring. An appropriate amount of catalyst (30 mmol) was added to the hot mixture and the reaction was continued. The progress of the reaction was determined by analyzing the reaction mixture by withdrawing small aliquots of the reaction mixture at specific intervals of time. With C42H36CuN4O2 (2+)*2Cl(1-), dihydrogen peroxide, Time= 3h, T= 69.84 °C , Heating, Catalytic behavior Bushra Begum; Rekha; Vasantha Kumar; Lakshmi Ranganatha; Khanum, Shaukath Ara; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 15; (2014); p. 3559 - 3564 View in Reaxys With Au/CeO2–TiO2 NT, Time= 8h, UV-irradiation, Reagent/catalyst, chemoselective reaction Zhang, Yajun; Zhao, Guohua; Zhang, Yanan; Huang, Xiaofeng; Green Chemistry; vol. 16; nb. 8; (2014); p. 3860 - 3869 View in Reaxys With PtNPs/Ca-ZSM-5 in water, Time= 20h, T= 25 °C , Reagent/catalyst Hong, Yejiang; Yan, Xiaoqing; Liao, Xiaofeng; Li, Renhong; Xu, Shaodan; Xiao, Liping; Fan, Jie; Chemical Communications; vol. 50; nb. 68; (2014); p. 9679 - 9682 View in Reaxys With tert.-butylnitrite, (5R)-2,2,3,5-tetramethyl-5-(p-tolyl)imidazolidin-4-one-1-oxyl, hydrogen bromide, oxygen in acetonitrile, Time= 24h, T= 80 °C , p= 760.051Torr , Inert atmosphere, Reagent/catalyst, Pressure, Temperature Carbo Lopez, Marta; Royal, Guy; Philouze, Christian; Chavant, Pierre Y.; Blandin, Veronique; European Journal of Organic Chemistry; vol. 2014; nb. 22; (2014); p. 4884 - 4896 View in Reaxys With C22H28ClN4ORu(1+)*C24H20B(1-), caesium carbonate, methoxybenzene in dimethyl sulfoxide, T= 110 °C , Sealed tube, Catalytic behavior, Reagent/catalyst, Solvent Leigh, Vivienne; Carleton, Daniel J.; Olguin, Juan; Mueller-Bunz, Helge; Wright, L. James; Albrecht, Martin; Inorganic Chemistry; vol. 53; nb. 15; (2014); p. 8054 - 8060 View in Reaxys 2.4. Oxidation of alcohols

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

202/438

2018-03-11 22:07:32


In a typical procedure, a mixture of 0.1 g catalyst (VPO or VPO-Co), with a grain size of 200–230 mesh 15 mL acetonitrile and10 mmol of alcohol was stirred in a three-necked flask under nitro-gen atmosphere at 50C for 30 min. The stirring rate of the solutionwas set at 750 cycle/min. Then 10 mmol of the oxidant (TBHP) wasadded and the mixture was refluxed at 90C for 8 h under nitrogenatmosphere. After filtration, the solid was washed with ethanol andthe reaction mixture was analyzed by GC. A GC (Perkin Elmer Model8500) equipped with a flame ionization detector (FID) connectedto a 3percent OV-17 column with a length of 2.5 m and diameter of 1/8in. was used for product analysis. Stage 1: in acetonitrile, Time= 0.5h, T= 50 °C , Inert atmosphere, Green chemistry Stage 2: With tert.-butylhydroperoxide, Time= 8h, T= 90 °C , Inert atmosphere, Green chemistry, Temperature, Solvent Mahdavi, Vahid; Hasheminasab, Hamid Reza; Applied Catalysis A: General; vol. 482; (2014); p. 189 - 197 View in Reaxys 91 %Chromat.

2.4. Aerial oxidation of alcohols General procedure: Five milligram of r-RuO2/MWCNT (0.68 molpercent) was stirred with3 mL of toluene taken in a round-bottomed flask equipped with a condenser and a magnetic stirrer. The substrate (1 mmol) was added to the stirring solution and then the mixture was refluxed at 110°C under atmospheric pressure of air. The completion of the reaction was checked by GC. After the reaction, the r-RuO2/MWCNTwas separated out from the reaction mixture by simple centrifugation and the products and unconverted reactants were analyzed by GC without any purification. Selectivity of the product for each reaction was also calculated. With air, multiwall carbon nanotube supported on r-ruthenium dioxide nanoparticle in toluene, Time= 12h, T= 110 °C Gopiraman; Babu, S. Ganesh; Karvembu; Kim; Applied Catalysis A: General; vol. 484; (2014); p. 84 - 96 View in Reaxys

> 99 General Procedure %Chromat. General procedure: The DMSO (0.23 g; 3 mmol) was added dropwise to the stirred mixture of tosyl chloride (0.29 g; 1.5 mmol) and dry toluene (2.0 ml) at °C for 10 min and stirring was continued for another 15 min. A solution of alcohol (1.0 mmol) in dry toluene (1 ml) was then injected into the solution, and the temperature of the resulting mixture was brought to the ambient temperature. The mixture was stirred at ambient temperature for 90 min before triethylamine (0.30 g; 3.0 mmol) was added dropwisein ca. 10 min. Once the reaction was complete, the complex was treated with water (5 mL) and the mixture was extracted using toluene (25 mL). The organic layer was dried over sodium sulfate (Na2SO4). Samples of the reaction mixture were monitored by GC. The products of the reaction were determined via comparison with those of authentic samples of carbonyl compounds.[26] Full experimental data are available in the online supplemental section. Stage 1: With dimethyl sulfoxide, p-toluenesulfonyl chloride in toluene, Time= 1.5h, T= 0 - 20 °C Stage 2: With triethylamine in toluene, Time= 0.333333h, T= 20 °C , Solvent, chemoselective reaction Saadati, Fariba; Yousefi, Kobra; Synthetic Communications; vol. 44; nb. 19; (2014); p. 2818 - 2825 View in Reaxys 2.3.1. Selective oxidation of benzyl alcohol The selective oxidation reactions of benzyl alcohols were carried out in a 25 mL round-bottomed flask with magnetic stirrer.50 mg catalyst, benzyl alcohol (3 mmol) and ethanol (10 mL) wereadded into the flask which was open to ambient air. The suspension was stirred magnetically at 40C. During the reactions 0.5 mLspecimens were periodically collected, filtered and analyzed byGC (Shimadzu GC-2014) with a capillary column of Rtx-5, temperature of column range from 100 to 220C (6C/min), injectortemperature 260C and flame ionization detector. The productswere identified by comparison with known standard samples. in ethanol, Time= 7h, T= 40 °C , Catalytic behavior, Reagent/catalyst, Solvent, Temperature Cui, Wenjing; Xiao, Qi; Sarina, Sarina; Ao, Wulan; Xie, Mengxia; Zhu, Huaiyong; Bao, Zhaorigetu; Catalysis Today; vol. 235; (2014); p. 152 - 159 View in Reaxys Catalytic experiments General procedure: All reactions were carried out in a 25 ml round-bottom flask equipped with magnetic stirrer and a reflux condenser. In a typical reaction, a certain amount catalyst and 30percent aqueous hydrogen peroxide were added to the solution of 5 ml toluene and 0.43 g (4 mmol) benzyl alcohol, and the reaction was carried out at 80 °C for a certain amount of time. At regular intervals, samples from the reaction mixture were separated and analyzed by a HP sp-6890 gas chromatograph equipped with a capillary column (FFAP 30 m × 0.32 μm × 0.30 μm) and an FID

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

203/438

2018-03-11 22:07:32


detector with the internal standard method. Assignments of products were made by comparison with authentic samples. With dihydrogen peroxide in water, toluene, Time= 8h, T= 80 °C , Solvent Dong, Xinbo; Wang, Danjun; Li, Kebin; Zhen, Yanzhong; Hu, Huaiming; Xue, Ganglin; Materials Research Bulletin; vol. 57; (2014); p. 210 - 220 View in Reaxys With oxygen in toluene, Time= 0.583333h, T= 101 - 103 °C , p= 760.051Torr Ali, Roushown; Assal; Al-Warthan, Abdulrahman; Rafiq; Siddiqui; Asian Journal of Chemistry; vol. 25; nb. 9; (2013); p. 4815 - 4819 View in Reaxys 99 %Chromat.

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, C92H116Cu4N4O8*0.5CH2Cl2, potassium carbonate in water, Time= 22h, T= 70 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst, Temperature, Solvent Zhang, Guoqi; Proni, Gloria; Zhao, Sherry; Constable, Edwin C.; Housecroft, Catherine E.; Neuburger, Markus; Zampese, Jennifer A.; Dalton Transactions; vol. 43; nb. 32; (2014); p. 12313 - 12320 View in Reaxys With sodium hypochlorite, potassium bromide in dichloromethane, water, Time= 0.166667h, T= 5 °C , pH= 9, Kinetics Saito, Kei; Hirose, Koji; Okayasu, Teruyuki; Nishide, Hiroyuki; Hearn, Milton T. W.; RSC Advances; vol. 3; nb. 25; (2013); p. 9752 - 9756 View in Reaxys With dihydrogen peroxide, T= 20 - 75 °C Baig, R.B. Nasir; Nadagouda, Mallikarjuna N.; Varma, Rajender S.; Green Chemistry; vol. 16; nb. 9; (2014); p. 4333 - 4338 View in Reaxys 2.3. Aerobic oxidation General procedure: A solution of alcohol substrate (1.0 mmol) in CH2Cl2 (6mL) was prepared in a 50 mL long‐ necked, round‐bottom flask equipped with a ground glass elbow to be in contact with the atmosphere. Then silica gel‐supported TEMPO/NOx (0.5 g) was added, and after that the resulting mixture was magnetically stirred at room temperature and ambient pressure. TLC and GC (GC Agilent 6890N) were applied to monitor the reaction.When the reaction was over, the mixture was vacuum filtered to get the product, which was examined by 1H and 13C NMR analysis (Bruker spectrometer, 400 MHz) with CDCl3 as the solvent and TMS as internal standard. The area normalization method was applied to calculate conversion and selectivity of the oxidation from GC results. With oxygen in dichloromethane, Time= 2h, T= 20 °C , p= 760.051Torr , Reagent/catalyst Zhang, Hua; Fu, Luoling; Zhong, Hongmin; Chinese Journal of Catalysis; vol. 34; nb. 10; (2013); p. 1848 - 1854 View in Reaxys With oxygen, Time= 6h, T= 160 °C , Catalytic behavior, Temperature Li; Ji; Cadigan; Richards; Catalysis Science and Technology; vol. 4; nb. 8; (2014); p. 2520 - 2525 View in Reaxys With C40H32Cl2Fe2N10O, dihydrogen peroxide in acetonitrile, Time= 2h, T= 20 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst Szavuly, Miklos; Szilvasi, Szilvio D.; Csonka, Robert; Klesitz, Daniel; Speier, Gabor; Giorgi, Michel; Kaizer, Jozsef; Journal of Molecular Catalysis A: Chemical; vol. 393; (2014); p. 317 - 324 View in Reaxys With zinc aluminate, dihydrogen peroxide in acetonitrile, Time= 10h, T= 80 °C , Green chemistry, Catalytic behavior, Reagent/catalyst Ragupathi; Judith Vijaya; Narayanan; John Kennedy; Ramakrishna, Seeram; Chinese Journal of Catalysis; vol. 34; nb. 10; (2013); p. 1951 - 1958

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

204/438

2018-03-11 22:07:32


View in Reaxys With oxygen, Time= 4h, T= 120 °C , p= 900.09Torr , Reagent/catalyst, Solvent, Temperature, Time, Pressure Moreno, Ines; Dummer, Nicholas F.; Edwards, Jennifer K.; Alhumaimess, Mosaed; Sankar, Meenakshisundaram; Sanz, Raul; Pizarro, Patricia; Serrano, David P.; Hutchings, Graham J.; Catalysis Science and Technology; vol. 3; nb. 9; (2013); p. 2425 - 2434 View in Reaxys 90 %Chromat.

With Methyltrichlorosilane, dimethyl sulfoxide, triethylamine in dichloromethane, T= -78 - -20 °C , Swern Oxidation, Reagent/catalyst, Temperature Wang, Yuanxun; Wang, Chao; Sun, Jian; Synthetic Communications; vol. 44; nb. 20; (2014); p. 2961 - 2965 View in Reaxys With dihydrogen peroxide, potassium carbonate in water, Time= 6h, T= 80 °C , Green chemistry, Reagent/catalyst Zhang, Mingmei; Sun, Qian; Yan, Zaoxue; Jing, Junjie; Wei, Wei; Jiang, Deli; Xie, Jimin; Chen, Min; Australian Journal of Chemistry; vol. 66; nb. 5; (2013); p. 564 - 571 View in Reaxys With [(C6H2Me3)CH2N2(NMe)C2Ph]RuCl2 in (2)H8-toluene, Time= 24h, T= 110 °C , Inert atmosphere, Schlenk technique, Glovebox, Reagent/catalyst Bagh, Bidraha; McKinty, Adam M.; Lough, Alan J.; Stephan, Douglas W.; Dalton Transactions; vol. 43; nb. 34; (2014); p. 12842 - 12850 View in Reaxys With dihydrogen peroxide in water, acetonitrile, T= 80 °C , Solvent Bhat, Pooja B.; Inam, Fawad; Bhat, Badekai Ramachandra; ACS Combinatorial Science; vol. 16; nb. 8; (2014); p. 397 - 402 View in Reaxys

100 2.4. Typical procedure for oxidation of alcohols %Chromat. In a typical reaction, to a mixture of benzyl alcohol (1 mmol, 108 mg) and hybrid compound1-POM(Zn) (0.05 mmol) in acetonitrile (3 mL), aqueous H2O2 30percent (1 mL) wasadded. The reaction mixture was stirred in a preheated oil bath at reflux and the progressof the reaction was monitored by TLC or GC. After completion of the reaction, the mixturewas cooled to room temperature and the catalyst was filtered, washed with n-hexane,and dried at room temperature to recover the catalyst. The solvent was evaporated and thepure product was obtained by chromatography on a short column of silica gel. With C21H33N3O6*3H(1+)*(PW11ZnO39)(5-), dihydrogen peroxide in acetonitrile, Time= 4.5h, Reflux, Catalytic behavior, Reagent/catalyst, Concentration, Solvent, Temperature Nadealian, Zahra; Mirkhani, Valiollah; Yadollahi, Bahram; Moghadam, Majid; Tangestaninejad, Shahram; Mohammadpoor-Baltork, Iraj; Journal of Coordination Chemistry; vol. 66; nb. 7; (2013); p. 1264 - 1275 View in Reaxys > 99 With palladium in UiO-67, air in toluene, Time= 20h, T= 100 °C , Green chemistry %Chromat. Chen, Liyu; Chen, Huirong; Luque, Rafael; Li, Yingwei; Chemical Science; vol. 5; nb. 10; (2014); p. 3708 - 3714 View in Reaxys 50 %Chromat.

With 6-methyl-2-pyridinecarboxylic acid, dihydrogen peroxide, iron(II) acetate in water, acetonitrile, Time= 0.25h, T= 25 °C , chemoselective reaction Tanaka, Shinji; Kon, Yoshihiro; Nakashima, Takuya; Sato, Kazuhiko; RSC Advances; vol. 4; nb. 71; (2014); p. 37674 - 37678 View in Reaxys Tanaka, Shinji; Kon, Yoshihiro; Nakashima, Takuya; Sato, Kazuhiko; RSC Advances; vol. 40; nb. 71; (2014); p. 37674 - 37678 View in Reaxys With oxygen, potassium carbonate in toluene, Time= 2h, T= 80 °C , Reagent/catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

205/438

2018-03-11 22:07:32


Liu, Kun; Chen, Zhaoxiang; Hou, Zhiqiang; Wang, Yuanyuan; Dai, Liyi; Catalysis Letters; vol. 144; nb. 5; (2014); p. 935 - 942 View in Reaxys 99 %Chromat.

With 5-chloro-1-indanone, potassium carbonate in nitrobenzene, Time= 15h, T= 160 °C , Inert atmosphere, Green chemistry, Solvent Wang, Hu; Zhang, Jin; Cui, Yu-Ming; Yang, Ke-Fang; Zheng, Zhan-Jiang; Xu, Li-Wen; RSC Advances; vol. 4; nb. 65; (2014); p. 34681 - 34686 View in Reaxys Catalytic One-Pot Oxidation-Olefination; General Procedure General procedure: CuCl (2.5 mg, 0.025 mmol) and 1,10-phenanthroline (4.5 mg, 0.025mmol) were placed in a vessel and toluene (5 mL) was added. The resulting solution was stirred at r.t. until the solution became green and clear (5 to 10 min). Then K2CO3 (138 mg, 1 mmol) and EtO2CNH-NHCO2Et (18.5 mg, 0.125 mmol) were added. The solution was stirred at r.t. for another 10 min. Alcohol (0.60 mmol) was added, the mixture was heated at 90 °C under an O2 atmosphere (O2 balloon) until the reaction was completed (TLC analysis). The vessel was backfilled with N2, Ph3P (157.2 mg, 0.6 mmol), CuI (9.5mg, 0.05 mmol), LiOt-Bu (56.0 mg, 0.7 mmol), and tosylhydrazone (0.5 mmol) were added. The solution was stirred at 90 °C for 10 h. The solvent was removed under reduced pressure and the crude alkene was purified by flash chromatography (silica gel). With 1,10-Phenanthroline, diethyl hydrazodicarboxylate, oxygen, potassium carbonate, copper(l) chloride in toluene, Time= 1h, T= 90 °C Sha, Qiang; Wei, Yunyang; Synthesis (Germany); vol. 46; nb. 17; (2014); p. 2353 - 2361; Art.No: SS-2014-H0185OP View in Reaxys With pyridine, oxygen in water, Time= 6h, T= 65 °C , Time, Reagent/catalyst Sahoo, Mitarani; Parida; Applied Catalysis A: General; vol. 460-461; (2013); p. 36 - 45 View in Reaxys To a solution of alcohols (1.0 mmol), and catalyst (1.0 mg) inCH3CN (1 mL) was bubbled O2as the oxidant. The reaction was vigorously stirred at room temperature for a defined time. After the reaction, the product mixtures were analyzed by gas chromatogra-phy (GC). With 2H2O*Ca0.16*MnO2, oxygen in acetonitrile, Time= 2h, T= 20 °C , Green chemistry, Catalytic behavior, Solvent, Reagent/catalyst, pH-value Amini, Mojtaba; Najafpour, Mohammad Mahdi; Zare, Maryam; Amini, Emad; Journal of Molecular Catalysis A: Chemical; vol. 394; (2014); p. 303 - 308 View in Reaxys 2. Experimental General procedure: The oxidation experiments were carried out in glass liners loaded into a pressurized steel autoclave. For a typical run, 0.97 mmol of benzyl alcohol, 0.38 molpercent Au/Al2O3 (48 mg) and the solvents were measured into the glass liners. Additional base was added as a solid when only organic solvent was used. The autoclave was pressurized with 10 bar oxygen, heated to 100∘C and the mixtures were stirred with magnetic stirring at 1000 rpm. After the reaction the autoclave was depressurized and the mixtures were extracted twice with ethyl acetate. After the first extraction the reaction mixtures were acidified with HCl to transfer benzoate salt to the organic phase as benzoic acid. Centrifuge (3000 rpm, 2 min) was used to separate the phases. The products were analyzed using GC (Agilent 6890N) equipped with a HP-Innowax column and a flame ionization detector. Molar selectivity and conversion were determined using acetophenone as astandard. GC-MS was used to identify the products. With oxygen, potassium carbonate in toluene, Time= 0.25h, T= 100 °C , p= 7500.75Torr , Autoclave, Catalytic behavior, Reagent/catalyst Rautiainen, Sari; Simakova, Olga; Guo, Hongfan; Leino, Anne-Riikka; Kordas, Krisztian; Murzin, Dmitry; Leskelae, Markku; Repo, Timo; Applied Catalysis A: General; vol. 485; (2014); p. 202 - 206 View in Reaxys Catalytic test: aerobic oxidation of benzyl alcohol General procedure: The reaction was carried out in a batch-type reaction withstirring. Typically, the catalyst powder (50 mg), benzyl alcohol(2 mmol) and solvent (10 mL) were placed in a 50 mL round-bottomflask; a LED lamp (200

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

206/438

2018-03-11 22:07:32


W, 400–800 nm) was used as a light source.The system was filled with pure oxygen and sealed. A small amountof reactant was separated at regular intervals and quantitativelyanalyzed by GC. Afterward, the products were identified with aGC–MS spectrometer. For comparison, the reaction was performedsimultaneously in the dark under the same conditions With oxygen, T= 39.84 °C , p= 760.051Torr , Irradiation, Solvent, Reagent/catalyst Yu, Jing; Li, Jingyi; Wei, Huili; Zheng, Jianwei; Su, Haiquan; Wang, Xiaojing; Journal of Molecular Catalysis A: Chemical; vol. 395; (2014); p. 128 - 136 View in Reaxys in acetonitrile, Time= 12h, T= 24.84 °C , Irradiation Higashimoto, Shinya; Nakai, Yuta; Azuma, Masashi; Takahashi, Masanari; Sakata, Yoshihisa; RSC Advances; vol. 4; nb. 71; (2014); p. 37662 - 37668 View in Reaxys 2 Experiment In a typical experiment, tungsten oxide was used as catalyst from a commercial source and calcined at 500°C overnight, which is mixed with solvents including ILs. The following amounts of reactants, oxidant, solvents and catalysts were used unless otherwise specified: aromatic alcohol (1 g), hydrogen peroxide (30 wt.percent, 2g), ILs (0.2 g)/ toluene, benzene, or n-heptane (10 g), and tungsten oxide (0.01 g). The optimal amount of solvents was defined in supplementary material Fig. S1. The liquid phase reaction was conducted in a round-bottom flask with a reflux condenser and stirred magnetically. Reaction time was varying from 0.25 h to 24 h in the range of 323.15 K to 363.15 K. After the reaction, each phase of the post-reaction liquid mixture was extracted with ether (3×5 ml), and analyzed on an Agilent GC 7890A with an OV-17 column. The errors in the yield measurements were estimated to be 3percent. With dihydrogen peroxide, tungsten(VI) oxide, 1-butyl-3-methylimidazolium Tetrafluoroborate in water, toluene, Time= 8h, T= 49.99 - 89.99 °C , chemoselective reaction Chen, Long; Chen, Lifang; Ye, Yinmei; Qi, Zhiwen; Freund, Hannsjoerg; Sundmacher, Kai; Catalysis Communications; vol. 28; (2012); p. 143 - 146 View in Reaxys General procedure for oxidation reaction To a clean dry 10 mL round-bottomed flask containing 1 mmol of alcohol, 70percent TBHP (3 mmol) was added. This was followed by the addition of 10 molpercent of CeCrO3 catalyst. The mixture was sonicated for 5 min and then stirred at 90 °C. The progress of the reaction was monitored by gas chromatograph. After an appropriate time, the reaction mass was cooled and the catalyst was separated by filtration. The yields of the products were based on GC analysis. The products were identified by GC–MS analysis. With tert.-butylhydroperoxide, cerium chromite in dimethyl sulfoxide, Time= 6h, T= 90 °C , Sonication Burange, Anand S.; Jayaram, Radha V.; Shukla, Rakesh; Tyagi, Avesh K.; Catalysis Communications; vol. 40; (2013); p. 27 - 31 View in Reaxys With sodium hypochlorite, β‐cyclodextrin in water, Time= 24h, T= 50 °C , Reagent/catalyst Kang, Yan; Zhou, Lilin; Li, Xia; Yuan, Jinying; Journal of Materials Chemistry; vol. 21; nb. 11; (2011); p. 3704 3710 View in Reaxys With O40PW12 (3-)*3C40H48Cl4N4P2Ru(1+), water, oxygen, Time= 1.5h, T= 100 °C , p= 7500.75Torr , Ionic liquid, Catalytic behavior, Reagent/catalyst, Solvent, Time Wang, Sa-Sa; Zhang, Jing; Zhou, Cheng-Liang; Vo-Thanh, Giang; Liu, Ye; Catalysis Communications; vol. 28; (2012); p. 152 - 154 View in Reaxys With oxygen in toluene, Time= 4h, T= 150 °C , p= 7500.75Torr , Reagent/catalyst Ishida, Tamao; Onuma, Yuta; Kinjo, Kota; Hamasaki, Akiyuki; Ohashi, Hironori; Honma, Tetsuo; Akita, Tomoki; Yokoyama, Takushi; Tokunaga, Makoto; Haruta, Masatake; Tetrahedron; nb. 36; (2014); p. 6150 - 6155 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

207/438

2018-03-11 22:07:32


75 %Chromat.

General procedure for oxidation of alcohols to the correspondingcarbonyl compound with 30percent H2O2 General procedure: In a two necked flask equipped with a condenser, alcohol (1 mmol), 30percent H2O2 (5 mmol) were added to an equal mixture of water and acetonitrile (1.5 ml). Then, WO4PMO-IL (0.23 g, ~1.5 mol percent) was added to the above solution and the resulting mixture was stirred at 90 °C for requisite time. The progress of the reaction was monitored by gas chromatography using standard addition method. After completion of the reaction, the mixture was allowed to cool down to the room temperature and the catalyst was successfully isolated with centrifugation and washed with CH2Cl2 (310 ml) and dried under the vacuum for 12 h. Then, the collected CH2Cl2 phase was first washed with water, dried over Na2SO4, and the solvent was concentrated with evaporation under the reduced pressure to give the corresponding carbonyl compounds. The recovered catalyst was used in the recycling procedure in the same manner as reported in the first run. With dihydrogen peroxide in water, acetonitrile, Time= 12h, T= 90 °C , Green chemistry, Catalytic behavior, Solvent Karimi, Babak; Rostami, Fatemeh Bakhshandeh; Khorasani, Mojtaba; Elhamifar, Dawood; Vali, Hojatollah; Tetrahedron; nb. 36; (2014); p. 6114 - 6119 View in Reaxys With silver nitrate, Irradiation, chemoselective reaction Qamar; Elsayed; Alhooshani; Ahmed; Bahnemann; Catalysis Communications; vol. 58; (2014); p. 34 - 39 View in Reaxys

100 2.3 Oxidation of benzyl alcohol %Chromat. A test tube was filled with benzyl alcohol as the substrate, H5IO6 (periodic acid) as the oxidant, Pd(II) complex as the catalyst and CH3CN (5 ml) as the solvent in a typical reaction. This tube was heated under reflux conditions for the appropriate time. After this time, the sample was treated with diethyl ether (10 ml) and filtered. The reactions were monitored by gas chromatography With bis-[N-(pyridine-2-ylmethyl)-4-methoxybenzenesulfonamido]palladium, periodic acid in acetonitrile, Time= 2h, Reflux, Catalytic behavior, Reagent/catalyst, Time Dayan, Serkan; etin, Ahmet; Arslan, N. Burcu; Özpozan, Nilgün Kalayciolu; Özdemir, Namik; Dayan, Osman; Polyhedron; vol. 85; (2015); p. 748 - 753 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, Trametes versicolor laccase, oxygen in acetonitrile, Time= 24h, T= 20 °C , pH= 5, Enzymatic reaction, Reagent/catalyst, pH-value, Temperature, Solvent Bechi, Beatrice; Herter, Susanne; McKenna, Shane; Riley, Christopher; Leimkühler, Silke; Turner, Nicholas J.; Carnell, Andrew J.; Green Chemistry; vol. 16; nb. 10; (2014); p. 4524 - 4529 View in Reaxys Catalytic Tests General procedure: In order to get effective results for the catalytic oxidation of alcohols, the reaction conditions were altered by studying the effect of sample composition (0–0.5 Sr(II) loading), effect of reaction time (0.5–8 h), effect of oxidant (NaOCl, H2O2, TBHP), effect of solvents (acetonitrile, n-hexane, DMF) and effect of temperature (50–90 C). For this purpose,benzyl alcohol was chosen as the model substrate. With dihydrogen peroxide in acetonitrile, Time= 8h, T= 80 °C , Kinetics, Solvent, Reagent/catalyst, Time, Temperature Kumar, R. Thinesh; Vijaya, J. Judith; Kennedy, L. John; Journal of Nanoscience and Nanotechnology; vol. 13; nb. 4; (2013); p. 2953 - 2960 View in Reaxys With oxygen in neat (no solvent), T= 119.84 °C , p= 750.075Torr , Catalytic behavior, Reagent/catalyst Hutchings, Graham J.; Catalysis Today; vol. 238; (2014); p. 69 - 73 View in Reaxys With iodine, oxygen in ethyl acetate, Time= 10h, T= 20 °C Nagasawa, Yoshitomo; Matsusaki, Yoko; Hotta, Toshiyuki; Nobuta, Tomoya; Tada, Norihiro; Miura, Tsuyoshi; Itoh, Akichika; Tetrahedron Letters; vol. 55; nb. 48; (2014); p. 6543 - 6546

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

208/438

2018-03-11 22:07:32


View in Reaxys 2.3. The test of catalytic activity The oxidation of benzyl alcohol over heterogeneous Pd/TiO2 catalysts was performed in 10 mL bottle using molecular oxygen as oxidant. In each experiment, 50 mg catalyst was added into 46.3 mmol benzyl alcohol. The mixture was heated to 120 °C for 3 h with oxygen bubbled in at a flow rate of 20 mL/min. After the system cooled to room temperature, the catalyst was removed from the reaction mixture by centrifugation and the products were analyzed by GC. The catalyst was washed with ethanol and dichloromethane for 3 times and dried at 60 °C in vacuum for the next use. With oxygen, Time= 3h, T= 120 °C , Reagent/catalyst, Time Liu, Kun; Yan, Xiaojun; Zou, Peipei; Wang, Yuanyuan; Dai, Liyi; Catalysis Communications; vol. 58; (2014); p. 132 - 136 View in Reaxys 90 %Chromat.

With [Fe(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-diaminoethane)(μ-O)FeCl3], dihydrogen peroxide in acetonitrile, T= 20 °C , Reagent/catalyst, chemoselective reaction Kejriwal, Ambica; Biswas, Achintesh Narayan; Choudhury, Amitava; Bandyopadhyay, Pinaki; Transition Metal Chemistry; vol. 39; nb. 8; (2014); p. 909 - 915 View in Reaxys

> 99 With oxygen, potassium carbonate in water, Time= 1.1h, T= 25 °C , p= 760.051Torr , Reagent/catalyst, Solvent %Chromat. Mahyari, Mojtaba; Shaabani, Ahmad; Behbahani, Mohammad; Bagheri, Akbar; Applied Organometallic Chemistry; vol. 28; nb. 8; (2014); p. 576 - 583 View in Reaxys With C27H29CuN3O2, oxygen, potassium hydoxide in acetonitrile, Time= 5h, T= 20 °C , p= 750.075Torr , Catalytic behavior, Kinetics, Reagent/catalyst, Solvent Alaji, Zahra; Safaei, Elham; Chiang, Linus; Clarke, Ryan M.; Mu, Changhua; Storr, Tim; European Journal of Inorganic Chemistry; vol. 2014; nb. 35; (2014); p. 6066 - 6074 View in Reaxys With formic acid, oxygen, T= 79.84 °C , p= 3750.38Torr , Reagent/catalyst Mehri, Afef; Kochkar, Hafedh; Chemistry Letters; vol. 43; nb. 7; (2014); p. 1046 - 1048 View in Reaxys With tert.-butylhydroperoxide in acetonitrile, Time= 9h, T= 60 °C , Sonication Meng, Yuying; Voiry, Damien; Goswami, Anandarup; Zou, Xiaoxin; Huang, Xiaoxi; Chhowalla, Manish; Liu, Zhongwu; Asefa, Tewodros; Journal of the American Chemical Society; vol. 136; nb. 39; (2014); p. 13554 - 13557 View in Reaxys With tert.-butylhydroperoxide, μ-O-[Fe(meso-tetra(4-carboxyphenyl)porphyrin)]2 16(N,N-dimethylformamide) in acetonitrile, Time= 0.5h, T= 70 °C , Catalytic behavior, Kinetics, Reagent/catalyst Fidalgo-Marijuan, Arkaitz; Barandika, Gotzone; Bazn, Begoa; Urtiaga, Miren Karmele; Larrea, Edurne S.; Iglesias, Marta; Lezama, Luis; Arriortua, Mara Isabel; Dalton Transactions; vol. 44; nb. 1; (2015); p. 213 - 222 View in Reaxys With tert.-butylhydroperoxide in neat (no solvent), Time= 12h, T= 70 °C , Catalytic behavior, Reagent/catalyst Saikia, Mrinal; Bhuyan, Diganta; Saikia, Lakshi; New Journal of Chemistry; vol. 39; nb. 1; (2015); p. 64 - 67 View in Reaxys With Iron(III) nitrate nonahydrate, 2C27H56N2O2 (1+)*2Br(1-)*CH4N2O, oxygen in neat (no solvent), Time= 1.5h, T= 60 °C , Green chemistry, Catalytic behavior, Reagent/catalyst Zhang, Yuecheng; Lü, Fenglian; Cao, Xiaohui; Zhao, Jiquan; RSC Advances; vol. 4; nb. 76; (2014); p. 40161 40169 View in Reaxys With dihydrogen peroxide in acetonitrile, Time= 1.5h, T= 40 °C , Catalytic behavior

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

209/438

2018-03-11 22:07:32


Feng, Yan; Moschetta, Eric G.; Jones, Christopher W.; Chemistry - An Asian Journal; vol. 9; nb. 11; (2014); p. 3142 - 3152 View in Reaxys 2.1.6. Catalytic performance The catalytic performance experiments were performed in the Schlenk-flask under pure O2 sphere. NaOH (0.2 g) was dissolved into Benzyl alcohol (20 ml) before the addition of complex(2 mg). The blank experiment was assembled the same aboveexcept without adding the complex. The mixture resulted withO2 bubbling and stirring in 20 h was analysed by a ShimadzuGC–MS spectrometer and the production of benzyl aldehyde wasdetermined on a Anglient 1100 series HPLC equipment using thedetecting wavelength at 248 nm, with mobile phases CH3CN:H2-O = 45:55. The results are the average of three runs. With C44H52CuN4O2, oxygen, sodium hydroxide in neat (no solvent), Time= 20h, T= 20 °C , Schlenk technique, Catalytic behavior, Reagent/catalyst Shi, Huatian; Yin, Yegao; Inorganica Chimica Acta; vol. 421; (2014); p. 446 - 450 View in Reaxys 47.8 With oxygen, nitric acid, Time= 2h, T= 90 °C , Catalytic behavior, Reagent/catalyst %Chromat. Shi, Ying; Nabae, Yuta; Hayakawa, Teruaki; Kakimoto, Masa-Aki; RSC Advances; vol. 5; nb. 3; (2015); p. 1923 1928 View in Reaxys With gold-copper bimetallic nanoparticles supported on a titanium dioxide-nanobelt, T= 220 °C , Flow reactor, Catalytic behavior, Temperature, Reagent/catalyst Jia, Qinqin; Zhao, Dongfang; Tang, Bin; Zhao, Na; Li, Haidong; Sang, Yuanhua; Bao, Nan; Zhang, Xiaomei; Xu, Xiaohong; Liu, Hong; Journal of Materials Chemistry A; vol. 2; nb. 38; (2014); p. 16292 - 16298 View in Reaxys With oxygen in neat (no solvent), Time= 8h, T= 100 °C , p= 7500.75Torr , Reagent/catalyst Zhang, Hua; Zheng, Zhijie; Ma, Changjian; Zheng, Jinbao; Zhang, Nuowei; Li, Yunhua; Chen, Bing H.; ChemCatChem; vol. 7; nb. 2; (2015); p. 245 - 249 View in Reaxys With oxygen, potassium hydoxide in water, Time= 24h, T= 60 °C , Schlenk technique Deraedt, Christophe; Wang, Dong; Salmon, Lionel; Etienne, Laetitia; LabrugA re, Christine; Ruiz, Jaime; Astruc, Didier; ChemCatChem; vol. 7; nb. 2; (2015); p. 303 - 308 View in Reaxys With palladium on silica, oxygen, Catalytic behavior, Reagent/catalyst Li, Lei; Zhao, Jianbo; Yang, Jinyue; Fu, Teng; Xue, Nianhua; Peng, Luming; Guo, Xuefeng; Ding, Weiping; RSC Advances; vol. 5; nb. 7; (2015); p. 4766 - 4769 View in Reaxys With oxygen, Time= 8h, Irradiation, Reagent/catalyst Xu, Jie; Luo, Liufeng; Xiao, Guangrui; Zhang, Zizhong; Lin, Huaxiang; Wang, Xuxu; Long, Jinlin; ACS Catalysis; vol. 4; nb. 9; (2014); p. 3302 - 3306 View in Reaxys With dihydrogen peroxide in acetonitrile, Time= 0.0833333h, T= 120 - 125 °C , p= 12376.2Torr , Microwave irradiation Yepez, Alfonso; Lam, Frank L. Y.; Romero, Antonio A.; Kappe, C. Oliver; Luque, Rafael; ChemCatChem; vol. 7; nb. 2; (2015); p. 276 - 282 View in Reaxys With oxygen in toluene, Time= 0.5h, T= 105 °C , p= 760.051Torr Kim, Daehyun; Kim, Youngyeong; Jung, Kyungmun; Choi, Myong Yong; Park, Minjun; Lee, Byung Yang; Kim, Tae Hyun; Kwon, Ki-Young; Bulletin of the Korean Chemical Society; vol. 36; nb. 1; (2015); p. 1 - 2

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

210/438

2018-03-11 22:07:32


View in Reaxys 34 %Chromat.

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], sodium acetate in water, acetic acid, toluene, Time= 24h, T= 100 °C Gunay, Ahmet; Mantell, Mark A.; Field, Kathleen D.; Wu, Wenbo; Chin, Michael; Emmert, Marion H.; Catalysis Science and Technology; vol. 5; nb. 2; (2015); p. 1198 - 1205 View in Reaxys

80 %Chromat.

With ((n-C4H9)4N)4[SiW11O39(Si(CH2)3-NCHC14H9)2O], oxygen in acetonitrile, Time= 4h, T= 25 °C , Irradiation, Catalytic behavior, Reagent/catalyst, Solvent, Concentration Karimian, Davud; Yadollahi, Bahram; Mirkhani, Valiollah; Dalton Transactions; vol. 44; nb. 4; (2015); p. 1709 1715 View in Reaxys With oxygen, potassium carbonate in water, Time= 5.5h, T= 60 °C Senthilnathan, Jaganathan; Rao, Kodepelly Sanjeeva; Lin, Wan-Hsien; Ting, Jyh-Ming; Yoshimura, Masahiro; Journal of Materials Chemistry A; vol. 3; nb. 6; (2015); p. 3035 - 3043 View in Reaxys 2.3. Photocatalytic activity The photocatalytic activity of g-C3N4-based catalysts was investigated by the selective oxidation of benzyl alcohol with molecular O2 as oxidant under visible light irradiation. In a typical reaction, photocatalytic activity measurements were carried out in a 25 mL glass reaction flask fitted with a condenser and a magnetic stirrer. The visible-light source for the reaction was provided by a 300 W Xenon lamp with a 420 nm cut-off filter. Benzyl alcohol(1 mmol), the catalyst (50 mg) and trifluorotoluene (10 mL) were added to the flask reactor. O2 (pressure ca. 1 bar) collected in a rubber bag was connected to the system. The resulting system was then stirred at 100 °C for 4 h under visible light irradiation. After the reaction, the solid catalyst was separated by centrifugation. The liquid phase was analyzed by a gas chromatograph (VARIAN 450) with anisole as the internal standard. In addition, different radical scavengers were used in the controlled photoactivity experiments, which involved -butyl alcohol (TBA, as trapping agent for hydroxyl radical species), benzoquinone (BQ, as trapping agent for superoxide radical species) and ammonium oxalate (AO, as trapping agent for holes). The amount of the above scavengers was 1 mmol. With oxygen, Time= 4h, T= 100 °C , p= 750.075Torr , Irradiation, Green chemistry, Reagent/catalyst Zhang, Ligang; Liu, Di; Guan, Jing; Chen, Xiufang; Guo, Xingcui; Zhao, Fuhua; Hou, Tonggang; Mu, Xindong; Materials Research Bulletin; vol. 59; (2014); p. 84 - 92 View in Reaxys With IrCl(CO)(rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene), sodium hydride in toluene, Time= 3h, T= 110 °C , Schlenk technique, Inert atmosphere Olsen, Esben P. K.; Singh, Thishana; Harris, Pernille; Andersson, Pher G.; Madsen, Robert; Journal of the American Chemical Society; vol. 137; nb. 2; (2015); p. 834 - 842 View in Reaxys With gold supported on zirconium oxide, oxygen, caesium carbonate in 1,4-dioxane, Time= 12h, T= 25 °C , p= 760.051Torr , Catalytic behavior, Solvent Wei, Huili; Li, Jingyi; Yu, Jing; Zheng, Jianwei; Su, Haiquan; Wang, Xiaojing; Inorganica Chimica Acta; vol. 427; (2015); p. 33 - 40 View in Reaxys With oxygen in toluene, Time= 9.5h, T= 100 °C , p= 3750.38Torr , Catalytic behavior Leus; Concepcion; Vandichel; Meledina; Grirrane; Esquivel; Turner; Poelman; Waroquier; Van Speybroeck; Van Tendeloo; García; Van Der Voort; RSC Advances; vol. 5; nb. 29; (2015); p. 22334 - 22342 View in Reaxys With silver(0) nanoparticles supported on silica-coated ferrite in toluene, Time= 24h, Inert atmosphere, Reflux Bayat, Ahmad; Shakourian-Fard, Mehdi; Ehyaei, Nona; Mahmoodi Hashemi, Mohammad; RSC Advances; vol. 5; nb. 29; (2015); p. 22503 - 22509

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

211/438

2018-03-11 22:07:32


View in Reaxys With 1-methyl-1H-imidazole, [2,2]bipyridinyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [(2,2’-bipyridine)Cu(II) (OH)]2(trifluoromethanesulfonate)2, oxygen in acetonitrile, Time= 0.0833333h, T= 20 °C , p= 3750.38Torr , Flow reactor, Kinetics, Catalytic behavior, Concentration, Reagent/catalyst Vanoye, Laurent; Pablos, Mertxe; De Bellefon, Claude; Favre-Réguillon, Alain; Advanced Synthesis and Catalysis; vol. 357; nb. 4; (2015); p. 739 - 746 View in Reaxys 2.4 Catalytic performance test [25] General procedure: Oxidation of alcohols was typically carried out as follows: a suspension with 5 mg of the synthesized catalyst in acetonitrile (2 mL) was magnetically stirred, and the substrate namely alcohols (0.1 mmol) and PhIO (2.5 equiv.) was then added. The resulting mixture was kept at 60 °C with magnetical stirring for a set time. The selectivity and conversion were determined by GC analysis. With iodosylbenzene in acetonitrile, Time= 5h, T= 60 °C , Reagent/catalyst, Temperature, Time, Solvent, chemoselective reaction Yang, Zhi-Wang; Zhao, Xia; Li, Tian-Jing; Chen, Wen-Long; Kang, Qiao-Xiang; Xu, Xue-Qing; Liang, Xi-Xi; Feng, Ying; Duan, Huan-Huan; Lei, Zi-Qiang; Catalysis Communications; vol. 65; (2015); p. 34 - 40 View in Reaxys With tris(2,2'-bipyridine)ruthenium(II) perchlorate, pentaaminechlorocobalt(III) dichloride, [MnIV(O)(H2O)(N,N'-dimethyl-N,N'-bis(8-quinolyl)cyclohexane-1,2-diamine)]2+ in acetonitrile, Time= 2h, T= 24.84 °C , pH= 4, Irradiation, Inert atmosphere, Schlenk technique, Mechanism, Solvent, pH-value Wu, Xiujuan; Yang, Xiaonan; Lee, Yong-Min; Nam, Wonwoo; Sun, Licheng; Chemical Communications; vol. 51; nb. 19; (2015); p. 4013 - 4016 View in Reaxys 75 %Spectr.

Stage 1: With C24H20B(1-)*C5H12NO2 (1+)*C5H11NO2 in acetonitrile, Time= 0.166667h, T= 20 °C , Ley-Griffith Ru Oxidation Stage 2: With tetrapropylammonium perruthennate in acetonitrile, T= 20 °C , Ley-Griffith Ru Oxidation Moore, Peter W.; Mirzayans, Paul M.; Williams, Craig M.; Chemistry - A European Journal; vol. 21; nb. 9; (2015); p. 3567 - 3571 View in Reaxys

99 %Chromat.

With phosphomolybdic acid, oxygen, tetrabutylammonium acetate, palladium diacetate in ethyl acetate, Time= 1h, T= 100 °C , p= 22502.3Torr , Pressure Dornan, Laura M.; Muldoon, Mark J.; Catalysis Science and Technology; vol. 5; nb. 3; (2015); p. 1428 - 1432 View in Reaxys

61 %Spectr.

With tert.-butylhydroperoxide, palladium(II) trifluoroacetate in 1,2-dichloro-ethane, Time= 20h, T= 100 °C , Sealed tube Hou, Lekai; Chen, Xiangxiang; Li, Shuang; Cai, Suxian; Zhao, Yanxia; Sun, Meng; Yang, Xiao-Juan; Organic and Biomolecular Chemistry; vol. 13; nb. 14; (2015); p. 4160 - 4164 View in Reaxys

73 %Chromat.

With oxygen in toluene, Time= 4h, T= 150 °C , Reagent/catalyst Ishida, Tamao; Onuma, Yuta; Kinjo, Kota; Hamasaki, Akiyuki; Ohashi, Hironori; Honma, Tetsuo; Akita, Tomoki; Yokoyama, Takushi; Tokunaga, Makoto; Haruta, Masatake; Tetrahedron; vol. 70; nb. 36; (2014); p. 6150 6155 View in Reaxys

75 %Chromat.

4.5 General procedure for oxidation of alcohols to the corresponding carbonyl compound with 30percent H2O2 General procedure: In a two necked flask equipped with a condenser, alcohol (1 mmol), 30percent H2O2 (5mmol) were added to an equal mixture of water and acetonitrile (1.5ml). Then, WO4 =PMO-IL (0.23g, ∼1.5 molpercent) was added to the above solution and the resulting mixture was stirred at 90°C for requisite time. The progress of the reaction was monitored by gas chromatography using standard addition method. After completion of the reaction, the

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

212/438

2018-03-11 22:07:32


mixture was allowed to cool down to the room temperature and the catalyst was successfully isolated with centrifugation and washed with CH2Cl2 (3×10ml) and dried under the vacuum for 12 h. Then, the collected CH2Cl2 phase was first washed with water, dried over Na2SO4, and the solvent was concentrated with evaporation under the reduced pressure to give the corresponding carbonyl compounds. The recovered catalyst was used in the recycling procedure in the same manner as reported in the first run. With dihydrogen peroxide in water, acetonitrile, Time= 12h, T= 90 °C , Green chemistry, Solvent, chemoselective reaction Karimi, Babak; Rostami, Fatemeh Bakhshandeh; Khorasani, Mojtaba; Elhamifar, Dawood; Vali, Hojatollah; Tetrahedron; vol. 70; nb. 36; (2014); p. 6114 - 6119 View in Reaxys 100 With dihydrogen peroxide in water, Time= 0.5h, T= 45 °C , Green chemistry %Chromat. Nikbakht, Elham; Yadollahi, Bahram; Farsani, Mostafa Riahi; Inorganic Chemistry Communications; vol. 55; (2015); p. 135 - 138 View in Reaxys With formaldehyd, oct-1-ene, palladium diacetate, toluene-4-sulfonic acid, 1,2-bis[di(t-butyl)phosphinomethyl]benzene, Time= 20h, T= 100 °C , Inert atmosphere, Sealed tube, Catalytic behavior Liu, Qiang; Yuan, Kedong; Arockiam, Percia-Beatrice; Franke, Robert; Doucet, Henri; Jackstell, Ralf; Beller, Matthias; Angewandte Chemie - International Edition; vol. 54; nb. 15; (2015); p. 4493 - 4497; Angew. Chem.; nb. 15; (2015); p. 4575 - 4580,6 View in Reaxys 45 :A 20 mL Schlenk tube was charged with 9 mL (11 g) of BTFDIA obtained in Example 1, 0.15 g of benzyl alcohol,and 0.067 g of platinum oxide. Next, a gas bag filled with oxygen gas was connected to the Schlenk tube, and theatmosphere in the system was replaced with the oxygen gas. Then the mixture was allowed to react at 100°C for 42 hours.[0081] After the reaction, the reaction solution was subjected to GC analysis. It was found that the conversion ratio ofbenzyl alcohol was 62percent and benzaldehyde was produced at a selectivity of 100percent. No decomposition of BTFDIA wasfound in the GC analysis.BTFDIA, which is the fluorine-containing phosphate ester-amide of the present invention, has high oxidationresistance and is non-flammable. Therefore, when BTFDIA is used as a solvent, a highly dangerous oxidation reactioncan be performed safely. With platinum(IV) oxide, phosphoric acid bis(2,2,2-trifluoroethyl)diisopropylamide, oxygen, Time= 42h, T= 100 °C , Schlenk technique Patent; Tosoh F-Tech, Inc.; MIMURA, Hideyuki; FUJITA, Hiroaki; EGUCHI, Hisao; EP2832737; (2015); (A1) English View in Reaxys With oxygen, Time= 4h, T= 25 °C , p= 750.075Torr , Irradiation, Catalytic behavior, Reagent/catalyst Shen, Lijuan; Luo, Mingbu; Huang, Linjuan; Feng, Pingyun; Wu, Ling; Inorganic Chemistry; vol. 54; nb. 4; (2015); p. 1191 - 1193 View in Reaxys With 2,6-dimethylpyridine, sodium perchlorate in acetonitrile, T= 20 °C , Electrochemical reaction, Reagent/catalyst Song, Dandan; Chen, Qiguo; Tang, Danyang; Shen, Zhenlu; Li, Meichao; Ma, Chunan; Journal of the Electrochemical Society; vol. 162; nb. 4; (2015); p. H251 - H255 View in Reaxys 90 %Chromat.

General Procedure for the Al–Amidate-Catalyzed Oxidationof Alcohol Substrates by Pivaldehyde General procedure: An 8-mL vial equipped with a magnetic stirring bar was charged with pre-catalyst (0.025 mmol for 2; 0.05 mmol for 3 or 4) and toluene (4 mL). Alcohol (1.0 mmol) was added neat and the vial was capped with a Teflon-lined silicone septum, and the reaction was stirred for 0.5 h. Pivaldehyde (163 mL, 1.5 mmol or 325 mL,3.0 mmol) was added and the reaction was stirred at room temperature. After 3 h, an aliquot (100 mL) of the reaction was collected with a gas-tight syringe, loaded onto a plug of alumina, rinsed with methanol (15 mL), and analyzed directly by GC. The GC retention times of the products were confirmed with those of commercially available samples.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

213/438

2018-03-11 22:07:32


With [κ2-N,O-(t-BuNCOPh)]3Al, pivalaldehyde in toluene, Time= 3h, T= 20 °C , Oppenauer Oxidation, Reagent/catalyst Yeagle, Kevin P.; Hester, Darryl; Piro, Nicholas A.; Dougherty, William G.; Kassel, W. Scott; Graves, Christopher R.; Australian Journal of Chemistry; vol. 68; nb. 3; (2015); p. 357 - 365 View in Reaxys With 4 wtpercent of Pd on TiO2 in water, Time= 4h, T= 24.84 °C , UV-irradiation, Inert atmosphere, Reagent/catalyst Selvam, Kaliyamoorthy; Sakamoto, Hirokatsu; Shiraishi, Yasuhiro; Hirai, Takayuki; New Journal of Chemistry; vol. 39; nb. 4; (2015); p. 2856 - 2860 View in Reaxys > 99 With Au nanoparticles on nanocomposite consisting of 1,3,5-tris[(3-methylimidazolio)methyl]-2,4,6-trimethylbenzene %Chromat. tribromide and polyoxometalate anion [PV2Mo10O40]5-, air in water, Time= 3h, T= 75 °C , Schlenk technique, Green chemistry, Catalytic behavior, Temperature, Reagent/catalyst Huang, Zhijun; Li, Fengbo; Chen, Bingfeng; Yuan, Guoqing; Green Chemistry; vol. 17; nb. 4; (2015); p. 2325 2329 View in Reaxys 97 %Spectr.

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, [Cu(4-(2-methyl-2-phenylhydrazono)pentan-2-one-H)2] in toluene, Time= 18h, T= 60 °C , Sealed tube Gaona, Miguel Ángel; Montilla, Francisco; Álvarez, Eleuterio; Galindo, Agustín; Dalton Transactions; vol. 44; nb. 14; (2015); p. 6516 - 6525 View in Reaxys With dihydrogen peroxide in neat liquid, Time= 4h, T= 90 °C , Catalytic behavior, Reagent/catalyst, Temperature Meng, Ling-Yan; Zhai, Shang-Ru; Li, Shi; Zhai, Bin; An, Qing-Da; Song, Xiao-Wei; European Journal of Inorganic Chemistry; vol. 2014; nb. 14; (2014); p. 2337 - 2344 View in Reaxys

> 99 With dmap, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, CuICuII(2,2':6',2"-terpyridine)Cl3 in water, Time= 5h, T= %Chromat. 25 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst, Temperature, Solvent Zhang, Guoqi; Liu; Yang, Chengxiong; Li, Li; Golen, James A.; Rheingold, Arnold L.; European Journal of Inorganic Chemistry; vol. 2015; nb. 6; (2015); p. 939 - 947 View in Reaxys With dihydrogen peroxide in acetonitrile, Time= 0.025h, T= 150 °C , p= 12411.9Torr , Microwave irradiation, Reagent/catalyst, Temperature Ojeda, Manuel; Grau-Atienza, Aida; Campos, Rafael; Romero, Antonio A.; Serrano, Elena; Maria Marinas, Jose; García Martínez, Javier; Luque, Rafael; ChemSusChem; vol. 8; nb. 8; (2015); p. 1328 - 1333 View in Reaxys 2.3 Catalytic tests The gas-phase oxidation of alcohols is performed on a fixed-bed quartz tube reactor (600mm length by 14 mm inner diameter) under atmospheric pressure. Catalyst used in each test is 0.27 g (200–300 mesh). Other conditions are described in the previous literature elaborately [16]. The products are analyzed by Gas Chromatography (Shimadzu GC-2014 with a Rtx-5 column) as well as GC–MS (Agilent 6890 equipped with a HP-5 column). The content of benzoic acid, benzyl benzoate, toluene and COx is 0.5percent, 0.2percent, 0.1percent and 0.6percent respectively, so the selectivity of benzylaldehyde in our reaction conditions is higher than 98percent. The carbon balance in the liquid phase is 99percent and other products are nearly negligible. With oxygen, T= 280 °C , p= 760.051Torr , Gas phase, Catalytic behavior, Reagent/catalyst, Temperature, chemoselective reaction Liu, Kun; Chen, Zhaoxiang; Zou, Peipei; Wang, Yuanyuan; Dai, Liyi; Catalysis Communications; vol. 67; (2015); p. 54 - 58; Art.No: 4285 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

214/438

2018-03-11 22:07:32


With dmap, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, {[Cu(4-phenyl-2,6-bis(2'-pyrazinyl)pyridine) (NO3)2]*[Cu(4-phenyl-2,6-bis(2'-pyrazinyl)pyridine)(NO3)(H2O)NO3]}*H2O in acetonitrile, Time= 10h, T= 20 °C , Catalytic behavior, Reagent/catalyst, Solvent Yin, Zhiwei; Zhang, Guoqi; Phoenix, Tonya; Zheng, Shengping; Fettinger, James C.; RSC Advances; vol. 5; nb. 45; (2015); p. 36156 - 36166 View in Reaxys 77 %Chromat.

2.3 Catalytic test General procedure: A certain amount of catalysts (30mg) was placedin the two necked, round-bottomed flask and then1 mmol of alcohol and 10mL of solvent (acetonitrile,dichloromethane and ethanol) were introduced into thereactor through a septum. The catalytic experimentswere carried out under reflux and microwave conditionunder atmospheric pressure and magnetic stirring,using t-BHP 70percent, (0.3–0.5mL) or hydrogen peroxide30percent (0.3 mL) as oxidant. The progress of the reactionwas followed using thin layer chromatography. Afterthe reaction was run for the desired time, the productswere filtered out from the catalyst and then oxidationproducts were analyzed using a gas chromatograph witha GC capillary column HP 6890 and a FID detector. With tert.-butylhydroperoxide in acetonitrile, Time= 0.5h, T= 80 °C , p= 760.051Torr , Temperature, Reagent/catalyst, Solvent Shojaei, A. Fallah; Tabatabaeian; Zanjanchi; Moafi, H. Fallah; Modirpanah; Journal of Chemical Sciences; vol. 127; nb. 3; (2015); p. 481 - 491 View in Reaxys Oxidation of alcohols with a 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxyl–iodine system General procedure: A solution of 4 mmol of the alcohol in 12 mL of CH2Cl2 was added to a mixture of 12 mL of 0.1 mol/L sodium hydrogen carbonate solution, 2 g (8 mmol) of crystalline iodine, and 0.085 g (0.4 mmol) of 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxyl (I) (alcohol–nitroxyl radical molar ratio of 10 : 1). The mixture was stirred during 1 h at 20 °C, extracted with CH2Cl2 (2 × 15 mL), treated with 20 wt percent solution of sodium thiosulfate (to remove iodine), and analyzed. The reaction in the presence of tetraalkylammonium salts was performed similarly adding 4 or 0.4 mmol of the salt to the reaction mixture; the components molar ratios are given in the table. With 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl, iodine, sodium hydrogencarbonate in dichloromethane, Time= 1h, T= 20 °C Kashparova; Kashparov; Zhukova; Astakhov; Kagan; Russian Journal of General Chemistry; vol. 85; nb. 3; (2015); p. 567 - 570; Art.No: 1666; Zh. Obshch. Khim.; vol. 85; nb. 3; (2015); p. 403 - 406,4 View in Reaxys With Ni(PtBu 2NtBu 2)(CH3CN)2(BF4)2, triethylamine in acetonitrile, T= 21 °C , Electrochemical reaction, Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst Weiss, Charles J.; Wiedner, Eric S.; Roberts, John A. S.; Appel, Aaron M.; Chemical Communications; vol. 51; nb. 28; (2015); p. 6172 - 6174 View in Reaxys With tert.-butylhydroperoxide, oxygen in water, Time= 24h, T= 90 °C , Catalytic behavior, Temperature, Reagent/ catalyst Singh, Sukriti; Narkhede, Nilesh; Patel, Anjali; RSC Advances; vol. 5; nb. 46; (2015); p. 36270 - 36278 View in Reaxys General procedure: The oxidation of benzyl alcohol was carried out with different initial concentrations of the oxidant and substrate in 20percent aq. acetic acid medium with 1.0 x 10-2mol dm-3 H2SO4 at 308 K and rates were measured. With potassium dichromate, sulfuric acid, acetic acid in water, T= 34.84 °C , Kinetics, Thermodynamic data, Reagent/catalyst, Temperature, Concentration Bijudas; Oriental Journal of Chemistry; vol. 30; nb. 3; (2014); p. 1391 - 1396 View in Reaxys

60 %Spectr.

With dihydrogen peroxide in water, Time= 2h, T= 80 °C , Sealed tube, Catalytic behavior, Time

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

215/438

2018-03-11 22:07:32


Lee, Li-Chen; Xiao, Chaoxian; Huang, Wenyu; Zhao, Yan; New Journal of Chemistry; vol. 39; nb. 4; (2015); p. 2459 - 2466 View in Reaxys With sodium hypochlorite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium bromide in dichloromethane, Time= 0.0166667h, T= 10 °C , pH= Ca. 9.1, Green chemistry, Reagent/catalyst Feng, Linbin; Wang, Jianli; Chen, Liang; Lu, Meizhen; Zheng, Zhi; Jing, Ren; Chen, Hualiang; Shen, Xianbo; ChemCatChem; vol. 7; nb. 4; (2015); p. 616 - 624 View in Reaxys With α-[Cu(1-methylimidazole)4]V2O6, dihydrogen peroxide in chlorobenzene, Time= 8h, T= 120 °C , Catalytic behavior, Reagent/catalyst Li, Jikun; Huang, Xianqiang; Yang, Song; Xu, Yanqing; Hu, Changwen; Crystal Growth and Design; vol. 15; nb. 4; (2015); p. 1907 - 1914 View in Reaxys 95 %Chromat.

With tetra-O-acetyl riboflavin, hydrogenchloride, scandium tris(trifluoromethanesulfonate) in water, acetonitrile, Time= 2.5h, UV-irradiation Mühldorf, Bernd; Wolf, Robert; Chemical Communications; vol. 51; nb. 40; (2015); p. 8425 - 8428 View in Reaxys

99 %Chromat.

With potassium carbonate in o-xylene, Time= 7h, T= 20 °C , p= 760.051Torr , Green chemistry, Catalytic behavior, Solvent, Reagent/catalyst Shaabani, Ahmad; Hezarkhani, Zeinab; Shaabani, Shabnam; RSC Advances; vol. 4; nb. 110; (2014); p. 64419 64428 View in Reaxys

257 μmol

With oxygen, Time= 15h, p= 760.051Torr , Irradiation, Catalytic behavior Nishino, Yuri; Tanaka, Atsuhiro; Hashimoto, Keiji; Kominami, Hiroshi; Chemistry Letters; vol. 44; nb. 4; (2015); p. 518 - 520 View in Reaxys With oxygen in toluene, Time= 16h, Darkness, Sealed tube, Irradiation, Catalytic behavior, Reagent/catalyst Li, Ang; Zhang, Peng; Chang, Xiaoxia; Cai, Weiting; Wang, Tuo; Gong, Jinlong; Small; vol. 11; nb. 16; (2015); p. 1892 - 1899 View in Reaxys With [Os(p-cymene)Cl(1-[2-(methylthio)phenyl]-4-phenyl-1H-1,2,3-triazole)]*hexafluorophosphate, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Hohloch, Stephan; Hettmanczyk, Lara; Sarkar, Biprajit; European Journal of Inorganic Chemistry; vol. 2014; nb. 20; (2015); p. 3164 - 3171 View in Reaxys With dihydrogen peroxide in acetonitrile, Time= 10h, T= 70 °C , Darkness Ede, Sivasankara Rao; Ramadoss, Ananthakumar; Nithiyanantham; Anantharaj; Kundu, Subrata; Inorganic Chemistry; vol. 54; nb. 8; (2015); p. 3851 - 3863 View in Reaxys Oxidation Procedure General procedure: Alcohol (1 mmol) was added to amixture of BAIB (1.1 mmol) and bromide anions (0.2 mmol) inEtOAc (1.5 mL), and the mixture was stirred at room temperaturefor 24 h. The solvent was removed under reduced pressureand the crude product was checked by 1H NMR spectroscopy. Incase of p-nitrobenzyl alcohol, anisole, and p-chlorobenzylalcohol oxidations, the residue was purified by chromatography[PE to separate iodobenzene and PE– EtOAc (10:1) to separatethe corresponding aldehyde]. With [bis(acetoxy)iodo]benzene, tetrabutylammomium bromide in dichloromethane, Time= 24h, T= 20 °C Salvo, Anna Maria Pia; Campisciano, Vincenzo; Beejapur, Hazi Ahmad; Giacalone, Francesco; Gruttadauria, Michelangelo; Synlett; vol. 26; nb. 9; (2015); p. 1179 - 1184

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

216/438

2018-03-11 22:07:32


View in Reaxys With 1-methyl-1H-imidazole, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper(I) bromide in water, acetonitrile, Time= 3h, T= 20 °C , Inert atmosphere, Catalytic behavior, Reagent/catalyst Sand, Henning; Weberskirch, Ralf; RSC Advances; vol. 5; nb. 48; (2015); p. 38235 - 38242 View in Reaxys 98 %Chromat.

With Pd-supported graphene oxide nanocomposite, air, pluronic P123 surfactant in water, Time= 3.5h, T= 80 °C , Solvent, Reagent/catalyst Rostamnia, Sadegh; Doustkhah, Esmail; Karimi, Ziba; Amini, Soraya; Luque, Rafael; ChemCatChem; vol. 7; nb. 11; (2015); p. 1678 - 1683 View in Reaxys With [Rh(OH)(cod)]2, (1R,5R)-1,5-dimethyl-2-methylene-6-oxabicyclo[3.2.1]octan-8-one, (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl in benzene-d6, T= 80 - 85 °C , Inert atmosphere Masarwa, Ahmad; Weber, Manuel; Sarpong, Richmond; Journal of the American Chemical Society; vol. 137; nb. 19; (2015); p. 6327 - 6334 View in Reaxys Typical procedure for the one-pot conversion of 4-nitrobenzyl alcohol to 1-dichloromethyl-4-nitrobenzene using ClPPh2 and DDQ: General procedure: 4-Nitrobenzyl alcohol (0.153 g, 1 mmol) was added to a flask containing DDQ(0.54 g, 2 mmol) in CH2Cl2 (5 mL) at room temperature. ClPPh2 (0.45 mL, 2.5 mmol) wasadded to the reaction mixture after TLC showed the complete conversion of this alcohol toits corresponding aldehyde and stirring was continued for 8 h. The solvent was evaporated.1-Dichloromethyl-4-nitrobenzene was obtained after short column chromatography of thecrude mixture on silica gel 60 (0.063–0.200 mm) using petroleum ether-ethyl acetate (40:1)as eluent in 90percent yield, 0.186 g; With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane, T= 20 °C Aghapour, Ghasem; Mohamadian, Samaneh; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 190; nb. 4; (2015); p. 520 - 527 View in Reaxys With 2C24H12N4O4*8C5H9NO*3Zn(2+)*4F(1-)*6H(1+)*2O40PW12 (3-) in acetonitrile, Time= 11h, T= 20 °C , Irradiation, Green chemistry, Reagent/catalyst Liao, Jian-Zhen; Zhang, Hai-Long; Wang, Sa-Sa; Yong, Jian-Ping; Wu, Xiao-Yuan; Yu, Rongmin; Lu, CanZhong; Inorganic Chemistry; vol. 54; nb. 9; (2015); p. 4345 - 4350 View in Reaxys With methoxybenzene in toluene, Time= 24h, T= 100 °C , Mechanism, Reagent/catalyst, Temperature, Time Poreddy, Raju; Engelbrekt, Christian; Riisager, Anders; Catalysis Science and Technology; vol. 5; nb. 4; (2015); p. 2467 - 2477 View in Reaxys

> 99 With 1-methyl-1H-imidazole, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, 2-[4-(2-pyridyl)-1,2,3-triazol-1-yl]pyri%Chromat. dine, copper(II) bis(trifluoromethanesulfonate), copper in acetonitrile, Time= 3h, T= 20 °C , Reagent/catalyst Thongkam, Pech; Jindabot, Sudarat; Prabpai, Samran; Kongsaeree, Palangpon; Wititsuwannakul, Taveechai; Surawatanawong, Panida; Sangtrirutnugul, Preeyanuch; RSC Advances; vol. 5; nb. 69; (2015); p. 55847 55855 View in Reaxys 98 %Chromat.

2.3 General procedure for alcohol oxidation General procedure: In a typical reaction, a mixture of benzyl alcohol (0.2mL, 2mmol) and the magnetic catalyst (0.03g) was loaded in a two-neck round bottom flask. Hydrogen peroxide (30percent, 6mmol) was then added dropwise to the mixture and stirred under organic-solvent-free condition at room temperature. The progress of reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the catalyst was separated by an external magnet and the liquid organic product was analysed by an Agilent gas chromatograph 6890 equipped with a HP-5 capillary column. Dodecane was used as the internal standard to calculate benzyl alcohol conversion and benzaldehyde selectivity.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

217/438

2018-03-11 22:07:32


With dihydrogen peroxide, Time= 0.166667h, T= 20 °C , Catalytic behavior, Solvent Heidarnezhad, Arash; Zamani, Farzad; Catalysis Communications; vol. 60; (2015); p. 105 - 109 View in Reaxys 97 %Chromat.

Typical procedure for catalytic oxidation of alcohols General procedure: The catalytic reactions were carried out in a 10-mL roundbottomflask equipped with a magnetic stirring bar and areflux condenser. The Co-STPOM catalyst (0.001 mmol),water (3 mL), alcohol (1 mmol), and H2O2 (9.8 mmol)were charged in the reaction vessel. The reaction was carriedout at reflux and progress of the reaction was detectedby TLC and GC. After completion of the reaction, organicproduct was isolated by ethyl acetate (3 × 2 mL) and theorganic layer was analyzed by gas chromatography or 1HNMR. Products were assigned by comparing experimentaldata with authentic samples. With 10Na(1+)*4Co(2+)*2O34PW9 (9-), dihydrogen peroxide in water, Time= 3h, Reflux, Green chemistry Farsani, Mostafa Riahi; Assady, Elham; Jalilian, Fariba; Yadollahi, Bahram; Rudbari, Hadi Amiri; Journal of the Iranian Chemical Society; vol. 12; nb. 7; (2015); p. 1207 - 1212; Art.No: 583 View in Reaxys General procedure of the catalytic reaction General procedure: 1 mmol benzyl alcohol, 1.375 g catalyst, 20 ml water, and15 ml ether were mixed in a flask (50 ml). A balloon wasused to introduce O2 at ambient pressure, keeping the temperatureat 30 °C for a given time. At the end of the reaction,a few drops of diluted HCl solution (1 mol/L) wereadded to the reaction system, and the pH of water wasadjusted to 3–4. After stirring, the catalyst was transferredinto the water and the upper organic layer was isolated forGC analysis. With oxygen in diethyl ether, water, Time= 15h, T= 30 °C , p= 760.051Torr , Solvent, Concentration, chemoselective reaction Zhu, Yaoqin; Xu, Jia; Lu, Ming; Journal of the Iranian Chemical Society; vol. 12; nb. 7; (2015); p. 1213 - 1219; Art.No: 584 View in Reaxys With 2-hydroxy-N,N,N-trimethyl ethanaminium peroxydisulfate in neat (no solvent), Time= 0.5h, T= 70 °C , Green chemistry Gadilohar, Balu L.; Kumbhar, Haribhau S.; Shankarling, Ganapati S.; New Journal of Chemistry; vol. 39; nb. 6; (2015); p. 4647 - 4657 View in Reaxys

75 %Chromat.

With tert.-butylhydroperoxide, C16H16N4 (2-)*2Cu(1+) in water, Time= 0.5h, T= 120 °C , Microwave irradiation, Catalytic behavior, Reagent/catalyst, Time Timokhin, Ivan; Pettinari, Claudio; Marchetti, Fabio; Pettinari, Riccardo; Condello, Francesca; Galli, Simona; Alegria, Elisabete C. B. A.; Martins, Luísa M.D.R.S.; Pombeiro, Armando J. L.; Crystal Growth and Design; vol. 15; nb. 5; (2015); p. 2303 - 2317 View in Reaxys

98 %Chromat.

With chitosan/polyacrylamide entrapped silver nanoparticles in para-xylene, Time= 12h, T= 130 °C , Inert atmosphere Kurhe, Deepak K.; Fernandes, Thomson A.; Deore, Tushar S.; Jayaram, Radha V.; RSC Advances; vol. 5; nb. 58; (2015); p. 46443 - 46447 View in Reaxys With oxygen in neat (no solvent), Time= 10h, T= 120 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst Nepak, Devadutta; Srinivas, Darbha; RSC Advances; vol. 5; nb. 59; (2015); p. 47740 - 47748 View in Reaxys 2.3.1 Aerobic alcohol oxidation General procedure: The oxidation reaction of alcohol was performed according to the following sequence: PdOSNP (40mg, Pd=3.3molpercent of substrate) with toluene (2mL) and alcohol (0.2mmol) was charged in the glass tube reactor. The mixture was stirred at 1000rpm using magnetic stirrer bar under atmospheric pressure of molecular oxygen at 90°C. The conversion and yield were obtained by taking the sample from a mixture at regular intervals and

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

218/438

2018-03-11 22:07:32


analyzing them with gas chromatography (GC, Younglin GC-6500) and at the end by GC-mass spectroscopy (GC– MS, JEOL GCMS-BU20) to compare with the standard samples. GC analyses were carried out using a flame ionization detector (FID) equipped with a DB-WAX capillary column. GC–MS were recorded at an ionization voltage of 70eV equipped with a DB-WAX capillary column (internal diameter=0.25mm, length=30m). With oxygen in toluene, Time= 6h, T= 90 °C , p= 760.051Torr Seok, Seunghwan; Hussain, Muhammad Asif; Park, Kyun Joo; Kim, Jung Won; Kim, Do Hyun; Ultrasonics Sonochemistry; vol. 28; (2016); p. 178 - 184; Art.No: 2954 View in Reaxys > 99 With oxygen in toluene, Time= 12h, T= 24.84 °C , p= 760.051Torr , Irradiation %Chromat. Sakamoto, Hirokatsu; Ohara, Tomoyuki; Yasumoto, Naoki; Shiraishi, Yasuhiro; Ichikawa, Satoshi; Tanaka, Shunsuke; Hirai, Takayuki; Journal of the American Chemical Society; vol. 137; nb. 29; (2015); p. 9324 - 9332 View in Reaxys With sodium hypochlorite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium hydrogencarbonate, potassium bromide in dichloromethane, water, Time= 0.208333h, T= 0 °C , Solvent Ghislieri, Diego; Gilmore, Kerry; Seeberger, Peter H.; Angewandte Chemie - International Edition; vol. 54; nb. 2; (2015); p. 678 - 682; Angew. Chem.; vol. 127; nb. 2; (2015); p. 688 - 692 View in Reaxys With potassium hydrogencarbonate, potassium bromide in dichloromethane, Time= 0.05h, T= 0 °C , Catalytic behavior, Reagent/catalyst Huangfu, Ying; Sun, Qi; Pan, Shuxiang; Meng, Xiangju; Xiao, Feng-Shou; ACS Catalysis; vol. 5; nb. 3; (2015); p. 1556 - 1559 View in Reaxys With dihydrogen peroxide in neat (no solvent), Time= 2.33333h, T= 20 °C , Green chemistry, Reagent/catalyst Bhat, Pooja B.; Bhat, Badekai Ramachandra; New Journal of Chemistry; vol. 39; nb. 6; (2015); p. 4933 - 4938 View in Reaxys With pyridine, oxygen in water, Time= 3h, T= 60 °C , p= 760.051Torr Rana, Surjyakanta; Maddila, Suresh; Jonnalagadda, Sreekantha B.; Catalysis Science and Technology; vol. 5; nb. 6; (2015); p. 3235 - 3241 View in Reaxys With 1-methyl-1H-imidazole, tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate, C34H40N7O4, oxygen in acetonitrile, Time= 3h, T= 20 °C , Catalytic behavior, Reagent/catalyst Prathap, Kaniraj Jeya; Maayan, Galia; Chemical Communications; vol. 51; nb. 55; (2015); p. 11096 - 11099 View in Reaxys 100 With dihydrogen peroxide in acetonitrile, Time= 0.75h, Reflux, Catalytic behavior, Reagent/catalyst, Solvent %Chromat. Assady, Elham; Yadollahi, Bahram; Riahi Farsani, Mostafa; Moghadam, Majid; Applied Organometallic Chemistry; vol. 29; nb. 8; (2015); p. 561 - 565 View in Reaxys With Na(x)TaO(y)*(n)H2O, oxygen in toluene, Time= 8h, T= 24.84 °C , p= 760.051Torr , UV-irradiation, Catalytic behavior, Reagent/catalyst, Temperature Su, Yiguo; Lang, Junyu; Du, Chunfang; Bian, Fenggang; Wang, Xiaojing; ChemCatChem; vol. 7; nb. 16; (2015); p. 2437 - 2441 View in Reaxys With oxygen, T= 280 °C , p= 760.051Torr , Flow reactor, Activation energy, Temperature, Reagent/catalyst, Concentration Zhao, Guofeng; Wu, Xin-Ping; Chai, Ruijuan; Zhang, Qiaofei; Gong, Xue-Qing; Huang, Jun; Lu, Yong; Chemical Communications; vol. 51; nb. 27; (2015); p. 5975 - 5978

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

219/438

2018-03-11 22:07:32


View in Reaxys With C30H24F3FeN5O(2+) in water, T= 25 °C , pH= 5.5, Kinetics, Reagent/catalyst Chantarojsiri, Teera; Sun, Yugie; Long, Jeff R.; Chang, Christopher J.; Inorganic Chemistry; vol. 54; nb. 12; (2015); p. 5879 - 5887 View in Reaxys 2.3. Catalytic studies Liquid phase oxidation of benzyl alcohol was carried out in a batch reactor at atmospheric pressure. In a typical experiment, 0.1 g of the zeolite catalyst (typically, 66MOR(AT-3.0)), 20 mmol benzyl alcohol (BzOH), 25 mmol aqueous tert-butyl hydroperoxide (TBHP) as the oxidant and 10 ml of acetonitrile as the solvent wereplaced in a round-bottom flask equipped with a water condenser and a thermometer. The resulting mixture was kept at 90 °C for 4 h under stirring, and then cooled to room temperature. The oxidized products after the catalytic reaction were separated by centrifugation. The products were analyzed in a gas chromatograph with a flame ionization detector, using a SGE BPX70 capillary column (70percent cyanopropyl polysilphenylene-siloxane, 30 m 0.53 mm 0.50 lm) and N2 as the carrier gas. With tert.-butylhydroperoxide in [(2)H6]acetone, Time= 3h, T= 90 °C , p= 760.051Torr , Catalytic behavior, Temperature, Reagent/catalyst Narayanan; Vijaya, J. Judith; Sivasanker; Alam, Mahboob; Tamizhdurai; Kennedy, L. John; Polyhedron; vol. 89; (2015); p. 289 - 296 View in Reaxys 84 %Chromat.

Catalytic oxidation General procedure: A solution of ruthenium complex (4) (0.01 mmol) in 20 cm3 CH2Cl2 was added to the solution of substrate (1 mmol) and NMO (3 mmol). The solution mixture was refluxed for 3-8 h. The filtrate obtained was evaporated under reduced pressure and the residual mass was dissolved in a mixture of ethyl acetate/hexane (1:4) and then passed through a short column of silica gel using hexane/ethyl acetate (4:1) as eluent. Removal of solvent and usual workup gave the corresponding aldehydes or ketones, which were identified by GC and 1HNMR. With C82H70As4Cl4N6Ru2S2, 4-methylmorpholine N-oxide in dichloromethane, T= 40 °C Mohamed Subarkhan; Ramesh; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 138; (2015); p. 264 - 270 View in Reaxys With oxygen, copper dichloride in acetone, Time= 1h, T= 25 °C , Irradiation, Catalytic behavior, Solvent, Time, Temperature, Wavelength, Reagent/catalyst Meng, Chao; Yang, Kai; Fu, Xianzhi; Yuan, Rusheng; ACS Catalysis; vol. 5; nb. 6; (2015); p. 3760 - 3766 View in Reaxys With iron(III) chloride hexahydrate, tris(p-chlorophenyl)methanol, Time= 1h, T= 60 °C , Microwave irradiation, Temperature Wang, Xiaoyu; Du, Chuan; Shi, Hui; Pang, Yadong; Jin, Shengfei; Hou, Yuqian; Wang, Yanshi; Peng, Xiaoshi; Xiao, Jianyong; Liu, Yang; Liu, Yongxiang; Cheng, Maosheng; Tetrahedron; vol. 71; nb. 38; (2015); p. 6744 6748 View in Reaxys With tert.-butylhydroperoxide, C96H56Fe2N8O17*16C3H7NO, Catalytic behavior, Reagent/catalyst Fidalgo-Marijuan, Arkaitz; Amayuelas, Eder; Barandika, Gotzone; Bazán, Begoña; Urtiaga, Miren Karmele; Arriortua, María Isabel; Molecules; vol. 20; nb. 4; (2015); p. 6683 - 6699 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Irradiation Yuan, Shuai; Liu, Tian-Fu; Feng, Dawei; Tian, Jian; Wang, Kecheng; Qin, Junsheng; Zhang, Qiang; Chen, Ying-Pin; Bosch, Mathieu; Zou, Lanfang; Teat, Simon J.; Dalgarno, Scott J.; Zhou, Hong-Cai; Chemical Science; vol. 6; nb. 7; (2015); p. 3926 - 3930 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

220/438

2018-03-11 22:07:32


With 6C16H36N(1+)*2Zn(2+)*4Na(1+)*[Bi2Zn2(ZnW9O34)2](14-), urea hydrogen peroxide adduct in acetonitrile, Time= 4.5h, T= 70 °C Amanchi, Srinivasa Rao; Khenkin, Alexander M.; Diskin-Posner, Yael; Neumann, Ronny; ACS Catalysis; vol. 5; nb. 6; (2015); p. 3336 - 3341 View in Reaxys Catalytic reaction General procedure: The alcohol aerobic oxidations were performed in a bath-type reactor under oxygen (101.3 kPa). In a typical reaction, a 25 mL three-necked round-bottomed flask containing alcohol (3 mmol), K2CO3 (1 mmol), a certain amount of catalyst, and p-xylene (10 mL) was kept at 120 °C, with magnetic stirring (1200 r/min). Oxygen was flowed into the suspension at a rate of 20 mL/min. The liquid products were obtained by centrifugation, and then analyzed using a gas chromatograph(GC-1690, Hangzhou Jiedao Technology Instrument Co., Ltd) equipped with a flame ionization detector (FID) and an ATOV-1701 capillary column, to determine the conversion and selectivity. Gas chromatography-mass spectrometry (GC-MS;450GC-320MS, Varian) was used to confirm the product compositions With oxygen, potassium carbonate in para-xylene, Time= 1.5h, T= 120 °C , p= 759.826Torr , Reagent/catalyst, Time Tian, Tao; Liu, Ying; Zhang, Xungao; Chinese Journal of Catalysis; vol. 36; nb. 8; (2015); p. 1358 - 1364 View in Reaxys 2.2. Typical procedure for the catalytic oxidation of alcohols General procedure: In a typical oxidation experiment, substrate (10 mmol), catalyst (as described in Table 1) and acetonitrile (20 mL) were added to a 25-mL three-neck round bottom glass reactor,which was fitted with a magnetic stirrer and O2 inlet tube. The reaction was performed at 25 °C in a water bath with magnetic stirring. O2 was introduced into the reactor at a constant flow rate (5 mL/min). A household w-filament bulb (250 W) and 420-nm cut-off filter were placed ~10 cm from the reactor as a visible-light source. To carry out the reaction in the dark, the glass reactor was covered with aluminum foil. After completion of the reaction, toluene was added to the mixture as an internal standard. Then, mpg-C3N4 was removed by filtration and thereaction mixture was injected into the GC for analysis. With N -hydroxyphthalimide, oxygen in acetonitrile, Time= 28h, T= 25 °C , p= 760.051Torr , Irradiation, Green chemistry, Reagent/catalyst Zhang, Pengfei; Deng, Jiang; Mao, Jianyong; Li, Haoran; Wang, Yong; Chinese Journal of Catalysis; vol. 36; nb. 9; (2015); p. 1580 - 1586 View in Reaxys With C19H18CrN4O3 (2+)*2BF4 (1-) in acetonitrile, T= -40.16 °C , Kinetics Kotani, Hiroaki; Kaida, Suzue; Ishizuka, Tomoya; Sakaguchi, Miyuki; Ogura, Takashi; Shiota, Yoshihito; Yoshizawa, Kazunari; Kojima, Takahiko; Chemical Science; vol. 6; nb. 2; (2015); p. 945 - 955 View in Reaxys With oxygen in neat (no solvent), Time= 0.5h, T= 120 °C , p= 750.075Torr , Catalytic behavior, Reagent/catalyst Wang, Jiacheng; Kondrat, Simon A.; Wang, Yingyu; Brett, Gemma L.; Giles, Cicely; Bartley, Jonathan K.; Lu, Li; Liu, Qian; Kiely, Christopher J.; Hutchings, Graham J.; ACS Catalysis; vol. 5; nb. 6; (2015); p. 3575 - 3587 View in Reaxys With 2,4-dihydroxyquinoline, oxygen, Time= 36h, T= 220 °C , Reagent/catalyst Zhang, Jian; Wang, Liang; Zhu, Longfeng; Wu, Qinming; Chen, Chunyu; Wang, Xiong; Ji, Yanyan; Meng, Xiangju; Xiao, Feng-Shou; ChemSusChem; vol. 8; nb. 17; (2015); p. 2867 - 2871 View in Reaxys 2.4. Typical catalytic procedure for selective aerobic oxidation of benzyl alcohol General procedure: The catalytic reaction was carried out under the follow-ing conditions: heterogeneous copper (II) catalyst (4 molpercent), base(0.50 mmol), TEMPO (0.25 mmol), benzyl alcohol (0.50 mmol) andCH3CN (2.5 mL). The air in the above reaction system was evacuatedand an oxygen balloon was supplied. The solution was centrifugedafter stirring for 24 h and the filtered liquid samples were analyzedvia gas chromatography–mass spectrometry (Agilent 7890/5975C-GC/MSD) using nitrobenzene as the internal standard. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, sodium hydrogencarbonate in acetonitrile, Time= 24h, T= 60 °C , p= 760.051Torr , Catalytic behavior, Solvent, Reagent/catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

221/438

2018-03-11 22:07:32


Hou, Junying; Luan, Yi; Tang, Jia; Wensley, Allison M.; Yang, Mu; Lu, Yunfeng; Journal of Molecular Catalysis A: Chemical; vol. 407; (2015); p. 53 - 59 View in Reaxys 43 %Spectr.

With R,R-Jacobsen's catalyst, potassium hydoxide in water, toluene Kurahashi, Takuya; Inorganic Chemistry; vol. 54; nb. 17; (2015); p. 8356 - 8366 View in Reaxys 2.5 General procedure for catalytic aerobic oxidation Under typical conditions, the reactions were performed in flasks fitted with water circulated condensors which are open to the air. 1.0mmol of substrate, 0.010mmol (1molpercent based on L) of metal complexes, 0.050mmol TEMPO (5molpercent) and DMAP or BPY (5molpercent) were placed in the flask, to which 5cm3 of solvents as indicated below was sequentially added. The reaction was allowed to stir at room temperature for 10h, after which time the products were diluted with dichloromethane and analysed by GC–MS to give the indicated conversions. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C20H16Cl4Cu2N4 in methanol, Time= 10h, T= 20 °C , p= 760.051Torr , Reagent/catalyst, Solvent Liu, E; Zhang, Yuan Zhuo; Li, Li; Yang, Chengxiong; Fettinger, James C.; Zhang, Guoqi; Polyhedron; vol. 99; (2015); p. 223 - 229; Art.No: 11466 View in Reaxys With sodium t-butanolate in toluene, Time= 24h, T= 100 °C , Schlenk technique, Sealed tube, Green chemistry Shi, Xinkang; Guo, Junmei; Liu, Jianping; Ye, Mingde; Xu, Qing; Chemistry - A European Journal; vol. 21; nb. 28; (2015); p. 9988 - 9993 View in Reaxys With tert.-butylhydroperoxide in decane, hexane, Time= 6h, T= 70 °C , Catalytic behavior Baskaran; Kumaravel; Christopher; Radhakrishnan; Sakthivel; Catalysis Letters; vol. 145; nb. 3; (2015); p. 851 - 859; Art.No: 1492 View in Reaxys The photo-catalytic selective oxidation of BA was performed in a 50 mL three-necked flask at room temperature and oxygen atmosphere. For each measurement, 50 mg of as-synthesized catalyst was dispersed in the mixed solution of acetonitrile (20 mL) and BA solution (2 mmol) and then stirred for 1 h in the dark to attain the adsorption–desorption equilibrium. The photo-catalysis reaction was performed under visible light for 4 h, using a 300 W Xenon arc lamp with a UV-cutoff filter (λ ≥ 420 nm) as the light source. After the reaction, the concentrations of BA and BAD in the solution were measured with a SHIMADZU SPDM20A high-performance liquid chromatograph (HPLC). The conversion rate of BA, the yield of BAD, and reaction selectivity were calculated with the equations as displayed in the Supporting information. With oxygen in acetonitrile, Time= 4h, T= 20 °C , Darkness, Irradiation, Reagent/catalyst Liu, Ya; Zhang, Ping; Tian, Baozhu; Zhang, Jinlong; Catalysis Communications; vol. 70; (2015); p. 30 - 33 View in Reaxys With potassium nitrite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 14h, T= 75 °C , p= 760.051Torr , Green chemistry, Catalytic behavior, Reagent/catalyst, Solvent, Temperature Jin, Zhaokui; Luan, Yi; Yang, Mu; Tang, Jia; Wang, Jingjing; Gao, Hongyi; Lu, Yunfeng; Wang, Ge; RSC Advances; vol. 5; nb. 96; (2015); p. 78962 - 78970 View in Reaxys With oxygen in ethanol, Time= 5h, T= 120 °C , p= 750.075Torr , Catalytic behavior, Reagent/catalyst Watanabe, Hiroyuki; Asano, Sayaka; Fujita, Shin-Ichiro; Yoshida, Hiroshi; Arai, Masahiko; ACS Catalysis; vol. 5; nb. 5; (2015); p. 2886 - 2894 View in Reaxys With Au-Pd/TiO2, carbon dioxide, hydrogen, oxygen in methanol, Time= 0.5h, T= 50 °C , p= 29995.4Torr , Solvent, Temperature, Reagent/catalyst, Time

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

222/438

2018-03-11 22:07:32


Santonastaso, Marco; Freakley, Simon J.; Miedziak, Peter J.; Brett, Gemma L.; Edwards, Jennifer K.; Hutchings, Graham J.; Organic Process Research and Development; vol. 18; nb. 11; (2014); p. 1455 - 1460 View in Reaxys With 1-methyl-1H-imidazole, [2,2]bipyridinyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate, oxygen in acetonitrile, Time= 0.666667h, T= 20 °C , Microwave irradiation Rabeah, Jabor; Bentrup, Ursula; Stösser, Reinhard; Brückner, Angelika; Angewandte Chemie - International Edition; vol. 54; nb. 40; (2015); p. 11791 - 11794; Angew. Chem.; vol. 127; nb. 40; (2015); p. 11957 - 11960,4 View in Reaxys 98 %Chromat.

With oxygen, potassium carbonate in o-xylene, Time= 8h, T= 20 °C Shaabani, Ahmad; Hezarkhani, Zeinab; Badali, Elham; RSC Advances; vol. 5; nb. 76; (2015); p. 61759 - 61767 View in Reaxys The liquid-phase aerobic oxidation of various alcohols with solventwas carried out using a 50 mL three-necked round-bottomflask with a reflux condenser. Each flask was charged with alcohol(2.0 mmol), toluene (10 mL), and catalysts (0.2 g). Molecular oxygenwas bubbled through the reaction mixture (20 mL/min). Theresulting mixture was heated at 100 C for 2 h and then cooled inan ice bath. The reaction products were also analyzed using anexternal standard. After centrifugal separation, the clear supernatantreaction mixture (0.5 mL) was mixed with mesitylene(0.05 mL). The analysis is similar to the process mentioned above,and the carbon balance was also within ±5percent. With oxygen in toluene, Time= 4h, T= 100 °C , Catalytic behavior, Solvent, Reagent/catalyst Du, Yiyun; Wang, Qian; Liang, Xiao; He, Yufei; Feng, Junting; Li, Dianqing; Journal of Catalysis; vol. 331; (2015); p. 154 - 161 View in Reaxys With oxygen, T= 140 °C , p= 750.075Torr , Kinetics, Catalytic behavior, Temperature Du, Yiyun; Wang, Qian; Liang, Xiao; He, Yufei; Feng, Junting; Li, Dianqing; Journal of Catalysis; vol. 331; (2015); p. 154 - 161 View in Reaxys With 1-methyl-1H-imidazole, [2,2]bipyridinyl, 2,2,6,6-tetramethyl-piperidine-N-oxyl, tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate, oxygen in acetonitrile, T= 100 °C , p= 6992.47Torr , Kinetics, Reagent/catalyst, Pressure, Temperature Greene, Jodie F.; Preger, Yuliya; Stahl, Shannon S.; Root, Thatcher W.; Organic Process Research and Development; vol. 19; nb. 7; (2015); p. 858 - 864 View in Reaxys With ammonium nitrate, hydrogenchloride, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in acetonitrile, Time= 6h, T= 60 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Solvent, Temperature, chemoselective reaction Prebil, Rok; Stavber, Gaj; Stavber, Stojan; European Journal of Organic Chemistry; vol. 2014; nb. 2; (2014); p. 395 - 402 View in Reaxys With oxygen, Time= 4h, T= 99.84 °C , p= 750.075Torr , Catalytic behavior He, Yufei; Yang, Pengfei; Fan, Jiaxuan; Liu, Yanan; Du, Yiyun; Feng, Junting; Fan, Faying; Li, Dianqing; RSC Advances; vol. 5; nb. 91; (2015); p. 74907 - 74915 View in Reaxys 2.4.1. Oxidative dehydrogenation of benzyl alcohol Catalytic evaluation was carried out in a 100-ml round-bottomflask equipped with a condenser and a magnetic stirrer. Benzylalcohol (BnOH, substrate, 1 mmol, 108.1 mg, 104 ll), dodecane(standard, 1 mmol, 170.3 mg, 228 ll), caesium carbonate (base,3 mmol, 977.5 mg), toluene (solvent, 20 ml) and the gold-basedcatalyst (Au: 2 lmol) were stirred together at 300 rpm and maintainedat 60 C (unless other indication) under atmospheric airpressure until complete conversion of the substrate (24–60 h inaverage) (Fig. 1).Reactions were monitored by regular samplings (0.2 ml) thatwere diluted 40 times in acetonitrile and analysed immediatelyby gas chromatography. Benzyl alcohol (BnOH) conversion wascalculated from the ratio of the number of mole of BnOH convertedover the initial quantity of BnOH introduced at the beginning of thereaction (nBnOH,0). Benzaldehyde (BnO) yield was calculated fromthe ratio of the

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

223/438

2018-03-11 22:07:32


number of moles of BnO produced over the initialquantity of BnOH introduced at the beginning of the reaction.Selectivity was defined as the ratio of yield over conversion.Turnover numbers (TON) were defined as the number of moleof BnOH converted per mole of surface gold atoms. Turnover frequencieswere defined as the number of mole of BnOH per moleof surface gold atoms per hour (Eq. (1)). Moles of surface goldatoms (nAu,surface) were calculated using the dispersion obtainedby TEM and assuming that gold particles adopt a cuboctahedrongeometry. The initial TOFs were calculated by fitting the TON–timecurve with an exponential curve (Eq. (2)) and by deriving it (s is theexponential time constant).TONt nBnOH;0nAu;surface 1 et=s 1TOF0 nBnOH;0nAu;surface 1 1=s 2 With caesium carbonate in toluene, T= 60 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst, Solvent, Temperature Lavenn, Christophe; Demessence, Aude; Tuel, Alain; Journal of Catalysis; vol. 322; (2015); p. 130 - 138 View in Reaxys 100 2.3 Typical procedure for catalytic oxidation of alcohols in the presence of LDH-PWFe %Chromat. General procedure: In a typical experiment 0.05g of LDH-PWFe, which contains about 0.01mmol of PWFe, was dispersed in an aqueous solution of benzyl alcohol (1mmol) and 30percent H2O2 (5mmol) in 3mL of water. The mixture was stirred for 2.5h at reflux and progress of the reaction was monitored by GC. At the end of oxidation reaction ethyl acetate (2×3mL) was added and the organic phase was extracted. Pure products were obtained by flash chromatography over a short column of silica gel (eluent: n-hexane/ethyl acetate). With Al(3+)*6HO(1-)*(x)H2O*0.6NO3 (1-)*2Zn(2+)*Fe0.1O3.9P0.1W1.1(0.4-), dihydrogen peroxide in water, Time= 2.5h, Reflux, Green chemistry, Reagent/catalyst, Solvent, Concentration Hasannia, Saeed; Yadollahi, Bahram; Polyhedron; vol. 99; (2015); p. 260 - 265 View in Reaxys With Oxone, C18H15Cl2MnN6O in acetonitrile, Mechanism, Reagent/catalyst, Solvent Najafpour, Mohammad Mahdi; Ebrahimi, Foad; Amini, Mojtaba; Rahimi, Mohammad; El-Sawy, Abdelhamid; Suib, Steven L.; Dalton Transactions; vol. 44; nb. 34; (2015); p. 15121 - 15125 View in Reaxys With sodium periodate in 1,4-dioxane, Time= 12h, T= 150 °C , Catalytic behavior, Reagent/catalyst, Solvent, Temperature Kim, Aram; Bae, Hee Seon; Park, Ji Chan; Song, Hyunjoon; Park, Kang Hyun; New Journal of Chemistry; vol. 39; nb. 10; (2015); p. 8153 - 8157 View in Reaxys With C40H56CuN4O2, potassium tert-butylate in dichloromethane, T= 19.84 °C , Reagent/catalyst De Bellefeuille, David; Orio, Maylis; Barra, Anne-Laure; Aukauloo, Ally; Journaux, Yves; Philouze, Christian; Ottenwaelder, Xavier; Thomas, Fabrice; Inorganic Chemistry; vol. 54; nb. 18; (2015); p. 9013 - 9026 View in Reaxys 2.3. Catalytic performance General procedure: Solvent-free aerobic oxidation of benzyl alcohol using molecular O2 was carried out in a batchtype reactor under mild conditions. 5 ml benzyl alcohol and 20 mg catalyst were added into a 25 ml three-necked glass flask equipped with a reflux condenser. Prior to reaction, the system was first charged with O2 by bubbling ultrahigh purity O2 at a flow rate of 15 ml min1 for 20 min to remove air. Under the continuous flow of O2, the reactor was immersed into a silicon oil bath at 90 °C to initiate the reaction. During the reaction, the mixture was vigorously stirred at a rateof 1250 rpm to exclude any mass transfer limitation [60]. Finally,the reaction products were analyzed using a Shimadzu GC-2014 gas chromatograph equipped with an Rtx-1 capillary column and an auto-injector. With oxygen in neat (no solvent), Time= 6h, T= 90 °C , Catalytic behavior, Reagent/catalyst, chemoselective reaction Wang, Hengwei; Wang, Chunlei; Yan, Huan; Yi, Hong; Lu, Junling; Journal of Catalysis; vol. 324; (2015); p. 59 68 View in Reaxys 2.3. Catalytic test General procedure: The catalytic test was carried out in a glass reactor with a volume of 13 mL. O2 was bubbled into the reactor under atmospheric pressure from a balloon for 20 min to eliminate trapped residual air. The desired

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

224/438

2018-03-11 22:07:32


amount of the benzyl alcohol (0.1 mol/L) substrate and catalyst were added. Next, the reactor was sealed and heated to 80 °C under vigorous stirring.After the reaction, the product mixture was extracted with toluene for analysis. The molar ratio of the substrate to Pd was 100. The reactants and products were analyzed by a GC 7890F gas chromatograph equipped with a flame ionization detector (FID). Quantification of the products was done by using the external calibration method. The carbon balance in liquid phase was >95percent for all the tests. With P(at)dPBFS‐500 in water, Time= 0.5h, T= 80 °C , p= 750.075Torr , Catalytic behavior Hao, Yan; Wang, Shuai; Sun, Qiang; Shi, Lei; Lu, An-Hui; Chinese Journal of Catalysis; vol. 36; nb. 4; (2015); p. 612 - 619 View in Reaxys With styrene, 1,3,5-trimethyl-benzene, Time= 24h, T= 150 °C , Inert atmosphere Lu, Tianliang; Du, Zhongtian; Liu, Junxia; Chen, Chen; Xu, Jie; Chinese Journal of Catalysis; vol. 35; nb. 12; (2014); p. 1911 - 1916 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, sodium carbonate in acetonitrile, Time= 24h, T= 75 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst, Solvent Yu, Jie; Luan, Yi; Qi, Yue; Hou, Junying; Dong, Wenjun; Yang, Mu; Wang, Ge; RSC Advances; vol. 4; nb. 98; (2014); p. 55028 - 55035 View in Reaxys With tert.-butylhydroperoxide, {[Ni(N,N′-bis-[(imidazol-4-yl)methylene]cyclohexane-1,2-diamine)]2(CuCN)9}n in acetonitrile, Time= 8h, T= 49.84 °C , Catalytic behavior, Mechanism, Reagent/catalyst, Time, Temperature Hou, Yun-Long; Li, Sheng-Xia; Sun, Raymond Wai-Yin; Liu, Xin-Yuan; Weng Ng, Seik; Li, Dan; Dalton Transactions; vol. 44; nb. 39; (2015); p. 17360 - 17365 View in Reaxys the alcohol oxidation process, 0.5 g of HNTs-g-CD (40.45 mg of CD) was added into deionized water (5 mL) at 50 °C under stirring, followed by benzyl alcohol (34 L, 0.3 mmol). Then, 2 mL of a 10percent NaOCl solution was added dropwise. The reaction was kept stirring at predetermined time intervals. The product was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was evaporated under vacumand the product was analyzed by FT-IR. With sodium hypochlorite solution in water, T= 50 °C Cao, Xuan Thang; Showkat, Ali Md.; Kim, Dong Woo; Jeong, Yeon Tae; Kim, Jong Su; Lim, Kwon Taek; Journal of Nanoscience and Nanotechnology; vol. 15; nb. 11; (2015); p. 8617 - 8621 View in Reaxys With air, graphene oxide like quantum dots in chloroform-d1, Time= 144h, T= 100 °C Chen, Guanxiong; Zhuo, Zhiwen; Ni, Kun; Kim, Na Yeon; Zhao, Yuan; Chen, Zongwei; Xiang, Bin; Yang, Lihua; Zhang, Qun; Lee, Zonghoon; Wu, Xiaojun; Ruoff, Rodney S.; Zhu, Yanwu; Small; vol. 11; nb. 39; (2015); p. 5296 - 5304 View in Reaxys With oxygen, potassium carbonate in water, Time= 5h, T= 80 °C , Green chemistry Zou, Houbing; Wang, Runwei; Dai, Jinyu; Wang, Yu; Wang, Xue; Zhang, Zongtao; Qiu, Shilun; Chemical Communications; vol. 51; nb. 78; (2015); p. 14601 - 14604 View in Reaxys 2.3. Aerobic oxidation of benzyl alcohol The catalytic reaction was carried out using molecular oxygen under solvent-free conditions. Benzyl alcohol (5.174 mL, 50 mmol) was loaded in a glass flask pre-charged with 0.01 g of catalyst. The mixture was immersed in a 160°C of oil bath while gaseous oxygen was purged (20 mL min−1) to initiate the reaction. The reaction was allowed to go on for 1 h under vigorous stirring (1200 rpm). After the reaction, the solid catalyst was filtered off while the liquid phase was analyzed by Agilent gas chromatograph 6890 equipped with HP-5 capillary column. Dodecane was used as the internal standard to measure the percentage of remaining reactant and products so as to calculate benzyl alcohol conversion and benzaldehyde selectivity values.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

225/438

2018-03-11 22:07:32


With oxygen in neat (no solvent), Time= 1h, T= 160 °C , Catalytic behavior, Reagent/catalyst Yan, Yibo; Jia, Xinli; Yang, Yanhui; Catalysis Today; vol. 259; nb. Part 2; (2016); p. 292 - 302 View in Reaxys 92 %Spectr.

With N-Bromosuccinimide in neat (no solvent), Time= 0.5h, Milling, Green chemistry, Reagent/catalyst Sahoo, Prasit Kumar; Bose, Anima; Mal, Prasenjit; European Journal of Organic Chemistry; vol. 2015; nb. 32; (2015); p. 6994 - 6998 View in Reaxys

90 %Chromat.

With oxygen, potassium carbonate in water, Time= 15h, T= 90 °C , p= 760.051Torr , Reagent/catalyst Karimi, Babak; Khorasani, Mojtaba; Vali, Hojatollah; Vargas, Carolina; Luque, Rafael; ACS Catalysis; vol. 5; nb. 7; (2015); p. 4189 - 4200 View in Reaxys

98 %Chromat.

With dihydrogen peroxide in acetonitrile, Time= 1h, T= 80 °C Naghdi, Zahra; Farzaeli, Razieh; Aliyan, Hamid; Russian Journal of Applied Chemistry; vol. 88; nb. 8; (2015); p. 1343 - 1350 View in Reaxys With C60H48As2Cl2N6O6Ru(1+)*Cl(1-), dihydrogen peroxide in acetonitrile, Time= 3h, T= 20 °C , Reagent/catalyst Shoair; El-Shobaky; Azab; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 151; (2015); p. 322 - 334 View in Reaxys With dihydrogen peroxide in acetonitrile, Time= 1.5h, T= 80 °C , Catalytic behavior, Solvent, Reagent/catalyst Heidari-Golafzani, Mahdi; Rabbani, Mahboubeh; Rahimi, Rahmatollah; Azad, Alireza; RSC Advances; vol. 5; nb. 121; (2015); p. 99640 - 99645 View in Reaxys Stage 1: With oxygen, Time= 1h, T= 20 °C , Darkness, Sealed tube Stage 2:Time= 8h, T= 20 °C , Irradiation, Sealed tube, Reagent/catalyst Xu, Jie; He, Sha; Zhang, Hualei; Huang, Jiancai; Lin, Huaxiang; Wang, Xuxu; Long, Jinlin; Journal of Materials Chemistry A; vol. 3; nb. 48; (2015); p. 24261 - 24271 View in Reaxys With galactose oxidase, copper(II) sulfate, catalase, horseradish peroxidase in aq. buffer, T= 25 °C , pH= 7.4, Enzymatic reaction, Reagent/catalyst Toftgaard Pedersen, Asbjorn; Birmingham, William R.; Rehn, Gustav; Charnock, Simon J.; Turner, Nicholas J.; Woodley, John M.; Organic Process Research and Development; vol. 19; nb. 11; (2015); p. 1580 - 1589 View in Reaxys

88 %Spectr.

With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy, sodium hydrogencarbonate, sodium carbonate in aq. buffer, Time= 2h, pH= 10, Electrochemical reaction, Catalytic behavior, Reagent/catalyst Rafiee, Mohammad; Miles, Kelsey C.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 137; nb. 46; (2015); p. 14751 - 14757 View in Reaxys With tert.-butylhydroperoxide in decane, T= 25 °C , Catalytic behavior Takahashi, Masaki; Imaoka, Takane; Yamamoto, Kimihisa; RSC Advances; vol. 5; nb. 122; (2015); p. 100693 100696 View in Reaxys With oxygen in N,N-dimethyl-formamide, Time= 2h, T= 110 °C , Catalytic behavior, Reagent/catalyst, Temperature Yang, Xiaoyuan; Wu, Shujie; Peng, Ling; Hu, Jing; Wang, Xiufang; Fu, Xiaoran; Huo, Qisheng; Guan, Jingqi; RSC Advances; vol. 5; nb. 124; (2015); p. 102508 - 102515 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

226/438

2018-03-11 22:07:32


2.5. Procedure for catalytic oxidation of alcohols with NMO General procedure: A solution of complex (0.01 mmol) in CH2Cl2 (25 mL) was addedto the mixture containing alcohol substrate (1 mmol), K2CO3(1.3 mmol), solid NMO (3 mmol) and molecular sieves. The reactionmixture was refluxed for 3 h, and the solvent was then evaporatedunder reduced pressure. The residue was then extracted withdiethyl ether (20 mL), concentrated to z 1 mL. The oxidizedproduct present in diethyl ether extract was analyzed by GC. With C31H27Cl2N2PRhS(1+)*F6P(1-), potassium carbonate, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Molecular sieve, Reflux Biswas, Sujan; Sarkar, Deblina; Kundu, Subhankar; Roy, Puspendu; Mondal, Tapan Kumar; Journal of Molecular Structure; vol. 1099; (2015); p. 297 - 303 View in Reaxys General procedure for the preparation of compounds 4: General procedure: A mixture of 4-methoxybenzyl alcohol (0.138 g, 1 mmol), I2 (0.254 g, 1 mmol), K2CO3(0.138 g, 1 mmol), isatoic anhydride (0.163 g, 1 mmol) and aniline (0.093 g,1 mmol) in water (5 mL) was stirred for 3 h at reflux. After reaction completion,the mixture was cooled to room temperature and stirred for 1 h. The resultingprecipitate was filtered, washed with water (3 3 mL), and purified by recrystallization from ethanol to give 4a as a white solid. With iodine, potassium carbonate in water, Time= 3h, Reflux, Green chemistry Azimi, Seyedeh Bahareh; Azizian, Javad; Tetrahedron Letters; vol. 57; nb. 2; (2016); p. 181 - 184 View in Reaxys 80 %Chromat.

2.4 General procedure for the oxidation of aromatic alcohols General procedure: Alcohols (1 mmol) were added in a two round bottomed glass flask containing a mixture of cobalt chitosan (5 mol percent, 0.023 g) and K2CO3 (0.5 mmol,0.069 g) in 10 mL p-xylene. The flask was fitted with a reflux condenser and mixture was heated at 80°C with continuous bubbling of air with flow rate of 15 mLmin−1. After completion of the reaction (progress of the reaction followed by TLC), catalyst was separated by an external magnet and the reaction mixture was analyzed by gas chromatography using a CP-Sil-8 fused silica capillary column. With potassium carbonate in para-xylene, Time= 1.5h, T= 85 °C Shaabani, Ahmad; Boroujeni, Mahmoud Borjian; Sangachin, Mona Hamidzad; Journal of Chemical Sciences; vol. 127; nb. 11; (2015); p. 1927 - 1935 View in Reaxys With oxygen in neat (no solvent), Time= 5h, T= 120 °C , Catalytic behavior, Time Lu, Yong-Ming; Zhu, Hai-Zhou; Liu, Jian-Wei; Yu, Shu-Hong; ChemCatChem; vol. 7; nb. 24; (2015); p. 4131 4136 View in Reaxys 2.5 General Procedure for the Peroxidative Oxidation of 1-Phenylethanol General procedure: Oxidation reactions of the alcohols were carried out in sealed cylindrical Pyrex tubes under focused MW irradiation as follows: the alcohol (2.5 mmol), TBHP (70 percent aqueous solution, 5.0 mmol) and catalyst precursor 1–3 (1–10 μmol, 0.04–0.4 molpercent vs. substrate) were introduced in the tube which was then placed in the MW reactor. In the experiments with radical traps, CBrCl3 (2.5 mmol) or NHPh2 (2.5 mmol) was added to the reaction mixture. In the experiments with other additives (TEMPO, nitric acid 1 M solution, or potassium carbonate 1 M solution), a 2.5 percent additive/substrate molar ratio was used. The system was stirred and irradiated (10 W) for 0.5–2 h at 50–150 °C. After the reaction, the mixture was allowed to cool down to room temperature. Typically, 150 μL of benzaldehyde (internal standard) and 2.5 mL of MeCN (to extract the substrate and the organic products from the reaction mixture) were added. The obtained mixture was stirred for 10 min, filtered and then a sample (1 μL) was taken from the organic phase and analysed by GC using the internal standard method. Blank tests indicate that only traces (<1 percent) of ketone or aldehyde are generated in a metal-free system. With tert.-butylhydroperoxide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [H(EtOH)][FeCl2(3-amino-2-pyrazinecarboxylate)2] in water, Time= 1.5h, T= 150 °C , Microwave irradiation, Sealed tube, Reagent/catalyst Karmakar, Anirban; Martins; Guedes Da Silva, M. Fátima C.; Hazra, Susanta; Pombeiro, Armando J. L.; Catalysis Letters; vol. 145; nb. 12; (2015); p. 2066 - 2076

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

227/438

2018-03-11 22:07:32


View in Reaxys With oxygen, Time= 2h, p= 750.075Torr , Irradiation, Reagent/catalyst Li, Xiuzhen; Zhang, Nan; Xu, Yi-Jun; ChemCatChem; vol. 7; nb. 14; (2015); p. 2047 - 2054 View in Reaxys 94 %Chromat.

With water, copper dichloride, Time= 0.5h, T= 250 °C , p= 30003Torr , Sealed tube, Green chemistry, Concentration Yang, Ziming; Hartnett, Hilairy E.; Shock, Everett L.; Gould, Ian R.; Journal of Organic Chemistry; vol. 80; nb. 24; (2015); p. 12159 - 12165 View in Reaxys 2.3. Catalytic oxidation of alcohol General procedure: Liquid-phase catalytic oxidation of benzyl alcohol was carriedout in a 25 mL two-neck flask with reflux condenser and magneticallystirred autoclave heated in an oil bath under atmospheric pressure. Dioxygen was bubbled (10 mL/min) through a solutionof acetonitrile (ACN, 8 mL), benzyl alcohol (108 mg, 1 mmol), IBA (216 mg, 3 mmol), and catalyst (1.9 106 mmol, calculated on the intercalated metlloporphyrin) at 60°C. The product samples were drawn at regular time intervals and analyzed with a gas chromatograph(Shimadzu GC-2010AF) having a Chromopak capillarycolumn and FID detector. The products were further confirmedusing GC–MS (Shimadzu GCMS-2010). The conversions of the reactions were calculated with no allowance for the background. After the reaction, the resulting mixture was cooled and the catalyst was separated by centrifugation and washed with solvent. After drying in vacuum, the recycled catalyst can be reused in the next run under the same conditions. The conversion, yield of benzaldehyde, and selectivity presented here are based on the GC calculations using chlorobenzene as the internal standard reference compound. With oxygen, isobutyraldehyde in acetonitrile, Time= 2h, T= 60 °C , p= 760.051Torr , Reflux, Autoclave, Reagent/ catalyst, Temperature, Solvent, Time Zhou, Wei-You; Tian, Peng; Sun, Fu'An; He, Ming-Yang; Chen, Qun; Journal of Catalysis; vol. 335; (2016); p. 105 - 116 View in Reaxys With trichloroisocyanuric acid in dichloromethane, Time= 3h, T= 20 °C , Inert atmosphere Gaspa, Silvia; Porcheddu, Andrea; De Luca, Lidia; Advanced Synthesis and Catalysis; vol. 358; nb. 1; (2016); p. 154 - 158 View in Reaxys General Procedure for the Synthesis of Benzimidazoles 2from Alcohols in PEG-200. General procedure: A 5mL flask equipped with astirrer bar was charged with the alcohol (1.2mmol), GO (300wtpercent) and 2mL of PEG-200. The resulting mixture was heatedat 110 °C until almost all alcohols were oxidized. After almostcomplete oxidation of the starting alcohol to aldehyde, 1mmolof o-phenylenediamine 1a was added and allow the reactionmixture to stir at 110 °C until the consumption of o-phenylenediamine was completed (reaction monitored by TLC). Uponcompletion of the reaction, the reaction mixture was dilutedwith water and filtered through a sintered funnel to separateGO. The aqueous solution was extracted with ethyl acetate(2 © 5 mL). Then GO was washed with warm ethanol (5 © 10mL). The combined organic phases (ethyl acetate and ethanol)were dried over anhydrous Na2SO4, sodium sulfate was filteredand the solvent was evaporated to obtain the product which waspurified by column chromatography. With graphene oxide, T= 110 °C , Green chemistry Khalili, Dariush; Banazadeh, Ali Reza; Bulletin of the Chemical Society of Japan; vol. 88; nb. 12; (2015); p. 1693 1706 View in Reaxys With tert.-butylhydroperoxide in acetonitrile, Time= 3h, T= 80 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst, Temperature, Solvent Mistri, Rajib; Das, Dipak; Llorca, Jordi; Dominguez, Montserrat; Mandal, Tapas Kumar; Mohanty, Paritosh; Ray, Bidhan Chandra; Gayen, Arup; RSC Advances; vol. 6; nb. 6; (2016); p. 4469 - 4477 View in Reaxys

50 %Chromat.

11. Oxidation of benzylalcohol

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

228/438

2018-03-11 22:07:32


The mixture of 1,2-dichloroethane (0.2 mL), GO (30.0 mg) and benzylalcohol (32.4 mg, 0.3 mmol) was stirred at 100 °C for 8 h under Ar or O2 atmosphere. After the reaction, the mixture was analyzed by GC using n-dodecane as an internal standard. With graphene oxide in 1,2-dichloro-ethane, Time= 8h, T= 100 °C , Inert atmosphere, Reagent/catalyst Morimoto, Naoki; Takeuchi, Yasuo; Nishina, Yuta; Chemistry Letters; vol. 45; nb. 1; (2016); p. 21 - 23 View in Reaxys 2.7 General procedure for catalytic aerobic oxidation General procedure: Under typical conditions, the catalytic reactions were performed in a small vial equiped with magnetic stirers and open to the air. 1.0mmol of benzyl alcohol, 0.010mmol (1molpercent based on ligand) of copper(II) CP, TEMPO (0.050mmol, 5molpercent) and DMAP (5molpercent) were placed in the vial, to which 5cm3 of water was sequentially added. The reaction was allowed to stir at room temperature for 10h, after which time the products were extracted with ethyl acetate. The organic layer was diluted with dichloromethane and analysed by GC–MS to give the indicated conversions. With dmap, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [Cu2(4′-(4-hexyloxyphenyl)-3,2′:6′,3″-terpyridine) (OAc)4]n in water, Time= 10h, T= 20 °C , p= 760.051Torr , Reagent/catalyst, Solvent Li, Li; Zhang, Yuan Zhuo; Yang, Chengxiong; Liu; Golen, James A.; Zhang, Guoqi; Polyhedron; vol. 105; (2016); p. 115 - 122 View in Reaxys 89 %Spectr.

Procedure for alcohol oxidation. General procedure: A 15ml test tube was charged with the amount of Cu-MOF-74 (5.2mg), TEMPO (0.05eq, 0.025mmol) and DMAP (1eq, 0.5mmol). With vacuumizing for 5min, the oxygen balloon was set up. To this mixture, alcohol (1eq, 0.5mmol) was added with 1 ml of acetonitrile. The mixture was stirred for the required time at 70°C under an O2 balloon. At the end of reaction, the mixture was filtered by silica and washed with ethyl acetate. The silica was washed several times with ethyl acetate, and the solvent was evaporated. A yield of the aldehyde product was confirmed by integration using an internal standard (1,1,2,2-tetrachloroethane) in the 1H-NMR spectrum. With dmap, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 12h, T= 70 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst, Time Kim, Bo Ram; Oh, Jung Suk; Kim, Jinho; Lee, Chang Yeon; Bulletin of the Korean Chemical Society; vol. 36; nb. 12; (2015); p. 2799 - 2800 View in Reaxys The vapor phase oxidation of benzyl alcohol was conductedat 320 C reaction temperature under atmosphericpressure in a fixed-bed vertical down-flow glass reactor(length= 520 mm, i.d.= 12 mm) using 1.0 g catalyst. Theupper portion of the reactor was filled with glass beadswhich serve as a preheater for the reactant. Prior to theoxidation reaction, each catalyst was activated at 250 Cfor 2 h in presence ofN2 flow (50 mL/min). Thereafter, thebenzyl alcohol (Sigma-Aldrich, 99.8percent) was fed into thereactor in a stoichiometric quantity (WHSV = 284 h−1)using a syringe pump (Perfusor, B. Braun, Germany) alongwith air, acting as an oxidant. The reaction products werecollected in an ice-cold trap at the bottom of the reactorfor every 1 h. With gold nano particles on the surface of MCM-41, T= 320 °C , p= 760.051Torr , Inert atmosphere, Flow reactor, Temperature, Reagent/catalyst Kumar, Ashish; Kumar, Vanama Pavan; Vishwanathan, Venkataraman; Chary, Komandur V. R.; Journal of Nanoscience and Nanotechnology; vol. 15; nb. 12; (2015); p. 9944 - 9953 View in Reaxys With titanium microfiber supported binary oxide nanocomposite, T= 300 °C , Inert atmosphere, Reagent/catalyst Zhao, Guofeng; Fan, Songyu; Tao, Longgang; Chai, Ruijuan; Zhang, Qiaofei; Liu, Ye; Lu, Yong; ChemCatChem; vol. 8; nb. 2; (2016); p. 313 - 317 View in Reaxys With dihydrogen peroxide in acetone, Time= 5h, T= 80 °C , Catalytic behavior, Solvent Chi, Hui; Cao, Liqin; Wang, Jide; RSC Advances; vol. 6; nb. 6; (2016); p. 4434 - 4441 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

229/438

2018-03-11 22:07:32


81 %Chromat.

With 7,8-dimethyl-10-(tetra-O-acetyl-D-xylitol-1-yl)-10H-benzo[g]pteridine-2,4-dione, (tris(2-pyridylmethyl)amine)bis(acetonitrile)iron(II) perchlorate in water, acetonitrile, Time= 2.5h, T= 20 °C , UV-irradiation Mühldorf, Bernd; Wolf, Robert; Angewandte Chemie - International Edition; vol. 55; nb. 1; (2016); p. 427 - 430; Angew. Chem.; vol. 128; nb. 1; (2015); p. 437 - 441,5 View in Reaxys 2.3 Catalytic Activity Test The solvent-free aerobic oxidation of benzyl alcohol using molecular O2 was carried out in a bath-type reactor operated under atmospheric conditions: a three-necked glass flask (capacity: 25 mL) precharged with certain amount of reactant and catalyst as well as a stirring bar was heated in a silicon oil bath, where a thermocouple was applied to control the reaction temperature. A reflux condenser was employed to condense the hot vapor of products. The amount of reactant and catalyst was constant at alcohol/Pd = 4.0 g/40 mg. In each reaction run, the mixture was heated to 120 °C under vigorous stirring (stirring rate: 1200 rpm). Oxygen flow was bubbled at 20 mL/min controlled by a mass flow controller into the mixture to initiate the reaction. After reaction for 3 h, the catalyst powder was filtered off, and the liquid organic products were analyzed by Gas chromatography (GC) was performed on GC-2014 with Rtx-5 capillary column. The catalyst was washed with deionized water and ethanol for three times and dried at 100 °C in vacuum for the next use. With oxygen, Time= 3h, T= 120 °C , Reagent/catalyst, Temperature Chen, Zhaoxiang; Zou, Peipei; Zhang, Ruizhe; Dai, Liyi; Wang, Yuanyuan; Catalysis Letters; vol. 145; nb. 12; (2015); p. 2029 - 2036 View in Reaxys With C29H33FeN5O3 (2+)*2CF3O3S(1-) in acetonitrile, Kinetics, Mechanism Rana, Sujoy; Dey, Aniruddha; Maiti, Debabrata; Chemical Communications; vol. 51; nb. 77; (2015); p. 14469 14472 View in Reaxys With bismuth oxychloride, T= 20 °C , Irradiation, chemoselective reaction Ding, Liyong; Chen, Huan; Wang, Qingqian; Zhou, Tengfei; Jiang, Qingqing; Yuan, Yuhong; Li, Jinlin; Hu, Juncheng; Chemical Communications; vol. 52; nb. 5; (2016); p. 994 - 997 View in Reaxys

92 %Chromat.

With water, Time= 65h, T= 110 °C , Schlenk technique Bai, Cuihua; Li, Aiqin; Yao, Xianfang; Liu, Hongli; Li, Yingwei; Green Chemistry; vol. 18; nb. 4; (2016); p. 1061 1069 View in Reaxys With niobium(V) oxide, oxygen, Time= 16h, p= 760.051Torr , Irradiation Furukawa, Shinya; Shishido, Tetsuya; Teramura, Kentaro; Tanaka, Tsunehiro; ChemPhysChem; vol. 15; nb. 13; (2014); p. 2665 - 2667 View in Reaxys 2.2.1.3. Catalytic activity of CuLNEOB complex in oxidation of alcohols. General procedure: In a typical experiment, alcohol (1 mmol), CuLNEOB (0.024 g,5 molpercent), TEMPO (0.024 g, 5 molpercent) and Cs2CO3 (0.650 g, 2 mmol)in 5 ml of oxygen saturated trifluorotoluene (TFT) were taken ina 15-ml two-necked round-bottom flask was equipped with oxygenballoon. The solution was magnetically stirred for some hoursat room temperature and the mixture was filtered through a plugof silica, and then diluted with TFT (2 ml). The progress of the reactionwas monitored by gas chromatography.In a separate blank test, a 15-ml two-necked roundbottomflask was charged with the solution of copper(II) acetate, TEMPOor ligand in mixed medium of Cs2CO3 (0.650 g, 2 mmol) in 5 mlof oxygen saturated TFT. Then the flask was equipped with an oxygenballoon at room temperature. The progress of the reaction wasmonitored by gas chromatography. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C18H18Cl4CuN2O2, caesium carbonate, Time= 12h, T= 23 °C Safaei, Elham; Hajikhanmirzaei, Leila; Karimi, Babak; Wojtczak, Andrzej; Cotič, Patricia; Lee, Yong-Ill; Polyhedron; vol. 106; (2016); p. 153 - 162 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

230/438

2018-03-11 22:07:32


2.2.1.3. Catalytic activity of CuLNEOB complex in oxidation of alcohols. In a typical experiment, alcohol (1 mmol), CuLNEOB (0.024 g,5 molpercent), TEMPO (0.024 g, 5 molpercent) and Cs2CO3 (0.650 g, 2 mmol)in 5 ml of oxygen saturated trifluorotoluene (TFT) were taken ina 15-ml two-necked round-bottom flask was equipped with oxygenballoon. The solution was magnetically stirred for some hoursat room temperature and the mixture was filtered through a plugof silica, and then diluted with TFT (2 ml). The progress of the reactionwas monitored by gas chromatography.In a separate blank test, a 15-ml two-necked round-bottomflask was charged with the solution of copper(II) acetate, TEMPOor ligand in mixed medium of Cs2CO3 (0.650 g, 2 mmol) in 5 mlof oxygen saturated TFT. Then the flask was equipped with an oxygenballoon at room temperature. The progress of the reaction wasmonitored by gas chromatography. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C18H18Cl4CuN2O2, caesium carbonate, Time= 12h, T= 23 °C Safaei, Elham; Hajikhanmirzaei, Leila; Karimi, Babak; Wojtczak, Andrzej; Cotič, Patricia; Lee, Yong-Ill; Polyhedron; vol. 106; (2016); p. 153 - 162 View in Reaxys Oxidation of benzyl alcohol In a typical procedure, a mixture of 0.1 g SBA-15-pr-NH2-Mn(Salen)Cl catalyst with the grain size of 200–230 mesh, 15 mL solvent (acetonitrile) and 10 mmol of benzyl alcohol was stirred in a three-necked flask under nitrogen atmosphere at 50 C for 30 min. The stirring rate of the solution was set at 750 cycle/min. Then, 10 mmol of the oxidant (TBHP) was added to the solution and the mixture was refluxed for 8 h under nitrogen atmosphere. After filtration, the reaction mixture was analyzed by GC. A GC–MS of model Thermo Finnigan (60 m, RTX-1 column) was used for the identification of products and a GC (Perkin Elmer Model 1800) was used for the product analysis. The GC was equipped with a flame ionization detector (FID) connected to a 3 percent OV-17 column with length of 2.5 m and diameter of 1/8 in. With tert.-butylhydroperoxide in acetonitrile, Time= 8h, T= 90 °C , Inert atmosphere, Reflux, Reagent/catalyst, Temperature, Time, Solvent Mahdavi, Vahid; Mardani, Mahdieh; Research on Chemical Intermediates; vol. 41; nb. 11; (2015); p. 8907 - 8927 View in Reaxys With carbon supported Fe3O4, air in toluene, Time= 8h, T= 80 °C , p= 760.051Torr , Reagent/catalyst Geng, Longlong; Zheng, Bin; Wang, Xiang; Zhang, Wenxiang; Wu, Shujie; Jia, Mingjun; Yan, Wenfu; Liu, Gang; ChemCatChem; vol. 8; nb. 4; (2016); p. 805 - 811 View in Reaxys 11 %Chromat.

With oxygen, potassium carbonate in water, Time= 24h, T= 60 °C , p= 759.826Torr , Green chemistry, Reagent/ catalyst Karimi, Babak; Naderi, Zahra; Khorasani, Mojtaba; Mirzaei, Hamid M.; Vali, Hojatollah; ChemCatChem; vol. 8; nb. 5; (2016); p. 906 - 910 View in Reaxys

99 %Chromat.

With potassium carbonate in water, Time= 18h, T= 100 °C , p= 760.051Torr , Green chemistry, Catalytic behavior, Reagent/catalyst, Solvent, Temperature, Time Pourjavadi, Ali; Safaie, Niloofar; Hosseini, Seyed Hassan; Bennett, Craig; New Journal of Chemistry; vol. 40; nb. 2; (2016); p. 1729 - 1736 View in Reaxys With C35H58CuN2O3 in acetonitrile, Catalytic behavior, Reagent/catalyst Debnath, Rajib Kumar; Kalita, Apurba; Sinha, Sourab; Bhattacharyya, Pradip Kr.; Mondal, Biplab; Ganguli, Jatindra Nath; Asian Journal of Chemistry; vol. 27; nb. 12; (2015); p. 4490 - 4500 View in Reaxys

50 %Chromat.

2.4. Procedure for Alcohol Oxidation General procedure: A typical reaction scheme for the alcohol oxidation isgiven in Scheme 1. Au–MgO nanorods (30 mg) and H2O2(945 L, 15 equivalence) were stirred in 20 mL of waterand the substrate alcohol (1 mM) was slowly added to thereaction mixture and continuously stirred at room temperature.After the requisite time, the catalyst was separatedby centrifugation. The centrifugate was extracted usingdiethyl ether. The ether extract was dried over anhydroussodium sulphate and evaporated. Then the product was dissolvedin ethyl acetate and then analysed by GC. Authenticsamples of reactants and respective products were used toverify the retention time and to confirm the prod-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

231/438

2018-03-11 22:07:32


uct formation.The used catalyst was washed with ethyl acetate and dried under vacuum. The dried catalyst was calcinedat 500 C before reuse. With dihydrogen peroxide in water, Time= 4h, T= 27 °C Emayavaramban; Ganesh Babu; Karvembu; Kadirvelu; Dharmaraj; Journal of Nanoscience and Nanotechnology; vol. 16; nb. 3; (2016); p. 2517 - 2526 View in Reaxys With air, hydrogen reduced 10 wtpercent alumina supported silver in para-xylene, Time= 4h, T= 120 °C , Reagent/ catalyst, Temperature Liu, Huihui; Tan, Hui-Ru; Tok, Eng Soon; Jaenicke, Stephan; Chuah, Gaik-Khuan; ChemCatChem; vol. 8; nb. 5; (2016); p. 968 - 975 View in Reaxys With oxygen, sodium hydroxide in cyclohexane, Time= 1h, T= 100 °C , p= 4500.45Torr Ferraz, Camila P.; Garcia, Marco Aurélio S.; Teixeira-Neto, Érico; Rossi, Liane M.; RSC Advances; vol. 6; nb. 30; (2016); p. 25279 - 25285 View in Reaxys With oxygen in water, Time= 20h, T= 24.84 °C , p= 760.051Torr , Irradiation, Sealed tube, Kinetics, Reagent/catalyst, Wavelength Tanaka, Atsuhiro; Hashimoto, Keiji; Kominami, Hiroshi; Chemistry - A European Journal; vol. 22; nb. 13; (2016); p. 4592 - 4599 View in Reaxys 2.1 : Catalytic oxidation of alcohols General procedure: Alcohols (3.0 mmol), MnP-AMP catalyst (3.0 × 10−3mmol) and acetonitrile (8 mL) were added to a three-neck flask, into which isobutyraldehyde (9.0 mmol) was also dropped in three portions (3.0 mmol each time) with stirring. The temperature and the air flow rate were maintained at 40°C and 150 mL/min respectively. The reaction time was 2–6 h. With oxygen, isobutyraldehyde in acetonitrile, Time= 2h, T= 40 °C , Catalytic behavior, Reagent/catalyst Li, Yongjin; Sun, Baoshuai; Yang, Weijun; Applied Catalysis A: General; vol. 515; (2016); p. 164 - 169 View in Reaxys With dihydrogen peroxide in water, Time= 72h, T= 110 °C , Schlenk technique, Green chemistry, Reagent/catalyst, Temperature, Solvent Yao, Xianfang; Bai, Cuihua; Chen, Junying; Li, Yingwei; RSC Advances; vol. 6; nb. 32; (2016); p. 26921 - 26928 View in Reaxys 1.2.5. General procedure for the photocatalytic aerobic oxidation ofalcohols General procedure: 1.2.5. General procedure for the photocatalytic aerobic oxidation ofalcoholsPhotocatalytic tests were performed by stirring the mixturesolutions of 1.0 mmol alcohol, 1 mg FeTSPPS, N: GQDs, and5.0 mL water in open air at room temperature for at least 10 minbefore irradiation. The samples were placed on narrow glass tubes(10.0 mL capacity) with magnetic stirring bar. The test tubes wereput in a water bath containing visible light source [fluorescent cir-cular lamp, 22 W, 230 V, 32400 LUX, intensity determined withlight meter (LT lutron model YK-2500 lx) and > 350 nm] or sun-light (62000 LUX) and irradiated for the required reaction time.The course of the irradiation was followed by taking one test tubeat the required reaction time and analyzing the products retainedin the solid. The solids were extracted by redispersing the powderin 3 mL of dichloromethane. The combined extracts (supernatantplus products recovered from the solid) were analyzed by gas chro-matography and spectral changes were monitored with ShimadzuUV-2100. GC conversions were obtained based on the amount ofremaining alcohol in the reaction mixture relative to the standardsample containing 1.0 mmol alcohol. With air, iron(III) tetra(4-sulfonatophenyl)porphyrin supported on sulfur and nitrogen co-doped graphene quantum dot in water, Time= 0.166667h, T= 20 °C , Solvent Mahyari, Mojtaba; Bide, Yasamin; Gavgani, Jaber Nasrollah; Applied Catalysis A: General; vol. 517; (2016); p. 100 - 109 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

232/438

2018-03-11 22:07:32


General procedure for the oxidation reaction General procedure: A mixture of benzyl alcohol (1 mmol), t-BHP 70 percent(0.3 ml) and RuO2(at)ZrO2 4 wtpercent (20 mg) in acetonitrile(5 ml) was stirred magnetically into the reactor through a septum. The progress of the reaction was followed using thin layer chromatography and after completion of the reaction, the products were filtered out from the catalyst.Then, the obtained oxidation products were analyzed using a gas chromatograph with a GC capillary column HP 6890and FID detector. in acetonitrile, Time= 0.0666667h, Microwave irradiation, Green chemistry Shojaei, Abdollah Fallah; Tabatabaeian, Khalil; Hamidiyan, Massome; Hejazi, Seyyedeh Zoha; Journal of the Iranian Chemical Society; vol. 13; nb. 5; (2016); p. 803 - 808 View in Reaxys 90 %Chromat.

With porous chitosan–manganese dioxide nanohybrid, air in para-xylene, Time= 0.5h, T= 80 °C , Green chemistry Shaabani, Ahmad; Borjian Boroujeni, Mahmoud; Laeini, Mohmmad Sadegh; Applied Organometallic Chemistry; vol. 30; nb. 3; (2016); p. 154 - 159 View in Reaxys With tungsten oxide loaded with a palladium oxide cocatalyst in water, Time= 3h, Irradiation, Reagent/catalyst Tomita, Osamu; Otsubo, Takahide; Higashi, Masanobu; Ohtani, Bunsho; Abe, Ryu; ACS Catalysis; vol. 6; nb. 2; (2016); p. 1134 - 1144 View in Reaxys With C33H40Cl2Ir2N5 (1+)*CF3O3S(1-) in 1,2-dichloro-benzene, Time= 96h, T= 150 °C , Sealed tube, Catalytic behavior, Time, Reagent/catalyst Valencia, Marta; Müller-Bunz, Helge; Gossage, Robert A.; Albrecht, Martin; Chemical Communications; vol. 52; nb. 16; (2016); p. 3344 - 3347 View in Reaxys

9.8 With oxygen in ethanol, Time= 5h, T= 120 °C , p= 750.075Torr , Green chemistry %Chromat. Ma, Zhishuang; Zhang, Hongye; Yang, Zhenzhen; Ji, Guipeng; Yu, Bo; Liu, Xinwei; Liu, Zhimin; Green Chemistry; vol. 18; nb. 7; (2016); p. 1976 - 1982 View in Reaxys 94 %Spectr.

2.3 Procedure for Alcohol Oxidation General procedure: A 15 mL test tube, which was equipped with a magnetic stirbar and charged with catalysts (0.05 equiv., 0.025 mmol) andTEMPO (0.05 equiv., 0.025 mmol), was evacuated andbackfilled with oxygen (this process was repeated a total ofthree times).To this mixture, alcohol (1 equiv., 0.5 mmol) andNMI (0.2 equiv., 0.1 mmol) was added with 1 mL of acetonitrile.Themixturewas stirred for the required time at 70 °C under an O2 balloon. At the end of the reaction, the mixturewas diluted by adding ethyl acetate and filtered through silicaplugs. The silica was washed several times with ethyl acetate,and the solvent was evaporated. A yield of the aldehyde productwas determined by integration using an internal standard(1,1,2,2-tetrachloroethane) in the 1H NMR spectrum. With 1-methyl-1H-imidazole, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, basolite C300, oxygen in acetonitrile, Time= 9h, T= 70 °C , Reagent/catalyst, Time Kim, Bo Ram; Oh, Jung Suk; Kim, Jinho; Lee, Chang Yeon; Catalysis Letters; vol. 146; nb. 4; (2016); p. 734 743 View in Reaxys With 5percent palladium nanoparticles loaded on Cu(II) 4,4,4-trifluoro-1-(4-(pyridin-4-yl)phenyl)butane-1,3-dionemetal organic frameworks, air in 5,5-dimethyl-1,3-cyclohexadiene, Time= 25h, T= 130 °C , Catalytic behavior, Temperature, Solvent, chemoselective reaction Chen, Gong-Jun; Wang, Jing-Si; Jin, Fa-Zheng; Liu, Ming-Yang; Zhao, Chao-Wei; Li, Yan-An; Dong, Yu-Bin; Inorganic Chemistry; vol. 55; nb. 6; (2016); p. 3058 - 3064 View in Reaxys

90 %Chromat.

With tert.-butylhydroperoxide in dimethyl sulfoxide, Time= 4h, T= 110 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

233/438

2018-03-11 22:07:32


Zhou, Qiangfei; Wan, Zijuan; Yuan, Xiaofeng; Luo, Jun; Applied Organometallic Chemistry; vol. 30; nb. 4; (2016); p. 215 - 220 View in Reaxys , Time= 1h, T= 350 °C , Catalytic behavior, Temperature Kumar, Ashish; Kumar, Vanama Pavan; Srikanth, Amirineni; Vishwanathan, Venkataraman; Chary, Komandur V. R.; Catalysis Letters; vol. 146; nb. 1; (2016); p. 35 - 46 View in Reaxys Stage 1: With oxygen in water, Time= 0.833333h, Darkness, Sealed tube Stage 2: in water, Time= 8h, T= 20 °C , p= 760.051Torr , Irradiation, Reagent/catalyst Yang, Juan; Shen, Xiaoxiao; Li, Yingjie; Bian, Linyan; Dai, Jun; Yuan, Dongsheng; ChemCatChem; vol. 8; nb. 7; (2016); p. 1399 - 1409 View in Reaxys > 99 With Iron(III) nitrate nonahydrate, 9-azabicyclolt;3.3.1gt;nonane-N-oxyl in acetonitrile, Time= 1.5h, T= 20 °C %Chromat. Wang, Lianyue; Shang, SenSen; Li, Guosong; Ren, Lanhui; Lv, Ying; Gao, Shuang; Journal of Organic Chemistry; vol. 81; nb. 5; (2016); p. 2189 - 2193 View in Reaxys 2.3 Catalytic Oxidation of Alcohols General procedure: The oxidation reactions were carried out in a 100 ml flask (with a condenser) containing 1 mmol alcohol, 0.1 g CQDs, and 25 mL deionized water as solvent. The mixture was stirred to form suspension. Then 5 mL of 10 percent NaClO was slowly added. The reactions were conducted at 70 °C under ambient pressure for 6 h. When the reaction was finished, the mixture was extracted by ethyl acetate (2 9 30 mL). Then ethyl acetate was removed in vacuum. Oxygenated products were analyzed by an Agilent 7890A Gas Chromatographer (GC). Furthermore, for the test ofreusability, the used catalyst was removed from the reaction by filtration and washed with deionized water and acetone, and dried in air. With sodium hypochlorite in water, Time= 6h, T= 70 °C , p= 760.051Torr , Reagent/catalyst Zhang, Xiao; Fu, Xiaobo; Zhang, Yuanming; Zhu, Yi; Yang, Jun; Catalysis Letters; vol. 146; nb. 5; (2016); p. 945 - 950 View in Reaxys With hydrogen, potassium carbonate in toluene, Time= 0.5h, T= 499.84 °C Okumura, Kazu; Synlett; vol. 27; nb. 8; (2016); p. 1223 - 1226; Art.No: ST-2015-U0854-C View in Reaxys 95 %Chromat.

With sodium hypochlorite, sodium hydrogencarbonate, potassium bromide in dichloromethane, water, T= 0 °C , pH= 8.9 Hepperle, Johannes A.M.; Mitschang, Fabian; Bier, Anna K.; Dettlaff, Barbara K.; Greiner, Andreas; Studer, Armido; RSC Advances; vol. 3; nb. 48; (2013); p. 25976 - 25981 View in Reaxys 1.3 Selective oxidation of benzyl alcohol Benzyl alcohol (AR, Sinopharm Chemical Reagent Co.,Ltd), Pd/FeC catalyst, K2CO3, and solvent were added at acertain proportion to a 25 ml three-neck flask with a refluxcondenser. The suspension was stirred magnetically at a certaintemperature under an O2 atmosphere in a thermostatic waterbath for several hours. The product was analyzed by highperformance liquid chromatography (HPLC, Agilent 1100) andthe conversion of benzyl alcohol and the selectivity for benzaldehydewere calculated by the peak area normalization method. After the reaction the solution was transferred into a vesseland a magnet was placed on the outside of the vessel wall. ThePd/FeC catalyst quickly adsorbed onto the wall of the vesseland the catalyst was then collected and washed with ethanoland deionized water three times and dried at 50 °C for reuse. With oxygen, potassium carbonate in acetonitrile, Time= 25h, T= 80 °C , Catalytic behavior, Solvent, Temperature Zhang, Hai; Liu, Ying; Zhang, Xungao; Chinese Journal of Catalysis; vol. 32; nb. 11-12; (2011); p. 1693 - 1701 View in Reaxys 3.2. Photocatalytic experiments

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

234/438

2018-03-11 22:07:32


The photocatalytic oxidation experiments were performed ina photochemical reactor (BL-GHX-V, Shanghai Bilon InstrumentManufacturing Co., Ltd) equipped with a 500 W Hg lamp, thewavelength of it is ∼ 365 nm. The system was cooled by a cir-culating water bath maintained at 20C. All the photocatalyticreactions were performed using the same initial conditions: 0.1 mL BA was mixed with 100 mg P25 and 50 mL Mill-Q ultrapurewater under constant magnetic stirring. The scavengers i-PrOH[V (i-PrOH:H2O = 1:16)], SO (c = 50 mM L−1), potassium bromate(c = 50 mM L−1), BQ (c = 50 mM L−1) were added to the different ves-sel. Before the irradiation, the mixture was stirred for 1 h in the darkto allow the system to reach adsorption equilibrium. All of the sam-ples, each of which was 4 mL in volume, were taken intermittentlyfor analysis. The solid was subsequently removed from the solutionusing a 0.45 m nitrocellulose filter.The purging N2was conducted at a flow rate of ∼0.08 L min−1for 40 min before the irradiation, and the gas was purged uniformlyduring the whole experiment. With potassium bromate, titanium dioxide, Time= 1h, UV-irradiation, Reagent/catalyst Zhao, Lei; Zhang, Baoyue; Xiao, Xin; Gu, Feng Long; Zhang, Rui-Qin; Journal of Molecular Catalysis A: Chemical; vol. 420; (2016); p. 82 - 87 View in Reaxys Catalytic activity tests The aerobic oxidation of benzyl alcohol was carried out toevaluate the catalytic activity of the NC materials (a–e). Thereaction was carried out in a 50 ml two-neck flask at atmosphericpressure. NC (0.3 g) was used as catalyst, which wassuspended in 10 ml toluene by stirring. Then 1.0 mmol benzylalcohol was added into the reactor. The mixture was contactedwith air and the reaction temperature was kept at 353 K. A gaschromatograph equipped with a capillary column was used toanalyze the products With oxygen in toluene, T= 79.84 °C , p= 750.075Torr Zhang, Min; Zhu, Wanchun; Liu, Gang; Zhang, Xiuyan; Zu, Yanhong; Zhang, Wenxiang; Yan, Wenfu; Jia, Mingjun; Chinese Journal of Catalysis; vol. 33; nb. 2-3; (2012); p. 465 - 472 View in Reaxys 0.313 mmol

General procedure for the synthesis of aldehydes and other oxidation derivatives General procedure: 500 μl CH2Cl2 solution of the porphyrin (1.00 × 10−3mmol) and evaporated solvent, were dissolved in 0.01 molof alcohols in a narrow glass tube. A stream of air at 1 atmpressure was bubbled through the solution and the samplewas irradiated using visible light [180 Power LED lamps ina circular manner, 1 W, 3.2 V, (79000 LUX) until degradationof sensitizers, the intensity was determined with a lightmeter (MASTECH model MS 6612 Digital Lux Meter) andλ > 350 nm]. The consumption of the starting alcohols andthe formation of the corresponding oxidized compoundsfrom alcohols were monitored by Thermo Quest FinniganAQA GC–MS, Agilent gas chromatograph and spectralchanges were monitored with a Shimadzu UV-2100. With oxygen, 5,15,10,20-tetraphenylporphyrin in neat (no solvent), Time= 80h, p= 760.051Torr , Irradiation, Green chemistry, Catalytic behavior, Reagent/catalyst Mehrabi-Kalajahi, Seyed Saeed; Hajimohammadi, Mahdi; Safari, Nasser; Journal of the Iranian Chemical Society; vol. 13; nb. 6; (2016); p. 1069 - 1076 View in Reaxys With oxygen, Time= 16h, T= 25 °C , p= 750.075Torr , Reagent/catalyst Martínez-Prieto; Ferry; Rakers; Richter; Lecante; Philippot; Chaudret; Glorius; Chemical Communications; vol. 52; nb. 26; (2016); p. 4768 - 4771 View in Reaxys 2.3. General procedure of catalytic oxidation reaction General procedure: Oxidation of alcohol was carried out in a 100 mL three-neckedflask equipped with a reflux condenser, a magnetic stirrer anda thermometer. typically, the reactor was loaded with alcohol(5 mmol), H2O (10 mL) and catalyst. then, 30percent aqueous hydro-gen peroxide (10 mmol) was added dropwise to the reactorunder the setting temperature under vigorous stirring for 300 min.after the finish of reaction, the products were extracted withdichloromethane from aqueous phase and were identified by aSP-3420A GC equipped with a KB-Wax column (30 m, 0.32 mm id,0.25 m film thickness) with toluene as internal standardAlcoholconversion(percent)=[(molesofalcoholadded−molesofunconvertedalcohol)/molealcoholadded]×100Productselectivity(percent)=[molesoftheproduct/(molesofalcoholadded−molesofunconvertedalcohol)]×100TOF : mmolketone/(mmolheteropolyanionincatalyst×reactiontime). With dihydrogen peroxide in water, Time= 6h, T= 80 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

235/438

2018-03-11 22:07:32


Wang, Hefang; Fang, Luping; Yang, Yongfang; Hu, Rongbin; Wang, Yanji; Applied Catalysis A: General; vol. 520; (2016); p. 35 - 43 View in Reaxys Oxidation reaction. General procedure: Substrate (benzyl alcohol or cyclohexane), catalystand aqueous H2O2 (30percent) were inserted into a 60 ml Parr reactor. Thereactor was heated to a desired temperature and the mixture was stirred.The catalyst was separated, and the products were extracted with diethylether, dried and analyzed by GC [chromatograph, Varian CP-3800 GC;column, CP-Sil (30 m × 0.25 mm)]. With dihydrogen peroxide in water, Time= 5h, T= 90 °C , Reagent/catalyst, Time Trakarnpruk, Wimonrat; Mendeleev Communications; vol. 26; nb. 3; (2016); p. 256 - 258 View in Reaxys 2.3 Oxidation of benzyl alcohol The liquid phase catalytic oxidation of benzyl alcohol was carried out in a round-bottom flask (50mL) connected with a reflux condenser. In a typical reaction, benzyl alcohol (30mmol) and catalyst (100mg) were added to the glass flask. The reaction was initiated by adding 30wtpercent H2O2 solution with vigorous stirring. The typical reaction temperature and time were 80°C and 6h respectively. After reaction, the mixture was centrifuged to remove catalyst and the water, the organic phase was analyzed by an HP 6890/5973 GC/MS instrument and quantified by an Agilent 6890 gas chromatography. With 4C8H15N2 (1+)*PMo11VO40 (4-), dihydrogen peroxide in water, Time= 6h, T= 80 °C , Catalytic behavior, Reagent/ catalyst, Temperature, Time Tong, Jinhui; Su, Lingdi; Li, Wenyan; Wang, Wenhui; Ma, Hengchang; Wang, Qizhao; Polyhedron; vol. 115; (2016); p. 282 - 287 View in Reaxys With oxygen in water, Time= 20h, Irradiation, Sealed tube Kitano, Sho; Tanaka, Atsuhiro; Hashimoto, Keiji; Kominami, Hiroshi; Applied Catalysis A: General; vol. 521; (2016); p. 202 - 207 View in Reaxys 5.3 : Oxidation of alcohols catalyzed by [Fe(N-N)3](OTf)2In General procedure: In a round-bottomed flask the solvent (3.0 mL) and the cat-alyst precursor [Fe(N-N)3] (OTf)2(0.050 mmol) were introduced, followed by the substrate (2.5 mmol). For reactions performed at temperatures higher than r.t., the resulting solution was heated ina thermostatted bath to the desired temperature. Slow addition of the oxidant was then carried out under stirring. After the desired time the reaction mixture was cooled at −18 °C and subsequently analized by GC and/or NMR. With tert.-butylhydroperoxide, [Fe(2,2'-bipyridine)3](OTf)2, Time= 24h, T= 25 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Temperature Chàvez, Jennifer E.; Crotti, Corrado; Zangrando, Ennio; Farnetti, Erica; Journal of Molecular Catalysis A: Chemical; vol. 421; (2016); p. 189 - 195 View in Reaxys With oxygen in toluene, T= 80 °C , p= 750.075Torr , Catalytic behavior, Reagent/catalyst Zhang, Na; Du, Yiyun; Yin, Min; Guan, Chaoyang; Feng, Junting; Li, Dianqing; RSC Advances; vol. 6; nb. 55; (2016); p. 49588 - 49596 View in Reaxys > 99 Catalytic oxidation. %Chromat. General procedure: Oxidation reaction was carried out in a 10 mL three-necked round bottom flask equipped with a mechanical stirrer and a condenser connected to a balloon filled with oxygen. Typically, to alcohol (2 mmol) dissolved in 3 mL of acetonitrile were added CuBr2 (0.1 mmol), TEMPO (0.08 mmol), and 0.11 g of the pyridinecarboxaldimine grafted to magnetic nanoparticles. The system was purged with oxygen and sealed. Stirring it for 0.5 h was followed by addition of the base (0.3 mmol). The process was monitored by GC. Upon completion of the reaction, the supported pyridinecarboxaldimine was collected by a magnet and washed with acetonitrile repeatedly. The following drying under vacuum to constant weight made the nanoparticles ready for another run.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

236/438

2018-03-11 22:07:32


With 1-methyl-1H-imidazole, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, copper(ll) bromide in acetonitrile, Time= 9h, T= 50 °C , Catalytic behavior, Reagent/catalyst, Temperature Zhang; Sun; Guo; Su; Zhao; Russian Journal of General Chemistry; vol. 86; nb. 4; (2016); p. 944 - 952; Zh. Obshch. Khim.; vol. 86; nb. 4; (2016); p. 944 - 952,9 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, Time= 5h Fernandes, Antony E.; Riant, Olivier; Jonas, Alain M.; Jensen, Klavs F.; RSC Advances; vol. 6; nb. 43; (2016); p. 36602 - 36605 View in Reaxys 99 %Chromat.

6.4.4. Oxidation of benzyl alcohol. NaOCl5H2O crystals (1.81 g,11.0 mmol) were added in one portion to a mixture of Bu4NHSO4(0.170 g, 0.50 mmol), TEMPO (15.6 mg, 0.10 mmol), benzyl alcohol(1.10 g, 10.2 mmol), in dichloromethane (30 mL) at 5 C. Afterstirring for 1 h, 0.5 mL of the organic layer and 0.03 g weighed of1,3-dichlorobenzene as an internal standard were added to 2 mL ofCH2Cl2. Benzaldehyde was determined in 99percent yield for GC analysis.GCeMS analysis of the product was identical with authentic sample. GCeMS: m/z106 (M, relative intensity 74percent), 105 (74percent), 85(0.4percent), 77(base peak), 63(2percent), 51 (27percent), 39 (8percent). With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium hypochlorite pentahydrate, tetra(n-butyl)ammonium hydrogensulfate in dichloromethane, Time= 1h, T= 5 °C Okada, Tomohide; Asawa, Tomotake; Sugiyama, Yukihiro; Iwai, Toshiaki; Kirihara, Masayuki; Kimura, Yoshikazu; Tetrahedron; vol. 72; nb. 22; (2016); p. 2818 - 2827 View in Reaxys With dihydrogen peroxide in water, Time= 2h, T= 25 °C Rostamnia, Sadegh; Doustkhah, Esmail; Golchin-Hosseini, Habib; Zeynizadeh, Behzad; Xin, Hongchuan; Luque, Rafael; Catalysis Science and Technology; vol. 6; nb. 12; (2016); p. 4124 - 4133 View in Reaxys

91 %Spectr.

2 : 2.6. PIC-mediated Montanari oxidation of alcohols General procedure: alcohol substrate (1.0 mmol), TEMPO(0.001 mmol, 0.068 mg) or PES-im-TEMPO (0.001 mmol, 5.0 mg), and CH2Cl2 (3.5 mL) were charged into a 25-mL round-bottom flask. The mixture was cooled to 10 °C, and NaBr (1.0 M, 0.15 mL) and NaClO(0.37M, 3.35mL, pH≈9.1) were added sequentially. The resulting mixture was magnetically stirred at 1400 rpm. After a certain period of time,the reaction was quenched by consuming hypochlorite with excess sodium sulfite, and the supernatant was analyzed by gas chromatography(GC) after dried with anhydrous sodium sulfate. The catalyst precipitated after adding HCl (1.0M) to adjust the pH to 2, and was collected by centrifugation and used for next cycles after drying in vacuum. The organic layer was separated and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to result in the crude product, which was purified by silica gel column chromatography (ethyl acetate/petroleum ether 10/1). The yield of the product was calculated by 1H NMR spectroscopy after careful determination of its weight. With sodium hypochlorite, sodium bromide in dichloromethane, water, Time= 0.025h, T= 10 °C , Catalytic behavior, Reagent/catalyst Chen, Liang; Tang, Jun; Zhang, Qi; Wang, Jianli; Reactive and Functional Polymers; vol. 105; (2016); p. 134 139 View in Reaxys 2.3. General procedure for alcohol dehydrogenation reaction General procedure: The catalytic experiments were carried out in a fixed bed reactor (1.5cm id) at atmospheric pressure under N2 flow. About 0.5g of the catalyst was loaded and pretreatment was done in N2 gas flow (purity 99.99percent, 30mL/min) at 723K for 4h. A thermocouple was inserted in the catalyst bed to measure the catalyst bed temperature. After pretreatment, the reactor was cooled to the desired reaction temperature and the reactant (benzyl alcohol) was fed at a flow rate of 3.0mLh−1 along with the N2 gas flow at a rate of 30mL/min to keep the WHSV at 8.56h −1. The product was collected in an ice cold trap periodically for every 60min and analyzed by a gas chromatograph (CIC, India) equipped with a flame ionization detector and SE-30 column. The oven temperature was kept at 483K, with ramp rate 10K/min whereas injector and detector temperature were kept at 503 K during the analysis. (0012) The regeneration of the catalyst was done by treating the spent catalyst with O2/N2 mixture (1:9vol ratios) in the same flow as reaction condition at 673 K temperature. Then reactor was flushed with N2 flow for one hour

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

237/438

2018-03-11 22:07:32


and feed mixture was introduced and product was collected and analyzed as described earlier. (0013) In the case of dehydrogenation of primary alcohol substrates (ethanol, 1-Propanol, 1-butanol and 1-octanol) the reactor effluent was analyzed online for first three substrates and offline for 1-octanol. We used a gas chromatograph (CIC, India) equipped with a flame ionization detector and SE-30 column. All transfer lines from the vaporizer to the reactor and gas chromatograph (GC) were heated to above 383K to avoid condensation of the reactants and products. The oven temperature was kept at 383K with ramp rate 5K/min whereas injector and detector temperature were kept at 403 K during the online analysis. For 1-octanol dehydrogenation product, the G.C conditions were kept same as for benzyl alcohol. With ZnO-CeO2 mixed oxide, Time= 1h, T= 299.84 °C , p= 760.051Torr , Inert atmosphere Enjamuri, Nagasuresh; Hassan, Shahid; Auroux, Aline; Pandey, Jai Krishna; Chowdhury, Biswajit; Applied Catalysis A: General; vol. 523; (2016); p. 21 - 30 View in Reaxys Typical procedure for catalytic oxidation of alcohols General procedure: The typical procedure is the following: 3 mL CH3CN,0.01 mmol catalyst, and 1 mmol Benzyl alcohol were added to round-bottomed flask equipped with a reflux condenser.Then, 1 mmol aqueous H2O2 was dropwise added with in 5 min under stirring. The reaction time was counted after the addition of aqueous H2O2, and the reaction mixture was sampled periodically. The typical reaction temperature is 85 °C, and reaction time is 3–7 h. The progress was monitored by TLC (EtOAc/n-hexane, 1/5). After completionof the reaction, the catalyst was separated from the product by filtration and the liquid was analyzed by a gas chromatograph. With dihydrogen peroxide in water, acetonitrile, Time= 5h, T= 85 °C , Reagent/catalyst, Solvent Babahydari, Ali Kazemi; Fareghi-Alamdari, Reza; Hafshejani, Shahrbanou Moradpour; Rudbari, Hadi Amiri; Farsani, Mostafa Riahi; Journal of the Iranian Chemical Society; vol. 13; nb. 8; (2016); p. 1463 - 1470 View in Reaxys With air, UiO-68-AP embedded Pd(0) nanoparticles in 5,5-dimethyl-1,3-cyclohexadiene, Time= 12h, T= 120 °C , Catalytic behavior, Solvent, Temperature, Reagent/catalyst Li, Yan-An; Yang, Song; Liu, Qi-Kui; Chen, Gong-Jun; Ma, Jian-Ping; Dong, Yu-Bin; Chemical Communications; vol. 52; nb. 39; (2016); p. 6517 - 6520 View in Reaxys With oxygen in toluene, Time= 3h, T= 110 °C , p= 760.051Torr , Catalytic behavior, Kinetics, Reagent/catalyst, Temperature Santra, Chiranjit; Auroux, Aline; Chowdhury, Biswajit; RSC Advances; vol. 6; nb. 51; (2016); p. 45330 - 45342 View in Reaxys 95 %Chromat.

With potassium hydoxide in para-xylene, Time= 4h, T= 80 °C , Green chemistry Shaabani, Ahmad; Shaabani, Shabnam; Afaridoun, Hadi; RSC Advances; vol. 6; nb. 54; (2016); p. 48396 48404 View in Reaxys

81.1 With tert.-butylhydroperoxide, [{Cu(5-{(pyridin-4-ylmethyl)-amino}isophthalic acid)(DMF)}·DMF·H2O]n in water, %Chromat. Time= 0.5h, T= 100 °C , Sealed tube, Microwave irradiation, Catalytic behavior, Reagent/catalyst Karmakar, Anirban; Martins, Luísa M. D. R. S.; Hazra, Susanta; Guedes Da Silva, M. Fátima C.; Pombeiro, Armando J. L.; Crystal Growth and Design; vol. 16; nb. 4; (2016); p. 1837 - 1849 View in Reaxys 95 %Chromat.

General procedure for the oxidation of alcohols General procedure: To a stirred suspension of the selected alcohol (0.5 mmol)and the heterogeneous catalyst VSBC(at)NS (0.1 mmol of V) in methanol (2 mL), H2O2 (0.06 mL, 0.6 mmol, 30 percentaq) was added in one portion. The slurry was stirred under reflux condition for 4 h. The catalyst was filtered off and washed with acetone (10 mL). The filtrate was diluted with ethyl acetate (10 mL) and the resulting solution was dried with anhydrous sodium sulfate, filtered and evaporated in vacuum to afford the crude product which was purified by column chromatography on silica gel (5 percent EtOAc in hexane)to afford the pure aldehyde. With dihydrogen peroxide in methanol, water, Time= 4h, Reflux, Green chemistry, Catalytic behavior, Solvent, Temperature

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

238/438

2018-03-11 22:07:32


Dabiri, Minoo; Koohshari, Majid; Shafipour, Fazeleh; Kasmaei, Melika; Salari, Parinaz; MaGee, David; Journal of the Iranian Chemical Society; vol. 13; nb. 7; (2016); p. 1265 - 1272 View in Reaxys 97 %Spectr.

Typical procedure for oxidationof alcohols using PIB-bound IBX. Thedesired alcohol (0.5 mmol) and 2 equivalents of of PIB-bound IBX were dissolved inheptane. Then 2 equivalents of boron trifluoride diethyl etherate was thenadded into the reaction mixture and the reaction mixture was stirred at roomtemperature for 30 min. Analiquot of the heptane reaction mixture was taken and diluted with CDCl3to determine the conversion of the substrate to product by 1H NMR spectroscopy. Kinetic studies where areaction mixture in CDCl3 was directly analyzed by 1H NMRspectroscopy had previously been used to show that this was a sufficient timefor complete conversion of alcohols to their product aldehyde or ketone Asdescribed above, the products were separated from the heptane solution of anyunreacted or spent oxidant by an extraction with acetonitrile. The heptane from the solution ofpolyisobutylene-bound substrates was then removed at reduced pressure and the PIBspecies isolated were reoxidized as described above. The reoxidized PIB-boundIBX was always characterized by 1H NMR and the ratio of PIB-boundIBX to the ester of PIB-bound 2-iodobenzoic acid was always calculated before asubsequent cycle. With boron trifluoride diethyl etherate, C79H149IO4 in n-heptane, Time= 0.5h, T= 25 °C , Solvent, Reagent/catalyst, Time, Temperature Samunual, Peerada; Bergbreiter, David E.; Tetrahedron Letters; vol. 57; nb. 30; (2016); p. 3272 - 3276 View in Reaxys

100 With dihydrogen peroxide in acetonitrile, Time= 1.5h, T= 80 °C , Irradiation, Catalytic behavior, Solvent, Reagent/ %Chromat. catalyst Rahimi, Rahmatollah; Moshari, Mahsa; Rabbani, Mahboubeh; Azad, Alireza; RSC Advances; vol. 6; nb. 47; (2016); p. 41156 - 41164 View in Reaxys With dihydrogen peroxide, Time= 6h, T= 100 °C , Catalytic behavior, Reagent/catalyst, Temperature, Time Alqurashi, Ghada K.; Al-Shehri, Abdulmohsen; Narasimharao, Katabathini; RSC Advances; vol. 6; nb. 75; (2016); p. 71076 - 71091 View in Reaxys With tungsten blue oxide modified with platinum nanoparticles in water, Irradiation Qamar; Fawakhiry; Azad; Ahmed; Khan; Saleh; RSC Advances; vol. 6; nb. 75; (2016); p. 71108 - 71116 View in Reaxys With La0.9Ce0.1CoO3, oxygen in toluene, T= 88 °C , p= 760.051Torr , Reagent/catalyst, Solvent Zhu, Junjiang; Zhao, Yanxi; Tang, Duihai; Zhao, Zhen; Carabineiro, Sónia A.C.; Journal of Catalysis; vol. 340; (2016); p. 41 - 48 View in Reaxys 2.4.2 Reaction with Molecular Oxygen General procedure: The oxidation reactions were performed in a batch-type reactor under atmospheric pressure. In a typical reaction appropriate amount of catalyst was added in a 50 mL two-necked flask containing substrates (100 mmol) and to that 0.2 mmol tertbutyl hydrogen peroxide (TBHP) was added in order to initiate the reaction. The reaction mixture was maintained at 80 °C (styrene) and 90 °C (benzyl alcohol) on REMI magnetic stirrer equipped with preheated oil bath at 600 rpm. The reaction was started by bubbling O2 (analytical grade) into the liquid. After completion of reaction, the catalyst was removed by simple centrifugation. The products were analysed on a GC using Rtx-5 capillary column by diluting with dichloromethane and drying with magnesium sulphate. Identification of the product was carried out by comparing it with authentic samples and then by gas chromatography-mass spectroscopy (GC-MS). With tert.-butylhydroperoxide, oxygen, Time= 24h, T= 90 °C , p= 760.051Torr , Green chemistry, Catalytic behavior, Reagent/catalyst Singh, Sukriti; Patel, Anjali; Catalysis Letters; vol. 146; nb. 6; (2016); p. 1059 - 1072 View in Reaxys With oxygen in neat (no solvent), Time= 7h, T= 99.84 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Temperature

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

239/438

2018-03-11 22:07:32


Kong, Liping; Wang, Chengcheng; Gong, Feilong; Zhu, Weidong; Zhong, Yijun; Ye, Xiangrong; Li, Feng; Catalysis Letters; vol. 146; nb. 7; (2016); p. 1321 - 1330 View in Reaxys With oxygen in toluene, Time= 16h, T= 80 °C Palo-Nieto, Carlos; Afewerki, Samson; Anderson, Mattias; Tai, Cheuk-Wai; Berglund, Per; Córdova, Armando; ACS Catalysis; vol. 6; nb. 6; (2016); p. 3932 - 3940 View in Reaxys 99 %Spectr.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, sodium carbonate in N,N-dimethyl-formamide, Time= 3h, T= 75 °C Ji, Guipeng; Yang, Zhenzhen; Zhang, Hongye; Zhao, Yanfei; Yu, Bo; Ma, Zhishuang; Liu, Zhimin; Angewandte Chemie - International Edition; vol. 55; nb. 33; (2016); p. 9685 - 9689; Angew. Chem.; vol. 128; nb. 33; (2016); p. 9837 - 9841,5 View in Reaxys 2.3. Oxidation of benzyl alcohol In a typical reaction, a test tube was filled with benzyl alcohol(1 mmol), periodic acid (0.5 mmol), C1-5 (0.01 mmol) and CH3CN(5 ml). This tube was refluxed for the appropriate time. The reactionswere monitored by gas chromatography. With [RuCl(2-[1H-benzimidazol-2-yl]quinoline)(p-cymene)]PF6, periodic acid in acetonitrile, T= 82 °C , Reagent/catalyst, Solvent Dayan, Osman; Tercan, Melek; Özdemir, Namik; Journal of Molecular Structure; vol. 1123; (2016); p. 35 - 43 View in Reaxys Catalytic Test The oxidation of benzyl alcohol using spinel NixMg1−xFe2O4x = 0.0, 0.2, 0.4, 0.6, 0.8 and 1.0) catalysts were carried out in a batch reactor operated under atmospheric conditions. 10 mmol of oxidant (H2O2 was added along with 1 g of nano-sized catalysts (MgFe2O4, Ni0.2Mg0.8Fe2O4, Ni0.4Mg0.6Fe2O4, Ni0.6Mg0.4Fe2O4, Ni0.8Mg0.2Fe2O4 and NiFe2O4 and the contents were heated at 80°C in an acetonitrile medium for 10 h in a three necked round bottom flask equipped with a reflux condenser and thermometer. The oxidized products after the catalytic reaction are collected and studied using Agilent GC spectrometer. The column used for the study was DB wax column (capillary column) of length 30 mm and helium was used as the carrier gas. With Ni0.6Mg0.4Fe2O4, dihydrogen peroxide in acetonitrile, Time= 5h, T= 80 °C , p= 760.051Torr , Green chemistry, Reagent/catalyst Hema; Manikandan; Karthika; Durka; Arul Antony; Venkatraman; Journal of Nanoscience and Nanotechnology; vol. 16; nb. 7; (2016); p. 7325 - 7336 View in Reaxys With air, 2 wtpercent Ni-Co oxide nanoparticle loaded nitrogen doped FDU-15 in N,N-dimethyl-formamide, Time= 7h, T= 110 °C , Catalytic behavior, Solvent, Temperature, Reagent/catalyst, Time Fu, Xiaoran; Wu, Shujie; Li, Zhifang; Yang, Xiaoyuan; Wang, Xiufang; Peng, Ling; Hu, Jing; Huo, Qisheng; Guan, Jingqi; Kan, Qiubin; RSC Advances; vol. 6; nb. 62; (2016); p. 57507 - 57513 View in Reaxys With C38H33BFeN6O3, oxygen, sodium benzoylformate in acetonitrile, Time= 8h, Catalytic behavior Sheet, Debobrata; Paine, Tapan Kanti; Chemical Science; vol. 7; nb. 8; (2016); p. 5322 - 5331 View in Reaxys

9 %Chromat.

With potassium carbonate in para-xylene, Time= 2h, T= 80 °C , Green chemistry Shaabani, Ahmad; Afaridoun, Hadi; Shaabani, Shabnam; Applied Organometallic Chemistry; vol. 30; nb. 9; (2016); p. 772 - 776 View in Reaxys

75 %Spectr.

With (90)Au006 (09)Ag094, oxygen in 1,4-dioxane, Time= 24h, T= 80 °C , p= 760.051Torr , Reagent/catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

240/438

2018-03-11 22:07:32


Takale, Balaram S.; Feng, Xiujuan; Lu, Ye; Bao, Ming; Jin, Tienan; Minato, Taketoshi; Yamamoto, Yoshinori; Journal of the American Chemical Society; vol. 138; nb. 32; (2016); p. 10356 - 10364 View in Reaxys With [MoO3(1,2,4-triazole)0.5], dihydrogen peroxide in water, T= 70 °C , Reagent/catalyst Amarante, Tatiana R.; Neves, Patrícia; Valente, Anabela A.; Paz, Filipe A. Almeida; Pillinger, Martyn; Gonçalves, Isabel S.; Journal of Catalysis; vol. 340; (2016); p. 354 - 367 View in Reaxys 89 %Chromat.

General procedure for the oxidation of benzyl alcohol Benzyl alcohol (1 mmol), catalyst (2 molpercent), base (5 molpercent) and solvent (20 mmol) were placed in a Schlenk tube under argon or nitrogen atmosphere. The mixture was stirred magnetically under reflux over the specified time. The yield of the benzaldehyde was determined by GC analysis using chlorobenzene as an internal standard. With [(1,2,3,4,5-pentamethylcyclopentadiene)*IrCl(N-(pyridin-2-ylmethylene)aniline)]PF6, caesium carbonate in toluene, Time= 48h, Reflux, Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst, Solvent Thangavel, Saravanan; Boopathi, Subramaniam; Mahadevaiah; Kolandaivel, Ponmalai; Pansuriya, Pramod B.; Friedrich, Holger B.; Journal of Molecular Catalysis A: Chemical; vol. 423; (2016); p. 160 - 171 View in Reaxys

96.51 2.3. Catalytic Test %Chromat. The oxidation of benzyl alcohol using spinel MnxZn1−xFe2O4 (x = 0.0, 0.2, 0.4, 0.6, 0.8 and 1.0) nano catalysts were carried out in a batch reactor operated under atmospheric conditions. 5 mmol of oxidant (H2O2 was added along with 0.5 g of nano-sized catalysts (ZnFe2O4,Mn02Zn08Fe2O4, Mn04Zn06Fe2O4, Mn06Zn04Fe2O4,Mn08Zn02Fe2O4 and MnFe2O4 and the contents were heated at 80 C in an acetonitrile medium for 10 h in a three necked round bottom flask equipped with a reflux condenser and thermometer. The oxidized products afterthe catalytic reaction are collected and studied using Agilent GC spectrometer. The column used for the study was DB wax column (capillary column) of length 30 mmand helium was used as the carrier gas. With Mn0.6Zn0.4Fe2O4, dihydrogen peroxide in acetonitrile, Time= 5h, T= 80 °C , Inert atmosphere, Catalytic behavior, Reagent/catalyst, Time Hema; Manikandan; Gayathri; Durka; Arul Antony; Venkatraman; Journal of Nanoscience and Nanotechnology; vol. 16; nb. 6; (2016); p. 5929 - 5943 View in Reaxys 72 %Chromat.

With tetra-n-butylammonium hydrogen monopersulfate in water, Time= 3h, T= 60 °C Rezaeifard, Abdolreza; Jafarpour, Maasoumeh; Farrokhi, Alireza; Parvin, Sousan; Feizpour, Fahimeh; RSC Advances; vol. 6; nb. 69; (2016); p. 64640 - 64650 View in Reaxys With tris(bipyridine)ruthenium(II) dichloride hexahydrate, pentaaminechlorocobalt(III) dichloride, (PPh4)2[Mn(N) (CN)4] in aq. phosphate buffer, Time= 0.5h, T= 23 °C , pH= 6.8, Inert atmosphere, Irradiation, Catalytic behavior Chen, Gui; Chen, Lingjing; Ma, Li; Kwong, Hoi-Ki; Lau, Tai-Chu; Chemical Communications; vol. 52; nb. 59; (2016); p. 9271 - 9274 View in Reaxys With oxygen in hexane, T= 19.84 °C , p= 760.051Torr , Green chemistry, Solvent, Reagent/catalyst Patent; Lee, Deok Rok; Kim, Jeong Won; (10 pag.); KR2016/9439; (2016); (A) Korean View in Reaxys 2.4. General procedure for the selective oxidation of benzylic alcohol General procedure: All oxidation experiments of benzylic alcohol were performed in a 120 mL stainless steel autoclave equipped with the magnetic stirring and a temperature controller. Typical procedure for oxidation of benzyl alcohol is as follows: benzyl alcohol (0.162 g, 1.5 mmol), alcoholic solvent (15 mL), catalyst (0.05 g) and additive (0.05 g) were added into the autoclave. After the reactor was sealed, the pure oxygen was pumped to replace the atmosphere for several times. Then under pressure of 0.3 MPa, the mixture was preheated to 110 °C with magnetic stirring and kept for a certain time. After the autoclave was cooled and the excess gas was released, the as-obtained mixture was analyzed by GC and GC–MS.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

241/438

2018-03-11 22:07:32


With oxygen, potassium carbonate in isopropyl alcohol, Time= 4h, T= 110 °C , p= 2250.23Torr , Autoclave, Solvent Sun, Jinyan; Tong, Xinli; Liu, Zonghui; Liao, Shengyun; Zhuang, Xuli; Xue, Song; Catalysis Communications; vol. 85; (2016); p. 70 - 74 View in Reaxys > 99 With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C28H22CuN2O10S2 (2-)*2Na(1+), oxygen, potassium carbonate %Chromat. in water, Time= 10h, T= 20 °C , Reagent/catalyst Wu, Jianglong; Liu, Yan; Ma, Xiaowei; Liu, Ping; Gu, Chengzhi; Dai, Bin; Applied Organometallic Chemistry; vol. 30; nb. 7; (2016); p. 577 - 580 View in Reaxys With C29H35Cl2IrN2O2, sodium acetate in 2,2,2-trifluoroethanol, Time= 20h, Reflux Gülcemal, Süleyman; Gülcemal, Derya; Whitehead, George F. S.; Xiao, Jianliang; Chemistry - A European Journal; vol. 22; nb. 30; (2016); p. 10513 - 10522 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, laccase from Trametes versicolor, N,N-didodecyl-N,N-dimethylammonium bromide in aq. phosphate buffer, Time= 24h, T= 20 °C , Enzymatic reaction Paprocki, Daniel; Koszelewski, Dominik; Zadło, Anna; Walde, Peter; Ostaszewski, Ryszard; RSC Advances; vol. 6; nb. 72; (2016); p. 68231 - 68237 View in Reaxys 86 %Chromat.

With C39H29N5ORu(2+)*2ClO4 (1-), dihydrogen peroxide in water, acetonitrile, Time= 12h, T= 70 °C , Reflux, Catalytic behavior, Reagent/catalyst, Solvent Singha Hazari, Arijit; Ray, Ritwika; Hoque, Md Asmaul; Lahiri, Goutam Kumar; Inorganic Chemistry; vol. 55; nb. 16; (2016); p. 8160 - 8173 View in Reaxys With oxygen, potassium carbonate in toluene, Time= 5h, T= 80 °C , Catalytic behavior, Solvent, Reagent/catalyst Gong, Xia; Liu, Baocang; Zhang, Geng; Xu, Guangran; Zhao, Tuo; Shi, Dichao; Wang, Qin; Zhang, Jun; CrystEngComm; vol. 18; nb. 27; (2016); p. 5110 - 5120 View in Reaxys With palladium nanoparticle immobilized mesoporous silica ZrSBA-15, Time= 4h, T= 60 °C , Green chemistry, Catalytic behavior Ji, Ran; Zhai, Shangru; Zheng, Wei; Xiao, Zuoyi; An, Qingda; Zhang, Feng; RSC Advances; vol. 6; nb. 74; (2016); p. 70424 - 70432 View in Reaxys With [Co(1,4-benzenedicarboxylate)(1,4-diazabicyclo[2.2.2]octane)0.5], oxygen in N,N-dimethyl-formamide, Time= 10h, T= 90 °C , Green chemistry, Reagent/catalyst Peng, Ling; Wu, Shujie; Yang, Xiaoyuan; Hu, Jing; Fu, Xiaoran; Huo, Qisheng; Guan, Jingqi; RSC Advances; vol. 6; nb. 76; (2016); p. 72433 - 72438 View in Reaxys

96 %Chromat.

With [NiIICl22,6-bis(phenylazo)pyridine(H2O)], potassium tert-butylate, oxygen, zinc in tetrahydrofuran, Time= 4h, T= 26.84 - 49.84 °C Sengupta, Debabrata; Bhattacharjee, Rameswar; Pramanick, Rajib; Rath, Santi Prasad; Saha Chowdhury, Nabanita; Datta, Ayan; Goswami, Sreebrata; Inorganic Chemistry; vol. 55; nb. 19; (2016); p. 9602 - 9610 View in Reaxys With oxygen in water, T= 60 °C , Inert atmosphere, Catalytic behavior Saeed, Adnan M.; Wisner, Clarissa A.; Donthula, Suraj; Majedi Far, Hojat; Sotiriou-Leventis, Chariklia; Leventis, Nicholas; Chemistry of Materials; vol. 28; nb. 13; (2016); p. 4867 - 4877 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

242/438

2018-03-11 22:07:32


76 %Spectr.

With 1-methyl-1H-imidazole, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, (x)C2H3N*C12H6N2O4 (2-)*4C16H12O4 (2-)*C

22H16O4

(2-)*Cu(1+)*4HO(1-)*I(1-)*4O(2-)*6Zr(4+)

in acetonitrile, Time= 6h, T= 20 °C , Catalytic behavior, Reagent/

catalyst Yuan, Shuai; Chen, Ying-Pin; Qin, Jun-Sheng; Lu, Weigang; Zou, Lanfang; Zhang, Qiang; Wang, Xuan; Sun, Xing; Zhou, Hong-Cai; Journal of the American Chemical Society; vol. 138; nb. 28; (2016); p. 8912 - 8919 View in Reaxys With tert.-butylhydroperoxide, [Mn(C6H5COO)(H2O)(1,10-phenanthroline)2](ClO4)(CH3OH) in water, acetonitrile, Time= 6h, T= 70 °C , Inert atmosphere, Catalytic behavior, Solvent Kani, Ibrahim; Bolat, Serkan; Applied Organometallic Chemistry; vol. 30; nb. 8; (2016); p. 713 - 721 View in Reaxys With oxygen in toluene, Time= 0.5h, T= 80 °C , Catalytic behavior, Reagent/catalyst Tan, Yu; Sun, Dalei; Chen, Libao; Li, Cheng Chao; New Journal of Chemistry; vol. 40; nb. 10; (2016); p. 8364 8370 View in Reaxys With C36H38Cu2N4O13*H2O, potassium tert-butylate, oxygen in acetonitrile, Time= 2h, T= 20 °C , Catalytic behavior, Time Benferrah, Nassima; Hammadi, Mohamed; Philouze, Christian; Berthiol, Florian; Thomas, Fabrice; Inorganic Chemistry Communications; vol. 72; (2016); p. 17 - 22 View in Reaxys 95 %Chromat.

With potassium hydoxide in para-xylene, Time= 4h, T= 80 °C , Green chemistry, Catalytic behavior Shaabani, Ahmad; Afaridoun, Hadi; Shaabani, Shabnam; Keramati Nejad, Mina; RSC Advances; vol. 6; nb. 99; (2016); p. 97367 - 97375 View in Reaxys

56 %Chromat.

General procedure: A 70.0 mL solution of acetonitrile/water (6:1, v/v) was used todissolve glycerol (1610.0 mg, 17.5 mmol). A 7.0 mL of this glyc-erol solution was next mixed with 25.0 mg of each catalyst in abatch reactor. A magnetic stirring bar was also placed inside eachone of the batch reactor. The containers were then placed in apressure chamber, and the setup was flushed with oxygen. A reac-tion condition of 60C and pressure at 20 psi was maintainedfor 6 h. After reaction, the reactor was cooled to room tempera-ture and the vessels were taken out for filtration. The mixtureswere filtered through syringe filters to remove the solid catalysts.The filtrates were collected in separate round bottom flasks. Thesolvent was removed under reduced pressure by using a rotaryevaporator, and the resulting product mixtures were analyzedusing gas chromatography (Agilent Gas Chromatograph (GC-FID)6850, column: Agilent 19091Z-433, flow rate: 1.6 mL/min) andthe high-performance liquid chromatography (Agilent, column:Aminex HPX-87H Column, wash solution: 0.02 N H2SO4, flow rate1.0 mL/min, column temperature 60C, UV detector 210 nm). Theyield was calculated according to the amount of glycerol added. Inaddition, the products were analyzed and identified by1H and13CNMR. Dihydroxyacetone, HOCH2C( O)CH2OH, yield 55percent (withdimer).1H NMR (D2O, ppm), = 4.29 (s, 4H, 2CH2).13C NMR (D2O,ppm), = 211.93 (CO), 64.77 (-CH2-). With Pd-Ce nanoparticles supported on functional Fe-MIL-101-NH2 in water, acetonitrile, T= 60 °C , p= 1034.32Torr Li, Xinhang; Tjiptoputro, Adrian Kaizen; Ding, Jun; Xue, Jun Min; Zhu, Yinghuai; Catalysis Today; vol. 279; (2017); p. 77 - 83 View in Reaxys 2.4. Catalytic oxidation of benzyl alcohol In a typical reaction, a test tube was filled with benzyl alcohol,periodic acid, synthesized complexes K1–7 and solvent. This tubewas refluxed for the appropriate time. The reactions were monitoredby gas chromatography With C22H25Cl2NO3RhS, periodic acid in N,N-dimethyl-formamide, Time= 0.0833333h, T= 110 °C , Catalytic behavior, Reagent/catalyst, Solvent, Temperature Kağıt, Reyhan; Dayan, Osman; Özdemir, Namık; Polyhedron; vol. 117; (2016); p. 504 - 512 View in Reaxys [3-(4-Bromophenyl)oxiran-2-yl](phenyl)methanone (3aa);9 Typical Procedure

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

243/438

2018-03-11 22:07:32


General procedure: I2 (0.315 mmol, 1.05 equiv) and styrene (0.6 mmol, 2 equiv) wereadded to a solution of 4-bromobenzyl alcohol (0.3 mmol, 1 equiv) andH2O (100 μL) in i-Pr2O (3 mL) in a Pyrex test tube under O2. The mixturewas stirred and externally irradiated with four 22 W fluorescentlamps for 22 h. LiOH·H2O (1.8 mmol, 6 equiv) was then added, and thesolution was stirred for a further 2 h under air. The reaction wasquenched with sat. aq Na2S2O3 and the mixture was extracted withEtOAc. The organic layers were combined, dried (MgSO4), and concentratedin vacuo. The crude residue was purified by column chromatography[silica gel, hexane–EtOAc (5:1)] to give a white solid; yield:61.9 mg (0.20 mmol, 68percent). With water, iodine, oxygen in isopropyl alcohol, Time= 22h, Irradiation, Reagent/catalyst Omura, Ryuji; Fujiya, Akitoshi; Yamaguchi, Eiji; Tada, Norihiro; Miura, Tsuyoshi; Itoh, Akichika; Synthesis (Germany); vol. 48; nb. 22; (2016); p. 3971 - 3975; Art.No: SS-2016-F0297-OP View in Reaxys 81 %Chromat.

With strontium manganate, oxygen in toluene, Time= 6h, T= 79.84 °C Kawasaki, Shuma; Kamata, Keigo; Hara, Michikazu; ChemCatChem; vol. 8; nb. 20; (2016); p. 3247 - 3253 View in Reaxys With oxygen in ethanol, Time= 16h, T= 80 °C , p= 760.051Torr , Autoclave, Reagent/catalyst Slot, Thierry K.; Eisenberg, David; van Noordenne, Dylan; Jungbacker, Peter; Rothenberg, Gadi; Chemistry A European Journal; vol. 22; nb. 35; (2016); p. 12307 - 12311 View in Reaxys With 1-methyl-1H-imidazole, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C20H30N8Si2*2Cl(1-)*Cu(2+), copper in acetonitrile, Time= 2h, T= 20 °C , Reagent/catalyst, Time Kongkaew, Manisa; Sitthisuwannakul, Kannika; Nakarajouyphon, Vasut; Pornsuwan, Soraya; Kongsaeree, Palangpon; Sangtrirutnugul, Preeyanuch; Dalton Transactions; vol. 45; nb. 42; (2016); p. 16810 - 16819 View in Reaxys With oxygen in acetonitrile, Time= 6h, T= 24.84 °C , p= 760.051Torr , Irradiation, Time Yang, Juan; Shen, Xiaoxiao; Wei, Jianping; Zhang, Lina; Zhao, Dan; Yao, Banghua; Catalysis Science and Technology; vol. 6; nb. 20; (2016); p. 7604 - 7614 View in Reaxys

99 %Chromat.

With hydrogenchloride, C18H38N2O(1+)*F6P(1-), 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate, sodium nitrite in water, Time= 1h, T= 20 °C , Reagent/catalyst Hirashita, Tsunehisa; Nakanishi, Makoto; Uchida, Tomoya; Yamamoto, Masakazu; Araki, Shuki; Arends, Isabel W. C. E.; Sheldon, Roger A.; ChemCatChem; vol. 8; nb. 16; (2016); p. 2704 - 2709 View in Reaxys

95 %Spectr.

With C21H26ClN4O2Ru(1+)*CF3O3S(1-), potassium hydoxide in 1,2-dichloro-benzene, Time= 16h, T= 150 °C , Reflux, Inert atmosphere, Catalytic behavior, Reagent/catalyst Sabater, Sara; Müller-Bunz, Helge; Albrecht, Martin; Organometallics; vol. 35; nb. 13; (2016); p. 2256 - 2266 View in Reaxys With potassium carbonate in water, Time= 5h, T= 40 °C , Irradiation Wang, Xiaohui; Baiyila, Dahu; Li, Xiaotian; RSC Advances; vol. 6; nb. 109; (2016); p. 107233 - 107238 View in Reaxys

90 %Chromat.

With Fe3O4-platinum nanoparticles supported on pyridinium based poly methyl methacrylate ionic liquid functionalized magnetic silica, air in water, T= 80 °C , Catalytic behavior, Activation energy, Solvent Vessally, Esmail; Ghasemisarabbadeih, Mostafa; Ekhteyari, Zeynab; Hosseinzadeh-Khanmiri, Rahim; Ghorbani-Kalhor, Ebrahim; Ejlali, Ladan; RSC Advances; vol. 6; nb. 108; (2016); p. 106769 - 106777 View in Reaxys

84 %Chromat.

General procedure for aerobic catalytic oxidation of alcohols to aldehydes General procedure: Reactions performed at atmospheric pressure were conducted in a 50 ml round bottom flask or in vials of 20 ml capacity, at the desired temperature (usually room temperature). The catalyst (0.025 mmol) and

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

244/438

2018-03-11 22:07:32


TEMPO (0.05 mmol) were first charged to the flask and the solvent (2 mL) and alcohol substrate (1.0 mmol) were then added and the mixture was stirred for the duration of the reaction. When the reaction had finished, the reaction mixture was filtered, added an internal standard (50 μl of dodecane or 50 mg of naphthalene) and diethyl ether up to 10 mL. The homogenized mixture was analyzed by gas chromatography. At least, two determinations were carried out for each catalytic essay. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C22H24CuN2O2 in toluene, Time= 18h, T= 25 °C , p= 760.051Torr , Inert atmosphere, Schlenk technique, Temperature, Solvent Conejo, María del Mar; Ávila, Paloma; Álvarez, Eleuterio; Galindo, Agustín; Inorganica Chimica Acta; vol. 455; (2017); p. 638 - 644 View in Reaxys With cobalt(II) tetrasulfophthalocyanine supported on wool, air in water, Time= 9h, T= 20 °C , Reagent/catalyst, Solvent, Temperature Shaabani, Ahmad; Hezarkhani, Zeinab; Journal of Porphyrins and Phthalocyanines; vol. 20; nb. 6; (2016); p. 677 688 View in Reaxys 2.3.2. Oxidation of benzyl alcohol Catalytic oxidation reactions of benzyl alcohol into benzaldehydewere carried out in a 10 ml round-bottomflask equipped areflux condenser. In a typical catalytic reaction [31], a certainamount of catalysts and aqueous of hydrogen peroxide (30percent) wereadded to 5 ml toluene solution containing 0.43 g benzyl alcohol,and the reaction was magnetically stirred at a specified tempera-ture for a given time. At regular intervals, a portion of sample wasanalyzed by GC analysis using authentic sample as a standard. With dihydrogen peroxide in water, toluene, Time= 1h, T= 80 °C , Catalytic behavior, Reagent/catalyst, Temperature Dong, Xinbo; Yu, Chengxing; Wang, Danjun; Zhang, Yanjie; Wu, Panfeng; Hu, Huaiming; Xue, Ganglin; Materials Research Bulletin; vol. 85; (2017); p. 152 - 160 View in Reaxys 3,3-Difluorocyclobutanecarbaldehyde (21) General procedure: To a solution of (3,3-difluorocyclobutyl)methanol (4.0 g, 32.8 mmol) in dichloromethane (109 ml) at room temperature was added Dess-Martin Periodinane (16.7 g, 39.3 mmol). After 2 h, the reaction was diluted with two volumes of ether and treated with sodiumthiosulfate (32 g) in water (160 mL). After stirring at room temperature for 10 min, the layers were separated. The ethereal was washed with saturated sodium bicarbonate (2X), dried over magnesium sulfate, and filtered. The resulting solution was concentrated via distillation of the solvent through a short path distillation apparatus. The distillation was discontinued when 6.56 g remained in the boiling flask. Integration of the 1H NMR showed product as a 28.4 wtpercent solution in diethyl ether (1.86 g, 47percent yield). The material was directly used without further concentration With Dess-Martin periodane in dichloromethane, Time= 2h, T= 20 °C , Inert atmosphere Degnan, Andrew P.; Maxwell, Darrell; Balakrishnan, Anand; Brown, Jeffrey M.; Easton, Amy; Gulianello, Michael; Hanumegowda, Umesh; Hill-Drzewi, Melissa; Miller, Regina; Santone, Kenneth S.; Senapati, Arun; Shields, Eric E.; Sivarao, Digavalli V.; Westphal, Ryan; Whiterock, Valerie J.; Zhuo, Xiaoliang; Bronson, Joanne J.; Macor, John E.; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 24; (2016); p. 5871 - 5876 View in Reaxys 75 %Spectr.

With (phthalocyaninato)iron(II), oxygen, 4-nitro-benzoic acid in tetrahydrofuran, Time= 48h, T= 70 °C , Molecular sieve, Sealed tube Hirose, Daisuke; Gazvoda, Martin; Košmrlj, Janez; Taniguchi, Tsuyoshi; Organic Letters; vol. 18; nb. 16; (2016); p. 4036 - 4039 View in Reaxys With dihydrogen peroxide in toluene, Time= 8h, T= 80 °C , Reagent/catalyst Dong, Xinbo; Zhang, Xi; Wu, Panfeng; Zhang, Yanjie; Liu, Bin; Hu, Huaiming; Xue, Ganglin; ChemCatChem; vol. 8; nb. 23; (2016); p. 3680 - 3687 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

245/438

2018-03-11 22:07:32


96 %Chromat.

With dihydrogen peroxide in water, Time= 18h, T= 90 °C , Green chemistry, Reagent/catalyst, Temperature Fan, Juan; Pu, Fan; Sun, Man; Liu, Zhong-Wen; Han, Xiao-Yan; Wei, Jun-Fa; Shi, Xian-Ying; New Journal of Chemistry; vol. 40; nb. 12; (2016); p. 10498 - 10503 View in Reaxys With C11H21N2 (1+)*Br(1-)*SnCl2, dihydrogen peroxide in water, Time= 0.25h, T= 65 °C , Catalytic behavior, Reagent/ catalyst, Temperature, Solvent, Time Wang, Bingtong; Hu, Yulin; Fang, Dong; Wu, Lin; Xing, Rong; Journal of the Chinese Chemical Society; vol. 63; nb. 12; (2016); p. 991 - 999 View in Reaxys

95 %Chromat.

With dihydrogen peroxide in water, Time= 3h, T= 90 °C , Catalytic behavior, Solvent, Temperature Zohreh, Nasrin; Tavakolizadeh, Maryam; Hosseini, Seyed Hassan; Jahani, Mahboobeh; Pourjavadi, Ali; Bennett, Craig; New Journal of Chemistry; vol. 40; nb. 12; (2016); p. 10325 - 10332 View in Reaxys With tert.-butylhydroperoxide in decane, [D3]acetonitrile, Time= 2h, T= 80 °C , Sealed tube, Reagent/catalyst Thompson, Anthony B.; Pahls, Dale R.; Bernales, Varinia; Gallington, Leighanne C.; Malonzo, Camille D.; Webber, Thomas; Tereniak, Stephen J.; Wang, Timothy C.; Desai, Sai Puneet; Li, Zhanyong; Kim, In Soo; Gagliardi, Laura; Penn, R. Lee; Chapman, Karena W.; Stein, Andreas; Farha, Omar K.; Hupp, Joseph T.; Martinson, Alex B. F.; Lu, Connie C.; Chemistry of Materials; vol. 28; nb. 18; (2016); p. 6753 - 6762 View in Reaxys With oxygen in toluene, T= 80 °C , Catalytic behavior, Reagent/catalyst Fernandes, Antony E.; Riant, Olivier; Jensen, Klavs F.; Jonas, Alain M.; Angewandte Chemie - International Edition; vol. 55; nb. 37; (2016); p. 11044 - 11048; Angew. Chem.; vol. 128; (2016); p. 11210 - 11214,5 View in Reaxys

60.1 With tert.-butylhydroperoxide in acetonitrile, Time= 2h, T= 60 °C , Catalytic behavior, Reagent/catalyst, Solvent, %Chromat. Temperature Zhou; Pan; Wu; Qian; He; Chen; RSC Advances; vol. 6; nb. 87; (2016); p. 84106 - 84112 View in Reaxys 98 %Spectr.

With dihydrogen peroxide in acetonitrile, Time= 0.75h, T= 80 °C , Catalytic behavior, Reagent/catalyst, Solvent Ramezanalizadeh; Manteghi; RSC Advances; vol. 6; nb. 101; (2016); p. 99096 - 99104 View in Reaxys With oxygen in acetonitrile, Time= 4h, T= 20 °C , Irradiation Zhang, Ping; Liu, Ya; Tian, Baozhu; Luo, Yusheng; Zhang, Jinlong; Catalysis Today; vol. 281; (2017); p. 181 188 View in Reaxys

50 %Spectr.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, laccase from Trametes versicolor, oxygen in water, Time= 72h, T= 20 °C , Enzymatic reaction Galletti, Paola; Pori, Matteo; Funiciello, Federica; Soldati, Roberto; Ballardini, Alberto; Giacomini, Daria; ChemSusChem; vol. 7; nb. 9; (2014); p. 2684 - 2689 View in Reaxys

99.9 With tert.-butylhydroperoxide, C26H26Cu2N6O12 in water, Time= 1h, T= 120 °C , Microwave irradiation, Catalytic be%Chromat. havior, Reagent/catalyst Martins, Nuno M. R.; Mahmudov, Kamran T.; Guedes Da Silva, M. Fátima C.; Martins, Luísa M. D. R. S.; Pombeiro, Armando J. L.; New Journal of Chemistry; vol. 40; nb. 12; (2016); p. 10071 - 10083 View in Reaxys > 99 With tert.-butylnitrite, oxygen, acetic acid in toluene, Time= 1.5h, T= 50 °C , p= 750.075Torr , Reagent/catalyst, Sol%Chromat. vent

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

246/438

2018-03-11 22:07:32


Karimi, Babak; Farhangi, Elham; Vali, Hojatollah; Vahdati, Saleh; ChemSusChem; vol. 7; nb. 9; (2014); p. 2735 2741 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C18H10CuN4O6, potassium carbonate in water, Time= 18h, T= 60 °C , p= 760.051Torr , Reagent/catalyst, Solvent Zhang, Guoqi; Li, Li; Yang, Chengxiong; Liu; Golen, James A.; Rheingold, Arnold L.; Inorganic Chemistry Communications; vol. 51; (2015); p. 13 - 16 View in Reaxys 54 %Chromat.

3.1 Procedure for Catalytic Oxidation Catalytic oxidation of benzyl alcohol to correspondingaldehydes and ketones by the titled copper complexes werestudied in the presence of H2O2. In a typical reaction, benzyl alcohol (0.1 cm3, 1.0 mmol) was added to a solution ofcopper complexes (Cunpap, Cubsisnph, Cunpisnph) contactedto air (0.05 mmol) in 10ml of acetonitrile at 50, 60, 70,80 or 90 °C in an water bath under magnetic stirring. Thereaction was initiated by charging with 5.54 mmol aqueousH2O2 (30 percent) at the typical temperature. The reaction wasmonitored by gas chromatographic analyses, using computerizedstandard calibration curve. The oxidation productswere identified by comparing their retention times with thoseof authentic samples. Control reactions were done by withdrawingsamples (ca. 2 ml) of the reaction mixture andtreatment of the reaction mixture with solidMnO2 (to quenchthe excess aqueous H2O2) and with anhydrous sodium sulfate(to absorb excess water molecules), under the sameconditions in the catalytic runs. The resulting slurry wasfiltered on Celite, and the filtrate was injected in the GC. Thisallowed independent measurements for each sample. Thechemo-conversion of benzoyl alcohol to benzaldehyde wascalculated according to computerized standard calibrationcurves. All the oxidation processes were run at least induplicate to confirm the yield of the products. With C32H22CuN4O2, dihydrogen peroxide in water, acetonitrile, Time= 2h, T= 70 °C , Catalytic behavior Abdel-Rahman, Laila H.; Abu-Dief, Ahmed M.; Adam, Mohamed Shaker S.; Hamdan, Samar Kamel; Catalysis Letters; vol. 146; nb. 8; (2016); p. 1373 - 1396 View in Reaxys

90 %Chromat.

3.1 Procedure for Catalytic Oxidation Catalytic oxidation of benzyl alcohol to correspondingaldehydes and ketones by the titled copper complexes werestudied in the presence of H2O2. In a typical reaction, benzyl alcohol (0.1 cm3, 1.0 mmol) was added to a solution ofcopper complexes (Cunpap, Cubsisnph, Cunpisnph) contactedto air (0.05 mmol) in 10ml of acetonitrile at 50, 60, 70,80 or 90 °C in an water bath under magnetic stirring. Thereaction was initiated by charging with 5.54 mmol aqueousH2O2 (30 percent) at the typical temperature. The reaction wasmonitored by gas chromatographic analyses, using computerizedstandard calibration curve. The oxidation productswere identified by comparing their retention times with thoseof authentic samples. Control reactions were done by withdrawingsamples (ca. 2 ml) of the reaction mixture andtreatment of the reaction mixture with solidMnO2 (to quenchthe excess aqueous H2O2) and with anhydrous sodium sulfate(to absorb excess water molecules), under the sameconditions in the catalytic runs. The resulting slurry wasfiltered on Celite, and the filtrate was injected in the GC. Thisallowed independent measurements for each sample. Thechemo-conversion of benzoyl alcohol to benzaldehyde wascalculated according to computerized standard calibrationcurves. All the oxidation processes were run at least induplicate to confirm the yield of the products. With C23H17BrCuN4O7, dihydrogen peroxide in water, acetonitrile, Time= 1h, T= 60 °C , Catalytic behavior Abdel-Rahman, Laila H.; Abu-Dief, Ahmed M.; Adam, Mohamed Shaker S.; Hamdan, Samar Kamel; Catalysis Letters; vol. 146; nb. 8; (2016); p. 1373 - 1396 View in Reaxys

79 %Chromat.

3.1 Procedure for Catalytic Oxidation Catalytic oxidation of benzyl alcohol to correspondingaldehydes and ketones by the titled copper complexes werestudied in the presence of H2O2. In a typical reaction, benzyl alcohol (0.1 cm3, 1.0 mmol) was added to a solution ofcopper complexes (Cunpap, Cubsisnph, Cunpisnph) contactedto air (0.05 mmol) in 10ml of acetonitrile at 50, 60, 70,80 or 90 °C in an water bath under magnetic stirring. Thereaction was initiated by charging with 5.54 mmol aqueousH2O2 (30 percent) at the typical temperature. The reaction wasmonitored by gas chromatographic analyses, using computerizedstandard calibration curve. The oxidation productswere identified by comparing their retention times with thoseof authentic samples. Control reactions were done by withdrawingsamples (ca. 2 ml) of the reaction mixture andtreatment of the reaction mixture with solidMnO2 (to quenchthe excess aqueous H2O2) and with anhydrous sodium sulfate(to absorb excess water molecules), under the sameconditions in the catalytic runs. The resulting slurry wasfiltered on Celite, and the filtrate was injected in the GC. Thisallowed independent measurements for each sample. Thechemo-conversion of benzoyl alcohol to benzaldehyde wascalculated according to computerized standard calibrationcurves. All the oxidation processes were run at least induplicate to confirm the yield of the products.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

247/438

2018-03-11 22:07:32


With C27H20CuN4O7, dihydrogen peroxide in water, acetonitrile, Time= 1h, T= 60 °C , Catalytic behavior Abdel-Rahman, Laila H.; Abu-Dief, Ahmed M.; Adam, Mohamed Shaker S.; Hamdan, Samar Kamel; Catalysis Letters; vol. 146; nb. 8; (2016); p. 1373 - 1396 View in Reaxys With 1-methyl-1H-imidazole, [2,2]bipyridinyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, copper(I) triflate in acetonitrile, Time= 0.183333h, T= 20 °C , Inert atmosphere, Reagent/catalyst Adomeit, Sven; Rabeah, Jabor; Surkus, Annette E.; Bentrup, Ursula; Brückner, Angelika; Inorganic Chemistry; vol. 56; nb. 1; (2017); p. 684 - 691 View in Reaxys With oxygen in toluene, Irradiation, Reagent/catalyst Li, Ang; Chang, Xiaoxia; Huang, Zhiqi; Li, Chengcheng; Wei, Yijia; Zhang, Lei; Wang, Tuo; Gong, Jinlong; Angewandte Chemie - International Edition; vol. 55; nb. 44; (2016); p. 13734 - 13738; Angew. Chem.; vol. 128; (2016); p. 13938 - 13942,5 View in Reaxys With [Fe2(μ-1,2-O2)(2-(2'-pyridyl)benzimidazole)4(acetonitrile)2]4+ in water, acetonitrile, Time= 1.38889h, T= 20 °C , Inert atmosphere, Schlenk technique, Time Szávuly, Miklós István; Surducan, Mihai; Nagy, Emoke; Surányi, Mátyás; Speier, Gábor; Silaghi-Dumitrescu, Radu; Kaizer, József; Dalton Transactions; vol. 45; nb. 37; (2016); p. 14709 - 14718 View in Reaxys 2.4. Evaluation of photocatalytic activity General procedure: 10 mg catalyst was suspended in 1.5 mL benzotrifluoride (BTF)solvent containing alcohol (0.1 mmol). The choice of BTF solventwas because it is inert to oxidation and has superior oxygen solubility[24]. The catalyst was blended evenly in the solution withmagnetic stirring for 30 min before illumination. Reaction temperaturewas kept at 20 °C with a water-cooling system. The reactionsolution was illuminated by a 300W Xe lamp with a UVcutoff filterwhere a majority of the light of wavelength shorter than420 nm was blocked. The reaction solution was analyzed with anAgilent Gas Chromatograph (GC7890) equipped with a flame ionizationdetector and a β-DEX 225 capillary column using dodecaneor undecane as the internal standard. The chemical structures ofproducts were confirmed by GC-mass spectrometry (MS) (AgilentTechnologies, GC6890N-MS5975). Stage 1: With oxygen, Time= 0.5h Stage 2:, Time= 1h, T= 20 °C , p= 750.075Torr , Irradiation, Reagent/catalyst Zhang, Bao; Li, Jun; Gao, Yuying; Chong, Ruifeng; Wang, Zhiliang; Guo, Lin; Zhang, Xianwen; Li, Can; Journal of Catalysis; vol. 345; (2017); p. 96 - 103 View in Reaxys 2.3. General procedure for oxidation of alcohols using Fe3O4-WO3 General procedure: To a mixture of Fe3O4-WO3 (0.005 g) and H2O2 30percent (2 mmol, 204 μL) in 2 mL CH3CN wasadded 0.5 mmol alcohol and stirred at 50 °C for 6 h. The reaction progress was monitoredby GC. After completion of the reaction, the catalyst was isolated using an external magneticfield. Assignments of products were made by comparison with authentic samples by GC. With dihydrogen peroxide in acetonitrile, Time= 6h, T= 50 °C , Catalytic behavior, Solvent, Temperature, Time Eftekhari-Sis, Bagher; Akbari, Masoud; Amini, Mojtaba; Ashouri, Fatemeh; Bagherzadeh, Mojtaba; Journal of Coordination Chemistry; vol. 70; nb. 2; (2017); p. 328 - 339 View in Reaxys > 95 %Spectr.

With 10-ethyl-9-iodo-3,7,8-trimethylbenzo[g]pteridine-2,4-(3H,10H)-dione, thiourea in dimethylsulfoxide-d6, [D3]acetonitrile, Time= 5h, Irradiation, Catalytic behavior, Reagent/catalyst, Solvent, Concentration Korvinson, Kirill A.; Hargenrader, George N.; Stevanovic, Jelena; Xie, Yun; Joseph, Jojo; Maslak, Veselin; Hadad, Christopher M.; Glusac, Ksenija D.; Journal of Physical Chemistry A; vol. 120; nb. 37; (2016); p. 7294 7300 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

248/438

2018-03-11 22:07:32


With tert.-butylhydroperoxide in N,N-dimethyl-formamide, Time= 3h, T= 50 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst Kamiloğlu, Ayşe Aktaş; Acar, İrfan; Biyiklioglu, Zekeriya; Saka, Ece Tuğba; Journal of Organometallic Chemistry; vol. 828; (2017); p. 59 - 67 View in Reaxys With oxygen in octanol, Time= 5h, T= 79.84 °C , Green chemistry, Catalytic behavior, Temperature, Solvent Siddique, Mohsin; Ilyas, Mohammad; Saeed, Muhammad; Journal of the Chemical Society of Pakistan; vol. 38; nb. 3; (2016); p. 454 - 462 View in Reaxys 2.3.1 Oxidation of Benzyl Alcohol The reactions were carried out in a 25 mL round-bottom flask equipped with magnetic stirrer and a reflux condenser. In a typical reaction, a certain amount catalyst and 30 percent H2O2 were added to the solution of 5 mL toluene and 0.43 g (4 mmol) benzyl alcohol at certain temperature for a certain amount of time. At regular intervals, samples from the reaction mixture were separated and analyzed by a HP sp-6890 gas chromatograph equipped with a capillary column (FFAP30 m × 0.32 × 0.30 μm) and an FID detector with the internal standard method. Assignments of products were made bycomparison with authentic samples [33]. With dihydrogen peroxide in toluene, Time= 8h, T= 80 °C , Reagent/catalyst, Time, Temperature Zhang, Yanjie; Wu, Lizhou; Dong, Xinbo; Wu, Panfeng; Hu, Huaiming; Xue, Ganglin; Catalysis Letters; vol. 146; nb. 12; (2016); p. 2468 - 2477 View in Reaxys With C44H31ClO2P2Pd, caesium carbonate in para-xylene, Time= 12h, Reflux, Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst De-Botton, Sophie; Romm, Ronit; Bensoussan, Guillaume; Hitrik, Maria; Musa, Sanaa; Gelman, Dmitri; Dalton Transactions; vol. 45; nb. 40; (2016); p. 16040 - 16046 View in Reaxys With oxygen in water, Time= 8h, T= 79.84 °C , p= 7500.75Torr , Catalytic behavior, Reagent/catalyst Xie, Jiahan; Yin, Kehua; Serov, Alexey; Artyushkova, Kateryna; Pham, Hien N.; Sang, Xiahan; Unocic, Raymond R.; Atanassov, Plamen; Datye, Abhaya K.; Davis, Robert J.; ChemSusChem; vol. 10; nb. 2; (2017); p. 359 - 362 View in Reaxys 2.2.5 General Procedure for the Oxidation of BenzylicAlcohols General procedure: A mixture of [Mn4(PW9O34)2]10−/Tb/TiO2 (40 mg), alcohols(1 mmol), 30percent H2O2 aqueous solution (6 mmol) andH2O (1 mL) was stirred at 80 °C for the time specified(Table 4). After the completion of the reaction, which wasmonitored by TLC (EtOAc/n-Hexane, 4/10), the catalystwas centrifuged. The product was extracted with CH2Cl2(3 × 5 mL) and the combined organic extractions washedwith brine (10 mL) and dried over anhydrous Na2SO4. Thesolvent was removed under reduced pressure to give thecorresponding pure carbonyl compound in most cases. With dihydrogen peroxide in water, Time= 5h, T= 80 °C , Reagent/catalyst Gholamyan, Sahar; Khoshnavazi, Roushan; Rostami, Amin; Bahrami, Leila; Catalysis Letters; vol. 147; nb. 1; (2017); p. 71 - 81 View in Reaxys With MnCo2O4 in toluene, Reagent/catalyst Yao, Lili; Zhang, Linlin; Liu, Yongxin; Tian, Long; Xu, Jin; Liu, Ting; Liu, Dan; Wang, Cheng; CrystEngComm; vol. 18; nb. 46; (2016); p. 8887 - 8897 View in Reaxys With oxygen in toluene, Time= 0.0833333h, T= 100 °C , Green chemistry, Catalytic behavior, Kinetics, Reagent/ catalyst, Temperature

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

249/438

2018-03-11 22:07:32


Assal, Mohamed E.; Kuniyil, Mufsir; Khan, Mujeeb; Al-Warthan, Abdulrahman; Siddiqui, Mohammed Rafiq H.; Tremel, Wolfgang; Nawaz Tahir, Muhammad; Adil, Syed Farooq; ChemistryOpen; vol. 6; nb. 1; (2017); p. 112 - 120 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, sodium hydrogencarbonate in acetonitrile, Time= 12h, T= 60 °C , p= 760.051Torr , Catalytic behavior, Solvent, Reagent/catalyst Hou, Junying; Luan, Yi; Yu, Jie; Qi, Yue; Wang, Ge; Lu, Yunfeng; New Journal of Chemistry; vol. 40; nb. 12; (2016); p. 10127 - 10135 View in Reaxys 99 %Chromat.

4.4. Catalytic performance General procedure: The catalytic oxidation of BzOH was carried out in a 50mL three necked flask fitted with a reflux condenser and a mechanical stirrer. In a typical procedure, BzOH (0.108 g, 1 mmol) and catalyst (0.8 g) was placed into the flask containing 25 mL of water and the reaction mixture was heated in an oil bath with continuous stirring at 60 °C. 2.5 mL of 30percent H2O2 together with 0.126 g (1.5 mmol) sodium bicarbonate was slowly introduced into the reactor and the mixture was stirred for 8 h. During the reaction, 0.5 mL of the sample was withdrawn periodically from the mixture and extracted by with 5mL ethyl acetate. After centrifugation, the extracted organic phase was analyzed by GC (Agilent7890). 0.5 mL water was then added to keep the volume of the reaction mixture constant. After the reaction, the catalyst was filtered and washed thoroughly with water. The separated catalyst was dried, and then reused again to test itsreusability. All the kinetic experiments were carried out for three times and good reproducibility was found with the error percentage within 5percent. With dihydrogen peroxide, sodium hydrogencarbonate in water, Time= 8h, T= 60 °C , Kinetics, Catalytic behavior, Temperature, Reagent/catalyst Yang, Zujin; Zhang, Xia; Yao, Xingdong; Fang, Yanxiong; Chen, Hongyan; Ji, Hongbing; Tetrahedron; vol. 72; nb. 14; (2016); p. 1773 - 1781 View in Reaxys With oxygen in methanol, T= 80 °C , p= 7500.75Torr Liguori, Francesca; Moreno-Marrodan, Carmen; Barbaro, Pierluigi; Sawa, Haruo; Applied Catalysis A: General; vol. 530; (2017); p. 217 - 225 View in Reaxys With C35H44CuN3O5, oxygen, caesium carbonate in tetrahydrofuran, Time= 12h, T= 24.84 °C , Reagent/catalyst, Temperature Safaei, Elham; Bahrami, Hadiseh; Wojtczak, Andrzej; Alavi, Saman; Jagličić, Zvonko; Polyhedron; vol. 122; (2017); p. 219 - 227 View in Reaxys Reaction procedure for benzyl alcohol oxidation Liquid-phase catalytic oxidation of benzyl alcohol was carriedout in a 25 mL two-neck-flask with reflux condenser and magnet-ically stirred autoclave heated in an oil bath under atmosphericpressure. Dioxygen was bubbled (10 mL/ min) through a solution oftoluene (8 mL), benzyl alcohol (216 mg, 2 mmol), and catalyst (1.0 g)at 80C. The product samples were drawn at regular time intervalsand analyzed with a gas chromatography (Shimadzu GC-2010AF)having SE-30 capillary column and FID detector. The products werefurther confirmed using GC–MS (Shimadzu GCMS-2010) with a DB-5MS capillary column. After the reaction, the resulting mixture wascooled with ice bath and the catalyst was separated by centrifuga-tion and washed with solvent. After drying at room temperature invacuum, the recycled catalyst can be reused in the next run underthe same conditions. The conversion, yield of benzaldehyde andselectivity presented here are based on the GC calculations usingchlorobenzene as the internal standard reference compound. With oxygen in toluene, Time= 8h, T= 80 °C , p= 760.051Torr , Autoclave, Heating, Inert atmosphere, Catalytic behavior, Temperature, Reagent/catalyst, Solvent Zhou, Weiyou; Tao, Qianyun; Pan, Jiugao; Liu, Jie; Qian, Junfeng; He, Mingyang; Chen, Qun; Journal of Molecular Catalysis A: Chemical; vol. 425; (2016); p. 255 - 265 View in Reaxys With iodobenzene, oxygen, caesium carbonate in toluene, Time= 24h, T= 150 °C , Schlenk technique, Reagent/ catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

250/438

2018-03-11 22:07:32


Abednatanzi, Sara; Derakhshandeh, Parviz Gohari; Abbasi, Alireza; Van Der Voort, Pascal; Leus, Karen; ChemCatChem; vol. 8; nb. 23; (2016); p. 3672 - 3679 View in Reaxys 100 With oxygen, Time= 4h, T= 60 °C , Green chemistry, Reagent/catalyst %Chromat. Liu, Gui; Liu, Junhua; Li, Wenxiu; Liu, Cheng; Wang, Fang; He, Junkai; Guild, Curtis; Jin, Jing; Kriz, David; Suib, Steven L.; Applied Catalysis A: General; vol. 535; (2017); p. 77 - 84 View in Reaxys With tert.-butylhydroperoxide in N,N-dimethyl-formamide, Time= 3h, T= 90 °C , Catalytic behavior, Reagent/catalyst, Temperature Aktaş, Ayşe; Acar, İrfan; Saka, Ece Tuğba; Biyiklioglu, Zekeriya; Kantekin, Halit; Journal of Inclusion Phenomena and Macrocyclic Chemistry; vol. 86; nb. 3-4; (2016); p. 183 - 190 View in Reaxys With dihydrogen peroxide in 1,4-dioxane, Time= 4h, T= 55 °C , Catalytic behavior Domínguez, María Isabel; Cojocaru, Bogdan; Tudorache, Madalina; Odriozola, José Antonio; Centeno, Miguel Angel; Parvulescu, Vasile I.; Comptes Rendus Chimie; vol. 19; nb. 10; (2016); p. 1156 - 1165 View in Reaxys With α,α,α-trifluorotoluene, indium sesquisulfide, T= 50 °C , p= 750.075Torr , Microwave irradiation Li, Tongtong; Zhang, Sujuan; Meng, Sugang; Ye, Xiangju; Fu, Xianliang; Chen, Shifu; RSC Advances; vol. 7; nb. 11; (2017); p. 6457 - 6466 View in Reaxys 2.5. Experimental procedure for oxidation of benzyl alcohol Oxidation experiments were carried out at 60°C. A solid catalyst of 1 or 2 (3.5 mg, 5 molpercent)was added to a 10 mL solution containing benzylic alcohol (10 μL, 0.1 mmol) with equivalentbase in a 25 mL open vial. The reaction mixture was stirred for 12 h in open air. Then theproducts of catalytic experiments were identified by comparing with the standard samples(purchased from J & K Chemical Technology). Yield and selectivity were calculated by GCanalysis via the internal method (bromobenzene was used as an internal standard). With C60H84Cl4Cu2N12O8*4C2H3N, 1,8-diazabicyclo[5.4.0]undec-7-ene in o-xylene, Time= 12h, T= 60 °C , Reagent/ catalyst, Solvent Lu, Xiaoshuang; Wu, Nini; Zhang, Bingguang; Deng, Kejian; Journal of Coordination Chemistry; vol. 70; nb. 3; (2017); p. 475 - 486 View in Reaxys 62 %Chromat.

With [{CyPN(H)P}Co(CH2SiMe3)]-BArF 4, acetophenone in toluene, Time= 24h, T= 120 °C , Inert atmosphere, Schlenk technique, Sealed tube, Green chemistry Zhang, Guoqi; Wu, Jing; Zeng, Haisu; Zhang, Shu; Yin, Zhiwei; Zheng, Shengping; Organic Letters; vol. 19; nb. 5; (2017); p. 1080 - 1083 View in Reaxys 2.3 Catalytic Test The selective oxidation reactions of benzyl alcohol (BZA) to benzaldehyde were conducted in two-necked flask (50 mL) in an oil bath, equipped with a condenser. 0.2 mL of BZA (ca. 2 mmol), and 100 μL of decane as an internal standard, were dissolved into 10 mL of toluene, followed by addition of 100 mg of catalyst. Afterwards, the mixture was heated up to 90 °C, and flushed with pure oxygen with a flow rate of 20 mL min−1 under vigorous stirring. After reaction, the mixture was centrifuged, and the products were analyzed by GC. With CeMn40O, oxygen in toluene, Time= 6h, T= 90 °C , Reagent/catalyst Xu, Jie; Shang, Jie-Kun; Wang, Yue; Chen, Ye; Li, Yong-Xin; Catalysis Letters; vol. 147; nb. 2; (2017); p. 328 334 View in Reaxys

88 %Chromat.

With C44H66O8P4Pd2, methyl vinyl ketone in water, toluene, Time= 12h, T= 105 °C , Inert atmosphere, Reagent/catalyst, chemoselective reaction

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

251/438

2018-03-11 22:07:32


Vasseur, Alexandre; Membrat, Romain; Gatineau, David; Tenaglia, Alphonse; Nuel, Didier; Giordano, Laurent; ChemCatChem; vol. 9; nb. 5; (2017); p. 728 - 732 View in Reaxys With dihydrogen peroxide in tetrahydrofuran, water, Time= 4h, Reflux, Green chemistry, Solvent Ma, Wenx; Tong, Qiaoling; Wang, Jian; Yang, Huali; Zhang, Meng; Jiang, Hailun; Wang, Qinghe; Liu, Yongxiang; Cheng, Maosheng; RSC Advances; vol. 7; nb. 11; (2017); p. 6720 - 6723 View in Reaxys With water, oxygen in tetrahydrofuran, Time= 24h, T= 25 °C , p= 760.051Torr Cheng, Hong-Gang; Miguélez, Javier; Miyamura, Hiroyuki; Yoo, Woo-Jin; Kobayashi, Shū; Chemical Science; vol. 8; nb. 2; (2017); p. 1356 - 1359 View in Reaxys 92 %Chromat.

17 : Synthesis of Benzaldehyde by Dehydrogenative Oxidation Reaction of Benzyl Alcohol General procedure: A 50 mL recovery flask was charged with 10 mL of tert-butyl alcohol, 54.0 mg (0.5 mmol) of benzyl alcohol, and 4.0 mg (0.0075 mmol, 1.5 mol percent) of complex 1, and stirring was carried out under reflux conditions for 20 hours. 10 mL of dichloromethane was added thereto and the mixture was made uniform, and when the reaction solution was then analyzed by GC it was confirmed that the corresponding benzaldehyde was formed with a conversion factor of 92percent and a yield of 92percent as shown in Table 4. With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) in tert-butyl alcohol, Time= 20h, Reflux, Inert atmosphere, Solvent, Temperature, Concentration Patent; Kanto Kagaku Kabushiki Kaisha; Yamaguchi, Ryohei; Fujita, Ken-ichi; (26 pag.); US2016/297844; (2016); (A1) English View in Reaxys 2.3 General procedure for one-pot tandem oxidation/Knoevenagel condensation catalyzed by MNP(at)PIL/W General procedure: In a round-bottomed flask, 0.5mmol alcohol, 0.75mmolH2O2, 2mL solvent water and 4molpercent MNPPIL/W (26mg) were mixed and stirred at 90°C for a defined time. After the completion of the reaction, monitored by TLC, the reaction was cooled down to room temperature and then 0.6mmol malononitrile was added to solution and the mixture was stirred for another 2h. Ethyl acetate was then added to the mixture and catalyst was separated by an external magnet and washed with methanol, dried at 50°C and stored for another run. The product was extracted by ethyl acetate and analyzed by gas chromatography (GC). With dihydrogen peroxide in water, Time= 4h, T= 90 °C , Green chemistry, Reagent/catalyst, Solvent Zohreh, Nasrin; Tavakolizadeh, Maryam; Hosseini, Seyed Hassan; Pourjavadi, Ali; Bennett, Craig; Polymer (United Kingdom); vol. 112; (2017); p. 342 - 350 View in Reaxys

94 %Chromat.

2.4 Catalytic Reactions The aerobic oxidations of benzyl alcohol were carried out using a 50 mL three-necked round-bottle flask equipped with a water-cooled condenser. Typically, the reactor wascharged with 0.1 g of catalyst, 1 mmol of benzyl alcoholand 8 mL of toluene at 100 °C for 3 h under an oxygen flow(25–30 mL min−1). After cooling to room temperature, Ndodecane (1 mmol), as internal standard, was added.The resulting mixture was diluted to constant volume by toluene in 25 mL volumetric flask. The reaction products were analyzed by using a Shimadzu GC-2014 (Rtx-5 column, 30 m × 0.320 mm, df = 0.25 μm) gas chromatograph equipped with a flame ionization detector. With oxygen in toluene, Time= 3h, T= 100 °C , Catalytic behavior, Reagent/catalyst Wang, Hanfei; Liu, Na; Xu, Chunli; Dong, Wensheng; Liu, Chunling; Catalysis Letters; vol. 147; nb. 2; (2017); p. 547 - 565 View in Reaxys 2.2 General procedure for the aerobic oxidation ofalcohols using NHPI/O2/CoTPP-Zn2Al-LDH system General procedure: In a typical experiment, a solution of NHPI (0.6 mmol,20 molpercent) and CoTPP-Zn2Al-LDH (0.01 mmol of CoTPP content, 30 mg) in PhCN or CH3CN (10 mL) was prepared in a 25mL round-bottom flask equippedwith magnetic stirrer. To this solution alcohol (3 mmol)was added and the resulting mixture was stirred at100 or 80 °C. Then dioxygen was bubbled through thesolution at a rate of 20mLmin−1. All the productswere identified by GC-MS and quantified at differentintervals during the reaction by GC-FID (ShimadzuGC-2010AF).

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

252/438

2018-03-11 22:07:32


With N -hydroxyphthalimide, oxygen in acetonitrile, Time= 7h, T= 80 °C , Reagent/catalyst Zhou, Weiyou; Chen, Dongwei; Cui, Aijun; Qian, Junfeng; He, Mingyang; Chen, Qun; Journal of Chemical Sciences; vol. 129; nb. 3; (2017); p. 295 - 299 View in Reaxys 3 : The catalyst prepared in Example 1 was used to catalyze the dehydrogenation reaction of benzyl alcohol The benzyl alcohol dehydrogenation reaction was carried out in a 10 ml two-necked flask, connected to a reflux condenser and a nitrogen atmosphere.The catalyst obtained by carbonizing at 850 ° C for 4 h in Example 1 was stirred at 20percent CH4/ H2The flow atmosphere was lowered to room temperature, switched to a nitrogen atmosphere, 2The

atmosphere is injected with dimethyl sulfoxide to prevent air oxidation of the catalyst.And then rapidly transfer-

red to a two-necked flask, and then 2 mmol of benzyl alcohol was added to the flask, and finally the volume of dimethylsulfoxide was maintained at 4 ml, about 60 mg of molybdenum carbide catalyst.The reaction system was frozen with liquid nitrogen and then the air of the reaction system was removed by means of a vacuum pump using 7 L of high purity N2Balloons provide nitrogen protection for the system.Placed in the oil bath pot, stirring conditions 120 reaction for a certain time (1-12h), the reaction product after centrifugal separation of the upper night, with gas chromatography analysis of its composition.Chromatographic analysis conditions are as follows: Agilent7890 gas chromatography, HP-5 capillary column (30m × 0.32mm × 0.25μm), equipped with hydrogen flame ionization detector (FID), chromatography with H2For the combustion gas, flow rate of 40ml / min, the air to help gas, flow rate of 400ml / min.The shielding gas is helium and the flow rate is 15ml / min.The inlet temperature is 240 , the pressure is 6.5756psi, the total flow rate is 504ml / min, the septum purge flow is 3ml / min, the temperature is kept at 100 for 10min. With molybdenum carbide in dimethyl sulfoxide, Time= 8h, T= 120 °C , Inert atmosphere, Reagent/catalyst, Time Patent; Dalian Institute of Chemical Physics, Chinese Academy of Sciences; Shen, WenJie; Li, ZhongCheng; Chen, chunhui; Zhan, EnSheng; Da, Na; Li, Yong; (9 pag.); CN104860806; (2016); (B) Chinese View in Reaxys 66 %Chromat.

2.6. Oxidation of olefins General procedure: The oxidation of olefins was performed in a 25-mL round-bottom flask equipped with a small magnetic bar. In a typical experiment experiment the flask was charged with the suspension of 2.0 mmol substrate, 1.0 mg Fe3O4-[MnCl(L)] nanocomposite (contains0.46 mmol Mn/g composite), 5.0 mmol isobutyraldehyde and 3 mL acetonitrile as solvent. The reaction was performed under oxygen atmosphere by using O2 balloon. At the end of 8 h, the catalyst was removed by an external magnet (1.2 T) and the product mixture analyzed by gas chromatography. Conversions and yields were calculated with respect to the starting substrate. The reaction products were quantified by gas chromatography and identified by comparison with the retention time and spectral data to those ofan authentic sample. To ensure reproducibility each catalytic reaction was carried out at least two times.For recycling experiments, after completion of the reaction, the nanocatalyst was recovered using a magnet, washed with acetonitrile,dried at 80 °C for 1 h and reused. With oxygen, isobutyraldehyde in acetonitrile, Time= 9h, T= 25 °C , Green chemistry Hadian-Dehkordi, Leila; Hosseini-Monfared, Hassan; Aleshkevych, Pavlo; Inorganica Chimica Acta; vol. 462; (2017); p. 142 - 151 View in Reaxys Photocatalytic activity and photocurrent measurements Photocatalytic oxidation of benzyl alcohol (BA) was performed in a 50-mL three-necked flask at room temperature under oxygen atmosphere (1 bar). A 300-W xenon arc lamp with a UV cutoff filter (λ ≥ 420 nm) was used as the visible-light source to trigger the photocatalytic reaction. Acetonitrile, a cheaper and nontoxic organic solvent, was chosen as the reaction medium. For each measurement, 50 mg as-synthesized photocatalyst was dispersed in mixed solution of acetonitrile (20 mL) and BA (208 μL, 2 mmol). Prior to light irradiation, the mixture was stirred for 1 h in the dark to reach adsorption-desorption equilibrium for BA and dissolved oxygen on the surface of photocatalyst. At a given time interval, about 4 mL suspension was withdrawn and centrifuged to remove remaining particles. The concentrations of BA and benzaldehyde (BAD) were measured using a Shimadzu SPD-M20A high performance liquid chromatograph (HPLC). The conversion rate of BA, the yield of BAD, and the reaction selectivity were calculated using the following equations: BA conversion (percent) = (C0 - C1)/C0 * 100, BAD Yield (percent) = (C2/C0) * 100, Selectivity (percent) = C2/(C0 - C1) * 100, where C0 is the initial concentration of BA, and C1 and C2 are the concentrations of BA and BAD, respectively, after the photocatalytic reaction [33]. Photocurrent measurements were conducted using a standard three-electrode system. The working electrode, counterelectrode, and reference electrode were the as-synthesized sample, Pt foil, and saturated calomel electrode (SCE), respectively. The electrolyte was

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

253/438

2018-03-11 22:07:32


0.5 M Na2SO4 aqueous solution. A 300-W xenon lamp with a UV cutoff filter (λ ≥ 420 nm) was used as the visiblelight source. With oxygen in acetonitrile, Time= 4h, T= 20 °C , p= 750.075Torr , Irradiation, Reagent/catalyst Si, Jingyan; Liu, Ya; Chang, Shunzhou; Wu, Di; Tian, Baozhu; Zhang, Jinlong; Research on Chemical Intermediates; vol. 43; nb. 4; (2017); p. 2067 - 2080 View in Reaxys Oxidation of benzyl alcohol A typical process was as follows. 50 mg of Fe3O4SiO2-GPTSCD was dispersed in 5 mL H2O with stirring at 50 C. Then 20 lL of benzyl alcohol and 1 mL of 10 percentNaClO aqueous were dropped into the suspension,respectively. After 24 h, the mixture was extracted with10 mL of ethyl acetate three times. The organic phase wasconcentrated and analyzed by GC–MS using ethyl acetateas the solvent. With sodium hypochlorite in water, ethyl acetate, Time= 24h, T= 50 °C , Catalytic behavior, Solvent, Reagent/catalyst Zhou, Mi; Cai, Songtao; Li, Jie; Qian, Xin; Zheng, Haha; Journal of Inclusion Phenomena and Macrocyclic Chemistry; vol. 87; nb. 1-2; (2017); p. 45 - 51 View in Reaxys 52 %Spectr.

With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II), 2,6-dimethoxy-p-quinone, tetrabutylammonium tetrafluoroborate, acetic acid in N,N-dimethyl-formamide, Time= 5h, T= 80 °C , Inert atmosphere, Electrochemical reaction Lybaert, Jeroen; Trashin, Stanislav; Maes, Bert U. W.; De Wael, Karolien; Abbaspour Tehrani, Kourosch; Advanced Synthesis and Catalysis; vol. 359; nb. 6; (2017); p. 919 - 925 View in Reaxys

46 %Chromat.

With potassium hexafluorophosphate, tetralin, C37H36ClN4PRu in toluene, Time= 48h, T= 100 °C Stubbs; Firth; Bridge; Berger; Hazlehurst; Boyle; Blacquiere; Dalton Transactions; vol. 46; nb. 3; (2017); p. 647 - 650 View in Reaxys

> 99 %Spectr.

2.3.1. Selective oxidation of alcohols General procedure: The catalyst (3 molpercent) was added to alcohol (5 mL) and dispersed by ultrasonication for 5 min. Then the suspension was added to a batch quartz reactor and photo-irradiated under magnetic stirring for appropriate times (see Table S1). After completion of reaction, the catalyst was recovered by centrifugation. The crude products were determined by 1H NMR and FT-IR. With NiO on anatase/rutile-TiO2 nanparticles, air, T= 20 °C , p= 760.051Torr , UV-irradiation, Green chemistry, Reagent/ catalyst Ziarati, Abolfazl; Badiei, Alireza; Mohammadi Ziarani, Ghodsi; Eskandarloo, Hamed; Catalysis Communications; vol. 95; (2017); p. 77 - 82 View in Reaxys

> 99 With oxygen in water, Time= 0.833333h, T= 36 °C , UV-irradiation, Catalytic behavior, Mechanism, Reagent/cata%Chromat. lyst, Time, Temperature Chen, Yu-Zhen; Wang, Zhiyong U.; Wang, Hengwei; Lu, Junling; Yu, Shu-Hong; Jiang, Hai-Long; Journal of the American Chemical Society; vol. 139; nb. 5; (2017); p. 2035 - 2044 View in Reaxys With tungsten oxide, oxygen, Time= 8h, T= 24.84 °C , UV-irradiation, Reagent/catalyst Ma, Bo; Huang, Erwei; Wu, Guangjun; Dai, Weili; Guan, Naijia; Li, Landong; RSC Advances; vol. 7; nb. 5; (2017); p. 2606 - 2614 View in Reaxys With potassium nitrite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 12h, p= 760.051Torr , Catalytic behavior, Reagent/catalyst, Solvent Miao, Zongcheng; Shu, Xin; Ramella, Daniele; RSC Advances; vol. 7; nb. 5; (2017); p. 2773 - 2779

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

254/438

2018-03-11 22:07:32


View in Reaxys 46 %Spectr.

With oxygen, benzo[c]cinnolin-5-ium-5-ylamide in 1,2-dichloro-ethane, Time= 36h, T= 20 °C , Irradiation Chatterjee, Tanmay; Roh, Geum-Bee; Shoaib, Mahbubul Alam; Suhl, Chang-Heon; Kim, Jun Soo; Cho, Cheon-Gyu; Cho, Eun Jin; Organic Letters; vol. 19; nb. 7; (2017); p. 1906 - 1909 View in Reaxys

100 %Spectr.

3.3 General procedure for the oxidation of alcohols General procedure: To 0.5 mmole of one of the chosen alcohols, dissolved in 5mL of DCM, was added 10percent mol of the free radical as catalyst (TEMPO, DN-DPPH or NHPI- as precursor of PINO) and one of the co-catalysts AD, and the mixture was stirred at room temperature for 24h under air. As co-catalyst A was used a mixture of 20percent mol sodium nitrite in 5mL of water and 0.2mL of acetic acid; co-catalyst B consisted in 20percent mol of nitrosonium tetrafluoroborate; co-catalyst C was a mixture of 0.5mL sodium hypochlorite (5percent) and 10mg of potassium bromide [19] dissolved in 5mL of water; co-catalyst D was gaseous nitrogen dioxide (5mL) bubbled slowly into DCM solution. After completion of the reaction, the solution was filtered of using a small cotton pad and the solvent was removed using a rotavap. The residue was dissolved in 1mL of deuterated chloroform and the NMR spectrum recorded. The yields of the reactions were calculated using the integral values obtained from 1H NMR spectra. With sodium hypochlorite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, potassium bromide in dichloromethane, water, Time= 24h, T= 20 °C Shakir, Ahmed J.; Madalan, Augustin M.; Ionita, Gabriela; Lupu, Stelian; Lete, Cecilia; Ionita, Petre; Chemical Physics; vol. 490; (2017); p. 7 - 11 View in Reaxys 2.2.4. Catalytic oxidation of alcohols by Cu(II) complex The complex [Cu(L1)(OAc)]H2O (0.0064 g, 0.01 mmol) wasdissolved in DMF (2 mL) and H2O (10 mL), then benzyl alcohol (2 mmol) was added with stirring for 30 min. Hydrogen peroxide (2.3 mL, 30percent, 10 mmol) was then added dropwise and reaction mixture was irradiated ultrasonically for further 30 min then reduced in vacuum. The carbonyl compound extracted by diethyl ether (3 10 mL), filtered through a bead of silica gel and dried over anhydrous MgSO4. The produced benzaldehyde were quantified as 2,4-dinitrophenylhydrazone derivative. Stage 1: With C15H15CuN3O3*H2O in water, N,N-dimethyl-formamide, Time= 0.5h, T= 20 °C Stage 2: With dihydrogen peroxide in water, N,N-dimethyl-formamide, Time= 0.5h, T= 20 °C , Sonication, Catalytic behavior, Reagent/catalyst El-Sonbati; Diab; El-Bindary, Ashraf El Bindary; Shoair; Hussein; El-Boz; Journal of Molecular Structure; vol. 1141; (2017); p. 186 - 203 View in Reaxys With oxygen in acetonitrile, Time= 8h, T= 25 °C , Irradiation, Catalytic behavior, Reagent/catalyst, Wavelength Li, Hao; Qin, Feng; Yang, Zhiping; Cui, Ximin; Wang, Jianfang; Zhang, Lizhi; Journal of the American Chemical Society; vol. 139; nb. 9; (2017); p. 3513 - 3521 View in Reaxys With oxygen, potassium carbonate, Time= 5h, T= 100 °C , p= 1500.15Torr , Autoclave Ciriminna, Rosaria; Scandura, Gabriele; Pandarus, Valerica; Delisi, Riccardo; Scurria, Antonino; Béland, François; Palmisano, Giovanni; Pagliaro, Mario; ChemCatChem; vol. 9; nb. 7; (2017); p. 1322 - 1328 View in Reaxys With air, metal organicframeworks Co-1,3,5-benzenetricarboxylic acid (Co-BTC) in N,N-dimethyl-formamide, Time= 10h, T= 95 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst, Temperature, Solvent, Time Peng, Ling; Wu, Shujie; Yang, Xiaoyuan; Hu, Jing; Fu, Xiaoran; Li, Min; Bai, Lu; Huo, Qisheng; Guan, Jingqi; New Journal of Chemistry; vol. 41; nb. 8; (2017); p. 2891 - 2894 View in Reaxys With C29H23Cl2FeN7O2 (1+)*Cl(1-), dihydrogen peroxide in acetonitrile, Time= 48h, T= 40 °C , Catalytic behavior, Time Tyagi, Nidhi; Singh, Ovender; Ghosh, Kaushik; Catalysis Communications; vol. 95; (2017); p. 83 - 87 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

255/438

2018-03-11 22:07:32


92 %Chromat.

Typical procedures of oxidation of alcohols to theircorresponding carbonyl compounds with NaIO4catalyzed by [Mn(salophen)nSTD] General procedure: A solution of NaIO4 (1 mmol) in H2O (2.5 ml) was addedto a mixture of alcohol (0.5 mmol) and [Mn(salophen)nSTD] (150 mg, 0.02 mmol) in CH3CN (5 ml). The mixturewas stirred at room temperature, and the progress ofthe reaction was monitored by GC. The products wereidentified by comparison with known standard samples. Atthe end of the reaction, organic compounds were extractedwith Et2O and purified with a silica gel plate or a silica gelcolumn. With sodium periodate in water, acetonitrile, Time= 2h, T= 20 °C , Catalytic behavior Asadniaye Fardjahromi, Mahsa; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Mohammadpoor-Baltork, Iraj; Journal of the Iranian Chemical Society; vol. 14; nb. 6; (2017); p. 1317 - 1323 View in Reaxys 2.3. Typical experimental procedure for photocatalytic test General procedure: In a general procedure for the photocatalytic test, a suspensionof 8 mg catalyst0.1 mmol aryl alcohol and 10 mL dodecane in1.5 mL of reagent grade benzotrifluoride (BTF) was transferred intoa 20 mL quartz bottle and magnetically stirred at 1000 rpm duringthe reaction. A stream of pure O2 at 1 atm pressure was bubbledinto the reaction system. The suspension was irradiated by a300-W Xenon Illuminator System with a UV cut-off filter in anair-conditioned room to maintain the reaction temperature at30 C. The photocatalytic reactions of fresh benzyl alcohol-BTFdodecanemixture under the same reaction conditions wererepeated 5 times to confirm the reliability of the data. After thereaction, reaction solutions (60 mL) were filtered by a one-timeplastic filter and added into 0.5 mL ethanol for gas chromatographanalysis (Agilent 7890A equipped with an FID detector). The specificGC parameters were as follows: HP-5 capillary column(30 m 0.32 mm 0.25 lm); detector temperature (300 C); splitratio (20:1); injector temperature (300 C). The oven temperaturewas maintained at 50 C for 5 min, and then raised to 120 C at arate of 10 C min1, finally the temperature increased to 300 C.Continuous nitrogen gas (20 mL min1) was used as a carrier gas.Here, dodecane was used as an internal standard to calculate theconversion of alcohol and selectivity for aldehyde. The carbon balancewas evaluated to be >99percent for all substrates. Thus, there is negligibleformation of volatile products, such as CO and CO2. Theproducts quantification were confirmed by comparison with theretention time of commercial samples and further confirmed bygas chromatography mass spectrometry (GC–MS) (430 GC Varian,USA). Controlled photoactivity experiments using a series of radicalscavengers, ammonium oxalate (AO) as the scavenger for photogeneratedholes, tertbutyl alcohol (TBA) as the scavenger forhydroxyl radicals, K2S2O8 as the scavenger for electrons, and benzoquinone(BQ) as scavenger for superoxide radical species wereperformed in a similar manner to the above photocatalytic experimentwith radical scavengers (0.1 mmol) added to the reactionsystem. With α,α,α-trifluorotoluene, oxygen in dodecane, Time= 2.5h, T= 30 °C , p= 760.051Torr , Irradiation, Reagent/catalyst Yang, Xue; Zhao, Hui; Feng, Jifei; Chen, Yanning; Gao, Shuiying; Cao, Rong; Journal of Catalysis; vol. 351; (2017); p. 59 - 66 View in Reaxys With oxygen, Time= 33h, T= 120 °C , p= 760.051Torr , Catalytic behavior, Time Wang, Tao; Zhang, Pengfei; Sun, Yan; Liu, Bing; Liu, Yunling; Qiao, Zhen-An; Huo, Qisheng; Dai, Sheng; Chemistry of Materials; vol. 29; nb. 9; (2017); p. 4044 - 4051 View in Reaxys With oxygen in toluene, Time= 2h, T= 120 °C , p= 1500.15Torr , Autoclave, Catalytic behavior, Kinetics, Solvent, Reagent/catalyst Li, Siqi; Li, Wei; Li, Yizhen; Fan, Guoli; Li, Feng; ChemPlusChem; vol. 82; nb. 2; (2017); p. 270 - 279 View in Reaxys 1.2 : Benzaldehyde was prepared by oxidation of benzyl alcohol Benzyl alcohol 2mmo 1 and toluene 10 mL were charged into a 50 mL three-necked flask and 100 mg of nano-V-Mn(η (V): η (Μη) = 3.0percent) was added to the above mixture , At 100 ° C. At the beginning of the reaction, the air is passed through the airway through the air supply pipe, and the flow rate of the air is controlled by the steady flow valve, and the air is bubbled into the reaction liquid (air flow rate: 30 mL / min). The reaction temperature is controlled by the oil bath , The temperature fluctuation is 1 ° C. After 1 h of reaction, the catalyst was filtered and the liquid product was analyzed by gas chromatograph. Under the above reaction conditions, the conversion of benzyl alcohol was 81.8percent, the selectivity of benzaldehyde was more than 99percent, and the catalyst was recycled more than

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

256/438

2018-03-11 22:07:32


6 times. The conversion of benzyl alcohol and the selectivity of benzaldehyde did not decrease significantly As shown in Figure 3) With nano-V-Mn-O, air in toluene, T= 100 °C , Temperature Patent; HENAN NORMAL UNIVERSITY; TANG, QINGHU; WANG, YANYAN; ZHAO, PEIZHENG; YIN, HONGQIANG; (9 pag.); CN106146270; (2016); (A) Chinese View in Reaxys 96 %Chromat.

With oxygen, Time= 3h, T= 110 °C , Reagent/catalyst, Time Liu, Na; Chen, Gui; Dong, Wensheng; Liu, Chunling; Xu, Chunli; Gold Bulletin; vol. 50; nb. 2; (2017); p. 163 175 View in Reaxys With oxygen, Time= 3h, T= 60 °C , p= 7500.75Torr , UV-irradiation Yang, Can; Wang, Bo; Zhang, Linzhu; Yin, Ling; Wang, Xinchen; Angewandte Chemie - International Edition; vol. 56; nb. 23; (2017); p. 6627 - 6631; Angew. Chem.; vol. 129; (2017); p. 6727 - 6731,5 View in Reaxys 2.6. Oxidation procedure General procedure: 1 *10-4 mmol(1 molpercent) of catalyst (complexes 1–4) was taken in a reaction vessel and 200 mL CH3CN was added to dissolve the catalyst. To the same reaction mixture 295 mL of a 1.3 M acetonitrile solution of H2O2(1.5 *10-2 mmol, 150 M equiv) was added. After this 1*10-2 mmol (100 M equiv) of respective substrates(cyclohexane, adamantane, benzyl alcohol) were added by a syringe over a period of 15 min, and each time the reaction mixture was kept stirring for a total time of 8 h at 40 deg.C. After addition of substrate, internal standard biphenyl was added. After 8 h of reaction,the solution was eluted with ethyl acetate through Al2O3 andanalyzed by GC. In the case of adamantane oxidation, due to solubility problems, total volume was 2 mL. Instead of the amounts described above the oxidation was performed with 1*10-5 mmol of the appropriate catalyst, 1*10-3 mmol of a 500 mL acetonitrile solution of adamantane, 500 mL of a 0.30 M solution of H2O2(1.5*10-3 mmol). Workup was carried out as describedpreviously. With C19H16Cl2FeN3O2, dihydrogen peroxide in acetonitrile, Time= 8h, T= 40 °C , Catalytic behavior, Reagent/catalyst Choudhary, Atul; Singh, Ovender; Singh, Udai P.; Ghosh, Kaushik; Inorganica Chimica Acta; vol. 464; (2017); p. 195 - 203 View in Reaxys Stage 1: With oxygen in water, Time= 1h, Green chemistry Stage 2: With oxygen in water, Time= 2h, T= 80 °C , p= 760.051Torr , Green chemistry, Catalytic behavior Du, Xin; Zhao, Caixia; Li, Xiaoyu; Huang, Hongwei; He, Junhui; Wen, Yongqiang; Zhang, Xueji; European Journal of Inorganic Chemistry; vol. 2017; nb. 19; (2017); p. 2517 - 2524 View in Reaxys

95 %Chromat.

2.2 Catalytic activity General procedure: To study the catalytic activity of the system, alcohol (0.5 mmol) and [ZnPOMAPIB-MWCNT] (50 mg, 0.004 mmol) in 3 mL CH3CN were introduced into a 25 mL round-bottom flask equipped with a magnetic stirrer (400 rpm). H2O2(5 mmol, 30percent) was added to this mixture and refluxed. The progress of the reactions was monitored by GC. At the end of the reaction, the catalyst was filtered and washed with Et2O (20 mL). The pure product was obtained after chromatography of organic layer on a short column of silica gel. With dihydrogen peroxide in water, acetonitrile, Time= 4h, Reflux, Catalytic behavior, Solvent, Reagent/catalyst, chemoselective reaction Hajian, Robabeh; Alghour, Zahra; Chinese Chemical Letters; vol. 28; nb. 5; (2017); p. 971 - 975 View in Reaxys

94 %Chromat.

2.7 Procedures for acceptorless dehydrogenation of primary alcohols catalyzed by 2bc (Table5) General procedure: A solution of an alcohol (0.5mmol) and catalyst 2bc (5.7mg, 0.01mmol) in toluene (9mL) was refluxed for 20hat 135°C (oil bath temperature). In the reaction of cyclohexylmethanol, p-xylene was used as the solvent and the solution was refluxed for 20hat 160°C (oil bath temperature). After the mixture was cooled to room tem-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

257/438

2018-03-11 22:07:32


perature, biphenyl (25mg) was added as an internal standard. The mixture was analyzed by GC using an authentic sample. The results are shown in Table5 . With [(pentamethylcyclopentadienyl)Ir(4-methyl-5-trifluoromethyl-2-pyridonate)Cl] in toluene, Time= 20h, T= 135 °C , Inert atmosphere, Schlenk technique Yamaguchi, Ryohei; Kobayashi, Daiki; Shimizu, Mineyuki; Fujita, Ken-ichi; Journal of Organometallic Chemistry; vol. 843; (2017); p. 14 - 19 View in Reaxys 2.4 Testing the catalyst In a typical reaction, a mixture of benzyl alcohol (0.87mL, 8.4mmol), p-xylene (2.0mL), and the SBA-15-supported Pd catalyst (9mg, 0.01mol.percent of Pd relative to benzyl alcohol) was stirred (at 800rpm) under flowing O2 (20 sccm) at 120°C for 3h. After the reaction, the solid catalyst was filtered off while the liquid phase (with decane added as internal standard) was analyzed on a gas chromatograph (Shimadzu GC-2014 equipped with a FID detector and a SGE BP-5 column). To test reuse, the catalysts were collected with centrifugation, washed with p-xylene, dried, and then reused in further runs. With oxygen in para-xylene, Time= 3h, T= 120 °C , Catalytic behavior, Temperature Liu, Chun-Hsia; Lin, Chih-Yu; Chen, Jeng-Lung; Lu, Kueih-Tzu; Lee, Jyh-Fu; Chen, Jin-Ming; Journal of Catalysis; vol. 350; (2017); p. 21 - 29 View in Reaxys Oxidation of 4-t-butylcyclohexanaol General procedure: O.1 mole of 4-t-butylcyclohexanol (ACROS) was weighed and placed in a 50 mL Erlenmeyer flask with stir bar and 10 mL ethyl acetate (Fisher). 1.0 g trichloroisocyanuric acid (Leslie’s Swimming Pool Supplies) was weighed into a 30 mL beaker and dissolved in 10 mL ethyl acetate. 1.0 mL (0.12 mol) pyridine (Aldrich) was delivered to the alcohol mixture by pipet. The TCICA solution was transferred to a dropping funnel and added dropwise to the stirring alcohol solution. Following addition, stirring was continued for 20 minutes and the mixture was filtered. The filtrate was washed with 10 mL 1 M HCl, 10 mL 5percent NaHCO3, and 5 mL saturated NaCl. The organic layer was dried over MgSO4, a GC sample removed, filtered and evaporated to dryness. Yield 1.50 g (100percent), nmr attached. With pyridine, trichloroisocyanuric acid in ethyl acetate, Time= 1h, T= 20 °C Dip, Irene; Gethers, Christina; Rice, Tonya; Straub, Thomas S.; Tetrahedron Letters; vol. 58; nb. 28; (2017); p. 2720 - 2722 View in Reaxys 80 %Chromat.

2.4 General procedure for catalytic oxidation of alcohols General procedure: Oxidation reactions were carried out under aerial conditions using 2mL of solvent and aqueous H2O2 (30wtpercent) as oxidant. In a typical experiment, complex 1 (1.186μmol, 0.001g), the solvent (2mL) and the substrate (1mmol) were placed in a 25mL round bottomed glass flask. The mixture was heated to the desired temperature, and after addition of H2O2, the resulting solution was kept stable at the selected temperature to continue the reaction. At appropriate intervals, aliquots were taken and analyzed immediately by GC. The oxidation products were identified by comparison of their retention times with those of authentic samples With C28H27Br3N4O6V2, dihydrogen peroxide in dichloromethane, water, T= 60 °C , Green chemistry, Catalytic behavior, Solvent, Temperature Bikas, Rahman; Shahmoradi, Elaheh; Noshiranzadeh, Nader; Emami, Marzieh; Reinoso, Santiago; Inorganica Chimica Acta; vol. 466; (2017); p. 100 - 109 View in Reaxys With oxygen in water, Time= 24h, T= 30 °C , Irradiation, Kinetics, Solvent, Time Zhang, Wuyuan; Bariotaki, Anna; Smonou, Ioulia; Hollmann, Frank; Green Chemistry; vol. 19; nb. 9; (2017); p. 2096 - 2100 View in Reaxys 2.4 General procedure of the catalytic oxidation experiments General procedure: The oxidation reactions were performed in a 50mL reaction flask with a reflux condenser under vigorous stirring at 70°C in a temperature-controlled oil bath. In a typical experiment, the reaction mixture was pre-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

258/438

2018-03-11 22:07:32


pared as follows: 7.6×10−3mmol of catalyst into a 10mL water solvent (0.76mmol) of substrate alcohol (substrate/ cat.=100) and an excess amount of H2O2 (30percent in water, 1.95mmol) in this order. The reactions were monitored by withdrawing small aliquots at certain time intervals and analyzed on a GC with an HP-5 quartz capillary column (30m×0.32 mm×0.25μm) and a flame ionization detector (FID). Each sample was repeated twice. Identification of peaks was made by comparing with chromatograms of authentic samples. With C30H25CuN2O3 (1+)*CH4O*ClO4 (1-), dihydrogen peroxide in water, Time= 6h, T= 70 °C , Green chemistry, Catalytic behavior Ünver, Hakan; Kani, Ibrahim; Polyhedron; vol. 134; (2017); p. 257 - 262 View in Reaxys 96 %Chromat.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [Cu([bis(3-tert-butyl-2-hydroxybenzyl)](2-pyridylmethyl)amine) (acetate)(acetic acid)] in water, Time= 24h, T= 25 °C , Catalytic behavior, Mechanism, Reagent/catalyst, Solvent, Concentration Zhan, Guangli; Zhong, Wei; Wei, Zhenhong; Liu, Zhenzhen; Liu, Xiaoming; Dalton Transactions; vol. 46; nb. 25; (2017); p. 8286 - 8297 View in Reaxys With air, Pt/Bi2O3-x in water, T= 26 °C , Reagent/catalyst Liu, Juanjuan; Zou, Shihui; Wang, Hui; Xiao, Liping; Zhao, Hongting; Fan, Jie; Catalysis Science and Technology; vol. 7; nb. 5; (2017); p. 1203 - 1210 View in Reaxys

84 %Spectr.

General procedure: General procedure: V1 (27.6 mg, 0.028 mmol) and substrate (0.5 mmol) were placed in a 20mL schlenk flask, and then the mixed MeCN/THF (1:1) solvent (3 mL) was added. The mixture was stirred at 60 C for an appropriate time under O2(balloon) or atmospheric air. After the reaction was completed, Et2O was added tothe reaction mixture. The resulting suspension was filtered and rinsed with Et2O. The combined filtrate was concentrated in vacuo. The yield of the oxidation products was confirmed by 1H NMR spectroscopy using 1,2-diphenylethane or 1,3,5-trimethoxybenzene as the internal standard. Purification of 2a–2c was performed by silica gel chromatography using hexane and EtOAc as the eluent to afford the analytically pure ketones. The isolated products were identified by comparing their 1H NMR spectra with those of authentic samples. With [VO(ReO4)(4,4'-di-tert-butyl-2,2'-bipyridine)2][0.25SO4*0.5ReO4], oxygen in tetrahydrofuran, acetonitrile, Time= 48h, T= 60 °C , p= 750.075Torr , Schlenk technique, chemoselective reaction Kobayashi, Daiki; Kodama, Shintaro; Ishii, Youichi; Tetrahedron Letters; vol. 58; nb. 33; (2017); p. 3306 - 3310 View in Reaxys Biotransformation in oxygen atmosphere In an Eppendorf tube purified HMFO (50 µg) was added to a sodium phosphate buffer solution (100 mM, pH 7.0) and an organic co-solvent at a given ratio (total volume 0.5 ml, solvent ratios 0, 10, 20, 30, 50, 70, 90 and 98 percent v/v) containing benzyl alcohol (1a, 25 mM) and catalase from M. lysodeikticus (1700 U). The mixture was placed into a pressure cylinder, 2 which was primed with O2 (technical grade) for 1 min and then adjusted to atmospheric pressure. The tubes were shaken at room temperature and 120 rpm for 24 h and products were extracted with ethyl acetate (0.5 ml). The combined organic phases were dried over anhydrous Na2SO4 and the samples were analyzed on GC. With catalase from M. lysodeikticus, (5-hydroxymethyl)furfural oxidase, oxygen in aq. phosphate buffer, Hexafluorobenzene, Time= 24h, T= 30 °C , pH= 7, Solvent Pickl, Mathias; Jost, Etta; Glueck, Silvia M.; Faber, Kurt; Tetrahedron; vol. 73; nb. 36; (2017); p. 5408 - 5410 View in Reaxys With [Fe2(LPh4 )(O2)(Ph3CCO2)]2+ in dichloromethane, T= 25 °C , Kinetics, Mechanism, Concentration Sekino, Mio; Furutachi, Hideki; Tojo, Rina; Hishi, Ayumi; Kajikawa, Hanako; Suzuki, Takatoshi; Suzuki, Kaito; Fujinami, Shuhei; Akine, Shigehisa; Sakata, Yoko; Ohta, Takehiro; Hayami, Shinya; Suzuki, Masatatsu; Chemical Communications; vol. 53; nb. 63; (2017); p. 8838 - 8841 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

259/438

2018-03-11 22:07:32


With potassium carbonate in water, Time= 4h, T= 80 °C Dai, Jinyu; Zou, Houbing; Wang, Runwei; Wang, Yu; Shi, Zhiqiang; Qiu, Shilun; Green Chemistry; vol. 19; nb. 5; (2017); p. 1336 - 1344 View in Reaxys With Au-TiO2, oxygen in water, Time= 10h, T= 24.84 °C , p= 760.051Torr , Irradiation, Catalytic behavior Tanaka, Atsuhiro; Hashimoto, Keiji; Kominami, Hiroshi; Chemical Communications; vol. 53; nb. 35; (2017); p. 4759 - 4762 View in Reaxys With iron(II) phthalocyanine, caesium carbonate, Time= 16h, T= 140 °C , Sealed tube Di Gregorio, Giovanni; Mari, Michele; Bartoccini, Francesca; Piersanti, Giovanni; Journal of Organic Chemistry; vol. 82; nb. 16; (2017); p. 8769 - 8775 View in Reaxys With rhodium contaminated with carbon, Time= 4h, T= 150 °C , p= 60006Torr , Supercritical conditions Chatterjee, Maya; Ishizaka, Takayuki; Chatterjee, Abhijit; Kawanami, Hajime; Green Chemistry; vol. 19; nb. 5; (2017); p. 1315 - 1326 View in Reaxys With dihydrogen peroxide in water, Time= 3h, T= 90 °C , Reagent/catalyst Wang, Hefang; Wang, Cunyue; Yang, Yongfang; Zhao, Meng; Wang, Yanji; Catalysis Science and Technology; vol. 7; nb. 2; (2017); p. 405 - 417 View in Reaxys 2.2. Experimental Procedures. General procedure: Amixture of an aromatic alcohol(3mmol), sodium nitrate (6mmol), and [DDPA][HSO4](1.2mmol) was heated with stirring at 80°C for 5–30 minin a round-bottomed flask. After oxidation of the aromaticalcohol (monitored by TLC), dicarbonyl compound (3mmol)and ammonium acetate (3mmol) were added. The mixture was heated with stirring at 80°C for 1–3h. The reaction wasmonitored by TLC after an interval of 15min. After completion,the reaction mixture was cooled to rt and extracted withethyl acetate. The organic layer was separated and washedwith brine solution and then dried over anhydrous Na2SO4.Solvent was removed in vacuo and the crude product waspurified by chromatography over silica gel.The aqueous layer(containing the ionic liquid) could be reused directly in thenext run without further purification. With sodium nitrate, 3-(N,N-dimethyldodecylammonium)propanesulfonic acid hydrogen sulphate, T= 80 °C , Green chemistry Liu, Xiaobing; Liu, Bin; Journal of Chemistry; vol. 2017; (2017); Art.No: 5646908 View in Reaxys With ZIF-derived porous carbon supported Pd nanoparticles within mesoporous silica shells, air in toluene, Time= 12h, T= 100 °C , Reagent/catalyst Zhang, Shaolong; Han, Aijuan; Zhai, Yanliang; Zhang, Jian; Cheong, Weng-Chon; Wang, Dingsheng; Li, Yadong; Chemical Communications; vol. 53; nb. 68; (2017); p. 9490 - 9493 View in Reaxys With C36H32Cl2N2O2P2Ru in toluene, Time= 16h, T= 150 °C , Inert atmosphere, Schlenk technique Sahoo; Jiang; Bruneau; Sharma; Suresh; Roisnel; Dorcet; Achard; Catalysis Science and Technology; vol. 7; nb. 16; (2017); p. 3492 - 3498 View in Reaxys 2.5. Catalyst testing The catalytic activities of 1percentAuPd/MgO catalysts were tested in a50 mL glass, stirred Radleys® carousel reactor for the solvent-free liquidphase oxidation of benzyl alcohol with oxygen. In a typical reaction,20 mg of the catalyst was suspended in 2 g of the substrate without anyadditional solvent. The reaction mixture was stirred at 1000 rpm with aconstant inlet pressure (1 barg) of pure oxygen. At the end of the reaction,the reactor was cooled in an ice bath until the temperature ofthe reaction mixture reaches below 5 °C. After de-pressuring the reactor,the catalyst was removed by centrifugation. An aliquot of theclear liquid reaction mixture along with a fixed amount of internalstandard

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

260/438

2018-03-11 22:07:32


(o-xylene) was injected in a GC (Agilent 7820A) fitted with aAgilent J &W HP-5 GC column and a flame ionization detector.Quantitative analyses of the substrates and products were performedwith the help of calibration plots and response factors. For reusabilitystudies, after the end of the reaction, the catalysts were filtered, washedwith acetone several times, and dried in an oven at 120 °C for overnight.These dried catalysts were calcined at 450 °C in static air for 4 hand used for the next reaction. The catalytic results are within an errorlimit of ± 5percent (determined from 5 separate catalytic experiments). With oxygen in neat (no solvent), Reagent/catalyst Guadix-Montero, Susana; Alshammari, Hamed; Dalebout, Remco; Nowicka, Ewa; Morgan, David J.; Shaw, Greg; He, Qian; Sankar, Meenakshisundaram; Applied Catalysis A: General; vol. 546; (2017); p. 58 - 66 View in Reaxys 100 With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, sodium nitrite in acetonitrile, Time= 5h, T= 75 °C , p= %Chromat. 760.051Torr , Reagent/catalyst Rapeyko, Anastasia; Arias, Karen S.; Climent, Maria J.; Corma, Avelino; Iborra, Sara; Catalysis Science and Technology; vol. 7; nb. 14; (2017); p. 3008 - 3016 View in Reaxys 100 With N-doped carbon encapsulated molybdenum carbide in dimethyl sulfoxide, Time= 4h, T= 120 °C , Inert atmos%Chromat. phere, Catalytic behavior, Reagent/catalyst, Solvent, Temperature Leng, Yan; Li, Jingjing; Zhang, Chenjun; Jiang, Pingping; Li, Yue; Jiang, Yuchen; Du, Shengyu; Journal of Materials Chemistry A; vol. 5; nb. 33; (2017); p. 17580 - 17588 View in Reaxys 80 %Chromat.

With tert.-butylhydroperoxide in acetonitrile, Time= 0.0583333h, p= 760.051Torr , Microwave irradiation, Reagent/ catalyst, Solvent Shojaei, Abdollah Fallah; Shirini, Farhad; Hedayati, Elaheh; Inorganic and Nano-Metal Chemistry; vol. 47; nb. 9; (2017); p. 1312 - 1317 View in Reaxys With α,α,α-trifluorotoluene in acetonitrile, Time= 10h, T= 25 °C , Irradiation, Green chemistry, Reagent/catalyst Fu, Yanghe; Yang, Huan; Du, Rongfei; Tu, Gaomei; Xu, Chunhui; Zhang, Fumin; Fan, Maohong; Zhu, Weidong; RSC Advances; vol. 7; nb. 68; (2017); p. 42819 - 42825 View in Reaxys With tert.-butylhydroperoxide, Time= 4h, T= 70 °C , Reagent/catalyst Lin, Yangming; Wu, Kuang-Hsu Tim; Yu, Linhui; Heumann, Saskia; Su, Dang Sheng; ChemSusChem; vol. 10; nb. 17; (2017); p. 3497 - 3505 View in Reaxys 2.3. Procedure for oxidation of benzylic alcohols by [CuNi(-OAc)(-OH)(-OH2)(bpy)2](ClO4)2 To a mixture of benzyl alcohol (0.5 mL, 4.64 mmol) and 15percent aqueous hydrogen peroxide(1.1 mL, 4.85 mmol), the catalyst [CuNi(-OAc)(-OH)(-OH2)(bpy)2](BF4)2 (8 mg, 0.01 mmol)was added and stirred at 70 °C for 5 h. The organic and aqueous phase were separated by aseparating funnel and then puried by column chromatography to aord benzaldehyde.The identity of the benzaldehyde was ascertained by comparison with authentic sampleusing IR, 1H NMR, and 13C NMR. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [CuNi(-OAc)(μ-OH)(μ-OH2)(bpy)2](ClO4)2, dihydrogen peroxide in water, Time= 5h, T= 70 °C Lal, Ram A.; Kumar, Arvind; Syiemlieh, Ibanphylla; Kurbah, Sunshine D.; Journal of Coordination Chemistry; vol. 70; nb. 15; (2017); p. 2722 - 2735 View in Reaxys

99 %Chromat.

With C44H39N2O5PRu, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux, Molecular sieve Viswanathamurthi; Iniya, R. Radha; Manikandan; Prakash; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 42; nb. 6; (2012); p. 771 - 778 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

261/438

2018-03-11 22:07:32


92 %Chromat.

2.5 Dehydrogenation of alcohols General procedure: Benzyl alcohol (108mg, 1.0mmol), AuSBA-15 (6wtpercent, 20mg) and K2CO3 (829mg, 6.0mmol) was dissoveled in toluene (6.0mL), the reaction mixture was stirred for 12hat 110°C. It was monitored by TLC. After the reaction was completed, the solvent was removed under reduced pressure and purified of the crude product by column chromatography on silica-gel afforded the title compound. With potassium carbonate in toluene, Time= 12h, T= 110 °C , Reagent/catalyst, Solvent Huang, Ronghui; Fu, Yong; Zeng, Wei; Zhang, Liang; Wang, Dawei; Journal of Organometallic Chemistry; vol. 851; (2017); p. 46 - 51 View in Reaxys With C82H68F2Fe2N4O7, dihydrogen peroxide, urea in dichloromethane, Time= 0.5h, T= 20 °C Wang, Fang; Becker, Sabine; Minier, Mikael A.; Loas, Andrei; Jackson, Megan N.; Lippard, Stephen J.; Inorganic Chemistry; vol. 56; nb. 18; (2017); p. 11050 - 11058 View in Reaxys 2.3. Evaluation of catalytic performance Liquid phase oxidation of benzyl alcohol was carried out using procedures that was reported previously with slight modification [20]. In a typical reaction, 2.6 mL (25 mmol) of benzyl alcohol, 3.3 mL (32 mmol)of 30percent H2O2 and 0.1 g of the catalyst powder was loaded in a 50 mL double neck round bottom flask containing 20 mL of toluene as solvent.The flask was connected to a reflux condenser, magnetically stirred and kept in an oil bath at 80 C for 2 h. After reaction, the solid catalysts were separated by centrifugation and the liquid samples were filtered and analysed by gas chromatography to evaluate the products by GC-MS(SHIDMADZU QP 5000) equipped with a flame ionization detector(FID) and a medium polarity capillary column (BPX-5 column(29.4 m 0.25 mm), with film thickness of 0.25 μm) with helium as the carrier gas. With dihydrogen peroxide in toluene, Time= 2h, T= 80 °C , Reagent/catalyst Kimi, Melody; Jaidie, Mohd Muazmil Hadi; Pang, Suh Cem; Journal of Physics and Chemistry of Solids; vol. 112; (2018); p. 50 - 53 View in Reaxys With C36H54CuN4 (1+)*F6Sb(1-), potassium tert-butylate, oxygen in dichloromethane, Time= 24h, T= 20 °C , p= 750.075Torr , Catalytic behavior, Reagent/catalyst, Solvent Kochem, Amélie; Molloy, Jennifer K.; Gellon, Gisèle; Leconte, Nicolas; Philouze, Christian; Berthiol, Florian; Jarjayes, Olivier; Thomas, Fabrice; Chemistry - A European Journal; vol. 23; nb. 56; (2017); p. 13929 - 13940 View in Reaxys With tert.-butylhydroperoxide, (ethylenediamine)[Cu3(5-(4-pyridyl)-1H-tetrazole)4(H2O)4][Co2Mo10H4O38]*24H2O in acetonitrile, Time= 8h, T= 75 °C An, Haiyan; Hou, Yujiao; Wang, Lin; Zhang, Yumeng; Yang, Wei; Chang, Shenzhen; Inorganic Chemistry; vol. 56; nb. 19; (2017); p. 11619 - 11632 View in Reaxys

73 %Chromat.

2.4. Photocatalytic reactions General procedure: Bismuth vanadate (32.3 mg, 100 mmol) was added to a Schlenkflask containing benzyl alcohol stock solution (1 mL, 0.1 mmol inacetonitrile) and acetonitrile (9 mL). The mixture was left to stirfor 30 min to disperse the catalyst under a dioxygen atmospherevia a balloon. The mixture was then irradiated with a 30W blueLED array at a distance of 2 cmwith an irradiance of 245mWcm2.The mixture reached ca. 40 °C by the end of the reaction and afterirradiation, the catalyst was removed using centrifugation at4000 rpm for 30 min. For GC analysis, 1 mL of supernatant wastaken and 1 lL injected. For NMR analysis, the supernatant wasreduced in volume using a rotary evaporator at 65 mbar at 20 °C,and the residue dissolved in d6-DMSO containing maleic acid asan internal standard. With bismuth vanadate, oxygen in acetonitrile, Time= 3h, T= 40 °C , p= 760.051Torr , Schlenk technique, Irradiation Unsworth, Christopher A.; Coulson, Ben; Chechik, Victor; Douthwaite, Richard E.; Journal of Catalysis; vol. 354; (2017); p. 152 - 159 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

262/438

2018-03-11 22:07:32


41 %Chromat.

With tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate, oxygen, bis(2-piperidinyl)methane in tetrahydrofuran, Time= 0.166667h, T= -80 °C , Glovebox Stumpf, Tim-Daniel J.; Steinbach, Manfred; Würtele, Christian; Becker, Jonathan; Becker, Sabine; Fröhlich, Roland; Göttlich, Richard; Schindler, Siegfried; European Journal of Inorganic Chemistry; vol. 2017; nb. 37; (2017); p. 4246 - 4258 View in Reaxys The oxidation of benzyl alcohol to benzaldehyde was performed using 25 mg of catalyst, 0.2 mL of benzyl alcohol, 0.3 mL of hydrogen peroxide, and 2 mL of acetonitrile as the solvent, for 5 and 10 min, respectively. With dihydrogen peroxide in acetonitrile, Time= 0.166667h, Microwave irradiation, Reagent/catalyst Rodríguez-Padrón, Daily; Balu, Alina M; Romero, Antonio A; Luque, Rafael; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 1982 - 1993 View in Reaxys With Cyclooctan, oxygen in toluene, Time= 4h, T= 100 °C , Kinetics, Reagent/catalyst Fu, Yu; Guo, Yanglong; Guo, Yun; Wang, Yunsong; Wang, Li; Zhan, Wangcheng; Lu, Guanzhong; Catalysis Science and Technology; vol. 7; nb. 18; (2017); p. 4136 - 4144 View in Reaxys With sodium anthraquinone-2-sulfonate, oxygen in water, Time= 24h, T= 30 °C , Irradiation, Catalytic behavior, Time, Solvent Zhang, Wuyuan; Gacs, Jenő; Arends, Isabel W. C. E.; Hollmann, Frank; ChemCatChem; vol. 9; nb. 20; (2017); p. 3821 - 3826 View in Reaxys With copper aluminate, dihydrogen peroxide in acetonitrile, T= 80 °C , Green chemistry, Catalytic behavior, Temperature, Reagent/catalyst, Solvent Ragupathi; Judith Vijaya; Thinesh Kumar; John Kennedy; Journal of Molecular Structure; vol. 1079; (2014); p. 182 - 188 View in Reaxys With oxygen, potassium carbonate in water, Time= 6h, T= 30 °C , p= 760.051Torr , Reagent/catalyst Yoskamtorn, Tatchamapan; Yamazoe, Seiji; Takahata, Ryo; Nishigaki, Jun-Ichi; Thivasasith, Anawat; Limtrakul, Jumras; Tsukuda, Tatsuya; ACS Catalysis; vol. 4; nb. 10; (2014); p. 3696 - 3700 View in Reaxys

80 %Chromat.

With tert.-butylhydroperoxide in acetonitrile, Time= 4h, T= 50 °C , Autoclave Skliri, Euaggelia; Lykakis, Ioannis N.; Armatas, Gerasimos S.; RSC Advances; vol. 4; nb. 86; (2014); p. 46170 46178 View in Reaxys

30 %Chromat.

2.3. Catalytic activity in open vessel General procedure: Microwave experiments were carried out using a CEM-DISCOVER model with PC control. In a 50 mL round-bottom flask equipped with a cooling system, benzyl alcohol (0.2 mL, 1.92 mmol) was solubilized in acetonitrile (2 mL), followed by the addition of 1.5 or 2.3 eq. oxidant (0.3 mL of a 33 or 50 w/vpercent aqueous H2O2 solution) and the catalyst. The reaction was stirred and heated with microwave irradiation at 300 W, achieving temperatures in the 90–132 °C range, as measured by an infra-red probe. After a certain time, the reaction was stopped and upon cooling the mixture was immediately filtered off and subsequently analyzed by GC-FID. With dihydrogen peroxide in water, acetonitrile, Time= 0.08h, T= 90 - 132 °C , p= 3750.38 - 12751.3Torr , Microwave irradiation, Catalytic behavior, Reagent/catalyst, Pressure Mangin, Floriane; Prinsen, Pepijn; Yepez, Alfonso; Gilani, Muhammad Rehan Hasan Shah; Xu, Guobao; Len, Christophe; Luque, Rafael; Catalysis Communications; vol. 104; (2018); p. 67 - 70 View in Reaxys With 2,2,6,6-tetramethyl-4-(2,2,2-trifluoroacetamido)-1-oxopiperidinium tetrafluoroborate, 4‐(acetylamino)‐2,2,6,6‐tetramethyl‐1‐oxopiperidinium tetrafluoroborate in acetonitrile, Kinetics

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

263/438

2018-03-11 22:07:32


Lambert, Kyle M.; Stempel, Zachary D.; Kiendzior, Sadie M.; Bartelson, Ashley L.; Bailey, William F.; Journal of Organic Chemistry; vol. 82; nb. 21; (2017); p. 11440 - 11446 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 1.5h, p= 750.075Torr , Irradiation, Kinetics, Catalytic behavior, Concentration, Reagent/catalyst, Solvent, Wavelength Zhang, Yichi; Wang, Zhan; Lang, Xianjun; Catalysis Science and Technology; vol. 7; nb. 21; (2017); p. 4955 4963 View in Reaxys With sodium tetrahydroborate, Time= 12h, T= 165 °C , Schlenk technique, Inert atmosphere Luo, Qi; Dai, Zengjin; Cong, Hengjiang; Li, Renjie; Peng, Tianyou; Zhang, Jing; Dalton Transactions; vol. 46; nb. 43; (2017); p. 15012 - 15022 View in Reaxys 83 %Chromat.

With N -hydroxyphthalimide, 4Gd(3+)*50H2O*[WZn{Cu(H2O)}2(ZnW9O34)2](12-), oxygen, tetramethylammonium bromide in acetonitrile, Time= 21h, T= 50 °C , Reagent/catalyst Zhao, Min; Zhang, Xian-Wei; Wu, Chuan-De; ACS Catalysis; vol. 7; nb. 10; (2017); p. 6573 - 6580 View in Reaxys With 10-molybdo-2-vanadophosphoric acid, oxygen in water, tert-butyl alcohol, Time= 16h, T= 25 °C , Irradiation, Solvent Krickl, Sebastian; Buchecker, Thomas; Meyer, Andreas Uwe; Grillo, Isabelle; Touraud, Didier; Bauduin, Pierre; König, Burkhard; Pfitzner, Arno; Kunz, Werner; Physical Chemistry Chemical Physics; vol. 19; nb. 35; (2017); p. 23773 - 23780 View in Reaxys

> 99 With 2,2,6,6-tetramethylpiperidin-1-ol, manganese (II) nitrate tetrahydrate, acetic acid, T= 25 °C , Glovebox, Inert at%Chromat. mosphere, Reagent/catalyst Lagerblom, Kalle; Lagerspets, Emi; Keskiväli, Juha; Cook, Chris; Ekholm, Filip; Parviainen, Arno; Repo, Timo; ChemCatChem; vol. 9; nb. 20; (2017); p. 3880 - 3887 View in Reaxys > 99 %Spectr.

11 : Example 11 Benzyl alcohol is oxidized to benzaldehyde Fe (NO3) 3.9H2O (40.4 mg, 10 molpercent), ABNO (1.4 mg, 1 molpercent),Benzyl alcohol (108 mg, 1 mmol) was added to a 10 ml reaction tube,Then, 2 ml of acetonitrile was added as a solvent and allowed to react openly at room temperature. The degree of reaction was then checked by GC-MS. After the reaction, the internal standard biphenyl was added and the yield of benzaldehyde was quantified by GC. Reaction 3h, benzaldehyde yield greater than 99percent, selectivity greater than 99percent. With Iron(III) nitrate nonahydrate, 9-azabicyclolt;3.3.1gt;nonane-N-oxyl in acetonitrile, Time= 3h, T= 20 °C , Green chemistry Patent; Dalian Institute of Chemical Physics; Gao Shuang; Wang Lianyue; Li Guosong; Lv Ying; (8 pag.); CN106800492; (2017); (A) Chinese View in Reaxys With Ni(PtBu 2NBn 2)(CH3CN)2(BF4)2, Cp*2FeBF4, triethylamine in [D3]acetonitrile, T= 25 °C , Sealed tube, Inert atmosphere Weiss, Charles J.; Das, Parthapratim; Miller, Deanna L.; Helm, Monte L.; Appel, Aaron M.; ACS Catalysis; vol. 4; nb. 9; (2014); p. 2951 - 2958 View in Reaxys

45 %Chromat.

3.1 : 4.2.1 General procedure for the synthesis of 2 in Table2 General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, PdCl2(CH3CN)2 (0.05mol, 5molpercent), Bi(OTf)3 (0.05mol, 5molpercent), K2CO3 (1mmol) were added. Substrates 1 (1mmol) and MeOH (2mL) were added subsequently. The reaction tube was vacuumed and backfilled with oxygen (3 times). Then the reaction mixture was stirred at 60°C for 3h in the presence of an oxygen balloon. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic lay-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

264/438

2018-03-11 22:07:32


er was dried over anhydrous magnesium sulfate. Subsequently, the combined organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography with hexane/ethyl acetate to afford the corresponding products 2. With bismuth(lll) trifluoromethanesulfonate, dichloro bis(acetonitrile) palladium(II), oxygen, triethylamine in methanol, Time= 5h, T= 60 °C , Schlenk technique Hu, Yongke; Li, Bindong; Tetrahedron; vol. 73; nb. 52; (2017); p. 7301 - 7307 View in Reaxys 99 %Chromat.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C12H8Cl3FeN2O4Zr4, oxygen, sodium nitrite in acetonitrile, Time= 12h, T= 20 °C , p= 760.051Torr , Reagent/catalyst, Solvent Shu, Xin; Yu, Ying; Jiang, Yi; Luan, Yi; Ramella, Daniele; Applied Organometallic Chemistry; vol. 31; nb. 12; (2017); Art.No: E3862 View in Reaxys With tert.-butylhydroperoxide in decane, chloroform, Time= 6h, T= 100 °C , Schlenk technique, Sealed tube, Catalytic behavior, Reagent/catalyst, Solvent Abednatanzi, Sara; Leus, Karen; Derakhshandeh, Parviz Gohari; Nahra, Fady; De Keukeleere, Katrien; Van Hecke, Kristof; Van Driessche, Isabel; Abbasi, Alireza; Nolan, Steven P.; Der Voort, Pascal Van; Catalysis Science and Technology; vol. 7; nb. 7; (2017); p. 1478 - 1487 View in Reaxys

97 %Chromat.

With oxygen, sodium carbonate in ethanol, Time= 24h, T= 60 °C , Catalytic behavior, Solvent, Reagent/catalyst, Temperature Kumar, Sandeep; Chaudhary, Abha; Bandna; Bhattacherjee, Dhananjay; Thakur, Vandna; Das, Pralay; New Journal of Chemistry; vol. 41; nb. 9; (2017); p. 3242 - 3245 View in Reaxys With [fac-N-(2-(diphenylphosphino)ethyl)-5,6,7,8-tetrahydroquinolin-8-amine]RuCl2(triphenylphosphine), potassium tert-butylate in para-xylene, Time= 48h, T= 50 °C , Inert atmosphere, Catalytic behavior Wang, Zheng; Pan, Bing; Liu, Qingbin; Yue, Erlin; Solan, Gregory A.; Ma, Yanping; Sun, Wen-Hua; Catalysis Science and Technology; vol. 7; nb. 8; (2017); p. 1654 - 1661 View in Reaxys With dihydrogen peroxide in acetonitrile, Time= 1h, T= 20 °C , Green chemistry Amini, Mojtaba; Najafpour, Mohammad Mahdi; Salimi, Saeideh; Ramezani, Sakine; Ashouri, Fatemeh; Mahmoudi, Ghodrat; Applied Organometallic Chemistry; vol. 31; nb. 12; (2017); Art.No: E3892 View in Reaxys 2.5 General Procedure of Catalytic Oxidation All oxidation reactions of alcohols were carried out in a round bottom flask fitted with reflux condenser and stir bar. Typically, 5mg of C1 and H2O2 30percent (2mmol, 204 μl) in 2 ml toluene were mixed, followed by the addition of 0.5 mmol substrate. The reaction mixture was stirred at 70 °C for 6h. With C2, the oxidation reaction was carried out in 2ml acetonitrile at 50 °C with the same procedure. In both cases, the work up process is easy. On the other hand, the solid nanocatalysts were separated by means of an external magnetic field and the solution was subjected to GC analysis. We have also used the same procedure for the oxidation of sulfides by C1 as a catalyst. With dihydrogen peroxide in toluene, Time= 6h, T= 70 °C , Reagent/catalyst, Solvent, Temperature, Time Eftekhari-Sis, Bagher; Akbari, Masoud; Akbari, Ali; Amini, Mojtaba; Catalysis Letters; vol. 147; nb. 8; (2017); p. 2106 - 2115 View in Reaxys With C25H34Cl2IrN3O5 in 1,2-dichloro-benzene, Time= 24h, T= 150 °C , Catalytic behavior, Reagent/catalyst Pretorius, René; Olguín, Juan; Albrecht, Martin; Inorganic Chemistry; vol. 56; nb. 20; (2017); p. 12410 - 12420 View in Reaxys With oxygen, potassium hydoxide in water, T= 120 °C , p= 3000.3Torr , Catalytic behavior, Temperature, Pressure, Reagent/catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

265/438

2018-03-11 22:07:32


Gu, Yulong; Li, Chunping; Bai, Jie; Liang, Haiou; Journal of Photochemistry and Photobiology A: Chemistry; vol. 351; (2018); p. 87 - 94 View in Reaxys 2.3 Catalytic test General procedure: The selective oxidation reactions of benzyl alcohol (BZA) were carried out in two-necked flask (50mL) in an oil bath, equipped with a condenser. 1.0mL of benzyl alcohol (9.6mmol), and 300μL of decane as an internal standard, were dissolved into 10mL of toluene, followed by addition of 25mg of catalyst. Afterwards, the mixture was heated up to 80°C, and flushed with pure oxygen with a flow rate of 20mLmin−1 under vigorous stirring. After reaction, the mixture was centrifuged, and the products were analyzed by GC equipped wih a FID detector. The carbon balance for the calculation method is 100±5percent. The values of both the catalytic conversion of BZA and selectivity to the target product were based on three parallel experiments. With oxygen in toluene, Time= 4h, T= 80 °C , Catalytic behavior, Reagent/catalyst Xu, Jie; Shang, Jie-Kun; Chen, Ye; Wang, Yue; Li, Yong-Xin; Applied Catalysis A: General; vol. 542; (2017); p. 380 - 388 View in Reaxys With oxygen, sodium sulfate, Irradiation, Reagent/catalyst Wu, Zhongyi; Wang, Jie; Zhou, Zhaoyu; Zhao, Guohua; Journal of Materials Chemistry A; vol. 5; nb. 24; (2017); p. 12407 - 12415 View in Reaxys 2.3. Typical Procedure for Alcohol Oxidation. General procedure: Liquid-phaseoxidation of 1-phenylethanol was performed in glass flaskequipped with a magnetic stirrer, reflux condenser, andthermometer. In a typical experiment, a mixture of the1-phenylethanol (2mmol), toluene (10 mL), and the catalyst(0.3 g) was transferred in a glass three-necked roundbottomedflask (100 mL); the resulting mixture was thenheated to desired temperature with vigorous stirring. Theoxidation experiment was started by bubbling oxygen gas ata flow rate of 20 mL/min into the reaction mixture. After thereaction, the solid catalyst was filtered off by centrifugationand the liquid productswere analyzed by gas chromatographyto determine the conversion of the alcohol and productselectivity by GC, 7890A,Agilent Technologies Inc., equippedwith a flame ionization detector (FID) and a 19019S-001 HPPONAcolumn. With oxygen in toluene, Time= 0.0666667h, T= 100 °C Assal, Mohamed E.; Kuniyil, Mufsir; Shaik, Mohammed Rafi; Khan, Mujeeb; Al-Warthan, Abdulrahman; Siddiqui, Mohammed Rafiq H.; Adil, Syed Farooq; Journal of Chemistry; vol. 2017; (2017); Art.No: 2937108 View in Reaxys With palladium nanoparticle supported on 3D porous carbon framework in neat (no solvent), Catalytic behavior, Reagent/catalyst Niu, Shuo; Guo, Wenyao; Lin, Tsung-Wu; Yu, Weizhen; Wu, Yifei; Ji, Xiaobo; Shao, Lidong; RSC Advances; vol. 7; nb. 42; (2017); p. 25885 - 25890 View in Reaxys With oxygen, isobutyraldehyde in acetic acid, Time= 0.75h, T= 50 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Solvent, Temperature Malakooti; Feghhi; New Journal of Chemistry; vol. 41; nb. 9; (2017); p. 3405 - 3413 View in Reaxys With potassium carbonate in para-xylene, Time= 2h, T= 80 °C , Reagent/catalyst, Solvent Shaabani, Ahmad; Tabatabaei, Azadeh Tavousi; Hajishaabanha, Fatemeh; Shaabani, Shabnam; Monatshefte fur Chemie; vol. 148; nb. 12; (2017); p. 2079 - 2090 View in Reaxys With oxygen, Time= 8h, UV-irradiation, Sealed tube Liang, Jun; Li, Li; Journal of Materials Chemistry A; vol. 5; nb. 22; (2017); p. 10998 - 11008 View in Reaxys With iron(III) 1,3,5-benzenetricarboxylate, T= 20 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

266/438

2018-03-11 22:07:32


Dhakshinamoorthy, Amarajothi; Santiago-Portillo, Andrea; Concepción, Patricia; Herance, José R.; Navalón, Sergio; Alvaro, Mercedes; Garcia, Hermenegildo; Catalysis Science and Technology; vol. 7; nb. 12; (2017); p. 2445 - 2449 View in Reaxys 2.3 Catalytic Oxidation of Alcohols General procedure: The selective oxidation reactions were carried out in a100mL flask (for a condenser) including 1mmol alcohol,0.09g CQDs-TiO2, and 25mL deionized water as solvent.The alcohols used were benzyl alcohol, cinnamyl alcohol,cyclohexanol, n-army alcohol and n-heptanol. The mixturewere stirred to form suspension. Then 7 mL of 10percentNaClO was gradually added. The reactions were conductedat 50 °C under ambient pressure for 7h. When the reactionwas fnished, the mixture was extracted by ethyl acetate(3 × 30 mL).Then ethyl acetate was removed in vacuum.Oxygenated products were analyzed by an Agilent 7890AGas Chromatographer (GC). Furthermore, for the test ofreusability, the used catalyst was removed from the reactionby filtration and washed with deionized water and acetone,and dried in the air for reuse. With sodium hypochlorite in water, Time= 7h, T= 50 °C , p= 760.051Torr , Reagent/catalyst Ren, Pu; Fu, Xiaobo; Zhang, Yuanming; Catalysis Letters; vol. 147; nb. 7; (2017); p. 1679 - 1685 View in Reaxys With potassium carbonate in toluene, Time= 6h, T= 60 °C , Catalytic behavior, Reagent/catalyst, Solvent, Temperature Karami, Kazem; Hashemi, Sara; Dinari, Mohammad; Applied Organometallic Chemistry; vol. 31; nb. 8; (2017); Art.No: E3672 View in Reaxys Reaction Steps: 2 1: 15 h / 85 °C / Inert atmosphere 2: lithium perchlorate / methanol / 0 °C / Inert atmosphere; Sealed tube; Electrochemical reaction; Cooling with ice With lithium perchlorate in methanol Barone, Mateus R.; Jones, Alan M.; Organic and Biomolecular Chemistry; vol. 15; nb. 47; (2017); p. 10010 10015 View in Reaxys 46 %Chromat.

4.3.4 Typical Procedure for Alcohol Oxidation General procedure: To a solution of ethyl acetate (0.5mL) containing 0.2mmolalcohol and 2mg STA-12(Co) (4μmol, 2molpercent) was added27.4μL TBHP (0.2mmol) and the mixture was stirred at60 °C for appropriated reaction time, which was monitoredby TLC or GC to afford the corresponding products. Theconversions and yields were determined by GC. Ethyl acetatewas added to the reaction mixture followed by centrifugationand filtration which led to easy isolation of Catalyst,and then directly reused in the next run under the samereaction conditions. With tert.-butylhydroperoxide, C6H12N2O6P2 (4-)*2Co(2+)*7.4H2O in ethyl acetate, Time= 2.5h, T= 60 °C , Green chemistry, Catalytic behavior, Time Farrokhi, Alireza; Jafarpour, Maasoumeh; Najafzade, Reihaneh; Catalysis Letters; vol. 147; nb. 7; (2017); p. 1714 - 1721 View in Reaxys 2.5. Catalytic Oxidation Reaction The oxidation of alcohols (benzyl alcohol, 4-methyl benzylalcohol and 4-methoxy benzyl alcohol) using nanocatalysts(ZnAl2O4-MIM and ZnAl2O4-CHM) was carried out in abatch reactor operated under atmospheric conditions. Toa clean dry round bottom flask (10 mL) equipped with areflux condenser and thermometer, and the flask containing5 mmol of oxidant (H2O2). This was followed by theaddition 0.5 g of ZnAl2O4 catalysts and 5 mmol solvent.The mixture was stirred at 80 °C for 5 h. The progressof the reaction was monitored by GC. After completionof the catalytic oxidation reaction, the reaction mixturewas cooled to room temperature and the catalyst was separated by filtration method. The products were identifiedby GC-MS. With extract of Abelmoschus esculentus, leaves, India, Tamil Nadu, Thanjavur, local agricultural fields, dihydrogen peroxide in acetonitrile, Time= 5h, T= 80 °C , p= 760.051Torr Bhavani; Manikandan; Paulraj; Dinesh; Durka; Antony, S. Arul; Journal of Nanoscience and Nanotechnology; vol. 18; nb. 6; (2018); p. 4072 - 4081

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

267/438

2018-03-11 22:07:32


View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [2-((pyridin-2-ylmethylene)amino)ethanol]copper(II) chloride, copper, sodium carbonate in water, Time= 16h, T= 20 °C , Reagent/catalyst Jehdaramarn, Attawit; Pornsuwan, Soraya; Chumsaeng, Phongnarin; Phomphrai, Khamphee; Sangtrirutnugul, Preeyanuch; New Journal of Chemistry; vol. 42; nb. 1; (2018); p. 654 - 661 View in Reaxys With dihydrogen peroxide, oxygen, Enzymatic reaction Pickl, Mathias; Winkler, Christoph K.; Glueck, Silvia M.; Fraaije, Marco W.; Faber, Kurt; Molecules; vol. 22; nb. 12; (2017); Art.No: 2205 View in Reaxys > 95 %Spectr.

With manganese(IV) oxide in acetonitrile, Time= 4h, T= 80 °C , Temperature Alegre-Requena, Juan V.; Marqués-López, Eugenia; Herrera, Raquel P.; Advanced Synthesis and Catalysis; vol. 360; nb. 1; (2018); p. 124 - 129 View in Reaxys With oxygen, T= 280 °C , p= 760.051Torr , Gas phase, Reagent/catalyst Liu, Kun; Long, Houkun; Wang, Guangyi; Sun, Yongbin; Hou, Chao; Dong, Jian; Cao, Xiaoqun; RSC Advances; vol. 7; nb. 86; (2017); p. 54861 - 54865 View in Reaxys 2.3. Catalytic Test The oxidation of benzyl alcohol using spinelMnxCo1−xAl2O4 (x = 0.0 to 1.0) catalysts were carriedout in a batch reactor operated under atmospheric conditions.10 mmol of oxidant (H2O2 was added along with1 g of nano-sized catalysts (CoAl2O4, Mn0.25Co0.75Al2O4,Mn0.5Co0.5Al2O4, Mn0.75Co0.25Al2O4 and MnAl2O4 andthe contents were heated at 80 °C in an acetonitrilemedium for 10 h in a three necked round bottom flaskequipped with a reflux condenser and thermometer. Theoxidized products after the catalytic reaction are collectedand studied using Agilent GC spectrometer. The columnused for the study was DB wax column (capillary column)of length 30 mm and helium was used as the carrier gas. With Mn0.75Co0.25Al2O4, dihydrogen peroxide in acetonitrile, Time= 10h, T= 80 °C , Green chemistry, Reagent/catalyst Bhavani; Manikandan; Jaganathan, Saravana Kumar; Shankar; Antony, S. Arul; Journal of Nanoscience and Nanotechnology; vol. 18; nb. 2; (2018); p. 1388 - 1395 View in Reaxys With C3H4N2*C44H20Cl8N4 (2-)*MnO(3+)*C2H3O2 (1-) in dichloromethane, T= -0.16 °C , Kinetics, Catalytic behavior, Temperature Nasrollahi, Rahele; Zakavi, Saeed; European Journal of Inorganic Chemistry; vol. 2017; nb. 13; (2017); p. 2002 2010 View in Reaxys

72 %Chromat.

With potassium tert-butylate, oxygen in dimethyl sulfoxide, toluene, Time= 12h, T= 160 °C , Schlenk technique, Sealed tube, Catalytic behavior, Reagent/catalyst, Temperature Li, Jinlei; Liu, Guoliang; Shi, Lijun; Xing, Qi; Li, Fuwei; Green Chemistry; vol. 19; nb. 24; (2017); p. 5782 - 5788 View in Reaxys With potassium ferrate(VI), sodium hydroxide in aq. phosphate buffer, T= 25 °C , pH= 9.5, Kinetics, pH-value, Temperature, Solvent Xie, Jianhui; Lo, Po-Kam; Lam, Chow-Shing; Lau, Kai-Chung; Lau, Tai-Chu; Dalton Transactions; vol. 47; nb. 1; (2018); p. 240 - 245 View in Reaxys With oxygen in neat (no solvent), Time= 48h, T= 100 °C , p= 760.051Torr , Sealed tube, Catalytic behavior

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

268/438

2018-03-11 22:07:32


Ye, Jianglin; Ni, Kun; Liu, Jie; Chen, Guanxiong; Ikram, Mujtaba; Zhu, Yanwu; ChemCatChem; vol. 10; nb. 1; (2018); p. 259 - 265 View in Reaxys 2.3. Catalytic Test The oxidation of benzyl alcohol using spinelNixCo1−xAl2O4 (x = 0.0, 0.2, 0.4, 0.6, 0.8 and 1.0) sampleswas carried out in a batch reactor operated underatmospheric conditions. 5 mmol of oxidant (H2O2 wasadded along with 0.5 g of spinel NixCo1−xAl2O4 (x = 0.0,0.2, 0.4, 0.6, 0.8 and 1.0) samples and the contents wereheated at 80 °C in an acetonitrile medium for 5 h in athree necked round bottom flask equipped with a refluxcondenser and thermometer. The oxidized products afterthe catalytic reaction are collected and studied usingAgilent GC spectrometer. The column used for the studywas DB wax column (capillary column) of length 30 mmand helium was used as the carrier gas. GC techniquewas carried out to know the conversion percentage of theproducts. With dihydrogen peroxide in acetonitrile, Time= 5h, T= 80 °C , Reagent/catalyst Suguna; Shankar; Jaganathan, Saravana Kumar; Manikandan, Ayyar; Journal of Nanoscience and Nanotechnology; vol. 18; nb. 2; (2018); p. 1019 - 1026 View in Reaxys 8 : Example 8 Activity Determination of Catalytic Oxidation of Benzyl Alcohol by CoPz (SBu) 7 (SOBu) With CoPz (SBu) 7 (SOBu) as catalyst,The performance of its catalytic oxidation of benzyl alcohol was determined in the absence of oxygen.The effects of solvent, reaction temperature and reaction time on the catalytic oxidation of benzyl alcohol were systematically investigated.With o-xylene as solvent, CoPz (SBu) 7 (SOBu) can catalyze the oxidation of benzyl alcohol to benzaldehyde under nitrogen atmosphere at room temperature. Under the condition that the molar ratio of catalyst to substrate is 1:10,The conversion of benzyl alcohol reached 14.2percent after 2 min reaction, and the selectivity of benzaldehyde was 99percent.It can be seen that the oxidized oxygen source of benzyl alcohol in the reaction comes from the catalyst CoPz (SBu) 7 (SOBu),This is the catalyst characteristics. With C48H72CoN8OS8 in o-xylene, T= 20 °C , Inert atmosphere Patent; South Central University for Nationalities; Deng Kejian; Zhang Bingguang; Liu Yang; Yang Changjun; Zhang Zehui; Zhou Xuanmu; Ren Xiaomei; (10 pag.); CN105175424; (2018); (B) Chinese View in Reaxys With dihydrogen peroxide in water, Time= 7h, T= 90 °C , Green chemistry, Reagent/catalyst Zhang, Wei-Hong; Shen, Jia-Jia; Wu, Jing; Liang, Xue-Yuan; Xu, Jie; Liu, Ping; Xue, Bing; Li, Yong-Xin; Molecular Catalysis; vol. 443; (2017); p. 262 - 269 View in Reaxys 4 : Example 4 In a Teflon reactor, add 2ml of carbon tetrachloride, 2mmol benzyl alcohol, cooled to minus 5 , rapid stirring, dropping 200mg concentration of 15percent nitrosyl sulfate, the reaction vessel closed, into the 1MPa oxygen , And reacted at 10 ° C for 4 hours. The conversion of benzyl alcohol was 100percent and the selectivity of benzaldehyde was 99percent. With nitrosylsulfuric acid, oxygen in tetrachloromethane, Time= 4h, T= -5 - 10 °C , p= 7500.75Torr , Pressure, Solvent, Temperature Patent; Liaoning University of Petroleum and Chemical Technology; Sheng Xuebin; Zhang Lu; Li Shenghui; Zheng Changyong; (4 pag.); CN106565440; (2017); (A) Chinese View in Reaxys With silver nanoparticles immobilized onto poly(4‐vinylpyridine)‐functionalized Fe3O4 nanoparticles in toluene, Time= 10h, Inert atmosphere, Reflux Bayat, Ahmad; Shakourian-Fard, Mehdi; Talebloo, Nazanin; Hashemi, Mohammed Mahmoodi; Applied Organometallic Chemistry; vol. 32; nb. 2; (2018); Art.No: E4061 View in Reaxys General procedure for oxidation of alcohols using (dichloroiodo)arenes General procedure: Alcohol 14 (0.250 mmol) was added to a solution of (dichloroiodo)arene (0.300 mmol) in acetonitrile (2 mL).The reaction was stirred at room temperature for 24 h. After completion of the reaction, a standard solutionof 1.5 mL of 2,4-dinitrophenylhydrazine (prepared from 200mg of 2,4-dinitrophenylhydrazine, 1 mL of H2SO4,10

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

269/438

2018-03-11 22:07:32


mL of EtOH, and 2 mL of H2O) was added. The precipitate of 2,4-dinitrophenylhydrazone derivative 15 wasfiltered, washed with water, and dried in vacuum. With 2-(dichloroiodo)pyridine in acetonitrile, Time= 24h, Inert atmosphere, Reagent/catalyst Yoshimura, Akira; Nguyen, Khiem C.; Nemykin, Victor N.; Zhdankin, Viktor V.; Arkivoc; vol. 2018; nb. 2; (2017); p. 40 - 49 View in Reaxys With Au/reduced graphene oxide nanocomposites, Time= 4h, T= 74.84 °C , Irradiation, Reagent/catalyst, Temperature Zhang, Yanhui; Guo, Hongxu; Weng, Wen; Fu, Ming-Lai; Physical Chemistry Chemical Physics; vol. 19; nb. 46; (2017); p. 31389 - 31398 View in Reaxys With α,α,α-trifluorotoluene, titanium(IV) oxide, oxygen, p= 750.075Torr , Irradiation, Reagent/catalyst Hu, Zengzeng; Quan, Huanhuan; Chen, Zhen; Shao, Yu; Li, Danzhen; Photochemical and Photobiological Sciences; vol. 17; nb. 1; (2018); p. 51 - 59 View in Reaxys With Co(at)N-doped carbon yolk-shell nanocomposite, air in water, Time= 4h, T= 110 °C , p= 750.075Torr , Schlenk technique Chen, Huirong; Shen, Kui; Mao, Qing; Chen, Junying; Li, Yingwei; ACS Catalysis; vol. 8; nb. 2; (2018); p. 1417 1426 View in Reaxys With high valent MnV(O) species, T= -0.16 °C Nasrollahi, Rahele; Zakavi, Saeed; New Journal of Chemistry; vol. 42; nb. 3; (2018); p. 1806 - 1815 View in Reaxys 60 %Spectr.

2.5. Electrolysis General procedure: A homemade airtight electrolysis cell was used equipped with areticulated vitreous carbon (RVC) as working electrode (basi, USA),a bridged Ag/AgCl reference electrode with 2 M LiCl ethanol solution as inner solution and a 0.1 M Bu4NBF4 DMSO as bridge solution was used and the counter electrode, a platinum rod electrode, was put in a divided cell separated from the anodic partby a ceramic frit. In a typical electrolysis experiment 4 mL of a 0.2 MBu4NBF4 DMSO solution was added to the divided part followed bythe addition of 200 mL of acetic acid. In the anodic part neocuproinePd(OAc)2 (0.1 equivalent), 2,6-dimethoxybenzoquinone(0.6 equivalent) and the alcohol (0.7 mmol) was added to a 14 mL solution of 0.2 M Bu4NBF4 in DMSO. The cell was closed andput under an argon atmosphere. Stirring was started, next apotential of 0.7 V was applied. After the appropriate reaction time30 mL of water was added to the reaction mixture. The resultingmixture was extracted with tert-butylmethylether (3 times 25 mL).The collected organic layer was washed with 15 mL of water tofurther remove DMSO. Next the organic layer was dried withMgSO4 filtered and evaporated. The resulting solution wasexamined with NMR. Isolated products were obtained usingcolumn chromatography with heptane/ethylacetate (7/3) aseluent. With (2,9-dimethyl-1,10-phenanthroline)-palladium(II) acetate, 2,6-dimethoxy-p-quinone, tetrabutylammonium tetrafluoroborate, acetic acid in dimethyl sulfoxide, Time= 8h, T= 20 °C , Electrolysis, Inert atmosphere Lybaert; Tehrani, K. Abbaspour; De Wael; Electrochimica Acta; vol. 247; (2017); p. 685 - 691 View in Reaxys

56%Chromat.

With tetrakis[3,5-bis(trifluoromethyl)phenyl]boric acid bis(diethyl ether) complex, 2,6-di-tert-butyl-4-(diphenylmethylene)-2,5-cyclohexadien-1-one in 1,2-dichloro-ethane, Time= 48h, T= 90 °C , Glovebox Fraser, Craig; Young, Rowan D.; Journal of Organic Chemistry; vol. 83; nb. 1; (2018); p. 505 - 509 View in Reaxys

90.9 With sodium hypochlorite, Cd2[4-((E)-((2-((E)-((3-methyl-phenyl)imino)methyl)phenyl)imino)methyl)-N-pentyl-N-(4%Chromat. ((E)-((2-((E)-(phenylimino)methyl)phenyl)imino)methyl)phenyl)aniline]Cl4, 1-ethyl-3-methyl imidazolium, Time= 0.25h, T= 20 °C , Reagent/catalyst Parsaee, Zohreh; Journal of Molecular Structure; vol. 1146; (2017); p. 644 - 659

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

270/438

2018-03-11 22:07:32


View in Reaxys With tert.-butylhydroperoxide in [D3]acetonitrile, water, Time= 48h, T= 25 °C , Solvent Dare, Nicola A.; Brammer, Lee; Bourne, Susan A.; Egan, Timothy J.; Inorganic Chemistry; vol. 57; nb. 3; (2018); p. 1171 - 1183 View in Reaxys With C21H25ClIrN4O(1+)*CF3O3S(1-) in 1,2-dichloro-benzene, Time= 72h, T= 150 °C , Inert atmosphere, Reagent/catalyst Mazloomi, Zahra; Pretorius, René; Pàmies, Oscar; Albrecht, Martin; Diéguez, Montserrat; Inorganic Chemistry; vol. 56; nb. 18; (2017); p. 11282 - 11298 View in Reaxys 99%Chromat.

With 1-methyl-1H-imidazole, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper(I) bromide in acetonitrile, Time= 1h, T= 23 °C Du, Xin; Luan, Yi; Yang, Fengxia; Ramella, Daniele; Shu, Xin; New Journal of Chemistry; vol. 41; nb. 11; (2017); p. 4400 - 4405 View in Reaxys

90 %Chromat.

With dihydrogen peroxide in water, Time= 4h, T= 100 °C , Catalytic behavior, Reagent/catalyst, Temperature Farhadi, Saeed; Hakimi, Mohammad; Maleki, Mansoureh; RSC Advances; vol. 8; nb. 13; (2018); p. 6768 - 6780 View in Reaxys

HO

H

O

O

HO

Rx-ID: 817415 View in Reaxys 2/435 Yield 95 %, 5 %

Conditions & References With tert.-butylhydroperoxide in acetonitrile, Time= 8h, Reflux Zendehdel; Khanmohamadi; Mokhtari; Journal of the Chinese Chemical Society; vol. 57; nb. 2; (2010); p. 205 212 View in Reaxys

93 %

With sodium acetate, 4,7-di-(NaSO3Ph)-[1.10]phenanthroline-Pd(OAc)2 in water, Time= 10h, T= 100 °C , p= 22502.3Torr , pH= 6.5 - 11.5 Ten Brink, Gerd-Jan; Arends, Isabel W. C. E.; Sheldon, Roger A.; Advanced Synthesis and Catalysis; vol. 344; nb. 3-4; (2002); p. 355 - 369 View in Reaxys

93 %, 7 %

With C25H28ClIrN3S(1+)*F6P(1-), 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Hohloch, Stephan; Hettmanczyk, Lara; Sarkar, Biprajit; European Journal of Inorganic Chemistry; nb. 20; (2014); p. 3164 - 3171 View in Reaxys

10.23 %, 89.77 %

With tert.-butylhydroperoxide in acetonitrile, Time= 8h, Reflux Zendehdel; Khanmohamadi; Mokhtari; Journal of the Chinese Chemical Society; vol. 57; nb. 2; (2010); p. 205 212 View in Reaxys

88.2 %, 11.8 %

With Cs5PMnW11O39, dihydrogen peroxide, Time= 5h, T= 80 °C , Green chemistry, Catalytic behavior, Temperature, chemoselective reaction Rana, Surjyakanta; Maddila, Suresh; Pagadala, Ramakanth; Parida; Jonnalagadda, Sreekantha B.; Catalysis Communications; vol. 59; (2014); p. 73 - 77 View in Reaxys

87 %, 3 %

With dihydrogen peroxide in water, acetone, Time= 2.5h, T= 56 °C , chemoselective reaction

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

271/438

2018-03-11 22:07:32


Kikukawa, Yuji; Yamaguchi, Kazuya; Mizuno, Noritaka; Angewandte Chemie - International Edition; vol. 49; nb. 35; (2010); p. 6096 - 6100 View in Reaxys 86 %

With sodium tungstate, dihydrogen peroxide in water, Time= 4h, T= 90 °C , Yields of byproduct given Sato, Kazuhiko; Aoki, Masao; Takagi, Junko; Noyori, Ryoji; Journal of the American Chemical Society; vol. 119; nb. 50; (1997); p. 12386 - 12387 View in Reaxys

85 %, 0.7 %

10 :Platinum black (19.5 mg, 0.100 mmol) and benzyl alcohol (1.0 ml, 10 mmol) were mixed and stirred at 90 °C for 10 minutes. A 30percent aqueous hydrogen peroxide solution (1.3 ml, 12 mmol) was gradually added dropwise to the mixed solution, followed by stirring at 90 °C for 15 hours, and then the reaction solution was cooled to room temperature. As a result of measurement by GLC, it was found that benzaldehyde was obtained in yield of 85percent. Benzoic acid was obtained in yield of 0.7percent. Stage 1: With platinum, Time= 0.166667h, T= 90 °C Stage 2: With dihydrogen peroxide in water, Time= 15h, T= 90 °C , Product distribution / selectivity Patent; National Institute of Advanced Industrial Science and Technology; EP1544188; (2005); (A1) English View in Reaxys

85 %, 5 %

With ammonium nitrate in dichloromethane, Time= 0.416667h, T= 20 °C Zarei, Amin; Bulletin of the Korean Chemical Society; vol. 33; nb. 7; (2012); p. 2149 - 2155 View in Reaxys

82.5%, 17.5 %

9 :REFERENCE EXAMPLE 9 865 mg (8 mmol) of benzyl alcohol, 25 mg of compound (14) obtained in Reference Example 3 (2,2,6,6-tetramethylpiperidine-1-oxyl-4-yl group: 0.08 mmol), 1.6 cc of a 0.5 normality aqueous solution of potassium bromide and 20 cc of methylene chloride were placed in a 100 ml reaction vessel. Then, with maintaining the temperature at 0 to 2° C., reaction was conducted while 74.48 g (20 mmol) of a 2.0percent by weight aqueous solution of sodium hypochlorite (adjusted to pH 8.6 by a 5percent by weight aqueous solution of sodium hydrogen carbonate) was dropped over 0.5 hour under stirring and stirring was conducted for another 0.5 hour. The reaction mixture after the reaction was completed was separated into the organic phase and the water phase and each phase was analyzed by liquid chromatography. By the reaction, benzaldehyde was produced with yield of 82.5percent (based on benzyl alcohol). As a by-product, 17.5percent (based on benzyl alcohol) of benzoic acid was produced. With sodium hypochlorite, C16H30N2O4Pol, sodium hydrogencarbonate, potassium bromide in dichloromethane, water, Time= 1h, T= 0 - 2 °C , pH= 8.6 Patent; Shiomi, Yasuhiro; Uno, Osamu; Ohta, Akio; Sunakami, Takeshi; US2005/124807; (2005); (A1) English View in Reaxys

82 %, 18 %

With tert.-butylhydroperoxide in water, acetonitrile, T= 80 °C Dhanalaxmi, Karnekanti; Singuru, Ramana; Kundu, Sudipta K.; Reddy, Benjaram Mahipal; Bhaumik, Asim; Mondal, John; RSC Advances; vol. 6; nb. 43; (2016); p. 36728 - 36735 View in Reaxys

81 %, 13 %

With oxygen in water, Time= 8h, T= 40 °C , p= 760.051Torr , Reagent/catalyst Long, Yu; Yuan, Bing; Niu, Jianrui; Tong, Xin; Ma, Jiantai; New Journal of Chemistry; vol. 39; nb. 2; (2015); p. 1179 - 1185 View in Reaxys

10 %, 80 %

With ammonium metavanadate, perchloric acid in water, Time= 8h, Heating, other arylmethanols; various reagents, Product distribution Banerjee; Dutt; Hazra; Datta; Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry; vol. 29; nb. 3; (1990); p. 257 - 262 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

272/438

2018-03-11 22:07:32


80 %, 20 %

With oxygen, cerium(IV) oxide, ruthenium, Time= 9h, T= 140 °C , Oxidation Vocanson; Guo; Namy; Kagan; Synthetic Communications; vol. 28; nb. 14; (1998); p. 2577 - 2582 View in Reaxys

79 %, 0.4 μmol

Stage 1: in toluene, Time= 0.0833333h, Ultrasonication Stage 2: With oxygen in toluene, T= 26.84 - 29.84 °C , Irradiation Tsukamoto, Daijiro; Shiraishi, Yasuhiro; Sugano, Yoshitsune; Ichikawa, Satoshi; Tanaka, Shunsuke; Hirai, Takayuki; Journal of the American Chemical Society; vol. 134; nb. 14; (2012); p. 6309 - 6315 View in Reaxys

21 %, 79 %

With [Os(p-cymene)Cl(1-[2-(methylthio)phenyl]-4-phenyl-1H-1,2,3-triazole)]*hexafluorophosphate, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux Hohloch, Stephan; Hettmanczyk, Lara; Sarkar, Biprajit; European Journal of Inorganic Chemistry; nb. 20; (2014); p. 3164 - 3171 View in Reaxys

77 %, 14 %

With dihydrogen peroxide, methyltrioctylammonium tetrakis(oxodiperoxotungsto)phosphate, Time= 0.75h, T= 90 °C Venturello, Carlo; Gambaro, Mario; Journal of Organic Chemistry; vol. 56; nb. 20; (1991); p. 5924 - 5931 View in Reaxys

75 %, Ca. 8%

in water, Time= 6h, Reflux Mamros, Audrey N.; Sharrow, Phillip R.; Weller, William E.; Luderer, Mark R.; Fair, Justin D.; Pazehoski, Kristina O.; Luderer, Matthew R.; Arkivoc; vol. 2011; nb. 5; (2011); p. 23 - 33 View in Reaxys

75 %, 20 %

2.2. Oxidation of alcohols under ultrasonic condition: a general procedure General procedure: A mixture of alcohol (10 mmol), Ni(NO3)2*6H2O (2.908 g, 10 mmol), I2 (1.3 g, 10 mmol) and water (2 mL) were sonicated in a sonic bath working at 35 kHz (constant frequency) maintained at 25 °C by circulating water. After completion of the reaction (Table 5, monitored on TLC), the product was taken into diethyl ether (10 mL), the organic matter was washed with sat. NaHCO3 (2.5 mL), water (5 mL) and then dried over anhydrous Na2SO4. The organic layer was evaporated in a fume hood to get almost pure aldehyde. The crude was then subjected to silica gel column chromatography to get the pure product. All the products were characterized by IR, GC– mass spectral analysis; and the physical properties were compared with the properties of authentic samples. With nickel(II) nitrate hexahydrate, iodine in water, Time= 0.166667h, T= 25 °C , Sonication Pasha, Mohamed Afzal; Nagashree, Shrivatsa; Ultrasonics Sonochemistry; vol. 20; nb. 3; (2013); p. 810 - 814 View in Reaxys

70 %, 12 %

With ruthenium trichloride, iodobenzene, potassium hydrogen persulfate in water, acetonitrile, Time= 1.5h, T= 20 °C Yusubov, Mekhman S.; Zagulyaeva, Aleksandra A.; Zhdankin, Viktor V.; Chemistry - A European Journal; vol. 15; nb. 42; (2009); p. 11091 - 11094 View in Reaxys

30 %, 70 %

2.2. Oxidation of alcohols under ultrasonic condition: a general procedure General procedure: A mixture of alcohol (10 mmol), Ni(NO3)2*6H2O (2.908 g, 10 mmol), I2 (1.3 g, 10 mmol) and water (2 mL) were sonicated in a sonic bath working at 35 kHz (constant frequency) maintained at 25 °C by circulating water. After completion of the reaction (Table 5, monitored on TLC), the product was taken into diethyl ether (10 mL), the organic matter was washed with sat. NaHCO3 (2.5 mL), water (5 mL) and then dried over anhydrous Na2SO4. The organic layer was evaporated in a fume hood to get almost pure aldehyde. The crude was then subjected to silica gel column chromatography to get the pure product. All the products were characterized by IR, GC– mass spectral analysis; and the physical properties were compared with the properties of authentic samples. With nickel(II) nitrate hexahydrate, iodine in water, Time= 0.133333h, T= 25 °C , Sonication Pasha, Mohamed Afzal; Nagashree, Shrivatsa; Ultrasonics Sonochemistry; vol. 20; nb. 3; (2013); p. 810 - 814 View in Reaxys

70 %, 28 %

With tert.-butylhydroperoxide, chromium tetra(tert-butoxide) in benzene, Time= 24h, T= 20 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

273/438

2018-03-11 22:07:32


Stepovik; Zaburdaeva; Fukin; Karaghiosoff; Russian Journal of General Chemistry; vol. 85; nb. 11; (2015); p. 2547 - 2559; Zh. Obshch. Khim.; vol. 85; nb. 11; (2015); p. 1805 - 1817,13 View in Reaxys 69 %

With 4‐(acetylamino)‐2,2,6,6‐tetramethyl‐1‐oxopiperidinium tetrafluoroborate in water, acetonitrile, Time= 480h, T= 20 °C Qiu, Joseph C.; Pradhan, Priya P.; Blanck, Nyle B.; Bobbitt, James M.; Bailey, William F.; Organic Letters; vol. 14; nb. 1; (2012); p. 350 - 353 View in Reaxys

23 %, 68 %

With C32H25Cl2N6O2Rh2 (1+)*Cl(1-), sodium carbonate in water, Time= 12h, T= 100 °C , Sealed tube, Inert atmosphere, Green chemistry, Catalytic behavior, Reagent/catalyst Wang, Xuewei; Wang, Chao; Liu, Yuxuan; Xiao, Jianliang; Green Chemistry; vol. 18; nb. 17; (2016); p. 4605 4610 View in Reaxys

66 %, 4 %

With potassium carbonate in Petroleum ether, Ambient temperature, electrolysis (Beaker type circulation cell): nickel anode, steel cathode, 0.2 A, current consumption 3.4 F/mol Schneider, Roy; Schaefer, Hans-J.; Synthesis; nb. 10; (1989); p. 742 - 743 View in Reaxys

65 %, 33 %

With trans-Na6lt;RuO2(H2TeO6)2gt; in water, Time= 24h, various type and concentration of catalysts; time, Product distribution El-Hendawy, Ahmed M.; Griffith, William P.; Piggott, Brian; Williams, David J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1988); p. 1983 - 1988 View in Reaxys

65 %, 34 %

With C30H24AgBr4N8 (1+)*AgBr2 (1-), potassium hydoxide in 1,2-dimethoxyethane, Time= 12h, T= 20 °C , Molecular sieve, Schlenk technique, Reagent/catalyst, Temperature, Time, Solvent Han, Lei; Xing, Ping; Jiang, Biao; Organic Letters; vol. 16; nb. 13; (2014); p. 3428 - 3431 View in Reaxys

65.4 %, 34.3 %

Stage 1: With tert.-butylhydroperoxide in diethylene glycol dimethyl ether, Time= 6h, T= 65 °C Stage 2:Time= 2h, T= 600 °C , Calcination, Activation energy Hinde, Christopher S.; Gill, Arran M.; Wells, Peter P.; Hor, T. S. Andy; Raja, Robert; ChemPlusChem; vol. 80; nb. 8; (2015); p. 1226 - 1230 View in Reaxys

10 %, 60 %

With superoxide, oxygen in N,N-dimethyl-formamide, Time= 15h, electrolysis, divided electrolytic cell, mercury pool cathode, platinum foil anode, Bu4N+Br-, cyclohexene, constant potential -1.0 V vs. SCE, current 85 (initial) to 25 (final) mA Singh; Dwivedi; Misra; Synthesis; nb. 4; (1991); p. 291 - 293 View in Reaxys

10 %, 60 %

With oxygen, Time= 12h, electrolysis: Hg cathode, plazinum foil anode, n-Bu4N(1+)*ClO4 (1-) / DMF, -1.0 V vs SCE Singh, Manorama; Misra, Ram A.; Synthesis; nb. 5; (1989); p. 403 - 404 View in Reaxys

28 %, 59 %

With peracetic acid, C24H29INO5 in acetic acid, Time= 24h, T= 30 °C Yakura, Takayuki; Ozono, Ayaka; Advanced Synthesis and Catalysis; vol. 353; nb. 6; (2011); p. 855 - 859 View in Reaxys

30 %, 59 %

With tert.-butylhydroperoxide in hexane, water, Time= 10.5h, T= 50 °C Zhang, Yuecheng; Huo, Wenge; Zhang, Hong-Yu; Zhao, Jiquan; RSC Advances; vol. 7; nb. 75; (2017); p. 47261 - 47270 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

274/438

2018-03-11 22:07:32


58 %, 23 %

With potassium permanganate, cetyltrimethylammonim bromide in dichloromethane, Time= 5h Kumar, Anil; Jain, Nidhi; Chauhan; Synthetic Communications; vol. 34; nb. 15; (2004); p. 2835 - 2842 View in Reaxys

57 %, 23 %

With 2-Ethylhexanoic acid, (R,R)-Mn-dpn, dihydrogen peroxide in acetonitrile, T= 0 °C , Inert atmosphere, chemoselective reaction Ottenbacher, Roman V.; Talsi, Evgenii P.; Bryliakov, Konstantin P.; Chemical Record; vol. 18; nb. 1; (2018); p. 78 - 90 View in Reaxys

56.5 %, 19.2 %

7 : Example 7 Oxidation of Benzyl Alcohol Oxidations of 1 mM benzyl alcohol with 2 mM H2O2 were carried with 30percent acetonitrile and 10 mM acetate (pH 3-5), phosphate (pH 7) or borate buffer (pH 8) at specified pH values using 0.01 mg/mL of purified peroxygenase (mature peroxygenase encoded by SEQ ID NO: 1) in a total reaction volume of 1 mL. Reactions were performed at room temperature for 25 minutes and stopped by adding 1 μL of catalase (Terminox Ultra 50 L, Novozymes). (0272) Samples were analyzed on an Agilent 1200 HPLC system equipped with a Diode Array Detector (Agilent, Santa Clara Calif., USA) and separated on a Zorbax Stable Bond C18 (2) (80 , 2.1×50 mm, 1.8 μm) column from Phenomenex (Torrance Calif., USA) thermostated at 40° C. Two mobile phases were used: (A) 0.1percent formic acid, and (B) 0.1percent formic acid in acetonitrile. (0273) Separations were run using stepwise gradient starting with 5percent B held for 4 min, then increasing to 100percent B within 6 min with a constant flow rate of 0.5 ml/min. (0274) Benzyl alcohol and its oxidation products benzaldehyde and benzoic acid were identified and quantified by external calibration using authentic standards, based on their retention times, UV absorbtion spectra (210 nm, 250 nm, and 230 nm respectively). (0275) The peroxygenase oxidised benzyl alcohol yielding two products benzaldehyde and benzoic acid. TABLE 7 Comparison of total product, benzaldehyde (B-CHO) and benzoic acid (B-COOH) yields calculated at various pH. B-CHO B-COOH Total product pH (percent) (percent) (percent) 3 14.1 0.6 14.6 5 50.9 17.9 68.7 7 56.5 19.2 75.8 8 7.7 0.0 7.7 With peroxygenase, dihydrogen peroxide in aq. phosphate buffer, acetonitrile, Time= 0.416667h, T= 20 °C , pH= 7, Enzymatic reaction, pH-value Patent; Novozymes A/S; Landvik, Sara; Oestergaard, Lars H.; Kalum, Lisbeth; (25 pag.); US9382559; (2016); (B2) English View in Reaxys

35 %, 55 %

With sodium hydroxide, bromine in water, Different amounts of NaOH and Br2, Mechanism, Product distribution Shapiro, Yu. M.; Pustovarova, O.P.; Baum, E.; Kul'nevich, V.G.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 11; (1982); p. 1132 - 1136; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 11; (1982); p. 1463 - 1467 View in Reaxys

53 %, 18 %

With C32H25Cl2N6O2Rh2 (1+)*Cl(1-), sodium acetate in water, Time= 12h, T= 100 °C , Sealed tube, Inert atmosphere, Green chemistry Wang, Xuewei; Wang, Chao; Liu, Yuxuan; Xiao, Jianliang; Green Chemistry; vol. 18; nb. 17; (2016); p. 4605 4610 View in Reaxys

52 %, 40 %

Oxidation reactions With 2O34W9Zn(12-)*W(6+)*3Zn(2+)*2H2O, dihydrogen peroxide in water, acetonitrile, Time= 0.25h, T= 135 °C , p= 2250.23Torr , Microwave irradiation Kasprzyk, Wiktor; Galica, Mateusz; Bednarz, Szczepan; Bogdal, Dariusz; Synlett; vol. 25; nb. 19; (2014); p. 2757 - 2760 View in Reaxys

50 %

With oxygen, potassium carbonate in water, Time= 1h, T= 80 °C , p= 760.051Torr Harada, Takashi; Ikeda, Shigeru; Hashimoto, Fumihiro; Sakata, Takao; Ikeue, Keita; Torimoto, Tsukasa; Matsumura, Michio; Langmuir; vol. 26; nb. 22; (2010); p. 17720 - 17725 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

275/438

2018-03-11 22:07:32


48 %, 49 %

With 1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene silver chloride, potassium hydoxide in toluene, Time= 12h, T= 20 °C , Molecular sieve, Schlenk technique, Reagent/catalyst, Temperature, Time, Solvent Han, Lei; Xing, Ping; Jiang, Biao; Organic Letters; vol. 16; nb. 13; (2014); p. 3428 - 3431 View in Reaxys

47 %

With dihydrogen peroxide in water, Time= 6h, T= 80 °C , Inert atmosphere Stolle, Achim; Ondruschka, Bernd; Morgenthal, Ingrid; Andersen, Olaf; Bonrath, Werner; Journal of Molecular Catalysis A: Chemical; vol. 335; nb. 1-2; (2011); p. 228 - 235 View in Reaxys

35 %, 46 %

With tert.-butylhydroperoxide, Rh2(Msip)4, sodium hydrogencarbonate in dichloromethane, water, Time= 24h, T= 40 °C , Sealed tube, chemoselective reaction Wusiman, Abudureheman; Lu, Chong-Dao; Applied Organometallic Chemistry; vol. 29; nb. 4; (2015); p. 254 - 258 View in Reaxys

42 %, 30 %

With diphenylether, Fe(TAML)Li, [bis(acetoxy)iodo]benzene, water in acetone, Time= 1h, T= 25 °C , Green chemistry, Kinetics Napoly, Francois; Jean-Gerard, Ludivine; Goux-Henry, Catherine; Draye, Micheline; Andrioletti, Bruno; European Journal of Organic Chemistry; vol. 2014; nb. 4; (2014); p. 781 - 787 View in Reaxys

6.4 %, 35.5 %

With 3-chloro-benzenecarboperoxoic acid, (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride in dichloromethane, acetonitrile, Time= 0.166667h, T= 20 °C Han, Jung Hee; Yoo, Sang-Kun; Seo, Jin Soo; Hong, Sung Jin; Kim, Seok Kyu; Kim, Cheal; Dalton Transactions; nb. 2; (2005); p. 402 - 406 View in Reaxys

35.2 %

2.3. Reaction procedure for benzyl alcohol oxidation Liquid-phase catalytic oxidation of benzyl alcohol was carried out ina 50 mL four-neck-flask with reflux condenser and magnetically stirredautoclave heated in an oil bath under atmospheric pressure. Acetonitrile(solvent, 10mL), catalyst (0.1 g) and 0.02mol benzyl alcoholwere magneticallystirred at 60 °C, followed by dropwise addition of 0.04 mol ofTBHP (70percent) in 30 min. The product samples were drawn at regulartime intervals and analyzed with a gas chromatography (ShimadzuGC-2010AF) having Chromopak capillary column and FID detector.The products were further confirmed using GC–MS (Shimadzu GCMS-2010). After the reaction, the resulting mixture was cooled with icebath and the catalyst was separated by centrifugation and washedwith solvent. After drying at roomtemperature in vacuum, the recycledcatalyst can be reused in the next run under the same conditions. Theconversion, yield of benzaldehyde and selectivity presented here are based on the GC calculations using cyclohexane as the internal standardreference compound. With tert.-butylhydroperoxide in acetonitrile, Time= 0.5h, T= 60 °C , p= 760.051Torr , Concentration, Reagent/catalyst, Solvent, Temperature, Time Zhou, Weiyou; Liu, Jie; Pan, Jiugao; Sun, Fu'An; He, Mingyang; Chen, Qun; Catalysis Communications; vol. 69; (2015); p. 1 - 4 View in Reaxys

28 %, 10 %

With copper(ll) sulfate pentahydrate, sulfuric acid, dihydrogen peroxide in water, Time= 1.5h, T= 80 °C Ahmad, Jahir Uddin; Raeisaenen, Minna T.; Leskelae, Markku; Repo, Timo; Applied Catalysis A: General; vol. 411-412; (2012); p. 180 - 187 View in Reaxys

Ca. 10 %

With iron(II) perchlorate monohydrate, oxygen, ozone, Overall yield = 85 percent Bataineh, Hajem; Pestovsky, Oleg; Bakac, Andreja; ACS Catalysis; vol. 5; nb. 3; (2015); p. 1629 - 1637 View in Reaxys

90 %Chromat., 9 %

With [bis(acetoxy)iodo]benzene, [Al(OH)(bpydc)·0.07RuCl3(DMSO)·0.5H2O] in dichloromethane, Time= 1.5h, T= 22 °C , Sealed tube, Catalytic behavior

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

276/438

2018-03-11 22:07:32


Carson, Fabian; Agrawal, Santosh; Gustafsson, Mikaela; Bartoszewicz, Agnieszka; Moraga, Francisca; Zou, Xiaodong; Martin-Matute, Belen; Chemistry - A European Journal; vol. 18; nb. 48; (2012); p. 15337 - 15344 View in Reaxys 3%

With ammonium cerium (IV) nitrate, sodium trimethylsilylpropionate-d4, C18H22N4O2Ru(2+)*2F6P(1-), water, Time= 0.5h, T= 20 °C Hirai, Yuichirou; Kojima, Takahiko; Mizutani, Yasuhisa; Shiota, Yoshihito; Yoshizawa, Kazunari; Fukuzumi, Shunichi; Angewandte Chemie - International Edition; vol. 47; nb. 31; (2008); p. 5772 - 5776 View in Reaxys

33.5 mg, 39.8 mg

With phosphate buffer, [Ru(2,2':6':2''-terpyridine)(2,2'-bipyridine)O](2+) in water, tert-butyl alcohol, Ambient temperature, electrooxidation, pH 6.8 Navarro, Marcelo; Giovani, Wagner F.De; Romero, J.R.; Synthetic Communications; vol. 20; nb. 3; (1990); p. 399 - 406 View in Reaxys

23 % Chromat., 6 % Chromat.

With oxygen in benzene, Time= 15h, Ambient temperature, Irradiation

41 % Chromat., 23 % Chromat.

With oxygen, N -hydroxyphthalimide in benzonitrile, Time= 5h, T= 100 °C , p= 760Torr

Suzuki; Yamazaki; Takabe; Morioka; Mizuno; Matsushima; Bulletin of the Chemical Society of Japan; vol. 57; nb. 7; (1984); p. 1870 - 1875 View in Reaxys

Ishii, Yasutaka; Nakayama, Kouichi; Takeno, Mitsuhiro; Sakaguchi, Satoshi; Iwahama, Takahiro; Nishiyama, Yutaka; Journal of Organic Chemistry; vol. 60; nb. 13; (1995); p. 3934 - 3935 View in Reaxys With nickel(II) sulphate, water, sodium phenylsulfonate, T= 70 °C , und Natronlauge an Nickel-Anoden McKee; Heard; ; vol. 65; (1934); p. 301,316 View in Reaxys With cobalt(II) sulfate, water, sodium phenylsulfonate, T= 70 °C , und Natronlauge an Nickel-Anoden McKee; Heard; ; vol. 65; (1934); p. 301,316 View in Reaxys With air, silica gel, T= 400 °C Patent; I.G. Farbenind.; DE520828; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 3011 View in Reaxys I.G. Farbenindustrie; Chem. Zentralbl.; vol. 102; nb. I; (1931); p. 3287 View in Reaxys With air, vanadium pentoxide-pumice stone, T= 400 - 480 °C Schorigin; Kisber; Smoljankowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 2; p. 150; Chem. Zentralbl.; vol. 100; nb. II; (1929); p. 730 View in Reaxys With sodium hydroxide, 3-methyl-10-ethyl-5-deazaisoalloxazine, Time= 20h, T= 90 °C , Yield given Yoneda, Fumio; Mori, Kenya; Matsuo, Sawako; Kadokawa, Yoko; Sakuma, Yoshiharu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 1836 - 1839 View in Reaxys bei der elektrolytischen Oxydation Koidzumi; Memoirs of the College of Science, Kyoto Imperial University; vol. <A> 11; p. 383; Chem. Zentralbl.; vol. 99; nb. II; (1928); p. 2331 View in Reaxys

60 % Chromat.,

With ammonium nitrate in sulfuric acid, water, T= 20 °C , var. ratio of reactants, Product distribution, Mechanism

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

277/438

2018-03-11 22:07:32


40 % Chromat.

Rodkin, M. A.; Shtern, M. M.; Cheprakov, A. V.; Makhon'kov, D. I.; Merdaleishvili, R. E.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 3; (1988); p. 434 - 440; Zhurnal Organicheskoi Khimii; vol. 24; nb. 3; (1988); p. 488 - 495 View in Reaxys With ruthenium trichloride, dihydrogen peroxide, N,N-didecyl-N,N-dimethylammonium bromide in dichloromethane, Time= 0.75h, T= 80 °C , other alipahtic primary and secondary alcohols and aliphatic allylic alcohol, other reaction time; selectivity of oxidation, effects of var. phase-transfer catalysts and some other metal salts, Product distribution Barak, Gabriela; Dakka, Jihad; Sasson, Yoel; Journal of Organic Chemistry; vol. 53; nb. 15; (1988); p. 3553 3555 View in Reaxys With bromate, sulfuric acid, mercury(II) diacetate in water, acetic acid, Time= 1.5h, T= 40 °C , ΔG(excit.), ΔH(excit.), ΔS(excit.), Ea at 40 deg C; added salts: NaClO4, NaHSO4, Rate constant, Mechanism, Thermodynamic data Reddy, Ch. Sanjeeva; Sundaram, E. V.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical; vol. 23; nb. 11; (1984); p. 911 - 916 View in Reaxys

23 % Chromat., 6 % Chromat.

With oxygen in benzene, Time= 15h, Ambient temperature, Irradiation, other time, other solvent,, Product distribution Suzuki; Yamazaki; Takabe; Morioka; Mizuno; Matsushima; Bulletin of the Chemical Society of Japan; vol. 57; nb. 7; (1984); p. 1870 - 1875 View in Reaxys With sodium hydroxide, benzyltrimethylammonium tribromide in tetrachloromethane, water, Time= 6h, Ambient temperature, variation of molar ratio on conditions; selective oxidation of further substituted benzyl alcohols, Product distribution Okamotom; Uesugi; Kakinami; Utsunomiya; Kajigaeshi; Bulletin of the Chemical Society of Japan; vol. 62; nb. 11; (1989); p. 3748 - 3749 View in Reaxys With ruthenium trichloride, sodium chloride in tetrachloromethane, water, T= 25 °C , electrochemical oxidation of alcohols and aldehydes by a biphasic ruthenium catalyzed phase transfer system; effect of pH, Product distribution Rajendran; Trivedi; Synthesis; nb. 2; (1995); p. 153 - 154 View in Reaxys

73.5 % Chromat., 25.6 % Chromat.

With dihydrogen peroxide, molecular sieve in water, Time= 18h, T= 79.9 °C , var. of solvent, Product distribution Bhaumik, Asim; Kumar, Rajiv; Journal of the Chemical Society, Chemical Communications; nb. 3; (1995); p. 349 350 View in Reaxys With tert.-butylhydroperoxide, CrAPO-5 in chlorobenzene, Time= 16h, T= 85 °C , other catalyst; oxidation of primary and secondary alcohols with TBHP and O2 catalyzed with chromium-substituted aluminophosphates; conversion; selectivity; possible mechanism; effect of radical scavengers, Product distribution Chen, Ji Dong; Lempers, Hans E. B.; Sheldon, Roger A.; Journal of the Chemical Society - Faraday Transactions; vol. 92; nb. 10; (1996); p. 1807 - 1813 View in Reaxys

73 % Chromat., 5 % Chromat.

With cis-lt;RuVI(6,6'-Cl2bpy)2O2gt;lt;ClO4gt; in acetonitrile, Time= 0.5h, T= 20 °C , Oxidation

45 % Chromat., 23 % Chromat.

With tert.-butylhydroperoxide, cis-[RuII(6,6'-Cl2bpy)2(OH)2](CF3SO3)2 in acetone, Time= 24h, T= 20 °C , Oxidation

Che; Cheng; Chan; Lau; Mak; Journal of Organic Chemistry; vol. 65; nb. 23; (2000); p. 7996 - 8000 View in Reaxys

Che; Cheng; Chan; Lau; Mak; Journal of Organic Chemistry; vol. 65; nb. 23; (2000); p. 7996 - 8000 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

278/438

2018-03-11 22:07:32


With potassium permanganate, copper(II) sulfate in dichloromethane, ultrasonic irradiation, Oxidation, Product distribution, Kinetics, Further Variations: Temperatures, Reagents, ultrasound effect Meciarova, Maria; Toma, Stefan; Heribanova, Andrea; Tetrahedron; vol. 56; nb. 43; (2000); p. 8561 - 8566 View in Reaxys Stage 1: With manganese(II) acetate, 1-bicyclo[2.2.1]hept-5-en-2-yl-CH2-4,7-diMe[1,4,7]triazonane in methanol, acetone, Time= 0.25h, T= 0 °C Stage 2: With oxalic buffer, dihydrogen peroxide in methanol, acetone, Time= 4.5h, T= 0 - 2 °C , Title compound not separated from byproducts Grenz; Ceccarelli; Bolm; Chemical Communications; nb. 18; (2001); p. 1726 - 1727 View in Reaxys With 2,2,6,6-tetramethyl-1-oxo-piperidinium; GENERIC INORGANIC ANION in acetonitrile, T= 10 °C , Product distribution, Kinetics Ganiev; Suvorkina; Igoshina; Kabal'nova; Imashev; Tolstikov; Russian Chemical Bulletin; vol. 51; nb. 6; (2002); p. 982 - 985 View in Reaxys With Ni-oxide in water, T= 19.85 - 39.85 °C , Activation energy, Kinetics Christoskova; Stoyanova; Water Research; vol. 36; nb. 9; (2002); p. 2297 - 2303 View in Reaxys With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione, Time= 3h, T= 60 - 90 °C Moorthy, Jarugu Narasimha; Singhal, Nidhi; Venkatakrishnan; Tetrahedron Letters; vol. 45; nb. 28; (2004); p. 5419 - 5424 View in Reaxys 26.6 % Chromat., 73.2 % Chromat.

With dihydrogen peroxide, tetrapropylammonium perruthennate in diethyl ether, T= 25 °C , Product distribution, Further Variations: Catalysts, rate of addition of H2O2 Campestrini, Sandro; Carraro, Massimo; Ciriminna, Rosaria; Pagliaro, Mario; Tonellato, Umberto; Tetrahedron Letters; vol. 45; nb. 39; (2004); p. 7283 - 7286 View in Reaxys With aqua(2,2'-bipyridine)(2,2':6',2''-terpyridine)ruthenium(II)(2+) in phosphate buffer, Time= 1h, pH= 7.2, Electrolysis, Product distribution, Kinetics, Further Variations: times Geneste, Florence; Moinet, Claude; New Journal of Chemistry; vol. 28; nb. 6; (2004); p. 722 - 726 View in Reaxys With tert.-butylhydroperoxide, streptavidin, biotinylated aminosulfonamide ruthenium piano stool in water, N,N-dimethyl-formamide, acetone, Time= 90h, T= 20 °C Thomas, Christophe M.; Letondor, Christophe; Humbert, Nicolas; Ward, Thomas R.; Journal of Organometallic Chemistry; vol. 690; nb. 20 SPEC. ISS.; (2005); p. 4488 - 4491 View in Reaxys

12.2 %Chromat., 36.2 %Chromat.

5 :In a 15 ml test tube type reaction vessel equipped with a magnetic stirrer and a reflux condenser, 0.43 g (4 mmols) of benzyl alcohol, 0.6 g (4 mmols) of sodium bromate, 0.32 g (6 mmols) of ammonium chloride, 5.6 ml of acetonitrile and 2.4 ml of water were charged, and then the resultant mixture was stirred at 80°C for one hour. After 20 minutes, bumping occurred and bromine was vigorously produced. After the completion of the reaction, bromine completely disappeared. With respect to the components in the reaction solution, an area ratio as determined by gas chromatography of the intended benzaldehyde was 12.2percent, that of a raw material benzyl alcohol was 36.1percent, and that of benzoic acid was 36.2percent. With sodium bromate, ammonium chloride in water, acetonitrile, Time= 1h, T= 80 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1661877; (2006); (A1) English View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

279/438

2018-03-11 22:07:32


With CrMCM-41, oxygen in carbon dioxide, Time= 14h, T= 59.84 - 99.84 °C , p= 120012Torr , Product distribution Dapurkar, Sudhir E.; Kawanami, Hajime; Suzuki, Toshishige M.; Yokoyama, Toshirou; Ikushima, Yutaka; Chemistry Letters; vol. 37; nb. 2; (2008); p. 150 - 151 View in Reaxys With tert.-butylhydroperoxide, [Cu2(triethanolamine)2(C6H5COO)2]*2H2O in acetonitrile, Time= 2h, T= 69.84 °C , Product distribution, Further Variations: Temperatures, Catalysts, Reagents, Solvents Zhu, Mingxia; Li, Bodong; He, Ping; Wei, Xin; Yuan, Youzhu; Tetrahedron; vol. 64; nb. 39; (2008); p. 9239 - 9243 View in Reaxys With 5-chloro-7-iodo-8-quinolinolatomanganese(III), dihydrogen peroxide in water, acetone, Time= 3h, T= 25 °C Ye, Zhengpei; Fu, Zaihui; Zhong, Sheng; Xie, Fang; Zhou, Xiaoping; Liu, Fenglan; Yin, Dulin; Journal of Catalysis; vol. 261; nb. 1; (2009); p. 110 - 115 View in Reaxys 86 %Chro- With tert.-butylhydroperoxide, diphenyl diselenide in decane, toluene, Time= 8h, T= 80 °C , Reactivity, Mechanism, mat., 5 Thermodynamic data, Reagent/catalyst, Solvent %Chromat. Van Der Toorn, John C.; Kemperman, Gerjan; Sheldon, Roger A.; Arends, Isabel W.C.E.; Journal of Organic Chemistry; vol. 74; nb. 8; (2009); p. 3085 - 3089 View in Reaxys With cerium(IV)diammonium nitrate, N-benzyl-N,N',N'-tris(2-pyridylmethyl)ethane-1,2-diamine, water in acetonitrile, Time= 0.5h, T= 25 °C Lee, Yong-Min; Dhuri, Sunder N.; Sawant, Sarvesh C.; Cho, Jaeheung; Kubo, Minoru; Ogura, Takashi; Fukuzumi, Shunichi; Nam, Wonwoo; Angewandte Chemie - International Edition; vol. 48; nb. 10; (2009); p. 1803 - 1806 View in Reaxys With CpMo(CO)3(CCPh), dihydrogen peroxide in water, Time= 8h, T= 80 °C , Reactivity, Solvent, Temperature, chemoselective reaction Biradar, Ankush V.; Dongare, Mohan K.; Umbarkar, Shubhangi B.; Tetrahedron Letters; vol. 50; nb. 24; (2009); p. 2885 - 2888 View in Reaxys With Iron(III) nitrate nonahydrate, potassium dihydrogenphosphate, dihydrogen peroxide in water, Time= 12h, T= 75 °C Shi, Feng; Tse, Man Kin; Li, Zuopeng; Beller, Matthias; Chemistry - A European Journal; vol. 14; nb. 29; (2008); p. 8793 - 8797 View in Reaxys With Iron(III) nitrate nonahydrate, oxygen, Time= 1h, T= 100 °C , Neat (no solvent), Mechanism, Concentration, Temperature, Time Dressen, Mark H. C. L.; Stumpel, Jelle E.; Van De Kruijs, Bastiaan H. P.; Meuldijk, Jan; Vekemans, Jef A. J. M.; Hulshof, Lumbertus A.; Green Chemistry; vol. 11; nb. 1; (2009); p. 60 - 64 View in Reaxys With oxygen in water, Time= 8h, T= 80 °C , p= 760.051Torr Maity, Prasenjit; Gopinath, Chinnakonda S.; Bhaduri, Sumit; Lahiri, Goutam Kumar; Green Chemistry; vol. 11; nb. 4; (2009); p. 554 - 561 View in Reaxys Stage 1: With gold on titanium oxide in water, Time= 0.166667h, T= 90 °C , Inert atmosphere Stage 2: With dihydrogen peroxide in water, Time= 1.08333h, T= 90 °C , Inert atmosphere, chemoselective reaction Ni, Ji; Yu, Wen-Jian; He, Lin; Sun, Hao; Cao, Yong; He, He-Yong; Fan, Kang-Nian; Green Chemistry; vol. 11; nb. 6; (2009); p. 756 - 759 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

280/438

2018-03-11 22:07:32


22 %Chro- With oxygen in carbon dioxide, Time= 12h, T= 100 °C , Autoclave mat., 50 %Chromat. Wang, Jin-Quan; He, Liang-Nian; Miao, Cheng-Xia; Green Chemistry; vol. 11; nb. 7; (2009); p. 1013 - 1017 View in Reaxys 49 %Chro- With (VO)4(3-hydrocypicolinate(2-))4, oxygen in ethanol, Time= 3h, T= 120 °C , p= 7500.75Torr , Autoclave mat., 22 %Chromat. Kodama, Shintaro; Ueta, Yukihiro; Yoshida, Jun; Nomoto, Akihiro; Yano, Shigenobu; Ueshima, Michio; Ogawa, Akiya; Dalton Transactions; nb. 44; (2009); p. 9708 - 9711 View in Reaxys With dihydrogen peroxide in water, Time= 6h, T= 89.84 °C Zhao, Wei; Zhang, Yingshuai; Ma, Baochun; Ding, Yong; Qiu, Wenyuan; Catalysis Communications; vol. 11; nb. 6; (2010); p. 527 - 531 View in Reaxys With water, oxygen, Time= 3h, T= 85 °C , p= 750.075Torr Yang, Xiaomin; Wang, Xiuna; Qiu, Jieshan; Applied Catalysis A: General; vol. 382; nb. 1; (2010); p. 131 - 137 View in Reaxys With cerium (IV) sulfate tetrahydrate, lithium bromide in water, T= 20 °C Nikishin; Sokova; Kapustina; Russian Chemical Bulletin; vol. 58; nb. 2; (2009); p. 303 - 308 View in Reaxys With hydrogen bromide, bromine, oxygen, sodium nitrite in water, acetonitrile, Time= 24h, T= 70 °C Uyanik, Muhammet; Fukatsu, Ryota; Ishihara, Kazuaki; Chemistry - An Asian Journal; vol. 5; nb. 3; (2010); p. 456 - 460 View in Reaxys 10 %Chro- With dihydrogen peroxide, potassium carbonate, Time= 1h, T= 60 °C , Microwave irradiation, Kinetics mat., 87 %Chromat. Liu, Yongmei; Tsunoyama, Hironori; Akita, Tomoki; Tsukuda, Tatsuya; Chemistry Letters; vol. 39; nb. 3; (2010); p. 159 - 161 View in Reaxys 14 %Chromat., 42 mg

With dihydrogen peroxide, potassium carbonate, Time= 1h, T= 60 °C , Microwave irradiation, Kinetics Liu, Yongmei; Tsunoyama, Hironori; Akita, Tomoki; Tsukuda, Tatsuya; Chemistry Letters; vol. 39; nb. 3; (2010); p. 159 - 161 View in Reaxys With graphene oxide, Time= 144h, T= 150 °C , Neat (no solvent) Dreyer, Daniel R.; Jia, Hong-Peng; Bielawski, Christopher W.; Angewandte Chemie - International Edition; vol. 49; nb. 38; (2010); p. 6813 - 6816 View in Reaxys With oxygen, Time= 1h, T= 160 °C , neat (no solvent) Chen, Yuanting; Guo, Zhen; Chen, Tao; Yang, Yanhui; Journal of Catalysis; vol. 275; nb. 1; (2010); p. 11 - 24 View in Reaxys With Oxone, C26H20N2O3V, tetrabutylammomium bromide in dichloromethane, water, Time= 0.5h, T= 20 °C Bagherzadeh, Mojtaba; Amini, Mojtaba; Journal of Coordination Chemistry; vol. 63; nb. 21; (2010); p. 3849 - 3858 View in Reaxys

7 %ChroWith tert.-butylhydroperoxide, [Co(4-nbz)2(py)2] in water, acetonitrile, Time= 5h, T= 82 °C mat., 77 %Chromat. Chakravorty, Stutee; Das, Birinchi K.; Polyhedron; vol. 29; nb. 8; (2010); p. 2006 - 2013 View in Reaxys With dihydrogen peroxide, acetic acid, sodium bromide in water, Time= 4h, T= 60 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

281/438

2018-03-11 22:07:32


Qi, Xingyi; Wang, Jing; Zheng, Liwei; Qi, Lin; Synlett; nb. 4; (2011); p. 555 - 558; Art.No: W17410ST View in Reaxys With dihydrogen peroxide in 1,4-dioxane, water, Time= 7h, T= 85 °C Ding, Yong; Zhao, Wei; Journal of Molecular Catalysis A: Chemical; vol. 337; nb. 1-2; (2011); p. 45 - 51 View in Reaxys With 2-Picolinic acid, manganese(II) perchlorate hexahydrate, dihydrogen peroxide, sodium acetate in [(2)H6]acetone, water, Time= 16h, T= 0 - 20 °C Pijper, Dirk; Saisaha, Pattama; De Boer, Johannes W.; Hoen, Rob; Smit, Christian; Meetsma, Auke; Hage, Ronald; Van Summeren, Ruben P.; Alsters, Paul L.; Feringa, Ben L.; Browne, Wesley R.; Dalton Transactions; vol. 39; nb. 43; (2010); p. 10375 - 10381 View in Reaxys With C8H10Cl2CuN4S, dihydrogen peroxide in acetonitrile, Time= 6h, T= 20 °C , chemoselective reaction Islam; Roy, Anupam Singha; Mondal, Paramita; Mubarak, Manir; Mondal, Sanchita; Hossain, Dildar; Banerjee, Satabdi; Santra; Journal of Molecular Catalysis A: Chemical; vol. 336; nb. 1-2; (2011); p. 106 - 114 View in Reaxys 24 %Spectr., 61 %Spectr.

With oxovanadium(IV) sulfate, 4-nitrophenyl(phenyl)methanol, oxygen, magnesium sulfate, 4,4'-di-tert-butyl-2,2'- bipyridine in water, Time= 22h, T= 90 °C , p= 750.075Torr Kodama, Shintaro; Hashidate, Suguru; Nomoto, Akihiro; Yano, Shigenobu; Ueshima, Michio; Ogawa, Akiya; Chemistry Letters; vol. 40; nb. 5; (2011); p. 495 - 497 View in Reaxys With oxygen in water, Time= 3h, T= 75 °C Zhou, Chunmei; Chen, Yuanting; Guo, Zhen; Wang, Xin; Yang, Yanhui; Chemical Communications; vol. 47; nb. 26; (2011); p. 7473 - 7475 View in Reaxys With Agrocybe aegerita aromatic peroxygenase, dihydrogen peroxide in acetonitrile, pH= 7, aq. phosphate buffer, Enzymatic reaction Kinne, Matthias; Zeisig, Christian; Ullrich, Rene; Kayser, Gernot; Hammel, Kenneth E.; Hofrichter, Martin; Biochemical and Biophysical Research Communications; vol. 397; nb. 1; (2010); p. 18 - 21 View in Reaxys With dihydrogen peroxide in water, Time= 8h, T= 84.84 °C Zhao, Wei; Ding, Yong; Ma, Baochun; Qiu, Wenyuan; Synthetic Communications; vol. 42; nb. 4; (2012); p. 554 562 View in Reaxys With dihydrogen peroxide, urea in water, Time= 8h, T= 84.84 °C Zhao, Wei; Ding, Yong; Ma, Baochun; Qiu, Wenyuan; Synthetic Communications; vol. 42; nb. 4; (2012); p. 554 562 View in Reaxys With 2C2H6O*C38H26CoN6S2 (2+)*H2O*2NO3 (1-), dihydrogen peroxide in water, Time= 8h, T= 20 °C , chemoselective reaction Nemati Kharat, Ali; Bakhoda, Abolghasem; Tamaddoni Jahromi, Bahareh; Polyhedron; vol. 30; nb. 17; (2011); p. 2768 - 2775 View in Reaxys With oxygen, T= 140 °C , p= 7500.75Torr Miedziak, Peter J.; He, Qian; Edwards, Jennifer K.; Taylor, Stuart H.; Knight, David W.; Tarbit, Brian; Kiely, Christopher J.; Hutchings, Graham J.; Catalysis Today; vol. 163; nb. 1; (2011); p. 47 - 54 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

282/438

2018-03-11 22:07:32


With oxygen, sodium hydroxide in water, Time= 3h, T= 80 °C , p= 3750.38Torr Guo, Hongfan; Kemell, Marianna; Al-Hunaiti, Afnan; Rautiainen, Sari; Leskelae, Markku; Repo, Timo; Catalysis Communications; vol. 12; nb. 13; (2011); p. 1260 - 1264 View in Reaxys 7 :Example 7 - Oxidation of Alcohols; [00228] Various alcohols may be oxidized to ketones or aldehydes using a graphene or graphit oxide catalyst. Specific examples are described below.[00229] Neat benzyl alcohol (PhCH2OH) was heated to 100 °C in the presence of 20 wtpercent graphene oxide or graphite oxide for 14 hours under ambient conditions. The general reaction scheme is shown in FIGURE 7. As FIGURE 8 indicates, acceptable variations in weight percentage graphene oxide or graphite oxide are between 5-200 wtpercent. Acceptable variations in reaction temperature are between 25-100°C. Acceptable variations in reaction time are between 3 -144 hours.[00230] Subsequent filtering of the reaction product afforded a mixture of benzylaldehyde (PhCHO):PhCH2OH in a 1 :3 molar ratio, as determined by 1H NMR spectroscopy. No over- oxidation to benzoic acid (PhC02H) or other by-products was detected under these conditions. NMR analysis and titrimetry of the reaction product mixture showed that water was released during the reaction.[00231] Atomic absorption and inductively coupled plasma mass spectrometry showed that the graphene oxide or graphite oxide catalyst used contained trace or no amounts of metals, indicating that the graphene oxide or graphite oxide and not a metal functioned as a catalyst. The catalytic activity of graphene oxide or graphite oxide was further confirmed by the inability of corresponding flake graphite to catalyze the alcohol oxidation reaction under identical conditions.[00232] The graphene oxide or graphite oxide used in the oxidation reaction was separated from the reaction mixture and filtered. The filtered material was characterized using FT-IR (KBr) and showed an attenuated signal relative to other peaks in the spectrum at υ = 3150 cm" l, corresponding to the O-H stretch as well as no diagnostic signals at 1685 cm"1,corresponding to the C=0 stretch and 1280 cm"1 or 1140 cm"1, corresponding to epoxide absorbances. C=0 and epoxide absorbance signals were seen in the unused catalyst. The FT- IR spectrum also showed signals at 1650 cm"1 and 1500 cm"1, corresponding to the presence of aromatic and olefin species. These signals were not seen in the unused catalyst. Power conductivity in the used graphene oxide or graphite oxide was also measured to be 15 S/m, which was a significant increase from the 2.2 x 10"5 S/m measured in the unused catalyst. Collectively, these results suggest that the graphene oxide or graphite oxide catalyst undergoes a partial reduction during the alcohol oxidation reaction. The used graphene oxide or graphite oxide is similar to r-graphene oxides or graphenes that have been synthesized by other methods.[00233] The catalytic function of the graphene oxide or graphite oxide, as opposed to direct oxidation of the alcohol by the graphene oxide or graphite oxide, was also confirmed. Under ambient conditions, when the graphene oxide or graphite oxide reacts with the alcohol as a catalyst, ambient oxygen is the terminal oxidant. In particular, the PhCH2OH to PhCHO reaction with a graphene oxide or graphite oxide was performed under a nitrogen atmosphere. After 24 hours of reaction time at 100 °C, an aliquot removed from the reaction mixture contained less than 5 molpercent PhCHO, indicating that the alcohol oxidation reaction was not able to proceed in the absence of oxygen. In contrast, if the graphene oxide or graphite oxide directly oxidized the alcohol, oxygen would not be needed and a higher PhCHO yield would be expected.[00234] The reaction was allowed to continue for another 24 hours at 100 °C and another aliquot was tested, showing only 23 molpercent conversion of the alcohol to PhCHO, further confirming the catalytic action of the graphene oxide or graphite oxide.[00235] Furthermore, when the graphene oxide or graphite oxide was separated from the reaction mixture by filtration, it was found to retain its oxidative properties and could be reused for multiple reaction cycles.[00236] The low yield under a nitrogen atmosphere also indicates that, in situations where it is desirable to diminish the oxidative capacity of the catalyst, an atmosphere lacking oxygen or other final oxidants may be used. [00237] To determine the role of radical species in the oxidation process, neat PhCH2OH was treated with 20 wtpercent graphene oxide or graphite oxide and 20 wtpercent butylatedhydroxytolulene (BHT). BHT affects the formation of radical species by forming a more stable, non-reactive radical that arrests the oxidation reaction or by inhibiting or preventing the formation of radicals. After 24 hours reaction time at 100 °C, less than 5 molpercent conversion of the alcohol to PhCHO was observed. However, when a 1 :1 : 1 mass ratio of graphene oxide or graphite oxide:PhCH2OH:BHT was heated for 14 hours at 100 °C, a 26 molpercent conversion of the alcohol to PhCHO was observed. This indicates that BHT likely does not inhibit the graphene oxide or graphite oxide's ability to oxidize the alcohol, but rather impedes the oxidation of the reduced catalyst. This assessment was further confirmed by heating graphene oxide or graphite oxide in the presence of cyclopropylcarbinol, which reacts in a very specific manner, evidenced by the formation of olefinic species, in the present of radicals. These olefinic species may be readily identified spectroscopically. This resulted in the formation of number of products including olefinic species, but no aldehydes. Similar results are obtained in chromic-acid mediated oxidation of the same substrate, which is known to proceed using radical species. Accordingly, the graphene or graphite catalysis of alcohol oxidation likely proceeds via radical species.[00238] The oxidation properties of graphene oxide or graphite oxide were studied under various conditions. In particular, in the oxidation of neat benzyl alcohol to benzylaldehyde or benzoic acid, catalyst loading was varied between 5-200 wtpercent, temperature was varied between 25-150 °C, and reaction time was varied between 3-144 hours.[00239] Selected reaction parameters and results are presented in Table 5. All reactions in Table 5 were allowed to proceed for 24 hours. Loading (wtpercent) refers to the amount of graphene oxide or graphite ox-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

283/438

2018-03-11 22:07:32


ide (GO) prepared by the Hummers method added to he reaction mixture, graphene oxide or graphite oxide was prepared by the Staudenmaier method. Graphite was natural flake graphite (Bay Carbon, Inc. or Alfa Aesar). PhCHO (percent) refers to the conversion of benzyl alcohol to benzylaldehyde. PhC02H (percent) refers to the conversion of benzyl alcohol to benzoic acid. TON refers to the turnover number, which was calculated as the ratio of the moles of oxidized product to mass of graphene oxide or graphite oxide.Table 5. Oxidation of benzyl alcohol to benzaldehyde and benzoic acid under various conditions. o 2 12 0 .00so 5 100 2 0 0:22G .sect. 150 0 0 11GO m 12 0 2:-SfGO m 100 24 2 1.1GO oo ifi 2? 2 1.2GO m ?:3/4 20 2 2.12GO 122 21 0:1 1.1SO m im. 22 12 1 ,2 O 200 00 22 0.22GO 200 100 22. 1 2:42GO 200 1 40 01 0:22[00240] At temperatures less than or equal to 75 °C, alcohol conversion peaked at 73 molpercent even with reaction times as long as 144 hours and catalyst loading as high as 200 wtpercent. At temperatures above 100 °C, conversion rates as high as 85 molpercent were observed with loading above 50 wtpercent. Conversion appeared to plateau at 6 hours under these conditions, indicating decomposition of the catalyst. At temperatures above or equal to 100 °C, an appreciable amount of PhC02H, which may not be desirable, was observed and the content of this acid increased with temperature, catalyst loading, and reaction time. Use of 200 wtpercent catalyst for a reaction time of 24 hours at 100 °C afforded a high conversion rate of 99percent with an aldehyde: acid ratio of 92:7.[00241] The turnover numbers in Table 5 remained relatively constant at 10" mol/g regardless of the reaction conditions, indicating that the catalyst consistently reached maximal activity.[00242] The scope and reactivity of the graphene oxide catalyst was confirmed using the reaction conditions of 200 wtpercent and 100 °C for 24 hours. A variety of primary and secondary benzylic and aliphatic alcohols were tested. The results of these tests are summarized in Table 6. For alcohol number 2 in the table, 2 molpercent benzaldehyde was also found. For alcohol number 3, a mixture of products was observed after 24 hours at 100 °C with 200 wtpercent graphene oxide or graphite oxide. The reported results are for a reaction for 24 hours at 75°C in 50 wtpercent graphene oxide or graphite oxide.Table 6. Oxidation of various alcohols.[00243] Overall, benzylic alcohols afforded the highest conversion, particularly dibenzylic alcohols such as benzhydrol (number 1 in Table 6). Cyclohexanol (number 4 in Table 6) showed conversion rates similar to benzyl alcohol. 2-thiophenemethanol (number 5 on Table 6) showed modest conversion rates with no sulfur oxidation, confirming the alcohol selectivity of the catalyst and its tolerance of functional groups. With oxygen, graphite oxide, Time= 24h, T= 100 °C , Product distribution / selectivity Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; BIELAWSKI, Christopher W.; DREYER, Daniel R.; JIA, Hong-Peng; WO2011/150329; (2011); (A2) English View in Reaxys With 4,4'-dimethyl-2,2'-bipyridines, copper(ll) sulfate pentahydrate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, dihydrogen peroxide, potassium carbonate in water, Time= 1.5h, T= 80 °C Ahmad, Jahir Uddin; Raeisaenen, Minna T.; Leskelae, Markku; Repo, Timo; Applied Catalysis A: General; vol. 411-412; (2012); p. 180 - 187 View in Reaxys 89 %Chro- Typical procedure for oxidation of benzyl alcohol (Table 3). mat., 7 To a mixture of benzyl alcohol (4a) (104 μL, 1 mmol), tridecane (50 μL, 0.205 mmol, internal standard), and solvent %Chromat. in a screw cap tube was added t-BuONO (198 μL, 1.5 mmol, 1.5 equiv.) under N2 atmosphere. The solution was stirred under the conditions indicated in table 3. The reaction mixture was analyzed by GC and the product was isolated by column chromatography (SiO2) for the characterization. With tert.-butylnitrite in 1,2-dimethoxyethane, Time= 17h, T= 100 °C , Inert atmosphere Hamasaki, Akiyuki; Kuwada, Hideyuki; Tokunaga, Makoto; Tetrahedron Letters; vol. 53; nb. 7; (2012); p. 811 814 View in Reaxys With dihydrogen peroxide in water, Time= 0.5h, T= 93.84 °C , Inert atmosphere Perez, Yolanda; Ballesteros, Ruth; Fajardo, Mariano; Sierra, Isabel; Del Hierro, Isabel; Journal of Molecular Catalysis A: Chemical; vol. 352; (2012); p. 45 - 56 View in Reaxys With oxone, tetrabutylammomium bromide in dichloromethane, water, Time= 0.5h, T= 20 °C Bagherzadeh, Mojtaba; Amini, Mojtaba; Boghaei, Davar M.; Najafpour, Mohammad Mahdi; McKee, Vickie; Applied Organometallic Chemistry; vol. 25; nb. 7; (2011); p. 559 - 563 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

284/438

2018-03-11 22:07:32


8 :Example 8Oxidation of alcoholsThe cyclopentadienyl dioxo molybdenum acetylide complex as prepared in example 2 was used as catalyst for catalytic oxidation of activated alcohols. Benzyl alcohol (10 mmol), hydrogen peroxide (20 mmol) and catalyst (O.lmmol, 30mg) was heated at 80°C for 8 h giving 86percent conversion with 92percent selectivity for benzaldehyde and 8percent selectivity for benzoic acid. With dihydrogen peroxide, dioxo molybdenum cyclopentadienyl phenyl acetylide complex, Time= 8h, T= 80 °C Patent; COUNCIL OF SCIENTIFIC and INDUSTRIAL RESEARCH; UMBARKAR, Shubhangi, Bhalchandra; DONGARE, Mohan Keraba; BIRADAR, Ankush; ACHAM, Vaibhav, Ravindrakumar; WO2012/35555; (2012); (A1) English View in Reaxys With dihydrogen peroxide in water, Time= 6h, T= 50 °C Islam, Sk. Manirul; Roy, Anupam Singha; Mondal, Paramita; Salam, Noor; Journal of Molecular Catalysis A: Chemical; vol. 358; (2012); p. 38 - 48 View in Reaxys With [Rh(III)(OEP)(Cl)]/C, sodium hydroxide in water, T= 25 °C , Electrochemical reaction, Inert atmosphere Yamazaki, Shin-Ichi; Yao, Masaru; Fujiwara, Naoko; Siroma, Zyun; Yasuda, Kazuaki; Ioroi, Tsutomu; Chemical Communications; vol. 48; nb. 36; (2012); p. 4353 - 4355 View in Reaxys With dihydrogen peroxide in water, Time= 0.5h, T= 90 °C , neat (no solvent) Leng, Yan; Zhao, Pingping; Zhang, Mingjue; Wang, Jun; Journal of Molecular Catalysis A: Chemical; vol. 358; (2012); p. 67 - 72 View in Reaxys With oxygen, potassium carbonate in water, Time= 24h, T= 90 °C Yang, Jianhu; Qiu, Lihua; Liu, Baoqiang; Peng, Yingjing; Yan, Feng; Shang, Songmin; Journal of Polymer Science, Part A: Polymer Chemistry; vol. 49; nb. 21; (2011); p. 4531 - 4538 View in Reaxys With 3-butyl-1,2-dimethyl-1H-imidazol-3-ium hydroxide in water, Time= 24h, Reflux, Inert atmosphere Feng, Bo; Chen, Chen; Yang, Hanmin; Zhao, Xiuge; Hua, Li; Yu, Yinyin; Cao, Ting; Shi, Yu; Hou, Zhenshan; Advanced Synthesis and Catalysis; vol. 354; nb. 8; (2012); p. 1559 - 1565 View in Reaxys 46 %Chro- With 13,17-bis(2-methoxycarbonylethyl)-2,7,12,18-tetramethylporphinatocobalt(II), oxygen, isovaleraldehyde in acemat., 54 tone, Time= 1h, T= 60 °C %Chromat. Sun, Chengguo; Hu, Bingcheng; Liu, Zuliang; Heteroatom Chemistry; vol. 23; nb. 3; (2012); p. 295 - 303 View in Reaxys With dihydrogen peroxide in water, acetonitrile, Time= 8h, T= 60 °C Islam, Sk Manirul; Mobarok, Manir; Mondal, Paramita; Roy, Anupam Singha; Salam, Noor; Hossain, Dildar; Mondal, Sanchita; Transition Metal Chemistry; vol. 37; nb. 1; (2012); p. 97 - 107 View in Reaxys Catalytic oxidation by TBHP General procedure: The liquid phase oxidation reactions were carried out in a two-necked round bottom flask fitted with a water condenser and placed in an oil bath at different temperatures under vigorous stirring for a certain period of time. Substrates (5 mmol) were taken in water (5 mL) for different sets of reactions together with catalyst in which 10 mmol of TBHP (70percent in aq.) was added. After the reaction, the organic products were separated from the reaction mixture by extraction with dichloromethane (5 mL×2). The combined organic portions were dried and concentrated. Product analysis was performed by Varian 3400 gas chromatograph equipped with a 30 m CP-SIL8CB capillary column and a Flame Ionization Detector using cyclohexanone as internal standard. All reaction products were identified by using Trace DSQ II GC-MS. With di-tert-butyl peroxide in water, Time= 6h, T= 60 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

285/438

2018-03-11 22:07:32


Islam; Roy, Anupam Singha; Mondal, Paramita; Paul, Sumantra; Salam, Noor; Inorganic Chemistry Communications; vol. 24; (2012); p. 170 - 176 View in Reaxys With dihydrogen peroxide in water, Time= 2h, T= 90 °C Leng, Yan; Wang, Jun; Jiang, Pingping; Catalysis Communications; vol. 27; (2012); p. 101 - 104 View in Reaxys 60.8 With [1,1′-(butane-1,4-diyl)-bis(3-methylimidazolium)]1.5 phosphotungstate, dihydrogen peroxide, Time= 12h, T= 90 %Chromat. °C , Time, Temperature, Solvent, Reagent/catalyst Leng, Yan; Zhao, Pingping; Zhang, Mingjue; Chen, Guojian; Wang, Jun; Science China Chemistry; vol. 55; nb. 9; (2012); p. 1796 - 1801 View in Reaxys With Na*Zn2Sb2, dihydrogen peroxide in water, Time= 7h, T= 85 °C View in Reaxys With {[(VIVO)(2,2'-bipyridine)(H2O)]2(μ-P2O7)}∙3H2O, triethylamine in neat (no solvent), T= 100 °C , Catalytic behavior, Concentration, Reagent/catalyst View in Reaxys With tert.-butylhydroperoxide, [Fe(1,10-phenanthroline)2Cl2]NO3 in aq. buffer, T= 55 °C , pH= 1 View in Reaxys With [Fe(1,10-phenanthroline)2Cl2]NO3, dihydrogen peroxide in aq. buffer, T= 55 °C , pH= 2, Concentration, Solvent, Reagent/catalyst, pH-value View in Reaxys With dihydrogen peroxide in acetonitrile, Time= 24h, T= 90 °C Reis, Michele C.; Barros, Suellen D.T.; Lachter, Elizabeth R.; San Gil, Rosane A.S.; Flores, Jhonny H.; Pais Da Silva, Maria I.; Onfroy, Thomas; Catalysis Today; vol. 192; nb. 1; (2012); p. 117 - 122 View in Reaxys With tert.-butylhydroperoxide, cis-(2,2'-bipyridine-κ2-N,N)bis(perchlorate)manganese(II), potassium bromide in acetonitrile, Time= 4h, T= 80 °C , Reagent/catalyst, Solvent Kani, Ibrahim; Kurtca, Mehmet; Turkish Journal of Chemistry; vol. 36; nb. 6; (2012); p. 827 - 840 View in Reaxys With dihydrogen peroxide in acetonitrile, Time= 5h, T= 29.84 °C , Temperature, Concentration Adam, Farook; Ooi, Wan-Ting; Applied Catalysis A: General; vol. 445-446; (2012); p. 252 - 260 View in Reaxys 43 %Chro- With potassium peroxymonosulfate, C72H58IN12O6Ru2 in dichloromethane, water, Time= 5h, T= 40 °C , pH= 1 mat., 38 %Chromat. Verho, Oscar; Dilenstam, Marlene D. V.; Kaerkaes, Markus D.; Johnston, Eric V.; Akermark, Torbjoern; Baeckvall, Jan-E.; Akermark, Bjoern; Chemistry - A European Journal; vol. 18; nb. 52; (2012); p. 16947 - 16954 View in Reaxys 22 %Chro- With potassium peroxymonosulfate, C72H58IN12O6Ru2 in dichloromethane, water, Time= 5h, T= 40 °C , pH= 1 mat., 78 %Chromat. Verho, Oscar; Dilenstam, Marlene D. V.; Kaerkaes, Markus D.; Johnston, Eric V.; Akermark, Torbjoern; Baeckvall, Jan-E.; Akermark, Bjoern; Chemistry - A European Journal; vol. 18; nb. 52; (2012); p. 16947 - 16954 View in Reaxys 60 %Chro- With dihydrogen peroxide, manganese(II) acetate in water, acetonitrile, Time= 0.666667h, T= 50 °C , Ionic liquid, mat., 31 Temperature, Time %Chromat.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

286/438

2018-03-11 22:07:32


Wong, Wing-Leung; Ho, Kam-Piu; Lee, Lawrence Yoon Suk; So, Ming-Him; Chan, Tak Hang; Wong, KwokYin; Applied Catalysis A: General; vol. 453; (2013); p. 244 - 249 View in Reaxys 14 %Chro- With dihydrogen peroxide, manganese(II) acetate in water, Time= 0.333333h, T= 25 °C , Ionic liquid mat., 74 %Chromat. Wong, Wing-Leung; Ho, Kam-Piu; Lee, Lawrence Yoon Suk; So, Ming-Him; Chan, Tak Hang; Wong, KwokYin; Applied Catalysis A: General; vol. 453; (2013); p. 244 - 249 View in Reaxys With dihydrogen peroxide in water, Time= 7h, T= 90 °C , Reflux Zhang, Zhenxin; Zhu, Qianqian; Ding, Yong; Synthetic Communications; vol. 43; nb. 9; (2013); p. 1211 - 1218 View in Reaxys 60 %Chro- 2.1. General procedure for oxidation of alcohols with tert-BuOOH catalyzed by [Mo(CO)5(at)APy-MWCNT] mat., 40 General procedure: In a 25 mL round bottom flask equipped with a magnetic stirrer bar and a condenser, alcohols (1 %Chromat. mmol),tert-BuOOH (2 mmol, 80percent solution in di-tert-butylperoxide), catalyst (90 mg, 0.015 mmol) and CCl4 (4 mL) were mixed and refluxed. The progress of the reaction was monitored by GLC. At the end of the reaction, the reaction mixture was diluted Et2O (20 mL) and filtered. The products were extracted with CH2Cl2 (2 10 mL) and were purified on silica-gel plates or a silica-gel column (CCl4-Et2O, 4:1). FT IR and 1H NMR spectral data was used to confirm the identities of the products.#10; With tert.-butylhydroperoxide in tetrachloromethane, Time= 1h, Reflux Araghi, Mehdi; Ghorbani, Azam; Yeganeh, Faten Eshrati; Comptes Rendus Chimie; vol. 16; nb. 2; (2013); p. 109 - 113 View in Reaxys With dihydrogen peroxide in water-d2, Time= 0.583333h, T= 20 °C , Reagent/catalyst, Time Eshtiagh-Hosseini, Hossein; Tabari, Taymaz; Eshghi, Hossein; Asian Journal of Chemistry; vol. 25; nb. 6; (2013); p. 3307 - 3312 View in Reaxys 2.5 Catalytic oxidation of benzyl alcohol General procedure: Complex, PhCH2OH and NaBrO3 were charged to a round bottomed flask. The mixture was stirred in a thermostat bath for a certain time. It was cooled down and extracted for three times with ethylacetate. The extracted sample was analyzed by a gas chromatograph (GC) to determine the contents of benzaldehyde (with nitrobenzene as internal standard) and benzoic acid (with dimethyl phthalate as internal standard). With sodium bromate, Ce(8-hydroxyquinolinate)4, T= 80 °C , Catalytic behavior, Reagent/catalyst, Temperature Li, Li; Yuan, Fugen; Li, Tingting; Zhou, Yuan; Zhang, Manman; Inorganica Chimica Acta; vol. 397; (2013); p. 69 74 View in Reaxys Microwave assisted oxidation of benzyl alcohol and aromatic alkenes General procedure: The reaction was carried out in a CEM Discover microwave reactor equipped with a PC-controlled interface. The method was power controlled in which samples (vessel size 10 mL) were irradiated at 300 W (maximum power output) to achieve different temperatures. In a typical reaction, a mixture containing 2 mmol of substrate, 0.4 mL of H2O2 (50 wt.percent), 2 mL of water and 0.05 g of catalyst was microwaved in a CEM-DISCOVER reactor for different times of reaction (typically between 3 and 15 min) at 300 W, reaching a maximum temperature between 100 and 120 °C (average temperature 100 °C). Dodecane was added to the mixture as internal standard. The microwave method was power-controlled and reactions were carried out in closed vessel mode (pressure 120– 200 psi-8.3 to 13.4 bar-developed in the system). Upon reaction completion (in both cases), samples were collected, extracted with an organic solvent (typically toluene) and subsequently analysed by GC and GC/MS in an Agilent 6890N fitted with an HP-5 capillary column (30 m × 0.32 mm × 0.25 μm) and a flame ionization detector (FID). With dihydrogen peroxide in water, Time= 0.25h, T= 120 °C , p= 6205.94 - 10343.2Torr , Microwave irradiation, Sealed tube, Green chemistry Balu, Alina Mariana; Lin, Carol Sze Ki; Liu, Hongli; Li, Yingwei; Vargas, Carolina; Luque, Rafael; Applied Catalysis A: General; vol. 455; (2013); p. 261 - 266 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

287/438

2018-03-11 22:07:32


86 %Chro- With potassium phosphate tribasic trihydrate, oxygen in water, Time= 12h, T= 60 °C mat., 7 %Chromat. Tang, Lin; Guo, Xuefeng; Li, Yunfeng; Zhang, Shuai; Zha, Zhenggen; Wang, Zhiyong; Chemical Communications; vol. 49; nb. 45; (2013); p. 5213 - 5215 View in Reaxys 2. Material and methods General procedure: All chemicals were of analytic grade and directly used as received. The four spinel ferrites were synthesized through one-pot sol–gel method [16,18], the typical process was as following: 1mol/L M (II, Cu2+, Co2+, Ni2+, Zn2+) nitrate salt solution and 0.5mol/L Fe(NO3)3·9H2O solution with a M2+/Fe3+ ratio of 1.0/2.0 was mixed together and stirred for 3h at room temperature. After stirring, pre-calculated amount of citrate and EDTA were added into the former solution, respectively. The final pH value was adjusted ∼7 through the addition of ammonia solution. The resulted solution was stirred for another 1h and followed by the evaporation of water and then a dried gel was formed. The obtained gel was calcined to remove template and other organic compounds using a temperature programmed rising procedure initially at 450°C for 5h and further to 950°C for 10h in the air oven at a heat rate of 2°C/ min. The phase compositions of the resultant spinel ferrites were determined by powder X-ray diffraction (XRD) on Bruker D8 to record a data set in a continuous scan mode in the range of 10–85° with intervals of 0.05°. Transmission electron microscopy (TEM) was used to investigate structural features of the catalysts with a Hitachi HF-2000 instrument. Scanning electron microscopy and energy-dispersive X-ray analysis (EDX) was obtained with Japanese JSM-6360LV operating at an acceleration voltage of 10kV. (0003) Oxidation of benzyl alcohol was conducted in a round flask (25mL) equipped with reflux condenser and magnetic stirrer under argon environment. In a typical reaction procedure, acetonitrile solvent (2mL), benzyl alcohol (2.0mL) and 30percent H2O2 (1mL) were mixed together and then spinel ferrite catalyst (0.40g) was added into the solution at room temperature. The zero time was recorded when the reaction temperature reached the desired temperature of 70°C. The whole reaction procedure was under the stirring speed of 1000rpm. Reaction products were collected after the reaction time of 10h through centrifugation for 30min and analyzed by Agilent 6890 gas chromatography equipped with a DV-101 column (0.2mm×0.25μm×50m) and FID detector. With CoFe2O4, dihydrogen peroxide in acetonitrile, Time= 10h, T= 20 - 70 °C , Inert atmosphere, Reagent/catalyst, chemoselective reaction Yan, Kai; Wu, Xu; An, Xia; Xie, Xianmei; Journal of Alloys and Compounds; vol. 552; (2013); p. 405 - 408 View in Reaxys With tetrakis(tetrabutylammonium)decatungstate(VI), dihydrogen peroxide in water, acetonitrile, Time= 0.25h, T= 135 - 140 °C , p= 25502.6 - 27002.7Torr , Microwave irradiation, Catalytic behavior, Temperature, Pressure, Solvent, Time Galica, Mateusz; Kasprzyk, Wiktor; Bednarz, Szczepan; Bogdal, Dariusz; Chemical Papers; vol. 67; nb. 9; (2013); p. 1240 - 1244 View in Reaxys With tert.-butylhydroperoxide, Cu(9-(2'-hydroxy-3'-phenylthio-5'-tert-butylphenyl)-6-methylthio-3-acetyl-5,7,8-triazanona-3,6,8-trien-2-one(2-)), potassium carbonate in water, acetonitrile, Time= 24h, T= 50 °C , Reagent/catalyst, Overall yield = 82.4 percentChromat. Arion, Vladimir B.; Platzer, Sonja; Rapta, Peter; Machata, Peter; Breza, Martin; Vegh, Daniel; Dunsch, Lothar; Telser, Joshua; Shova, Sergiu; Mac Leod, Tatiana C. O.; Pombeiro, Armando J. L.; Inorganic Chemistry; vol. 52; nb. 13; (2013); p. 7524 - 7540 View in Reaxys With dihydrogen peroxide in water, Time= 6h, T= 50 °C , Green chemistry, Catalytic behavior, Reagent/catalyst Salam, Noor; Sinha, Arjyabaran; Mondal, Paramita; Roy, Anupam Singha; Jana, Nikhil R.; Islam, Sk. Manirul; RSC Advances; vol. 3; nb. 39; (2013); p. 18087 - 18098 View in Reaxys With oxygen in neat (no solvent), Time= 2.5h, T= 100 °C , p= 4500.45Torr , Autoclave, Pressure, Temperature Silva, Tiago A. G.; Landers, Richard; Rossi, Liane M.; Catalysis Science and Technology; vol. 3; nb. 11; (2013); p. 2993 - 2999 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

288/438

2018-03-11 22:07:32


With tert.-butylhydroperoxide, oxygen in neat (no solvent), Time= 24h, T= 90 °C , Catalytic behavior, Reagent/catalyst, Temperature, Time Narkhede, Nilesh; Patel, Anjali; Singh, Sukriti; Dalton Transactions; vol. 43; nb. 6; (2014); p. 2512 - 2520 View in Reaxys 0.84 mol, 0.15 mol

With tert.-butylhydroperoxide, chromium tetra(tert-butoxide) in benzene, T= 20 °C Stepovik; Potkina; Poddelskii; Russian Journal of General Chemistry; vol. 83; nb. 11; (2013); p. 2005 - 2017; Zh. Obshch. Khim.; vol. 83; nb. 11; (2013); p. 1805 - 1818,14 View in Reaxys With tert.-butylhydroperoxide, [Fe(N-(2-pyridylmethyl)iminodiethanolate)(NO3)]2(NO3)2*2CH3OH in methanol, dodecane, Time= 24h, T= 50 °C , Catalytic behavior, Reagent/catalyst Shin, Jong Won; Bae, Jeong Mi; Kim, Cheal; Min, Kil Sik; Dalton Transactions; vol. 43; nb. 10; (2014); p. 3999 4008 View in Reaxys With tert.-butylhydroperoxide, Cs5[PCo(H2O)Mo11O39]*6H2O, oxygen, Time= 24h, T= 90 °C , Reagent/catalyst, Temperature, Time, chemoselective reaction Pathan, Soyeb; Patel, Anjali; Catalysis Science and Technology; vol. 4; nb. 3; (2014); p. 648 - 656 View in Reaxys 2.3. Procedure for the catalytic oxidation of benzyl alcohol in acetone General procedure: A 50 mL three-necked glass flask was charged with a mixture ofDPPH (98.6 mmg, 0.25 mmol),WO3/Al2O3 (0.844 g,W: 3 mmol), alcohol(50 mmol), and 30 mL acetone. One neck was connected with awater condenser to reflux. Besides, there must be a deflated balloonon the top of the condenser to collect the evaporated acetone. And anotherneck was connected with a dropping funnel to add acetone.Then an oxygen steel cylinder was used to slowly provide the oxygenfor the reaction through the third neck with an air duct. The ventilationspeed must be adjusted according to the size of the balloon. Moreover,to maintain the airtightness of the whole reaction, the liquid level inthe dropping funnel should be kept in a certain height. Then themixturewas stirred at 80 °C for 4 h. The reaction mixture was subjected to GCanalysis to supervise the reaction process till the oxidation ended. With 2,2-diphenyl-1-picrylhydrazyl, tungusten oxide/alumina, oxygen in acetone, Time= 4h, T= 80 °C , Reagent/ catalyst, Solvent Zhu, Yaoqin; Xu, Jian; Lu, Ming; Catalysis Communications; vol. 48; (2014); p. 78 - 84 View in Reaxys With (pyridinium)H3PMo11VO40, dihydrogen peroxide in acetonitrile, Time= 1h, T= 70 °C Palermo, Valeria; Villabrille, Paula I.; Vazquez, Patricia G.; Caceres, Carmen V; Tundo, Pietro; Romanelli, Gustavo P.; Journal of Chemical Sciences; vol. 125; nb. 6; (2013); p. 1375 - 1383 View in Reaxys With tert.-butylhydroperoxide in neat (no solvent), Time= 24h, T= 69.84 °C , Green chemistry, Catalytic behavior, Reagent/catalyst Pal, Nabanita; Cho, Eun-Bum; Kim, Dukjoon; RSC Advances; vol. 4; nb. 18; (2014); p. 9213 - 9222 View in Reaxys General procedure for aerobic oxidation reaction catalysed by PS-teta–VO General procedure: The aerobic oxidation reactions were carried out in a 50mL stainless steel autoclave at different temperatures under vigorous stirring for a certain period of time. We examined the catalytic activity of vanadium complex using alcohol as the substrate and molecular oxygen as the primary oxidant. The oxidation of alcohol (5mmol) was conducted under oxygen pressure (5.0bar) at 60°C for 5h in the presence of vanadium complex (5mg) in water (5mL). After the reaction, the organic products were separated from the reaction mixture by extraction with dichloromethane (5mL×2). The combined organic portions were dried and concentrated. Product analysis was performed by Varian 3400 gas chromatograph equipped with a 30m CP-SIL8CB capillary column. With oxygen in dimethyl sulfoxide, Time= 5h, T= 60 °C , p= 3750.38Torr , Autoclave, Catalytic behavior

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

289/438

2018-03-11 22:07:32


Islam, Sk. Manirul; Molla, Rostam Ali; Roy, Anupam Singha; Ghosh, Kajari; Salam, Noor; Iqubal, Md. Asif; Tuhina; Journal of Organometallic Chemistry; vol. 761; (2014); p. 169 - 178 View in Reaxys With Ti0.85V0.15O2, dihydrogen peroxide in methanol, Time= 2h, T= 20 °C , Reagent/catalyst Amini, Mojtaba; Naslhajian, Hadi; Farnia, S. Morteza F.; New Journal of Chemistry; vol. 38; nb. 4; (2014); p. 1581 - 1586 View in Reaxys With dihydrogen peroxide in neat (no solvent), Time= 4h, T= 90 °C , Solvent Meng, Ling-Yan; Zhai, Shang-Ru; Li, Shi; Zhai, Bin; An, Qing-Da; Song, Xiao-Wei; European Journal of Inorganic Chemistry; nb. 14; (2014); p. 2337 - 2344 View in Reaxys With dihydrogen peroxide in neat (no solvent), Time= 4h, T= 90 °C Meng, Ling-Yan; Zhai, Shang-Ru; Li, Shi; Zhai, Bin; An, Qing-Da; Song, Xiao-Wei; European Journal of Inorganic Chemistry; nb. 14; (2014); p. 2337 - 2344 View in Reaxys With tert.-butylhydroperoxide in acetonitrile, Time= 6h, T= 75 °C , Solvent, Reagent/catalyst Mobinikhaledi, Akbar; Zendehdel, Mojgan; Safari, Parvin; Transition Metal Chemistry; vol. 39; nb. 4; (2014); p. 431 - 442 View in Reaxys With tert.-butylhydroperoxide in acetonitrile, Time= 6h, T= 75 °C Mobinikhaledi, Akbar; Zendehdel, Mojgan; Safari, Parvin; Transition Metal Chemistry; vol. 39; nb. 4; (2014); p. 431 - 442 View in Reaxys General Procedure for Oxidation of Alcohols General procedure: Chemicals and reagents were purchased fromAldrich or Fisher and used without further purification unless noted. The required amount of H5IO6(see Table 2) and CrO2 (0.042 g, 0.5 mmol) were ground together in amortar to produce a uniform gray-black mixture, which was then transferred to a50 mL round-bottomed flask along with a magnetic stir bar. Water (5.0 mL) was added, and the mixture wasstirred for 5-10 minutes to dissolve the H5IO6. Then 20.0 mL acetonitrile (ACN) was added andthe mixture was stirred vigorously to disperse the black CrO2solid. At this point the solution phasewas dark yellow. The alcohol reactant(5.0 mmol, weighed if solid, via pipette if liquid) was added in one portionwith vigorous stirring, and within one minute the solution phase became muchlighter (although it gradually darkened during the reaction period). With chromium (VI) oxide, periodic acid in toluene, Time= 16h, T= 20 °C , Reagent/catalyst, Solvent Few, Chip S.; Williams, Kathryn R.; Wagener, Kenneth B.; Tetrahedron Letters; vol. 55; nb. 32; (2014); p. 4452 4454 View in Reaxys 2.4. Oxidation of alcohols In a typical procedure, a mixture of 0.1 g catalyst (VPO or VPO-Co), with a grain size of 200–230 mesh 15 mL acetonitrile and10 mmol of alcohol was stirred in a three-necked flask under nitro-gen atmosphere at 50C for 30 min. The stirring rate of the solutionwas set at 750 cycle/min. Then 10 mmol of the oxidant (TBHP) wasadded and the mixture was refluxed at 90C for 8 h under nitrogenatmosphere. After filtration, the solid was washed with ethanol andthe reaction mixture was analyzed by GC. A GC (Perkin Elmer Model8500) equipped with a flame ionization detector (FID) connectedto a 3percent OV-17 column with a length of 2.5 m and diameter of 1/8in. was used for product analysis. Stage 1: in acetonitrile, Time= 0.5h, T= 50 °C , Inert atmosphere, Green chemistry Stage 2: With tert.-butylhydroperoxide, Time= 8h, T= 90 °C , Inert atmosphere, Green chemistry, Temperature Mahdavi, Vahid; Hasheminasab, Hamid Reza; Applied Catalysis A: General; vol. 482; (2014); p. 189 - 197 View in Reaxys With tert.-butylhydroperoxide, N,N'-(ethylene)bis(4-[2-(ethylthio)ethoxy]salicylideneimine), manganese(II) acetate, trifluoroacetic acid in acetonitrile, Time= 8h, T= 80 °C , p= 15001.5Torr , Mechanism, chemoselective reaction

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

290/438

2018-03-11 22:07:32


Raeisaenen, Minna T.; Al-Hunaiti, Afnan; Atosuo, Elisa; Kemell, Marianna; Leskelae, Markku; Repo, Timo; Catalysis Science and Technology; vol. 4; nb. 8; (2014); p. 2564 - 2573 View in Reaxys With dihydrogen peroxide, potassium carbonate in water, Time= 1h, T= 80 °C , Green chemistry, Time, Temperature Zhang, Mingmei; Sun, Qian; Yan, Zaoxue; Jing, Junjie; Wei, Wei; Jiang, Deli; Xie, Jimin; Chen, Min; Australian Journal of Chemistry; vol. 66; nb. 5; (2013); p. 564 - 571 View in Reaxys With 2O39PW11 (7-)*11K(1+)*Pr(3+)*22H2O, dihydrogen peroxide in water, Time= 3h, T= 90 °C , Green chemistry Saini, Mukesh Kumar; Gupta, Rakesh; Parbhakar, Swati; Singh, Surendra; Hussain, Firasat; RSC Advances; vol. 4; nb. 72; (2014); p. 38446 - 38449 View in Reaxys 2. Experimental General procedure: The oxidation experiments were carried out in glass liners loaded into a pressurized steel autoclave. For a typical run, 0.97 mmol of benzyl alcohol, 0.38 molpercent Au/Al2O3 (48 mg) and the solvents were measured into the glass liners. Additional base was added as a solid when only organic solvent was used. The autoclave was pressurized with 10 bar oxygen, heated to 100∘C and the mixtures were stirred with magnetic stirring at 1000 rpm. After the reaction the autoclave was depressurized and the mixtures were extracted twice with ethyl acetate. After the first extraction the reaction mixtures were acidified with HCl to transfer benzoate salt to the organic phase as benzoic acid. Centrifuge (3000 rpm, 2 min) was used to separate the phases. The products were analyzed using GC (Agilent 6890N) equipped with a HP-Innowax column and a flame ionization detector. Molar selectivity and conversion were determined using acetophenone as astandard. GC-MS was used to identify the products. With oxygen, potassium carbonate in toluene, Time= 2h, T= 100 °C , p= 7500.75Torr , Autoclave Rautiainen, Sari; Simakova, Olga; Guo, Hongfan; Leino, Anne-Riikka; Kordas, Krisztian; Murzin, Dmitry; Leskelae, Markku; Repo, Timo; Applied Catalysis A: General; vol. 485; (2014); p. 202 - 206 View in Reaxys 2 Experiment In a typical experiment, tungsten oxide was used as catalyst from a commercial source and calcined at 500°C overnight, which is mixed with solvents including ILs. The following amounts of reactants, oxidant, solvents and catalysts were used unless otherwise specified: aromatic alcohol (1 g), hydrogen peroxide (30 wt.percent, 2g), ILs (0.2 g)/ toluene, benzene, or n-heptane (10 g), and tungsten oxide (0.01 g). The optimal amount of solvents was defined in supplementary material Fig. S1. The liquid phase reaction was conducted in a round-bottom flask with a reflux condenser and stirred magnetically. Reaction time was varying from 0.25 h to 24 h in the range of 323.15 K to 363.15 K. After the reaction, each phase of the post-reaction liquid mixture was extracted with ether (3×5 ml), and analyzed on an Agilent GC 7890A with an OV-17 column. The errors in the yield measurements were estimated to be 3percent. With water, dihydrogen peroxide, tungsten(VI) oxide, 1-methyl-3-octylimidazol-3-ium chloride in toluene, Time= 8h, T= 49.99 - 89.99 °C , Reagent/catalyst, Solvent, Time, chemoselective reaction Chen, Long; Chen, Lifang; Ye, Yinmei; Qi, Zhiwen; Freund, Hannsjoerg; Sundmacher, Kai; Catalysis Communications; vol. 28; (2012); p. 143 - 146 View in Reaxys 22 %Chro- With dihydrogen peroxide in neat liquid, Time= 12h, T= 90 °C , Green chemistry mat., 50 %Chromat. Karimi, Babak; Rostami, Fatemeh Bakhshandeh; Khorasani, Mojtaba; Elhamifar, Dawood; Vali, Hojatollah; Tetrahedron; nb. 36; (2014); p. 6114 - 6119 View in Reaxys 65 %Chro- With dihydrogen peroxide in water, Time= 12h, T= 90 °C , Green chemistry, Solvent mat., 32 %Chromat. Karimi, Babak; Rostami, Fatemeh Bakhshandeh; Khorasani, Mojtaba; Elhamifar, Dawood; Vali, Hojatollah; Tetrahedron; nb. 36; (2014); p. 6114 - 6119 View in Reaxys With dihydrogen peroxide, T= 70 °C , Catalytic behavior, Reagent/catalyst, Temperature, Solvent Rathore, Puran Singh; Patidar, Rajesh; Thakore, Sonal; RSC Advances; vol. 4; nb. 77; (2014); p. 41111 - 41121

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

291/438

2018-03-11 22:07:32


View in Reaxys With oxygen, potassium hydoxide in water, Time= 24h, T= 60 °C , Schlenk technique Deraedt, Christophe; Wang, Dong; Salmon, Lionel; Etienne, Laetitia; LabrugA re, Christine; Ruiz, Jaime; Astruc, Didier; ChemCatChem; vol. 7; nb. 2; (2015); p. 303 - 308 View in Reaxys With (poly ionic liquid)PIL(at)SiO2-Pd in water, Time= 5h, T= 65 °C , Green chemistry, Reagent/catalyst Yang, Yan; Ambrogi, Martina; Kirmse, Holm; Men, Yongjun; Antonietti, Markus; Yuan, Jiayin; Chemistry of Materials; vol. 27; nb. 1; (2015); p. 127 - 132 View in Reaxys With dihydrogen peroxide in acetonitrile, Time= 0.0833333h, T= 120 - 125 °C , p= 12376.2Torr , Microwave irradiation, Reagent/catalyst Yepez, Alfonso; Lam, Frank L. Y.; Romero, Antonio A.; Kappe, C. Oliver; Luque, Rafael; ChemCatChem; vol. 7; nb. 2; (2015); p. 276 - 282 View in Reaxys With oxygen in neat (no solvent), Time= 2.5h, T= 100 °C , p= 1520.1Torr , Reagent/catalyst De Moura, Edmilson M.; Garcia, Marco A. S.; Gonalves, Renato V.; Kiyohara, Pedro K.; Jardim, Renato F.; Rossi, Liane M.; RSC Advances; vol. 5; nb. 20; (2015); p. 15035 - 15041 View in Reaxys With oxygen, potassium carbonate in neat (no solvent), Time= 2.5h, T= 100 °C , p= 1520.1Torr De Moura, Edmilson M.; Garcia, Marco A. S.; Gonalves, Renato V.; Kiyohara, Pedro K.; Jardim, Renato F.; Rossi, Liane M.; RSC Advances; vol. 5; nb. 20; (2015); p. 15035 - 15041 View in Reaxys 65 %Chro- With α,α,α-trifluorotoluene, oxygen, Time= 2h, T= 20 °C , UV-irradiation, Kinetics mat., 13 %Chromat. Koutsouroubi, Eirini D.; Xylouri, Alexandra K.; Armatas, Gerasimos S.; Chemical Communications; vol. 51; nb. 21; (2015); p. 4481 - 4484 View in Reaxys 22 %Chro- 4.5 General procedure for oxidation of alcohols to the corresponding carbonyl compound with 30percent mat., 50 H2O2 %Chromat. General procedure: In a two necked flask equipped with a condenser, alcohol (1 mmol), 30percent H2O2 (5mmol) were added to an equal mixture of water and acetonitrile (1.5ml). Then, WO4 =PMO-IL (0.23g, ∼1.5 molpercent) was added to the above solution and the resulting mixture was stirred at 90°C for requisite time. The progress of the reaction was monitored by gas chromatography using standard addition method. After completion of the reaction, the mixture was allowed to cool down to the room temperature and the catalyst was successfully isolated with centrifugation and washed with CH2Cl2 (3×10ml) and dried under the vacuum for 12 h. Then, the collected CH2Cl2 phase was first washed with water, dried over Na2SO4, and the solvent was concentrated with evaporation under the reduced pressure to give the corresponding carbonyl compounds. The recovered catalyst was used in the recycling procedure in the same manner as reported in the first run. With dihydrogen peroxide in neat (no solvent), Time= 12h, T= 90 °C , Green chemistry, chemoselective reaction Karimi, Babak; Rostami, Fatemeh Bakhshandeh; Khorasani, Mojtaba; Elhamifar, Dawood; Vali, Hojatollah; Tetrahedron; vol. 70; nb. 36; (2014); p. 6114 - 6119 View in Reaxys 65 %Chro- 4.5 General procedure for oxidation of alcohols to the corresponding carbonyl compound with 30percent mat., 32 H2O2 %Chromat. General procedure: In a two necked flask equipped with a condenser, alcohol (1 mmol), 30percent H2O2 (5mmol) were added to an equal mixture of water and acetonitrile (1.5ml). Then, WO4 =PMO-IL (0.23g, ∼1.5 molpercent) was added to the above solution and the resulting mixture was stirred at 90°C for requisite time. The progress of the reaction was monitored by gas chromatography using standard addition method. After completion of the reaction, the mixture was allowed to cool down to the room temperature and the catalyst was successfully isolated with centrifugation and washed with CH2Cl2 (3×10ml) and dried under the vacuum for 12 h. Then, the collected CH2Cl2 phase

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

292/438

2018-03-11 22:07:32


was first washed with water, dried over Na2SO4, and the solvent was concentrated with evaporation under the reduced pressure to give the corresponding carbonyl compounds. The recovered catalyst was used in the recycling procedure in the same manner as reported in the first run. With dihydrogen peroxide in water, Time= 12h, T= 90 °C , Green chemistry, Solvent, chemoselective reaction Karimi, Babak; Rostami, Fatemeh Bakhshandeh; Khorasani, Mojtaba; Elhamifar, Dawood; Vali, Hojatollah; Tetrahedron; vol. 70; nb. 36; (2014); p. 6114 - 6119 View in Reaxys 13 %Spectr., 47 %Spectr.

With cesiumhydroxide monohydrate, oxygen in 1,3,5-trimethyl-benzene, Time= 24h, T= 140 °C , p= 760.051Torr Wang, Chao; Chen, Changpeng; Han, Jian; Zhang, Jingyu; Yao, Yingming; Zhao, Yingsheng; European Journal of Organic Chemistry; vol. 2015; nb. 13; (2015); p. 2972 - 2977 View in Reaxys With dihydrogen peroxide in neat liquid, Time= 4h, T= 90 °C , Catalytic behavior, Reagent/catalyst, Temperature Meng, Ling-Yan; Zhai, Shang-Ru; Li, Shi; Zhai, Bin; An, Qing-Da; Song, Xiao-Wei; European Journal of Inorganic Chemistry; vol. 2014; nb. 14; (2014); p. 2337 - 2344 View in Reaxys With phosphoric acid, dihydrogen peroxide, sodium hydroxide in water, Time= 2h, T= 50 °C , pH= 8.5 Wu, Xiaochen; Guo, Shouwu; Zhang, Jingyan; Chemical Communications; vol. 51; nb. 29; (2015); p. 6318 - 6321 View in Reaxys With manganese(IV) oxide, oxygen in octanol, Time= 0.333333h, T= 89.84 °C , p= 757.576Torr , Kinetics, Temperature, Reagent/catalyst, Pressure Saeed, Muhammad; Ilyas, Mohammad; Siddique, Mohsin; International Journal of Chemical Kinetics; vol. 47; nb. 7; (2015); p. 447 - 460 View in Reaxys With dihydrogen peroxide in water, Time= 18h, T= 80 °C , Sealed tube, Catalytic behavior, Reagent/catalyst, Overall yield = 96 percentSpectr. Lee, Li-Chen; Xiao, Chaoxian; Huang, Wenyu; Zhao, Yan; New Journal of Chemistry; vol. 39; nb. 4; (2015); p. 2459 - 2466 View in Reaxys in water, Time= 8h, T= 20 °C , p= 760.051Torr , Irradiation, Green chemistry, Reagent/catalyst Yang, Juan; Wang, Xiaohan; Chen, Yumei; Dai, Jun; Sun, Shihao; RSC Advances; vol. 5; nb. 13; (2015); p. 9771 - 9782 View in Reaxys

58 %Chro- Catalytic Oxidation mat., 15 General procedure: For the catalytic oxidation by [RuIILCl2] complex, theorganic substrate (1.0 mmol) was added to %Chromat. NaIO4(2.5 mmol) in CCl4-CH3CN-H2O (1:1:2; 20 mL) and the catalyst (0.02 mmol). The reaction mixture was stirred underreflex at 70C, then cooled and extracted with diethyl ether(3 £20 mL). The ethereal layer was then dried with anhydrous Na2SO4and the aldehyde or ketone content quantifiedas its 2,4-dinitrophenylhydrazone derivatives. The aqueouslayer was acidified with 5M H2SO4 to PH2, extracted withdiethylether (3£20 mL), dried and evaporated to give theacid. With sodium periodate, C42H38Cl2N8O2Ru in tetrachloromethane, water, acetonitrile, Time= 3h, T= 70 °C , Catalytic behavior El-Shobaky, Amira R.; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 45; nb. 10; (2015); p. 1481 - 1488 View in Reaxys With [Ru(p-cymene)Cl(1-[2-(methylthio)phenyl]-4-phenyl-1H-1,2,3-triazole)]*hexafluorophosphate, 4-methylmorpholine N-oxide in dichloromethane, Time= 3h, Reflux, Reagent/catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

293/438

2018-03-11 22:07:32


Hohloch, Stephan; Hettmanczyk, Lara; Sarkar, Biprajit; European Journal of Inorganic Chemistry; vol. 2014; nb. 20; (2015); p. 3164 - 3171 View in Reaxys With [Os(p-cymene)Cl(1-[2-(methylthio)phenyl]-4-phenyl-1H-1,2,3-triazole)]*hexafluorophosphate, 4-methylmorpholine N-oxide in dichloromethane, Time= 1h, Reflux Hohloch, Stephan; Hettmanczyk, Lara; Sarkar, Biprajit; European Journal of Inorganic Chemistry; vol. 2014; nb. 20; (2015); p. 3164 - 3171 View in Reaxys With pyridine, oxygen in water, Time= 3h, T= 60 °C , p= 760.051Torr Rana, Surjyakanta; Maddila, Suresh; Jonnalagadda, Sreekantha B.; Catalysis Science and Technology; vol. 5; nb. 6; (2015); p. 3235 - 3241 View in Reaxys 60 %Chro- With sodium periodate, C14H30Cl2FeN4 (1+)*F6P(1-) in 2,2,2-trifluoroethanol, water, Time= 22h, T= 23 °C mat., 10 %Chromat. Tan, Peng; Kwong, Hoi-Ki; Lau, Tai-Chu; Chemical Communications; vol. 51; nb. 61; (2015); p. 12189 - 12192 View in Reaxys With Au NCs/TiO2, oxygen in cyclohexane, T= 60 °C , p= 1500.15Torr Villa, Alberto; Ferri, Davide; Campisi, Sebastiano; Chan-Thaw, Carine E.; Lu, Ye; Kröcher, Oliver; Prati, Laura; ChemCatChem; vol. 7; nb. 16; (2015); p. 2534 - 2541 View in Reaxys in N,N-dimethyl-formamide, Time= 4h, T= 120 °C , Inert atmosphere, Catalytic behavior, Reagent/catalyst Zhu, Yaoqin; Shen, Mengnan; Xia, Yonggen; Lu, Ming; Applied Organometallic Chemistry; vol. 29; nb. 3; (2015); p. 152 - 156 View in Reaxys 2.2. Typical procedure for the catalytic oxidation of alcohols General procedure: In a typical oxidation experiment, substrate (10 mmol), catalyst (as described in Table 1) and acetonitrile (20 mL) were added to a 25-mL three-neck round bottom glass reactor,which was fitted with a magnetic stirrer and O2 inlet tube. The reaction was performed at 25 °C in a water bath with magnetic stirring. O2 was introduced into the reactor at a constant flow rate (5 mL/min). A household w-filament bulb (250 W) and 420-nm cut-off filter were placed ~10 cm from the reactor as a visible-light source. To carry out the reaction in the dark, the glass reactor was covered with aluminum foil. After completion of the reaction, toluene was added to the mixture as an internal standard. Then, mpg-C3N4 was removed by filtration and thereaction mixture was injected into the GC for analysis. With N -hydroxyphthalimide, oxygen in acetonitrile, Time= 28h, T= 25 °C , p= 760.051Torr , Irradiation, Green chemistry Zhang, Pengfei; Deng, Jiang; Mao, Jianyong; Li, Haoran; Wang, Yong; Chinese Journal of Catalysis; vol. 36; nb. 9; (2015); p. 1580 - 1586 View in Reaxys 26 %Chro- With C60H62Fe2Li2N10O7 (2+)*2ClO4 (1-), dihydrogen peroxide, acetic acid in water, acetonitrile, Time= 3h, T= 30 °C mat., 30 %Chromat. Das, Biswanath; Al-Hunaiti, Afnan; Haukka, Matti; Demeshko, Serhiy; Meyer, Steffen; Shteinman, Albert A.; Meyer, Franc; Repo, Timo; Nordlander, Ebbe; European Journal of Inorganic Chemistry; vol. 2015; nb. 21; (2015); p. 3590 - 3601 View in Reaxys Catalytic tests The catalyst (0.05 g), benzyl alcohol (3 ml, 28.8 mmol), 30 percent H2O2 (4 ml) and solvent (water, acetone, or acetonitrile) (10 ml) were placed into a reaction vessel. The resulting mixture was vigorously stirred at 80° C under nitrogen. After certain times, the catalysts were separated by filtration. The products were analyzed with a gas chromatography (Shimadzu, GC-8A) equipped with a XE60 capillary columnand FID detector. With dihydrogen peroxide in water, Time= 6h, T= 80 °C , Inert atmosphere, Solvent, Reagent/catalyst, Temperature, Time

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

294/438

2018-03-11 22:07:32


Hu, Jing; Zou, Yongcun; Liu, Jing; Sun, Jian; Yang, Xiaoyuan; Kan, Qiubin; Guan, Jingqi; Research on Chemical Intermediates; vol. 41; nb. 8; (2015); p. 5703 - 5712 View in Reaxys 83 %Spectr., 10 %Spectr.

With dmap, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, sodium dodecyl-sulfate in water, Time= 1h, T= 25 °C , Reagent/catalyst, chemoselective reaction Chen, Ba-Tian; Bukhryakov, Konstantin V.; Sougrat, Rachid; Rodionov, Valentin O.; ACS Catalysis; vol. 5; nb. 2; (2015); p. 1313 - 1317 View in Reaxys

21 %Chro- With oxygen, potassium carbonate in water, Time= 15h, T= 90 °C , p= 760.051Torr , Reagent/catalyst mat., 78 %Chromat. Karimi, Babak; Khorasani, Mojtaba; Vali, Hojatollah; Vargas, Carolina; Luque, Rafael; ACS Catalysis; vol. 5; nb. 7; (2015); p. 4189 - 4200 View in Reaxys With tert.-butylhydroperoxide, C27H22N4*3Co(2+)*2.5C8H4O4 (2-)*C2H3O2 (1-) in acetonitrile, Time= 24h, T= 60 °C Wang, Jian-Cheng; Ding, Feng-Wen; Ma, Jian-Ping; Liu, Qi-Kui; Cheng, Jun-Yan; Dong, Yu-Bin; Inorganic Chemistry; vol. 54; nb. 22; (2015); p. 10865 - 10872 View in Reaxys With potassium carbonate in toluene, Time= 6h, T= 90 °C Karami, Kazem; Naeini, Nasrin Haghighat; Eigner, Vaclav; Dusek, Michal; Lipkowski, Janusz; Hervés, Pablo; Tavakol, Hossein; RSC Advances; vol. 5; nb. 124; (2015); p. 102424 - 102435 View in Reaxys With oxygen in N,N-dimethyl-formamide, Time= 6h, T= 120 °C , Catalytic behavior, Reagent/catalyst, Temperature Yang, Xiaoyuan; Wu, Shujie; Peng, Ling; Hu, Jing; Wang, Xiufang; Fu, Xiaoran; Huo, Qisheng; Guan, Jingqi; RSC Advances; vol. 5; nb. 124; (2015); p. 102508 - 102515 View in Reaxys With dihydrogen peroxide in acetone, Time= 5h, T= 80 °C , Catalytic behavior, Solvent Chi, Hui; Cao, Liqin; Wang, Jide; RSC Advances; vol. 6; nb. 6; (2016); p. 4434 - 4441 View in Reaxys 47 %Chro- With oxygen, potassium carbonate in water, Time= 16h, T= 80 °C , p= 759.826Torr , Green chemistry, Reagent/ mat., 53 catalyst %Chromat. Karimi, Babak; Naderi, Zahra; Khorasani, Mojtaba; Mirzaei, Hamid M.; Vali, Hojatollah; ChemCatChem; vol. 8; nb. 5; (2016); p. 906 - 910 View in Reaxys With oxygen, potassium carbonate, Time= 1h, T= 100 °C , p= 4500.45Torr , Reagent/catalyst Ferraz, Camila P.; Garcia, Marco Aurélio S.; Teixeira-Neto, Érico; Rossi, Liane M.; RSC Advances; vol. 6; nb. 30; (2016); p. 25279 - 25285 View in Reaxys With Cumene hydroperoxide, C12H16BrMo6NO18 (2-)*2C16H36N(1+) in toluene, Time= 48h, T= 80 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst Jangir, Ritambhara; Antony, Rajendran; Murugavel, Ramaswamy; New Journal of Chemistry; vol. 40; nb. 2; (2016); p. 1004 - 1013 View in Reaxys 36 %Spectr., 59 %Spectr.

With C33H33N5O8Ru, dihydrogen peroxide in dichloromethane, water, Time= 4h, T= 25 °C , Schlenk technique, Inert atmosphere Isozaki, Katsuhiro; Yokoi, Tomoya; Yoshida, Ryota; Ogata, Kazuki; Hashizume, Daisuke; Yasuda, Nobuhiro; Sadakane, Koichiro; Takaya, Hikaru; Nakamura, Masaharu; Chemistry - An Asian Journal; vol. 11; nb. 7; (2016); p. 1076 - 1091

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

295/438

2018-03-11 22:07:32


View in Reaxys 1.3. General procedurefor the oxidation of benzyl alcohol General procedure: Experiments were carried out in a thermostatedSchlenk vessel equipped with a condenser and stirrer. The solution of benzylalcohol and catalyst in solvent was purified with bubbling nitrogen gas toremove the oxygen. A mixture of benzyl alcohol (1.89×10-3 mol),catalyst (3.16×10-6 mol) and solvent (0.01 L) was stirred in aSchlenk vessel for few minutes at room temperature. The oxidant TBHP (1.58×10-3mol) was then added and the reaction mixture was stirred for the desiredtime. The samples (0.0005 L)were withdrawn periodically from the mixture todetermine the percentage conversion by analyzing them with GC equipped with DBWax (30 mx 0.32 nm ID) using 20 µL of cyclohexanone as an internal standart. With tert.-butylhydroperoxide, Inert atmosphere, Schlenk technique, Catalytic behavior Aktaş, Ayşe; Acar, Irfan; Saka, Ece Tuǧba; Biyiklioglu, Zekeriya; Journal of Organometallic Chemistry; vol. 815-816; (2016); p. 1 - 7 View in Reaxys The aerobic oxidation reaction of benzyl alcohol (Merck) was carried out in a 25 ml PARR reactor (3 cm diameter),where, 0.65 g of the catalyst, 13.0 g of benzyl alcohol were mixed under stirring at 550 RPM, with air flow rate of 2.2 ml·sec−1, at 1–5 bar pressure with reaction temperatures ranging from 40 to 100 °C.At the end of the reaction, the mixture was cooled to room temperature and the product was analyzed using a gas chromatograph (GC,PerkinElmer) connected with an EQUITY column and a flame ionizationdetector (FID). With trimagnesium phosphate, oxygen in neat liquid, Time= 8h, T= 100 °C , p= 3000.3Torr , Autoclave, Green chemistry, Catalytic behavior, Temperature, Pressure, Reagent/catalyst Debnath, Suman; Saxena, Sandeep K.; Nagabhatla, Viswanadham; Catalysis Communications; vol. 84; (2016); p. 129 - 133 View in Reaxys 44.8 %Chromat., 22.4 %Chromat.

catalytic alcohol oxidations by t-BuOOH in the presence of iron complexes General procedure: t-BuOOH (0.075 mmol) was added to a mixture of substrate(0.05 mmol), iron complex (1.0 103 mmol), imidazole (0.01 mmol), NHPI (0.02 mmol), and solvent (CH3CN; 1 mL). The mixture was stirred for the given time at 50 °C. Each reaction was monitored by GC/MS analysis of 20 lL aliquots withdrawn periodically from the reaction mixture. Dodecane was used as an internal standard to quantify the yields of products and conversions of substrates. All reactions were run at least in triplicate, and the average conversions and product yields have been presented. Conversions and product yields were calculated with respect to substrates. With 1H-imidazole, tert.-butylhydroperoxide, N -hydroxyphthalimide, [Fe(bpc)Cl2][Et4N] in acetonitrile, Time= 7h, T= 50 °C , Reagent/catalyst Bae, Jeong Mi; Lee, Myoung Mi; Lee, Seul Ah; Lee, Sun Young; Bok, Kwon Hee; Kim, Jinheung; Kim, Cheal; Inorganica Chimica Acta; vol. 451; (2016); p. 8 - 15 View in Reaxys

24 %Chro- With tert.-butylhydroperoxide, Cs5V14As8O42Cl in water, acetone, Time= 24h, T= 20 °C mat., 20 %Chromat. Campbell, McKenzie L.; Sulejmanovic, Dino; Schiller, Jacqueline B.; Turner, Emily M.; Hwu, Shiou-Jyh; Whitehead, Daniel C.; Catalysis Science and Technology; vol. 6; nb. 9; (2016); p. 3208 - 3213 View in Reaxys With dihydrogen peroxide, T= 90 °C , Reagent/catalyst Alqurashi, Ghada K.; Al-Shehri, Abdulmohsen; Narasimharao, Katabathini; RSC Advances; vol. 6; nb. 75; (2016); p. 71076 - 71091 View in Reaxys With oxygen, potassium hydoxide in water, Time= 2h, T= 60 °C , p= 760.051Torr Gao, Wenjun; Li, Siwen; Pal, Manas; Liu, Yong; Wan, Xiaoyue; Li, Wei; Wang, Shuai; Wang, Changyao; Zheng, Gengfeng; Zhao, Dongyuan; RSC Advances; vol. 6; nb. 66; (2016); p. 61064 - 61072 View in Reaxys With [MoO3(1,2,4-triazole)0.5], dihydrogen peroxide in water, Time= 48h, T= 70 °C , Reagent/catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

296/438

2018-03-11 22:07:32


Amarante, Tatiana R.; Neves, Patrícia; Valente, Anabela A.; Paz, Filipe A. Almeida; Pillinger, Martyn; Gonçalves, Isabel S.; Journal of Catalysis; vol. 340; (2016); p. 354 - 367 View in Reaxys With tert.-butylhydroperoxide, [Mn(C6H5COO)(H2O)(1,10-phenanthroline)2](ClO4)(CH3OH) in water, acetonitrile, Time= 24h, T= 70 °C , Inert atmosphere, Catalytic behavior, Reagent/catalyst, Solvent Kani, Ibrahim; Bolat, Serkan; Applied Organometallic Chemistry; vol. 30; nb. 8; (2016); p. 713 - 721 View in Reaxys With (copper(II))(di-methyl-Salen), dihydrogen peroxide in acetonitrile, Time= 18h, T= 79.84 °C , Catalytic behavior, Reagent/catalyst Godhani, Dinesh R.; Nakum, Haresh D.; Parmar, Digvijaysinh K.; Mehta, Jignasu P.; Desai, Nisheeth C.; Inorganic Chemistry Communications; vol. 72; (2016); p. 105 - 116 View in Reaxys 86 %Chro- With dihydrogen peroxide in water, Time= 12h, T= 90 °C , Solvent, Reagent/catalyst mat., 13 %Chromat. Zohreh, Nasrin; Tavakolizadeh, Maryam; Hosseini, Seyed Hassan; Jahani, Mahboobeh; Pourjavadi, Ali; Bennett, Craig; New Journal of Chemistry; vol. 40; nb. 12; (2016); p. 10325 - 10332 View in Reaxys 50 %Spectr., 50 %Spectr.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, laccase from Trametes versicolor, oxygen in water, Time= 192h, T= 20 °C , Enzymatic reaction, Temperature Galletti, Paola; Pori, Matteo; Funiciello, Federica; Soldati, Roberto; Ballardini, Alberto; Giacomini, Daria; ChemSusChem; vol. 7; nb. 9; (2014); p. 2684 - 2689 View in Reaxys

38 %Chro- 3.1 Procedure for Catalytic Oxidation mat., 30 Catalytic oxidation of benzyl alcohol to correspondingaldehydes and ketones by the titled copper complexes were%Chromat. studied in the presence of H2O2. In a typical reaction, benzyl alcohol (0.1 cm3, 1.0 mmol) was added to a solution ofcopper complexes (Cunpap, Cubsisnph, Cunpisnph) contactedto air (0.05 mmol) in 10ml of acetonitrile at 50, 60, 70,80 or 90 °C in an water bath under magnetic stirring. Thereaction was initiated by charging with 5.54 mmol aqueousH2O2 (30 percent) at the typical temperature. The reaction wasmonitored by gas chromatographic analyses, using computerizedstandard calibration curve. The oxidation productswere identified by comparing their retention times with thoseof authentic samples. Control reactions were done by withdrawingsamples (ca. 2 ml) of the reaction mixture andtreatment of the reaction mixture with solidMnO2 (to quenchthe excess aqueous H2O2) and with anhydrous sodium sulfate(to absorb excess water molecules), under the sameconditions in the catalytic runs. The resulting slurry wasfiltered on Celite, and the filtrate was injected in the GC. Thisallowed independent measurements for each sample. Thechemo-conversion of benzoyl alcohol to benzaldehyde wascalculated according to computerized standard calibrationcurves. All the oxidation processes were run at least induplicate to confirm the yield of the products. With C32H22CuN4O2, dihydrogen peroxide in water, acetonitrile, Time= 4h, T= 60 °C , Catalytic behavior Abdel-Rahman, Laila H.; Abu-Dief, Ahmed M.; Adam, Mohamed Shaker S.; Hamdan, Samar Kamel; Catalysis Letters; vol. 146; nb. 8; (2016); p. 1373 - 1396 View in Reaxys 29 %Chro- 3.1 Procedure for Catalytic Oxidation mat., 33 Catalytic oxidation of benzyl alcohol to correspondingaldehydes and ketones by the titled copper complexes were%Chromat. studied in the presence of H2O2. In a typical reaction, benzyl alcohol (0.1 cm3, 1.0 mmol) was added to a solution ofcopper complexes (Cunpap, Cubsisnph, Cunpisnph) contactedto air (0.05 mmol) in 10ml of acetonitrile at 50, 60, 70,80 or 90 °C in an water bath under magnetic stirring. Thereaction was initiated by charging with 5.54 mmol aqueousH2O2 (30 percent) at the typical temperature. The reaction wasmonitored by gas chromatographic analyses, using computerizedstandard calibration curve. The oxidation productswere identified by comparing their retention times with thoseof authentic samples. Control reactions were done by withdrawingsamples (ca. 2 ml) of the reaction mixture andtreatment of the reaction mixture with solidMnO2 (to quenchthe excess aqueous H2O2) and with anhydrous sodium sulfate(to absorb excess water molecules), under the sameconditions in the catalytic runs. The resulting slurry wasfiltered on Celite, and the filtrate was injected in the GC. Thisallowed independent measurements for each sample. Thechemo-conversion of benzoyl alcohol to benzaldehyde wascalculated according to computerized standard calibrationcurves. All the oxidation processes were run at least induplicate to confirm the yield of the products. With C32H22CuN4O2, dihydrogen peroxide in water, acetonitrile, Time= 4h, T= 90 °C , Catalytic behavior

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

297/438

2018-03-11 22:07:32


Abdel-Rahman, Laila H.; Abu-Dief, Ahmed M.; Adam, Mohamed Shaker S.; Hamdan, Samar Kamel; Catalysis Letters; vol. 146; nb. 8; (2016); p. 1373 - 1396 View in Reaxys 57 %Chro- 3.1 Procedure for Catalytic Oxidation mat., 43 Catalytic oxidation of benzyl alcohol to correspondingaldehydes and ketones by the titled copper complexes were%Chromat. studied in the presence of H2O2. In a typical reaction, benzyl alcohol (0.1 cm3, 1.0 mmol) was added to a solution ofcopper complexes (Cunpap, Cubsisnph, Cunpisnph) contactedto air (0.05 mmol) in 10ml of acetonitrile at 50, 60, 70,80 or 90 °C in an water bath under magnetic stirring. Thereaction was initiated by charging with 5.54 mmol aqueousH2O2 (30 percent) at the typical temperature. The reaction wasmonitored by gas chromatographic analyses, using computerizedstandard calibration curve. The oxidation productswere identified by comparing their retention times with thoseof authentic samples. Control reactions were done by withdrawingsamples (ca. 2 ml) of the reaction mixture andtreatment of the reaction mixture with solidMnO2 (to quenchthe excess aqueous H2O2) and with anhydrous sodium sulfate(to absorb excess water molecules), under the sameconditions in the catalytic runs. The resulting slurry wasfiltered on Celite, and the filtrate was injected in the GC. Thisallowed independent measurements for each sample. Thechemo-conversion of benzoyl alcohol to benzaldehyde wascalculated according to computerized standard calibrationcurves. All the oxidation processes were run at least induplicate to confirm the yield of the products. With C23H17BrCuN4O7, dihydrogen peroxide in water, acetonitrile, Time= 2h, T= 60 °C , Catalytic behavior Abdel-Rahman, Laila H.; Abu-Dief, Ahmed M.; Adam, Mohamed Shaker S.; Hamdan, Samar Kamel; Catalysis Letters; vol. 146; nb. 8; (2016); p. 1373 - 1396 View in Reaxys 18 %Chro- 3.1 Procedure for Catalytic Oxidation mat., 55 Catalytic oxidation of benzyl alcohol to correspondingaldehydes and ketones by the titled copper complexes were%Chromat. studied in the presence of H2O2. In a typical reaction, benzyl alcohol (0.1 cm3, 1.0 mmol) was added to a solution ofcopper complexes (Cunpap, Cubsisnph, Cunpisnph) contactedto air (0.05 mmol) in 10ml of acetonitrile at 50, 60, 70,80 or 90 °C in an water bath under magnetic stirring. Thereaction was initiated by charging with 5.54 mmol aqueousH2O2 (30 percent) at the typical temperature. The reaction wasmonitored by gas chromatographic analyses, using computerizedstandard calibration curve. The oxidation productswere identified by comparing their retention times with thoseof authentic samples. Control reactions were done by withdrawingsamples (ca. 2 ml) of the reaction mixture andtreatment of the reaction mixture with solidMnO2 (to quenchthe excess aqueous H2O2) and with anhydrous sodium sulfate(to absorb excess water molecules), under the sameconditions in the catalytic runs. The resulting slurry wasfiltered on Celite, and the filtrate was injected in the GC. Thisallowed independent measurements for each sample. Thechemo-conversion of benzoyl alcohol to benzaldehyde wascalculated according to computerized standard calibrationcurves. All the oxidation processes were run at least induplicate to confirm the yield of the products. With C23H17BrCuN4O7, dihydrogen peroxide in water, acetonitrile, Time= 6h, T= 70 °C , Catalytic behavior Abdel-Rahman, Laila H.; Abu-Dief, Ahmed M.; Adam, Mohamed Shaker S.; Hamdan, Samar Kamel; Catalysis Letters; vol. 146; nb. 8; (2016); p. 1373 - 1396 View in Reaxys 47 %Chro- 3.1 Procedure for Catalytic Oxidation mat., 25 Catalytic oxidation of benzyl alcohol to correspondingaldehydes and ketones by the titled copper complexes were%Chromat. studied in the presence of H2O2. In a typical reaction, benzyl alcohol (0.1 cm3, 1.0 mmol) was added to a solution ofcopper complexes (Cunpap, Cubsisnph, Cunpisnph) contactedto air (0.05 mmol) in 10ml of acetonitrile at 50, 60, 70,80 or 90 °C in an water bath under magnetic stirring. Thereaction was initiated by charging with 5.54 mmol aqueousH2O2 (30 percent) at the typical temperature. The reaction wasmonitored by gas chromatographic analyses, using computerizedstandard calibration curve. The oxidation productswere identified by comparing their retention times with thoseof authentic samples. Control reactions were done by withdrawingsamples (ca. 2 ml) of the reaction mixture andtreatment of the reaction mixture with solidMnO2 (to quenchthe excess aqueous H2O2) and with anhydrous sodium sulfate(to absorb excess water molecules), under the sameconditions in the catalytic runs. The resulting slurry wasfiltered on Celite, and the filtrate was injected in the GC. Thisallowed independent measurements for each sample. Thechemo-conversion of benzoyl alcohol to benzaldehyde wascalculated according to computerized standard calibrationcurves. All the oxidation processes were run at least induplicate to confirm the yield of the products. With C27H20CuN4O7, dihydrogen peroxide in water, acetonitrile, Time= 2h, T= 60 °C , Catalytic behavior Abdel-Rahman, Laila H.; Abu-Dief, Ahmed M.; Adam, Mohamed Shaker S.; Hamdan, Samar Kamel; Catalysis Letters; vol. 146; nb. 8; (2016); p. 1373 - 1396 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

298/438

2018-03-11 22:07:32


41 %Chro- 3.1 Procedure for Catalytic Oxidation mat., 43 Catalytic oxidation of benzyl alcohol to correspondingaldehydes and ketones by the titled copper complexes were%Chromat. studied in the presence of H2O2. In a typical reaction, benzyl alcohol (0.1 cm3, 1.0 mmol) was added to a solution ofcopper complexes (Cunpap, Cubsisnph, Cunpisnph) contactedto air (0.05 mmol) in 10ml of acetonitrile at 50, 60, 70,80 or 90 °C in an water bath under magnetic stirring. Thereaction was initiated by charging with 5.54 mmol aqueousH2O2 (30 percent) at the typical temperature. The reaction wasmonitored by gas chromatographic analyses, using computerizedstandard calibration curve. The oxidation productswere identified by comparing their retention times with thoseof authentic samples. Control reactions were done by withdrawingsamples (ca. 2 ml) of the reaction mixture andtreatment of the reaction mixture with solidMnO2 (to quenchthe excess aqueous H2O2) and with anhydrous sodium sulfate(to absorb excess water molecules), under the sameconditions in the catalytic runs. The resulting slurry wasfiltered on Celite, and the filtrate was injected in the GC. Thisallowed independent measurements for each sample. Thechemo-conversion of benzoyl alcohol to benzaldehyde wascalculated according to computerized standard calibrationcurves. All the oxidation processes were run at least induplicate to confirm the yield of the products. With C27H20CuN4O7, dihydrogen peroxide in water, acetonitrile, Time= 4h, T= 80 °C , Catalytic behavior Abdel-Rahman, Laila H.; Abu-Dief, Ahmed M.; Adam, Mohamed Shaker S.; Hamdan, Samar Kamel; Catalysis Letters; vol. 146; nb. 8; (2016); p. 1373 - 1396 View in Reaxys With potassium carbonate in water, Time= 1h, T= 26.84 °C , p= 760.051Torr , Reagent/catalyst Ishida, Ryo; Arii, Setsuka; Kurashige, Wataru; Yamazoe, Seiji; Koyasu, Kiichirou; Negishi, Yuichi; Tsukuda, Tatsuya; Chinese Journal of Catalysis; vol. 37; nb. 10; (2016); p. 1656 - 1661 View in Reaxys With tert.-butylhydroperoxide in N,N-dimethyl-formamide, Time= 3h, T= 50 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Temperature, Reagent/catalyst Kamiloğlu, Ayşe Aktaş; Acar, İrfan; Biyiklioglu, Zekeriya; Saka, Ece Tuğba; Journal of Organometallic Chemistry; vol. 828; (2017); p. 59 - 67 View in Reaxys With oxygen, Time= 1h, T= 99.84 °C , Green chemistry, Catalytic behavior, Temperature Siddique, Mohsin; Ilyas, Mohammad; Saeed, Muhammad; Journal of the Chemical Society of Pakistan; vol. 38; nb. 3; (2016); p. 454 - 462 View in Reaxys With tert.-butylhydroperoxide in N,N-dimethyl-formamide, Time= 3h, T= 90 °C , Catalytic behavior Aktaş, Ayşe; Acar, İrfan; Saka, Ece Tuğba; Biyiklioglu, Zekeriya; Kantekin, Halit; Journal of Inclusion Phenomena and Macrocyclic Chemistry; vol. 86; nb. 3-4; (2016); p. 183 - 190 View in Reaxys 83 %Spectr., 17 %Spectr.

With 1,1,1,3',3',3'-hexafluoro-propanol, nitric acid, Time= 4h, T= 20 °C Možina, Štefan; Stavber, Stojan; Iskra, Jernej; European Journal of Organic Chemistry; vol. 2017; nb. 3; (2017); p. 448 - 452 View in Reaxys With oxygen in toluene, T= 110 °C , p= 760.051Torr , Reagent/catalyst Buxaderas, Eduardo; Graziano-Mayer, Marilyn; Volpe, María Alicia; Radivoy, Gabriel; Synthesis (Germany); vol. 49; nb. 6; (2017); p. 1387 - 1393; Art.No: SS-2016-M0473-OP View in Reaxys

6 %Chromat.

With dihydrogen peroxide in water, Time= 12h, T= 90 °C , Green chemistry Zohreh, Nasrin; Tavakolizadeh, Maryam; Hosseini, Seyed Hassan; Pourjavadi, Ali; Bennett, Craig; Polymer (United Kingdom); vol. 112; (2017); p. 342 - 350 View in Reaxys Oxidation of benzyl alcohol A typical process was as follows. 50 mg of Fe3O4SiO2-GPTSCD was dispersed in 5 mL H2O with stirring at 50 C. Then 20 lL of benzyl alcohol and 1 mL of 10 percentNaClO aqueous were dropped into the suspension,respectively.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

299/438

2018-03-11 22:07:32


After 24 h, the mixture was extracted with10 mL of ethyl acetate three times. The organic phase wasconcentrated and analyzed by GC–MS using ethyl acetateas the solvent. With sodium hypochlorite in water, Time= 24h, T= 50 °C Zhou, Mi; Cai, Songtao; Li, Jie; Qian, Xin; Zheng, Haha; Journal of Inclusion Phenomena and Macrocyclic Chemistry; vol. 87; nb. 1-2; (2017); p. 45 - 51 View in Reaxys 2.2. Oxidation of benzylic alcohols by NGO To study the catalytic effect of the NGO sheets on the oxidationof benzylic alcohols, we used H2O2 as an oxidant in anaqueous solution. Various mass fractions of the NGO sheets((5–200)percent) and different reaction temperatures (RT to 100 °C)were investigated. In a preliminary experiment, benzyl alcoholwas heated in the presence of H2O as solvent, an excess amountof H2O2 as oxidant, and 200percent (mass fraction) of NGO as catalystat 100 °C for 24 h. To ensure that the only oxidant present wasH2O2, the reaction was carried out under N2 atmosphere. Tostudy the role of H2O2, the oxidation of benzyl alcohol was alsoconducted with different concentrations of H2O2 (10, 2.2, 1, 0.5and 0 equivalents (eq.)) in the presence of 100percent (mass fraction)NGO in 2 mL of DI water at 100 °C for 24 h. To optimizethe different reaction parameters, the effects on the yield wereinvestigated for different benzyl alcohol derivatives (benzylalcohol, and 4‐chloro, 4‐methoxy, and 4‐nitro derivatives), NGOmass fractions ((10–200)percent) reaction temperatures (RT to 100°C with (20–100)percent (mass fraction) of NGO and 2.2 eq. of H2O2),and reaction time (1–24 h with 20percent (mass fraction) of NGOand 2.2 eq. of H2O2 at 80 °C). The role of substituents on thebenzylic carbon in the oxidation process was investigated bystudying the oxidation of 1‐phenylethanol and diphenylmethanolin the presence of 20percent (mass fraction) of NGO and1.1 eq. of H2O2 at 80 °C for 24 h. Finally, to highlight the catalyticperformance of the NGO, the oxidation reactions of all of thebenzyl alcohol derivatives were conducted with H2O2 butwithout NGO at 100 °C for 24 h. The progress of all reactionswas monitored by thin layer chromatography (aluminumsheets, 20 × 20 cm, Merck Millipore) and gas chromatography(PHILIPS PU4500). After completion of the reaction the product was extracted into CH2Cl2 (3 × 10 mL). With dihydrogen peroxide in water, Time= 1h, T= 80 °C , p= 760.051Torr , Inert atmosphere Sedrpoushan, Alireza; Heidari, Masoud; Akhavan, Omid; Chinese Journal of Catalysis; vol. 38; nb. 4; (2017); p. 745 - 757 View in Reaxys 2.2. Oxidation of benzylic alcohols by NGO To study the catalytic effect of the NGO sheets on the oxidationof benzylic alcohols, we used H2O2 as an oxidant in anaqueous solution. Various mass fractions of the NGO sheets((5–200)percent) and different reaction temperatures (RT to 100 °C)were investigated. In a preliminary experiment, benzyl alcoholwas heated in the presence of H2O as solvent, an excess amountof H2O2 as oxidant, and 200percent (mass fraction) of NGO as catalystat 100 °C for 24 h. To ensure that the only oxidant present wasH2O2, the reaction was carried out under N2 atmosphere. Tostudy the role of H2O2, the oxidation of benzyl alcohol was alsoconducted with different concentrations of H2O2 (10, 2.2, 1, 0.5and 0 equivalents (eq.)) in the presence of 100percent (mass fraction)NGO in 2 mL of DI water at 100 °C for 24 h. To optimizethe different reaction parameters, the effects on the yield wereinvestigated for different benzyl alcohol derivatives (benzylalcohol, and 4‐chloro, 4‐methoxy, and 4‐nitro derivatives), NGOmass fractions ((10–200)percent) reaction temperatures (RT to 100°C with (20–100)percent (mass fraction) of NGO and 2.2 eq. of H2O2),and reaction time (1–24 h with 20percent (mass fraction) of NGOand 2.2 eq. of H2O2 at 80 °C). The role of substituents on thebenzylic carbon in the oxidation process was investigated bystudying the oxidation of 1‐phenylethanol and diphenylmethanolin the presence of 20percent (mass fraction) of NGO and1.1 eq. of H2O2 at 80 °C for 24 h. Finally, to highlight the catalyticperformance of the NGO, the oxidation reactions of all of thebenzyl alcohol derivatives were conducted with H2O2 butwithout NGO at 100 °C for 24 h. The progress of all reactionswas monitored by thin layer chromatography (aluminumsheets, 20 × 20 cm, Merck Millipore) and gas chromatography(PHILIPS PU4500). After completion of the reaction the product was extracted into CH2Cl2 (3 × 10 mL). With dihydrogen peroxide in water, Time= 9h, T= 80 °C , p= 760.051Torr , Inert atmosphere Sedrpoushan, Alireza; Heidari, Masoud; Akhavan, Omid; Chinese Journal of Catalysis; vol. 38; nb. 4; (2017); p. 745 - 757 View in Reaxys With water, sodium sulfate, Time= 1h, T= 20 °C , Irradiation, Electrochemical reaction, Green chemistry Zhang, Ruikang; Shao, Mingfei; Li, Zhenhua; Ning, Fanyu; Wei, Min; Evans, David G.; Duan, Xue; Chemistry A European Journal; vol. 23; nb. 34; (2017); p. 8142 - 8147

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

300/438

2018-03-11 22:07:32


View in Reaxys 2.4 General procedure for catalytic oxidation of alcohols General procedure: Oxidation reactions were carried out under aerial conditions using 2mL of solvent and aqueous H2O2 (30wtpercent) as oxidant. In a typical experiment, complex 1 (1.186μmol, 0.001g), the solvent (2mL) and the substrate (1mmol) were placed in a 25mL round bottomed glass flask. The mixture was heated to the desired temperature, and after addition of H2O2, the resulting solution was kept stable at the selected temperature to continue the reaction. At appropriate intervals, aliquots were taken and analyzed immediately by GC. The oxidation products were identified by comparison of their retention times with those of authentic samples With C28H27Br3N4O6V2, dihydrogen peroxide in water, acetonitrile, T= 70 °C , Green chemistry, Catalytic behavior, Solvent, Temperature Bikas, Rahman; Shahmoradi, Elaheh; Noshiranzadeh, Nader; Emami, Marzieh; Reinoso, Santiago; Inorganica Chimica Acta; vol. 466; (2017); p. 100 - 109 View in Reaxys 67 %Chro- With Nitrogen dioxide in acetonitrile, Time= 5h, T= 140 °C , p= 760.051Torr , Sealed tube mat., 16 %Chromat. Ren, Fangping; Tian, Xinzhe; Ren, Yun-Lai; Zhao, Shuang; Wang, Jianji; Zhao, Bo; Catalysis Communications; vol. 101; (2017); p. 98 - 101 View in Reaxys With sodium hydroxide in water, toluene, Time= 4h, T= 100 °C , p= 760.051Torr , Reagent/catalyst Weston, Jack O.; Miyamura, Hiroyuki; Yasukawa, Tomohiro; Sutarma, Dedi; Baker, Chloe A.; Singh, Preabjot K.; Bravo-Sanchez, Mariela; Sano, Naoko; Cumpson, Peter J.; Ryabenkova, Yulia; Kobayashi, Shu; Conte, Marco; Catalysis Science and Technology; vol. 7; nb. 18; (2017); p. 3985 - 3998 View in Reaxys With oxygen, potassium carbonate in water, Time= 6h, T= 30 °C , p= 760.051Torr , Reagent/catalyst Yoskamtorn, Tatchamapan; Yamazoe, Seiji; Takahata, Ryo; Nishigaki, Jun-Ichi; Thivasasith, Anawat; Limtrakul, Jumras; Tsukuda, Tatsuya; ACS Catalysis; vol. 4; nb. 10; (2014); p. 3696 - 3700 View in Reaxys With Ru(2,4,6-tris(2-pyridyl)-s-triazine)Cl3, Electrolysis, Reagent/catalyst Yamaguchi, Shingi; Kamiya, Kazuhide; Hashimoto, Kazuhito; Nakanishi, Shuji; Chemical Communications; vol. 53; nb. 75; (2017); p. 10437 - 10440 View in Reaxys With Na*Zn2Sb2, dihydrogen peroxide in water, Time= 7h, T= 85 °C Ni, Lubin; Patscheider, Joerg; Baldridge, Kim K.; Patzke, Greta R.; Chemistry - A European Journal; vol. 18; nb. 42; (2012); p. 13293 - 13298 View in Reaxys With 2O33W10Zn(2-)*46H2O*4Zn(2+)*2Sb(3+)*10Na(1+), dihydrogen peroxide in water, Time= 7h, T= 85 °C , Reagent/ catalyst Ni, Lubin; Patscheider, Joerg; Baldridge, Kim K.; Patzke, Greta R.; Chemistry - A European Journal; vol. 18; nb. 42; (2012); p. 13293 - 13298 View in Reaxys With oxygen, potassium hydoxide in water, Time= 8h, T= 20 °C , p= 760.051Torr , UV-irradiation, Catalytic behavior, Reagent/catalyst, Temperature Gu, Yulong; Li, Chunping; Bai, Jie; Liang, Haiou; Journal of Photochemistry and Photobiology A: Chemistry; vol. 351; (2018); p. 87 - 94 View in Reaxys Benzyl alcohol (BzOH) oxidation reactions with H2O2 were carried out in a glass reactor with a magnetic stirrer and a reflux condenser,immersed in a thermally controlled bath at 70 °C for 7 h. In a typical reaction, benzyl alcohol (Fluka>95percent) (9.11 mmol), was stirred with hydrogen peroxide (H2O2, Riedel de Han, 35 wt.percent in water)(2.28 mmol), using acetonitrile (AcN, Sintorgan, 99.5percent) (91.15 mmol)as solvent and M-M(60) as catalyst (100 mg).

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

301/438

2018-03-11 22:07:32


Reaction progress was followed taking samples at different times by a lateral tabulation without opening the reactor. Liquid samples were immediately filtered and analyzed by gas chromatography equipped with FID detector (HP-1capillary column) and identified by comparison with known standards. With dihydrogen peroxide in water, acetonitrile, Time= 7h, T= 70 °C , Green chemistry, Catalytic behavior Cánepa, Analía L.; Elías, Verónica R.; Vaschetti, Virginia M.; Sabre, Ema V.; Eimer, Griselda A.; Casuscelli, Sandra G.; Applied Catalysis A: General; vol. 545; (2017); p. 72 - 78 View in Reaxys With oxygen, Time= 4h, T= 60 °C , p= 750.075Torr , UV-irradiation, Reagent/catalyst Zhou, Min; Yang, Pengju; Yuan, Rusheng; Asiri, Abdullah M.; Wakeel, Muhammad; Wang, Xinchen; ChemSusChem; vol. 10; nb. 22; (2017); p. 4451 - 4456 View in Reaxys With oxygen, potassium carbonate in neat (no solvent), Time= 2.5h, T= 100 °C , p= 1500.15Torr , Green chemistry, Reagent/catalyst De Abreu, Wiury C.; Garcia, Marco A. S.; Nicolodi, Sabrina; De Moura, Carla V. R.; De Moura, Edmilson M.; RSC Advances; vol. 8; nb. 7; (2018); p. 3903 - 3909 View in Reaxys With [Mo2O6(m-trtzH)(H2O)2], dihydrogen peroxide in water, acetonitrile, Time= 24h, T= 70 °C , Reagent/catalyst Neves, Patrícia; Lysenko, Andrey B.; Gomes, Ana C.; Pillinger, Martyn; Gonçalves, Isabel S.; Valente, Anabela A.; Catalysis Letters; vol. 147; nb. 5; (2017); p. 1133 - 1143 View in Reaxys With dihydrogen peroxide, Time= 0.5h, T= 60 °C , Green chemistry, Temperature Karimi, Hirbod; Journal of the Chinese Chemical Society; vol. 62; nb. 7; (2015); p. 604 - 613 View in Reaxys 2H

2H

2H

2H

2H

2H

2H

2H

2H

O

HO 2H

2H

2H

2H

Rx-ID: 8565355 View in Reaxys 3/435 Yield 50 %

Conditions & References With manganese(IV) oxide in dichloromethane, Time= 24h, T= 20 °C , Oxidation Veith; Oldham; Dettner; Pasteels; Boland; Journal of Chemical Ecology; vol. 23; nb. 2; (1997); p. 429 - 443 View in Reaxys With oxygen, aluminum oxide, ruthenium in various solvent(s), T= 59.85 °C , p= 760Torr , Activation energy Yamaguchi, Kazuya; Mizuno, Noritaka; Angewandte Chemie - International Edition; vol. 41; nb. 23; (2002); p. 4538 - 4542 View in Reaxys With C33H32N7O7P2Ru, sodium acetate, T= 23 °C , pH= 5, Electrochemical reaction, Kinetics Vannucci, Aaron K.; Hull, Jonathan F.; Chen, Zuofeng; Binstead, Robert A.; Concepcion, Javier J.; Meyer, Thomas J.; Journal of the American Chemical Society; vol. 134; nb. 9; (2012); p. 3972 - 3975 View in Reaxys With FeII(1,3-bis(2'-pyridylimino)isoindoline)(CH3CN)3(H2O)0.5(ClO4)2, dihydrogen peroxide in acetonitrile, T= 25 °C , Inert atmosphere, Kinetics Pap, Jozsef S.; Cranswick, Matthew A.; Balogh-Hergovich; Barath, Gabor; Giorgi, Michel; Rohde, Gregory T.; Kaizer, Jozsef; Speier, Gabor; Que Jr., Lawrence; European Journal of Inorganic Chemistry; nb. 22-23; (2013); p. 3858 - 3866 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

302/438

2018-03-11 22:07:32


KIE study on competitive oxidation of benzyl alcohol and deuterated benzyl alcohol by t-BuOOH in the presence of iron complexes General procedure: This reaction was performed in presence of excess substrate to avoid further oxidation of the benzaldehyde, derived from benzyl alcohol, to benzoic acid which inhibits the determination of the exact KIE value. More over, in order to improve the accuracy in measuring the amount of deuterated benzyl alcohol product, a 1:6 mixture of benzyl alcohol and deuterated benzyl alcohol was used. The reaction procedure: t-BuOOH (0.075 mmol) was added to a mixture of benzyl alcohol (0.1 mmol) and benzyl-d7-alcohol(0.6 mmol), imidazole (0.01 mmol), NHPI (0.02 mmol), catalysts1a or 1b (1.0 103 mmol), and solvent (CH3CN, 1 mL). The mixture was stirred for the given time at 50 °C. Reaction conversion was monitored by GC/MS analysis of 20 lL aliquots with drawn periodically from the reaction mixture. All the reactions were run at least in triplicate and the average KIE values have been presented. With 1H-imidazole, tert.-butylhydroperoxide, N -hydroxyphthalimide, [Fe(bpc)Cl2][Et4N] in acetonitrile, Time= 1h, T= 50 °C , Reagent/catalyst Bae, Jeong Mi; Lee, Myoung Mi; Lee, Seul Ah; Lee, Sun Young; Bok, Kwon Hee; Kim, Jinheung; Kim, Cheal; Inorganica Chimica Acta; vol. 451; (2016); p. 8 - 15 View in Reaxys With potassium ferrate(VI), sodium hydroxide in aq. phosphate buffer, tert-butyl alcohol, T= 25 °C , pH= 9.5, Kinetics Xie, Jianhui; Lo, Po-Kam; Lam, Chow-Shing; Lau, Kai-Chung; Lau, Tai-Chu; Dalton Transactions; vol. 47; nb. 1; (2018); p. 240 - 245 View in Reaxys

O

HO

H O

Rx-ID: 9272168 View in Reaxys 4/435 Yield 90 %

Conditions & References With polystyrene-supported(catecholato) oxoRe cat. act. by iPrOH, dimethyl sulfoxide in toluene, Time= 2h, Heating, Dean-Stark apparatus Arterburn, Jeffrey B.; Liu, Minghua; Perry, Marc C.; Helvetica Chimica Acta; vol. 85; nb. 10; (2002); p. 3225 3236 View in Reaxys

10 %Spectr., 80 %Spectr.

With Cp*Ir(Cl)2(nBu2Im), silver trifluoromethanesulfonate, Time= 12h, T= 130 °C Prades, Amparo; Corberan, Rosa; Poyatos, Macarena; Peris, Eduardo; Chemistry - A European Journal; vol. 14; nb. 36; (2008); p. 11474 - 11479 View in Reaxys With ruthenium trichloride, 1,3-bis-(diphenylphosphino)propane, nitrobenzene, Time= 16h, T= 150 °C , Inert atmosphere Feng, Chao; Liu, Yong; Peng, Shengming; Shuai, Qi; Deng, Guojun; Li, Chao-Jun; Organic Letters; vol. 12; nb. 21; (2010); p. 4888 - 4891 View in Reaxys

54 %Chro- Typical procedure for the oxidation of alcohols mat., 46 General procedure: To a solution of alcohol (0.1 g) in2 mL of solvent was added the appropriate amount of GO (as %Chromat. indicated in Table2). The resulting mixture was irradiated in an ultrasonic bath or with an ultrasonic probe (methods A to G) for the time indicated in Table 2 prior to GC/MS analysis. The mixture was filtered through a sintered funnel and evaporated under reduced pressure. Purification was achieved by column chromatography using hexane as the eluent. The spectroscopic data of the obtained aldehydes were compared with authentic samples.16 Other products were also known compounds10–12 and were characterized by 1H NMR, mass spectrometry, and FT-IR spectroscopy. With Graphite oxide in hexane, Time= 0.5h, Sonication

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

303/438

2018-03-11 22:07:32


Mirza-Aghayan, Maryam; Kashef-Azar, Elnaz; Boukherroub, Rabah; Tetrahedron Letters; vol. 53; nb. 37; (2012); p. 4962 - 4965 View in Reaxys 44 %Chro- Typical procedure for the oxidation of alcohols mat., 55 General procedure: To a solution of alcohol (0.1 g) in2 mL of solvent was added the appropriate amount of GO (as %Chromat. indicated in Table2). The resulting mixture was irradiated in an ultrasonic bath or with an ultrasonic probe (methods A to G) for the time indicated in Table 2 prior to GC/MS analysis. The mixture was filtered through a sintered funnel and evaporated under reduced pressure. Purification was achieved by column chromatography using hexane as the eluent. The spectroscopic data of the obtained aldehydes were compared with authentic samples.16 Other products were also known compounds10–12 and were characterized by 1H NMR, mass spectrometry, and FT-IR spectroscopy. With Graphite oxide in chloroform, Time= 0.75h, Sonication Mirza-Aghayan, Maryam; Kashef-Azar, Elnaz; Boukherroub, Rabah; Tetrahedron Letters; vol. 53; nb. 37; (2012); p. 4962 - 4965 View in Reaxys With C23H27ClIrN5 (2+)*2CF3O3S(1-) in 1,2-dichloro-benzene, Time= 24h, T= 150 °C , Sealed tube, Reagent/catalyst Valencia, Marta; Müller-Bunz, Helge; Gossage, Robert A.; Albrecht, Martin; Chemical Communications; vol. 52; nb. 16; (2016); p. 3344 - 3347 View in Reaxys With C20H27ClIrN4 (1+)*CF3O3S(1-) in 1,2-dichloro-benzene, Time= 24h, T= 150 °C , Sealed tube, Reagent/catalyst Valencia, Marta; Müller-Bunz, Helge; Gossage, Robert A.; Albrecht, Martin; Chemical Communications; vol. 52; nb. 16; (2016); p. 3344 - 3347 View in Reaxys With 6-hydroxy-2-methylpyridine, bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] in tetrahydrofuran, Time= 24h, T= 150 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst Sahoo; Jiang; Bruneau; Sharma; Suresh; Achard; RSC Advances; vol. 6; nb. 102; (2016); p. 100554 - 100558 View in Reaxys 50 %Spectr., 50 %Spectr.

With 1,1,1,3',3',3'-hexafluoro-propanol, nitric acid, Time= 24h, T= 20 °C Možina, Štefan; Stavber, Stojan; Iskra, Jernej; European Journal of Organic Chemistry; vol. 2017; nb. 3; (2017); p. 448 - 452 View in Reaxys With C19H28IrN5 (2+)*2CF3O3S(1-) in 1,2-dichloro-benzene, Time= 24h, T= 150 °C , Sealed tube, Catalytic behavior, Reagent/catalyst, Time Vivancos, Ángela; Petronilho, Ana; Cardoso, Joao; Müller-Bunz, Helge; Albrecht, Martin; Dalton Transactions; vol. 47; nb. 1; (2018); p. 74 - 82 View in Reaxys H

HO

O

Cl

Rx-ID: 28752406 View in Reaxys 5/435 Yield 84.7 %, 6.3 %

Conditions & References 3.2. Experimental procedure General procedure: The continuous ow microreactor system was assembled as shown in Figure 1. The Me2SO, activator, and benzyl alcohol were loaded into HPLC pumps with appropriate ow rates. After a stable period of 10 min, the effluent was collected in a separation funnel through which we could observe the color and layering by controlling the valve. Then effluent was finally collected into a continuously stirred ask containing an excess amount of triethylamine. The temperatures were kept constant by a water bath with constant circulation temperatures and a thermostat magnetism agitator. All of the reactions were monitored offline by GC-MS; the yields and selectivities were calculated by the method of area normalization. Upon completion of the reaction, the mixture of triethylamine and effluent was washed with 5percent HCl and the organic layer was separated. Then the organic layer was washed 2 or 3 times

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

304/438

2018-03-11 22:07:32


until the mixture in the separation funnel reached neutral. In the process, the aqueous layers were always extracted twice with dichloromethane. At last, the organic layers were collected together and dried by anhydrous MgSO4 for 4 h. The final product, benzaldehyde, was obtained after filtration and reduced pressure distillation. Stage 1: With oxalyl dichloride, dimethyl sulfoxide, T= 15 °C , Flow reactor, Swern Oxidation Stage 2: With triethylamine, T= 15 °C , Flow reactor, Swern Oxidation, Temperature Zhu, Lin; Xu, Xiaohui; Zheng, Fuping; Turkish Journal of Chemistry; vol. 42; nb. 1; (2018); p. 75 - 85 View in Reaxys 65 %, 35 %

Stage 1: With bis(trichloromethyl) carbonate, 4-(2-(2-(methylsulfinyl)ethyl)-4-nitrophenyl)morpholine in dichloromethane, Time= 1h, T= -30 °C , Inert atmosphere, Swern Oxidation Stage 2: With triethylamine in dichloromethane, T= -30 °C , Inert atmosphere, Swern Oxidation, Temperature Ye, Xiaojing; Fu, Hongliang; Ma, Jiahao; Zhong, Weihui; Synthetic Communications; vol. 46; nb. 10; (2016); p. 885 - 892 View in Reaxys

36 %, 63 %

Stage 1: With bis(trichloromethyl) carbonate, 4-(2-(2-(methylsulfinyl)ethyl)-4-nitrophenyl)morpholine in dichloromethane, Time= 1h, T= -5 °C , Inert atmosphere, Swern Oxidation Stage 2: With triethylamine in dichloromethane, T= -5 °C , Inert atmosphere, Swern Oxidation Ye, Xiaojing; Fu, Hongliang; Ma, Jiahao; Zhong, Weihui; Synthetic Communications; vol. 46; nb. 10; (2016); p. 885 - 892 View in Reaxys

54 %Chro- With vanadium(V) oxychloride in acetonitrile, Time= 3h, T= 80 °C , Inert atmosphere mat., 24 %Chromat. Du, Zhongtian; Miao, Hong; Hong, Ma.; Sun, Zhiqiang; Jiping, Ma.; Xu, Jie; Advanced Synthesis and Catalysis; vol. 351; nb. 4; (2009); p. 558 - 562 View in Reaxys 2H

O

2H

2H

O

Rx-ID: 45241101 View in Reaxys 6/435 Yield

Conditions & References With triethylamine, pyridinium chlorochromate in dichloromethane, T= 20 °C , Sealed tube Bera, Sourav Sekhar; Debbarma, Suvankar; Ghosh, Avick Kumar; Chand, Santanu; Maji, Modhu Sudan; Journal of Organic Chemistry; vol. 82; nb. 1; (2017); p. 420 - 430 View in Reaxys With pyridinium chlorochromate in dichloromethane, T= 20 °C Sk, Md Raja; Bera, Sourav Sekhar; Maji, Modhu Sudan; Organic Letters; vol. 20; nb. 1; (2018); p. 134 - 137 View in Reaxys H

HO

O

Rx-ID: 817413 View in Reaxys 7/435 Yield 61 %, 38 %

Conditions & References With reusable unsupported rhenium nanocrystalline particle in neat (no solvent), Time= 3h, T= 180 °C , Inert atmosphere, Green chemistry Yi, Jing; Miller, Jeffrey T.; Zemlyanov, Dmitry Y.; Zhang, Ruihong; Dietrich, Paul J.; Ribeiro, Fabio H.; Suslov, Sergey; Abu-Omar, Mahdi M.; Angewandte Chemie - International Edition; vol. 53; nb. 3; (2014); p. 833 - 836; Angew. Chem.; vol. 126; nb. 03; (2013); p. 852 - 855,4 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

305/438

2018-03-11 22:07:32


56 %, 26 %

With water, palladium diacetate, sodium 3-(diphenylphosphanyl)benzenesulfonate, Time= 16h, T= 100 °C , Sealed tube Hikawa, Hidemasa; Matsuda, Naoya; Suzuki, Hideharu; Yokoyama, Yuusaku; Azumaya, Isao; Advanced Synthesis and Catalysis; vol. 355; nb. 11-12; (2013); p. 2308 - 2320 View in Reaxys

53.4 %, 33.8 %

With 1 Pd/C Selcat Q6, oxygen, Time= 2h, T= 120 °C , p= 7757.43Torr , chemoselective reaction Lopez-Sanchez, Jose Antonio; Dimitratos, Nikolaos; Glanville, Neil; Kesavan, Lokesh; Hammond, Ceri; Edwards, Jennifer K.; Carley, Albert F.; Kiely, Christopher J.; Hutchings, Graham J.; Applied Catalysis A: General; vol. 391; nb. 1-2; (2011); p. 400 - 406 View in Reaxys

31 %, 18 %

With Cu–Al hydrotalcite in 1,4-dioxane, Time= 0.045h, T= 220 °C , p= 12001.2Torr Aellig, Christof; Jenny, Florian; Scholz, David; Wolf, Patrick; Giovinazzo, Isabella; Kollhoff, Fabian; Hermans, Ive; Catalysis Science and Technology; vol. 4; nb. 8; (2014); p. 2326 - 2331 View in Reaxys Time= 6h, T= 176 °C , Heating Berthon, Bruno; Forestiere, Alain; Leleu, Gerard; Sillion, Bernard; Tetrahedron Letters; vol. 22; nb. 41; (1981); p. 4073 - 4076 View in Reaxys T= 150 - 300 °C , Leiten ueber einen Kupfer-Zink-Aluminium-Katalysator Sultanow et al.; Zhurnal Obshchei Khimii; vol. 28; (1958); p. 787,788; engl. Ausg. S. 765 View in Reaxys With palladium(II) acetylacetonate, triphenylphosphine, Product distribution Moreno-Manas, M.; Trius, A.; Tetrahedron; vol. 37; nb. 17; (1981); p. 3009 - 3016 View in Reaxys With palladium on activated charcoal, hydrogen in ethanol, Time= 0.3h, solvent and catalysts dependence, hydrogenolysis, Product distribution, Rate constant Rusina, S. V.; Litvin, E. F.; Sharf, V. Z.; Russian Chemical Bulletin; vol. 42; nb. 7; (1993); p. 1200 - 1203; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 7; (1993); p. 1257 - 1261 View in Reaxys With copper chromite, Time= 1h, T= 250 °C , var. temp. and time, Product distribution Pillai; Journal of the Indian Chemical Society; vol. 74; nb. 2; (1997); p. 169 - 170 View in Reaxys With air, phosphomolybdic acid hydrate, p= 760Torr , Disproportionation, dehydrogenation, Kinetics, Further Variations: Reagents Athilakshmi; Olaofe; Viswanathan; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 36; nb. 4; (1997); p. 332 - 334 View in Reaxys With tetraaquapalladium(II), T= 38 °C , p= 750.06Torr Potekhin; Matsura; Ukraintsev; Russian Journal of General Chemistry; vol. 70; nb. 6; (2000); p. 828 - 831 View in Reaxys With lanthanum copper oxide, T= 219.85 °C , Product distribution, Further Variations: Temperatures, Catalysts Srinivasan; Viswanathan; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 41; nb. 7; (2002); p. 1349 - 1354 View in Reaxys With Pd147(o-phenanthroline)32O60(OC(O)tBu)30, T= 60 °C , Kinetics, Further Variations: Catalysts

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

306/438

2018-03-11 22:07:32


Stolyarov; Gaugash; Kryukova; Kochubei; Vargaftik; Moiseev; Russian Chemical Bulletin; vol. 53; nb. 6; (2004); p. 1194 - 1199 View in Reaxys With palladium/alumina, oxygen, T= 100 °C , Base condition, neat (no solvent) Wang, Hu; Deng, Shao-Xin; Shen, Zhu-Rui; Wang, Jin-Gui; Ding, Da-Tong; Chen, Tie-Hong; Green Chemistry; vol. 11; nb. 10; (2009); p. 1499 - 1502 View in Reaxys With oxygen in cyclohexane, T= 80 °C , p= 1520.1Torr Villa, Alberto; Wang, Di; Dimitratos, Nikolaos; Su, Dangsheng; Trevisan, Valentina; Prati, Laura; Catalysis Today; vol. 150; nb. 1-2; (2010); p. 8 - 15 View in Reaxys With 10 palladium on activated charcoal, oxygen in cyclohexane, T= 80 °C , p= 1520.1Torr Chan-Thaw, Carine E.; Villa, Alberto; Prati, Laura; Thomas, Arne; Chemistry - A European Journal; vol. 17; nb. 3; (2011); p. 1052 - 1057 View in Reaxys With carbon nanotube-supported TiO2 nanoparticles in para-xylene, Time= 6h, T= 119.84 °C , Inert atmosphere Fang, Wenhao; Chen, Jiashu; Zhang, Qinghong; Deng, Weiping; Wang, Ye; Chemistry - A European Journal; vol. 17; nb. 4; (2011); p. 1247 - 1256 View in Reaxys With oxygen, Time= 2h, T= 120 °C , p= 7757.43Torr Dimitratos, Nikolaos; Lopez-Sanchez, Jose Antonio; Morgan, David; Carley, Albert F.; Tiruvalam, Ramchandra; Kiely, Christopher J.; Bethell, Donald; Hutchings, Graham J.; Physical Chemistry Chemical Physics; vol. 11; nb. 25; (2009); p. 5142 - 5153 View in Reaxys 2.3. Catalytic activity General procedure: The solvent-free aerobic oxidation of benzyl alcohol using molecular O2 was carried out in a batch-type reactor operated under atmospheric conditions. Experiments were conducted using a three-necked glass flask (capacity 25 mL) precharged with 5.4 g of benzyl alcohol and 20 mg of catalyst. The mixture was stirred using a magnetic stirrer and heated in a silicon oil bath. The system was equipped with a thermocouple to control the temperature and a reflux condenser. In each reaction run, the mixture was heated to 160 °C under vigorous stirring (stirring rate 1000 rpm). Oxygen was bubbled into the mixture at a constant flow rate of 20 mL/min using a mass flow controller to initiate the reaction. After the allowed reaction time, the catalyst powder was filtered off and the liquid organic products were analyzed using an Agilent 6890 gas chromatograph equipped with an HP-5 capillary column (30 m long and 0.32 mm in diameter, packed with silica-based Supel-cosil). With Pd/CeO2, oxygen, Time= 1h, T= 160 °C , chemoselective reaction Chen, Yuanting; Zheng, Huijian; Guo, Zhen; Zhou, Chunmei; Wang, Chuan; Borgna, Armando; Yang, Yanhui; Journal of Catalysis; vol. 283; nb. 1; (2011); p. 34 - 44 View in Reaxys With oxygen, Time= 4h, T= 100 °C , p= 7500.75Torr , Autoclave Miedziak, Peter; Sankar, Meenakshisundaram; Dimitratos, Nikolaos; Lopez-Sanchez, Jose A.; Carley, Albert F.; Knight, David W.; Taylor, Stuart H.; Kiely, Christopher J.; Hutchings, Graham J.; Catalysis Today; vol. 164; nb. 1; (2011); p. 315 - 319 View in Reaxys , T= 80 °C , p= 1520.1Torr Chan-Thaw, Carine E.; Villa, Alberto; Veith, Gabriel M.; Kailasam, Kamalakannan; Adamczyk, Leslie A.; Unocic, Raymond R.; Prati, Laura; Thomas, Arne; Chemistry - An Asian Journal; vol. 7; nb. 2; (2012); p. 387 - 393 View in Reaxys With oxygen in cyclohexane, T= 100 °C , p= 1520.1Torr

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

307/438

2018-03-11 22:07:32


Villa; Plebani; Schiavoni; Milone; Piperopoulos; Galvagno; Prati; Catalysis Today; vol. 186; nb. 1; (2012); p. 76 - 82 View in Reaxys With Pd0.3wt/TiO2, Time= 6h, T= 24.84 °C , p= 760.051Torr , Irradiation, Inert atmosphere Shiraishi, Yasuhiro; Fujiwara, Keisuke; Sugano, Yoshitsune; Ichikawa, Satoshi; Hirai, Takayuki; ACS Catalysis; vol. 3; nb. 3; (2013); p. 312 - 320 View in Reaxys in neat (no solvent), T= 120 °C , p= 15001.5Torr , Inert atmosphere Nowicka, Ewa; Hofmann, Jan P.; Parker, Stewart F.; Sankar, Meenakshisundaram; Lari, Giacomo M.; Kondrat, Simon A.; Knight, David W.; Bethell, Donald; Weckhuysen, Bert M.; Hutchings, Graham J.; Physical Chemistry Chemical Physics; vol. 15; nb. 29; (2013); p. 12147 - 12155 View in Reaxys With oxygen in neat (no solvent), Time= 2.5h, T= 100 °C , p= 4500.45Torr , Autoclave, Reagent/catalyst Silva, Tiago A. G.; Landers, Richard; Rossi, Liane M.; Catalysis Science and Technology; vol. 3; nb. 11; (2013); p. 2993 - 2999 View in Reaxys With oxygen in neat (no solvent), Time= 20h, T= 120 °C , p= 760.051Torr , Catalytic behavior Qiao, Zhen-An; Zhang, Pengfei; Chai, Song-Hai; Chi, Miaofang; Veith, Gabriel M.; Gallego, Nidia C.; Kidder, Michelle; Dai, Sheng; Journal of the American Chemical Society; vol. 136; nb. 32; (2014); p. 11260 - 11263 View in Reaxys With oxygen, Time= 2h, T= 120 °C , p= 750.075Torr , Catalytic behavior, Reagent/catalyst Morad, Moataz; Sankar, Meenakshisundaram; Cao, Enhong; Nowicka, Ewa; Davies, Thomas E.; Miedziak, Peter J.; Morgan, David J.; Knight, David W.; Bethell, Donald; Gavriilidis, Asterios; Hutchings, Graham J.; Catalysis Science and Technology; vol. 4; nb. 9; (2014); p. 3120 - 3128 View in Reaxys With oxygen in neat (no solvent), T= 119.84 °C , p= 750.075Torr , Catalytic behavior, Reagent/catalyst Hutchings, Graham J.; Catalysis Today; vol. 238; (2014); p. 69 - 73 View in Reaxys With oxygen in cyclohexane, T= 80 °C , p= 1520.1Torr , Catalytic behavior, Reagent/catalyst Chan-Thaw, Carine E.; Villa, Alberto; Veith, Gabriel M.; Prati, Laura; ChemCatChem; vol. 7; nb. 8; (2015); p. 1338 - 1346 View in Reaxys With Pd nanoparticles and TiO2, oxygen in cyclohexane, T= 60 °C , p= 1500.15Torr Villa, Alberto; Ferri, Davide; Campisi, Sebastiano; Chan-Thaw, Carine E.; Lu, Ye; Kröcher, Oliver; Prati, Laura; ChemCatChem; vol. 7; nb. 16; (2015); p. 2534 - 2541 View in Reaxys 2.3. Aerobic oxidation of benzyl alcohol The catalytic reaction was carried out using molecular oxygen under solvent-free conditions. Benzyl alcohol (5.174 mL, 50 mmol) was loaded in a glass flask pre-charged with 0.01 g of catalyst. The mixture was immersed in a 160°C of oil bath while gaseous oxygen was purged (20 mL min−1) to initiate the reaction. The reaction was allowed to go on for 1 h under vigorous stirring (1200 rpm). After the reaction, the solid catalyst was filtered off while the liquid phase was analyzed by Agilent gas chromatograph 6890 equipped with HP-5 capillary column. Dodecane was used as the internal standard to measure the percentage of remaining reactant and products so as to calculate benzyl alcohol conversion and benzaldehyde selectivity values. With oxygen in neat (no solvent), Time= 1h, T= 160 °C , Catalytic behavior, Reagent/catalyst Yan, Yibo; Jia, Xinli; Yang, Yanhui; Catalysis Today; vol. 259; nb. Part 2; (2016); p. 292 - 302 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

308/438

2018-03-11 22:07:32


With Au-Pd/TiO2, oxygen in o-xylene, T= 120 °C , p= 2400.24Torr , Flow reactor, Solvent, Temperature Constantinou, Achilleas; Wu, Gaowei; Corredera, Albert; Ellis, Peter; Bethell, Donald; Hutchings, Graham J.; Kuhn, Simon; Gavriilidis, Asterios; Organic Process Research and Development; vol. 19; nb. 12; (2015); p. 1973 - 1979 View in Reaxys 34 %Spectr., 34 %Spectr.

With palladium diacetate, sodium 3-(diphenylphosphanyl)benzenesulfonate in water, Time= 16h, T= 80 °C , Sealed tube, Inert atmosphere Hikawa, Hidemasa; Koike, Toshitaka; Izumi, Kyoko; Kikkawa, Shoko; Azumaya, Isao; Advanced Synthesis and Catalysis; vol. 358; nb. 5; (2016); p. 784 - 791 View in Reaxys 2.3. General procedure for alcohol dehydrogenation reaction General procedure: The catalytic experiments were carried out in a fixed bed reactor (1.5cm id) at atmospheric pressure under N2 flow. About 0.5g of the catalyst was loaded and pretreatment was done in N2 gas flow (purity 99.99percent, 30mL/min) at 723K for 4h. A thermocouple was inserted in the catalyst bed to measure the catalyst bed temperature. After pretreatment, the reactor was cooled to the desired reaction temperature and the reactant (benzyl alcohol) was fed at a flow rate of 3.0mLh−1 along with the N2 gas flow at a rate of 30mL/min to keep the WHSV at 8.56h −1. The product was collected in an ice cold trap periodically for every 60min and analyzed by a gas chromatograph (CIC, India) equipped with a flame ionization detector and SE-30 column. The oven temperature was kept at 483K, with ramp rate 10K/min whereas injector and detector temperature were kept at 503 K during the analysis. (0012) The regeneration of the catalyst was done by treating the spent catalyst with O2/N2 mixture (1:9vol ratios) in the same flow as reaction condition at 673 K temperature. Then reactor was flushed with N2 flow for one hour and feed mixture was introduced and product was collected and analyzed as described earlier. (0013) In the case of dehydrogenation of primary alcohol substrates (ethanol, 1-Propanol, 1-butanol and 1-octanol) the reactor effluent was analyzed online for first three substrates and offline for 1-octanol. We used a gas chromatograph (CIC, India) equipped with a flame ionization detector and SE-30 column. All transfer lines from the vaporizer to the reactor and gas chromatograph (GC) were heated to above 383K to avoid condensation of the reactants and products. The oven temperature was kept at 383K with ramp rate 5K/min whereas injector and detector temperature were kept at 403 K during the online analysis. For 1-octanol dehydrogenation product, the G.C conditions were kept same as for benzyl alcohol. With ZnO-CeO2 mixed oxide, Time= 1h, T= 499.84 °C , p= 760.051Torr , Inert atmosphere, Temperature Enjamuri, Nagasuresh; Hassan, Shahid; Auroux, Aline; Pandey, Jai Krishna; Chowdhury, Biswajit; Applied Catalysis A: General; vol. 523; (2016); p. 21 - 30 View in Reaxys With hydrogen, T= 299.84 °C Li, Maoshuai; Wang, Xiaodong; Cárdenas-Lizana, Fernando; Keane, Mark A.; Catalysis Today; vol. 279; (2017) View in Reaxys With bis(tetrabutylammonium) hexamolybdate, isopropyl alcohol, Time= 6h, T= 200 °C , Microwave irradiation Larsen, Daniel B.; Petersen, Allan R.; Dethlefsen, Johannes R.; Teshome, Ayele; Fristrup, Peter; Chemistry - A European Journal; vol. 22; nb. 46; (2016); p. 16621 - 16631 View in Reaxys With oxygen in neat (no solvent), T= 120 °C , p= 750.075Torr Abis, Laura; Freakley, Simon J.; Dodekatos, Georgios; Morgan, David J.; Sankar, Meenakshisundaram; Dimitratos, Nikolaos; He, Qian; Kiely, Christopher J.; Hutchings, Graham J.; ChemCatChem; vol. 9; nb. 15; (2017); p. 2914 - 2918 View in Reaxys With oxygen, Time= 1h, T= 120 °C , p= 3000.3Torr , Catalytic behavior, Reagent/catalyst, Temperature, Pressure Khawaji, Motaz; Chadwick, David; ChemCatChem; vol. 9; nb. 23; (2017); p. 4353 - 4363 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

309/438

2018-03-11 22:07:32


H 13 2 C HO

H 13C O

Rx-ID: 2034614 View in Reaxys 8/435 Yield 99 %

Conditions & References With Dess-Martin periodane Xiang, Jason S.; Fuchs; Tetrahedron Letters; vol. 37; nb. 30; (1996); p. 5269 - 5272 View in Reaxys

99 %

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide, Time= 0.333333h, T= 20 °C An, Wan-Kai; Han, Man-Yi; Wang, Chang-An; Yu, Si-Min; Zhang, Yuan; Bai, Shi; Wang, Wei; Chemistry--A European Journal; vol. 20; nb. 35; (2014); p. 11019 - 11028,10 View in Reaxys

84 %

With pyridinium chlorochromate in dichloromethane, T= 20 °C Blake, Michael E.; Bartlett, Kevin L.; Jones Jr., Maitland; Journal of the American Chemical Society; vol. 125; nb. 21; (2003); p. 6485 - 6490 View in Reaxys

80 %

With Dess-Martin periodane in dichloromethane, Time= 4h, T= 20 °C Davies, Paul W.; Martin, Nicolas; Spencer, Neil; Beilstein Journal of Organic Chemistry; vol. 7; (2011); p. 839 846 View in Reaxys

64 %

With pyridinium chlorochromate in dichloromethane, T= 0 - 25 °C , Inert atmosphere West, Thomas H.; Walden, Daniel M.; Taylor, James E.; Brueckner, Alexander C.; Johnston, Ryne C.; Cheong, Paul Ha-Yeon; Lloyd-Jones, Guy C.; Smith, Andrew D.; Journal of the American Chemical Society; vol. 139; nb. 12; (2017); p. 4366 - 4375 View in Reaxys

54 %

With pyridinium chlorochromate in dichloromethane, T= 0 - 20 °C , Inert atmosphere, Schlenk technique Wang, Pan; Feng, Liang-Wen; Wang, Lijia; Li, Jun-Fang; Liao, Saihu; Tang, Yong; Journal of the American Chemical Society; vol. 137; nb. 14; (2015); p. 4626 - 4629 View in Reaxys

60 % Turn- With manganese(IV) oxide, benzyl alcohol in hexane, T= 20 °C ov. Cavaleiro, Jose A. S.; Neves, Maria G. P. S.; Hewlins, Michael J. E.; Jackson, Anthony H.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 7; (1990); p. 1937 - 1943 View in Reaxys With pyridinium chlorochromate Huan, Zhenwei; Landgrebe, John A.; Peterson, Kimberly; Tetrahedron Letters; vol. 24; nb. 28; (1983); p. 2829 2832 View in Reaxys With dipyridinium dichromate in dichloromethane, Time= 16h Bjorklund, Jeffrey A.; Leete, Edward; Phytochemistry (Elsevier); vol. 31; nb. 11; (1992); p. 3883 - 3888 View in Reaxys With Swern's oxidizing agent Geletneky, Christian; Foersterling, Frank-Holger; Bock, Willi; Berger, Stefan; Chemische Berichte; vol. 126; nb. 11; (1993); p. 2397 - 2402 View in Reaxys With dipyridinium dichromate, Oxidation

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

310/438

2018-03-11 22:07:32


Yamataka, Hiroshi; Sasaki, Daizo; Kuwatani, Yoshiyuki; Mishima, Masaaki; Tsuno, Yuho; Journal of the American Chemical Society; vol. 119; nb. 42; (1997); p. 9975 - 9979 View in Reaxys With dipyridinium dichromate Yamataka, Hiroshi; Shimizu, Makoto; Mishima, Masaaki; Bulletin of the Chemical Society of Japan; vol. 75; nb. 1; (2002); p. 127 - 129 View in Reaxys 400 mg

With Dess-Martin periodane in dichloromethane, Time= 4h, T= 20 °C Huang, Bo; Shen, Yangyong; Mao, Zhenjun; Liu, Yu; Cui, Sunliang; Organic Letters; vol. 18; nb. 19; (2016); p. 4888 - 4891 View in Reaxys

2H

2H

2H

HO

O

Rx-ID: 2063917 View in Reaxys 9/435 Yield 94 %

Conditions & References With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide, Time= 3h, T= 20 °C , Inert atmosphere Ramachandran, P. Veeraraghavan; Nicponski, Daniel R.; Chemical Communications; vol. 50; nb. 96; (2014); p. 15216 - 15219 View in Reaxys

81 %

With 3 A molecular sieve, pyridinium chlorochromate in dichloromethane, Time= 4h, T= 25 °C O'Hagan, David; Goss, Rebecca J. M.; Meddour, Abdelkrim; Courtieu, Jacques; Journal of the American Chemical Society; vol. 125; nb. 2; (2003); p. 379 - 387 View in Reaxys

73 %

With dipyridinium dichromate in dichloromethane, Time= 24h, T= 20 °C , Inert atmosphere Watanabe, Yohsuke; Yamazaki, Takashi; Journal of Organic Chemistry; vol. 76; nb. 6; (2011); p. 1957 - 1960 View in Reaxys

67 %

With bis-triphenylphosphine-palladium(II) chloride, potassium carbonate in tetrahydrofuran, Time= 20h, T= 65 - 70 °C , Inert atmosphere, Schlenk technique Liu, Chao; Tang, Shan; Lei, Aiwen; Chemical Communications; vol. 49; nb. 13; (2013); p. 1324 - 1326 View in Reaxys

63 %

With pyridinium chlorochromate in dichloromethane, Time= 3h, T= 0 - 20 °C Bejot, Romain; Tisserand, Steve; Li, De Run; Falck; Mioskowski, Charles; Tetrahedron Letters; vol. 48; nb. 22; (2007); p. 3855 - 3858 View in Reaxys

29 %

With aluminum oxide, pyridinium chlorochromate in dichloromethane, Time= 2.5h, Ambient temperature Kawai, Yasushi; Saitou, Kentarou; Hida, Kouichi; Dao, Duc Hai; Ohno, Atsuyoshi; Bulletin of the Chemical Society of Japan; vol. 69; nb. 9; (1996); p. 2633 - 2638 View in Reaxys With ammonium cerium(IV) nitrate in water McMahon, Robert J.; Abelt, Christopher J.; Chapman, Orville L.; Johnson, Jeffery W.; Kreil, Curits L.; et al.; Journal of the American Chemical Society; vol. 109; nb. 8; (1987); p. 2456 - 2469 View in Reaxys With pyridine, chromium(VI) oxide Rhodes, Christopher J.; Agirbas, Hikmet; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 3; (1992); p. 397 - 402

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

311/438

2018-03-11 22:07:32


View in Reaxys With lt;RuVL(O)gt;2+-complex lt;HL = lt;2-hydroxy-2-(2-pyridyl)ethylgt;bislt;2-(2-pyridyl)ethylgt;aminegt; in perchloric acid, T= 24.9 °C , Mechanism, Rate constant Che, Chi-Ming; Ho, Clare; Lau, Tai-Chu; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 5; (1991); p. 1259 - 1263 View in Reaxys With quinolinium dichromate(VI) in N,N-dimethyl-formamide, T= 39.9 °C , Rate constant Dey, Doyamoy; Mahanti, Mahendra K.; Journal of Organic Chemistry; vol. 55; nb. 23; (1990); p. 5848 - 5850 View in Reaxys With chloramine-B in water, acetic acid, Rate constant Mukherjee, Jogeshwar; Banerji, Kalyan K.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 676 - 678 View in Reaxys With tripropylammonium fluorochromate (VI) in dimethyl sulfoxide, T= 24.9 °C , ΔH(excit.), ΔS(excit.); primari kinetic isotope effect, Rate constant, Kinetics, Thermodynamic data Banerji, Kalyan K.; Journal of Organic Chemistry; vol. 53; nb. 10; (1988); p. 2154 - 2159 View in Reaxys With cis-nitrous acid in sulfuric acid, T= 25 °C , acidity dependence, Rate constant Moodie, Roy B.; Richards, Stuart N.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1986); p. 1833 - 1838 View in Reaxys With perchloric acid, {Ru(IV)(2,2'-bipyridine)2(pyridine)O}(2+) in water, T= 25 °C , ΔH and -ΔS; var. solv.: D2O, aq. acetone, Rate constant, Product distribution Roecker, Lee; Meyer, Thomas J.; Journal of the American Chemical Society; vol. 109; nb. 3; (1987); p. 746 - 754 View in Reaxys With perchloric acid, N-bromoacetamide in water, acetic acid, T= 29.9 °C , kinetic isotope effects, Rate constant, Mechanism Negi, Suresh C.; Bhatia, Indu; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 11; (1981); p. 3966 - 3980 View in Reaxys With lead(IV) acetate, acetic acid in benzene, T= 29.9 °C , presence of pyridine, Rate constant, Mechanism Bhatia, Indu; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 4; (1982); p. 1076 - 1092 View in Reaxys With cis-lt;Ru(VI)(N,N,N',N'-tetramethyl-3,6-diazaoctane-1,8-diamine)O2gt;(2+) in acetonitrile, T= 24.9 °C , Rate constant Cheng, Wing-Chi; Yu, Wing-Yiu; Li, Chi-Kueng; Che, Chi-Ming; Journal of Organic Chemistry; vol. 60; nb. 21; (1995); p. 6840 - 6846 View in Reaxys With bis(2,2'-bipyridyl) copper(II) permanganate in acetic acid, T= 9.9 - 29.9 °C , Kinetics, Mechanism Vyas; Kothari; Banerji; International Journal of Chemical Kinetics; vol. 29; nb. 1; (1997); p. 9 - 16 View in Reaxys With toluene-4-sulfonic acid, quinolinium chlorochromate(VI) in dimethyl sulfoxide, Time= 24h, T= 24.9 °C , ΔH(excit.), ΔS(excit.), ΔG(excit.); var. temp., Rate constant, Kinetics, Thermodynamic data Oezguen, Beytiye; Degirmenbas, Nebahat; Journal of Chemical Research, Miniprint; nb. 1; (1997); p. 220 - 227 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

312/438

2018-03-11 22:07:32


With potassium permanganate, Tris(3,6-dioxaheptyl)amine in dichloromethane, primary kinetic isotope effect investigated, Rate constant, Mechanism Rankin, Kathryn N.; Liu, Qing; Hendry, Jennifer; Yee, Henry; Noureldin, Nazih A.; Lee, Donald G.; Tetrahedron Letters; vol. 39; nb. 10; (1998); p. 1095 - 1098 View in Reaxys With N,N,N-trimethylbenzenemethanaminium dichloroiodate, acetic acid, zinc(II) chloride, Time= 15h, T= 24.85 °C , ΔH(excit.), ΔS(excit.); isotope effect, Rate constant, Kinetics, Thermodynamic data Rao, P. Surya Chandra; Suri, Deepa; Kothari, Soona; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 9; (1998); p. 2251 - 2272 View in Reaxys With benzyltrimethylammonium tribromide, acetic acid in water, Oxidation, Kinetics, Activation energy, Further Variations: Temperatures Anjana; Kothari, Seema; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 8; (1999); p. 2118 2135 View in Reaxys With sodium hydroxide, sodium perchlorate, potassium hexacyanoferrate(III), (2,2':6',2''-terpyridine)trichlororuthenium(III) in water, T= 25 °C , Kinetics Kelson, Eric P.; Phengsy, Proma P.; International Journal of Chemical Kinetics; vol. 32; nb. 12; (2000); p. 760 - 770 View in Reaxys With 3,3-dimethyldioxirane in acetone, T= 0 °C , Kinetics Angelis, Yiannis S.; Hatzakis, Nikos S.; Smonou, Ioulia; Orfanopoulos, Michael; Tetrahedron Letters; vol. 42; nb. 22; (2001); p. 3753 - 3756 View in Reaxys With Mn(N,N'-ethylenebis(salicylaldiminato))O in acetonitrile, Time= 12h, T= 24.85 °C , Kinetics Kumbhat, Vinita; Sharma, Pradeep K.; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; (2001); p. 562 - 585 View in Reaxys With benzyltrimethylammonium chlorobromate, acetic acid, T= 34.85 °C , Kinetics, Further Variations: Temperatures Sita Rama Raju; Sharma; Banerji; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 39; nb. 12; (2000); p. 1258 - 1263 View in Reaxys With quinolinium monofluorochromate(VI) in dimethyl sulfoxide, T= 14.85 °C , Kinetics, Further Variations: Temperatures Dave, Itishri; Sharma, Vinita; Banerji, Kalyan K.; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 41; nb. 3; (2002); p. 493 - 499 View in Reaxys With TBATB in water, acetic acid, T= 14.85 °C , Kinetics, Activation energy, Further Variations: Temperatures Kumar, Ashok; Sharma, Pradeep K.; Banerji, Kalyan K.; Journal of Physical Organic Chemistry; vol. 15; nb. 10; (2002); p. 721 - 727 View in Reaxys With toluene-4-sulfonic acid, quinoxalinium dichromate in dimethyl sulfoxide, Time= 24h, T= 24.85 °C , Kinetics, Thermodynamic data, Further Variations: Temperatures Oezguen, Beytiye; Degirmenbasi, Nebahat; Monatshefte fuer Chemie; vol. 135; nb. 5; (2004); p. 483 - 492 View in Reaxys With bis-[(trifluoroacetoxy)iodo]benzene in water, acetic acid, T= 14.85 °C , Kinetics, Further Variations: Temperatures

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

313/438

2018-03-11 22:07:32


Kansara, Alpna; Sharma, Pradeep K.; Banerji, Kalyan K.; Journal of Chemical Research; nb. 9; (2004); p. 581 584 View in Reaxys With air, cis-{NBu(n)4}{Os(N)(CH2SiMe3)2(CrO4)} in benzene, Time= 10h, T= 70 °C , Catalytic oxidation Shapley, Patricia A.; Zhang, Najie; Allen, Jana L.; Pool, Douglas H.; Liang, Hong-Chang; Journal of the American Chemical Society; vol. 122; nb. 6; (2000); p. 1079 - 1091 View in Reaxys Reaction Steps: 2 1: 73 percent / thionyl chloride / benzene 2: 29 percent / 2-nitropropane, 10 percent NaOH / 2 h / Heating With sodium hydroxide, thionyl chloride, 2-nitropropane in benzene Terol, A.; Subra, G.; Fernandez, J. P.; Robbe, Y.; Chapat, J. P.; Granger, R.; Organic Magnetic Resonance; vol. 17; nb. 1; (1981); p. 68 - 70 View in Reaxys With pyridine, sulfur trioxide, dimethyl sulfoxide Fristrup, Peter; Kreis, Michael; Palmelund, Anders; Norrby, Per-Ola; Madsen, Robert; Journal of the American Chemical Society; vol. 130; nb. 15; (2008); p. 5206 - 5215 View in Reaxys With morpholinium chlorochromate in dimethyl sulfoxide, T= 24.84 °C , Kinetics, Temperature Soni, Neelam; Tiwari, Vandana; Sharma, Vinita; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 47; nb. 5; (2008); p. 669 - 676 View in Reaxys With 2,2'-bipyridinium chlorochromate in dimethyl sulfoxide, T= 24.84 °C , Kinetics, Temperature Yajurvedi, Deeksha; Baghmar, Manju; Sharma, Pradeep K.; Journal of the Indian Chemical Society; vol. 85; nb. 5; (2008); p. 496 - 501 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, N,N′-{1,3-bis[(pyridine-2-ylmethyl)amino]propan-2-al}atodicopper(II)(μ-acetato)diperchlorate, oxygen, sodium hydroxide in water, acetonitrile, T= 20 °C , Kinetics, Concentration Striegler, Susanne; Dunaway, Natasha A.; Gichinga, Moses G.; Milton, Lisa K.; Tetrahedron; vol. 66; nb. 40; (2010); p. 7927 - 7932 View in Reaxys With oxygen, caesium carbonate, copper dichloride in toluene, Time= 12h, T= 25 °C Liang, Lei; Rao, Guodong; Sun, Hao-Ling; Zhang, Jun-Long; Advanced Synthesis and Catalysis; vol. 352; nb. 14-15; (2010); p. 2371 - 2377 View in Reaxys With 2CF3O3S(1-)*C12H32Cu2N4O2 (2+) in acetone, T= -30.16 °C Kang, Peng; Bobyr, Elena; Dustman, John; Hodgson, Keith O.; Hedman, Britt; Solomon, Edward I.; Stack, T. Daniel P.; Inorganic Chemistry; vol. 49; nb. 23; (2010); p. 11030 - 11038 View in Reaxys With tetraethylammonium bromochromate in dimethyl sulfoxide, T= 24.84 °C , Mechanism, Temperature Mansoor, S. Sheik; Shafi, S. Syed; Zeitschrift fur Physikalische Chemie; vol. 225; nb. 2; (2011); p. 249 - 263 View in Reaxys With oxygen, titanium(IV) oxide in acetonitrile, T= 24.84 °C , Visible light irradiation, Kinetics Higashimoto, Shinya; Kitao, Naoya; Yoshida, Norio; Sakura, Teruki; Azuma, Masashi; Ohue, Hiroyoshi; Sakata, Yoshihisa; Journal of Catalysis; vol. 266; nb. 2; (2009); p. 279 - 285 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

314/438

2018-03-11 22:07:32


With oxygen, potassium carbonate in water, Time= 2h, T= 80 °C , p= 760.051Torr Harada, Takashi; Ikeda, Shigeru; Hashimoto, Fumihiro; Sakata, Takao; Ikeue, Keita; Torimoto, Tsukasa; Matsumura, Michio; Langmuir; vol. 26; nb. 22; (2010); p. 17720 - 17725 View in Reaxys With pyridinium chlorochromate in dichloromethane, T= 20 °C Meng, Ling-Guo; Wang, Lei; Chemical Communications; vol. 48; nb. 26; (2012); p. 3242 - 3244 View in Reaxys 4.1.1. (R)-α-Deuteriobenzyl alcohol [(R)-5a-d] TPAP (56 mg, 0.16 mmol) was added to a mixture of α,α-dideuteriobenzyl alcohol 3a (1.76 g, 16.0 mmol), 4 A molecular sieves (8.0 g), and NMO (2.88 g, 24.0 mmol) in CH2Cl2 (56 mL) with stirring at rt under Ar and the whole was stirred at the temperature for 16 h. After diluted with CH2Cl2, the mixture was filtered through a pad of Celite and the filtrate was washed with 10percent HCl, water, saturated NaHCO3, and brine prior to drying (Na2SO4) and solvent evaporation. The crude was used without further purification because of instability of the product for air oxidation to give benzaldehyde-α-d4a (1.70 g) as a gray oil. A 1 M THF solution of catecholborane (24.0 mL, 24.0 mmol) was added dropwise to a mixture of (S)-2-methyl-CBS-oxazaborolidine (1 m toluene solution) (4.96 mL, 4.96 mmol) and 4a (1.70 g) in a mixed solvent of toluene-methylcyclohexane-CH2Cl2 (2 : 2: 1, v/v) (178 mL) with stirring at -78 °C. After the mixture was stirred for 3.5 h at this temperature, 4 M HCl in AcOEt (3 mL) and MeOH (19 mL) were added to the mixture. The mixture was washed with 1 M NaOH aqueous solution (30 mL) prior to drying (MgSO4) and solvent evaporation. The residue was chromatographed on silica gel eluting with n-hexane/EtOAc (3:1) to give (R)-5a-d (1.15 g, 66percent in two steps) as a colorless oil. With tetrapropylammonium perruthennate, 4-methylmorpholine N-oxide in dichloromethane, Time= 16h, T= 20 °C , Inert atmosphere, Molecular sieve Kitamura, Maria; Hirokawa, Yoshimi; Yoshioka, Yuki; Maezaki, Naoyoshi; Tetrahedron; vol. 68; nb. 22; (2012); p. 4280 - 4285 View in Reaxys With oxygen, copper dichloride in acetonitrile, Time= 1h, T= 25 °C , Irradiation, Molecular sieve, Reagent/catalyst, Wavelength Meng, Chao; Yang, Kai; Fu, Xianzhi; Yuan, Rusheng; ACS Catalysis; vol. 5; nb. 6; (2015); p. 3760 - 3766 View in Reaxys With [FeV(O)(biuret-TAML)]− in acetonitrile, T= 26.84 °C , Kinetics, Reagent/catalyst, Temperature Ghosh, Munmun; Nikhil; Dhar, Basab B.; Sen Gupta, Sayam; Inorganic Chemistry; vol. 54; nb. 24; (2015); p. 11792 - 11798 View in Reaxys With C29H33FeN5O3 (2+)*2CF3O3S(1-), Kinetics, Mechanism Rana, Sujoy; Dey, Aniruddha; Maiti, Debabrata; Chemical Communications; vol. 51; nb. 77; (2015); p. 14469 14472 View in Reaxys Kinetic Isotope Effect Experiments Two separate solutions of substrate 1a and d2-1a (15.0 μmol, 1.0 equivalent) were made using 5 mM aqueous αcyclodextrin solution (1.0 mL, 5.0 μmol, 0.33 equivalents) in D2O. DBDMH 3 (4.3 mg, 15.0 μmol, 1.0 equivalent) was added to the reaction mixtures and sonicated to make sure that the reagents were well suspended. The reaction mixtures were heated at 60 oC with occasional shaking to maintain the homogeneity of the solutions for 1 hour. 1H NMR spectra of the reaction mixtures were recorded to determine the percent conversions. With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione, water-d2, alpha cyclodextrin, Time= 1h, T= 60 °C , Green chemistry Chaudhuri, Sauradip; Zaki, Hossam; Levine, Mindy; Synthetic Communications; vol. 46; nb. 7; (2016); p. 636 644 View in Reaxys With oxygen in water, T= 79.84 °C , p= 7500.75Torr , Catalytic behavior

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

315/438

2018-03-11 22:07:32


Xie, Jiahan; Yin, Kehua; Serov, Alexey; Artyushkova, Kateryna; Pham, Hien N.; Sang, Xiahan; Unocic, Raymond R.; Atanassov, Plamen; Datye, Abhaya K.; Davis, Robert J.; ChemSusChem; vol. 10; nb. 2; (2017); p. 359 - 362 View in Reaxys O

H

O

O

HO

HO

Rx-ID: 3838183 View in Reaxys 10/435 Yield 90 %, 10 %

Conditions & References With Oxone, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, tetrabutylammomium bromide, Time= 48h, T= 60 °C , Sealed tube Ray, Ritwika; Jana, Rahul Dev; Bhadra, Mayukh; Maiti, Debabrata; Lahiri, Goutam Kumar; Chemistry - A European Journal; vol. 20; nb. 47; (2014); p. 15618 - 15624 View in Reaxys

71 %Chromat., 42 %

2.6. General procedure for the aerobic oxidative esterification ofbenzylic alcohols with methanol General procedure: In a typical aerobic oxidation, a mixture of benzylic alcohol(0.145 ml, 2.5 mmol), K2CO3(87 mg, 0.4 mmol), methanol (6.0 ml)and Ag-MPTA-1 catalyst (50 mg) were taken in a 50 ml RB flask. Thereaction was carried out for 12 h under O2atmosphere at 45C.After the completion of the reaction, the catalyst was filtered offand washed with water followed by acetone and dried in oven. Thefiltrate was extracted four times with ethyl acetate (4 × 15 ml) andthe combined organic layers were dried with anhydrous Na2SO4by vacuum. The filtrate was concentrated and the resulting residuewas purified by column chromatography on silica gel to obtain thefinal product. With oxygen, potassium carbonate, Time= 12h, T= 45 °C , Green chemistry Salam, Noor; Banerjee, Biplab; Roy, Anupam Singha; Mondal, Paramita; Roy, Susmita; Bhaumik, Asim; Islam, Sk. Manirul; Applied Catalysis A: General; vol. 477; (2014); p. 184 - 194 View in Reaxys

24 %Chromat., 37 %

2.6. General procedure for the aerobic oxidative esterification ofbenzylic alcohols with methanol General procedure: In a typical aerobic oxidation, a mixture of benzylic alcohol(0.145 ml, 2.5 mmol), K2CO3(87 mg, 0.4 mmol), methanol (6.0 ml)and Ag-MPTA-1 catalyst (50 mg) were taken in a 50 ml RB flask. Thereaction was carried out for 12 h under O2atmosphere at 45C.After the completion of the reaction, the catalyst was filtered offand washed with water followed by acetone and dried in oven. Thefiltrate was extracted four times with ethyl acetate (4 × 15 ml) andthe combined organic layers were dried with anhydrous Na2SO4by vacuum. The filtrate was concentrated and the resulting residuewas purified by column chromatography on silica gel to obtain thefinal product. With oxygen, potassium carbonate in water, Time= 12h, T= 45 °C , Green chemistry Salam, Noor; Banerjee, Biplab; Roy, Anupam Singha; Mondal, Paramita; Roy, Susmita; Bhaumik, Asim; Islam, Sk. Manirul; Applied Catalysis A: General; vol. 477; (2014); p. 184 - 194 View in Reaxys

30 % Spectr., 62 % Spectr.

4 % Turnov., 63 % Turnov.

With pyridine, tert-butylhypochlorite in dichloromethane, Time= 1h Milovanovic, Jovan N.; Vasojevic, Miorad; Gojkovic, Svetislav; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 8; (1991); p. 1231 - 1233 View in Reaxys With sodium carbonate in dichloromethane, acetonitrile, T= 15 °C , electrolysis Brinkhaus, Karl-Heinz Grosse; Steckham, Eberhard; Schmidt, Werner; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 37; nb. 6; (1983); p. 499 - 508 View in Reaxys

3 %ChroWith oxygen, potassium carbonate, Time= 3h, T= 80 °C , p= 3750.38Torr mat., 48 %Chromat. Ishida, Tamao; Nagaoka, Megumi; Akita, Tomoki; Haruta, Masatake; Chemistry - A European Journal; vol. 14; nb. 28; (2008); p. 8456 - 8460 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

316/438

2018-03-11 22:07:32


77 %Chro- With oxygen, potassium carbonate, Time= 23h, T= 80 °C , p= 3750.38Torr mat., 2 %Chromat. Ishida, Tamao; Nagaoka, Megumi; Akita, Tomoki; Haruta, Masatake; Chemistry - A European Journal; vol. 14; nb. 28; (2008); p. 8456 - 8460 View in Reaxys 65 %Chro- With silver(I) hexafluorophosphate, oxygen, palladium diacetate, potassium carbonate, T= 50 - 60 °C , p= mat., 14 750.075Torr %Chromat. Gowrisankar, Saravanan; Neumann, Helfried; Beller, Matthias; Angewandte Chemie - International Edition; vol. 50; nb. 22; (2011); p. 5139 - 5143 View in Reaxys 15 %Chro- With pyridine, silver(I) hexafluorophosphate, oxygen, palladium diacetate, potassium carbonate, T= 50 - 60 °C , p= mat., 36 750.075Torr %Chromat. Gowrisankar, Saravanan; Neumann, Helfried; Beller, Matthias; Angewandte Chemie - International Edition; vol. 50; nb. 22; (2011); p. 5139 - 5143 View in Reaxys 44 %Chro- With bis-triphenylphosphine-palladium(II) chloride, oxygen, sodium carbonate, T= 45 °C mat., 51 %Chromat. Liu, Chao; Wang, Jing; Meng, Lingkui; Deng, Yi; Li, Yao; Lei, Aiwen; Angewandte Chemie - International Edition; vol. 50; nb. 22; (2011); p. 5144 - 5148 View in Reaxys With oxygen, potassium carbonate, Time= 4h, T= 130 °C , p= 7600.51Torr Parreira, Luciana A.; Bogdanchikova, Nina; Pestryakov, Alexey; Zepeda; Tuzovskaya, Inga; Farias; Gusevskaya, Elena V.; Applied Catalysis A: General; vol. 397; nb. 1-2; (2011); p. 145 - 152 View in Reaxys 23 %Chro- With Pyridine-2,6-dicarboxylic acid, dihydrogen peroxide, trifluoroacetic acid, zinc dibromide in water, Time= 16h, T= mat., 61 20 °C %Chromat. Wu, Xiao-Feng; Chemistry - A European Journal; vol. 18; nb. 29; (2012); p. 8912 - 8915 View in Reaxys With diethoxymethylane, palladium diacetate, sodium carbonate in methanol, Time= 24h, T= 40 °C , chemoselective reaction Bai, Xing-Feng; Ye, Fei; Zheng, Long-Sheng; Lai, Guo-Qiao; Xia, Chun-Gu; Xu, Li-Wen; Chemical Communications; vol. 48; nb. 68; (2012); p. 8592 - 8594 View in Reaxys 2.3. Catalytic oxidation experiments General procedure:The reactions were carried out in a stainless steel reactor equipped with a magnetic stirrer. In a typical run, a mixture of the substrate (0.4-1.2 mmol), solvent (if any) (2 mL), and the catalyst (10-40 mg; ca. 0.6-2.4 wt.percent; Au: 0.01-0.75 molpercent) was transferred in the reactor. The reactor was pressurized with oxygen to the total pressure of 10 atm and placed in an oil bath; then, the solution was intensively stirred at 80-130 °C for the reported time. The reactions were followed by gas chromatography (GC) (Shimadzu 17 instrument, Carbowax 20 M capillary column). At appropriate time intervals, stirring was stopped and after catalyst settling aliquots were taken and analyzed by GC. To ensure correct GC results in solvent-free reactions and in those with high initial substrate concentrations, the aliquots were diluted with methanol before the analysis. The structures of the products were confirmed by GC/MS (Shimadzu QP2010-PLUS instrument, 70 eV). With oxygen, Time= 1h, T= 110 °C , p= 7600.51Torr , Stainless steel reactor, chemoselective reaction Costa, Vinicius V.; Estrada, Miguel; Demidova, Yulia; Prosvirin, Igor; Kriventsov, Vladimir; Cotta, Rafaela F.; Fuentes, Sergio; Simakov, Andrey; Gusevskaya, Elena V.; Journal of Catalysis; vol. 292; (2012); p. 148 - 156 View in Reaxys 92 %Chro- 2.3. Catalytic oxidation experiments mat., 8 General procedure:The reactions were carried out in a stainless steel reactor equipped with a magnetic stirrer. In a %Chromat. typical run, a mixture of the substrate (0.4-1.2 mmol), solvent (if any) (2 mL), and the catalyst (10-40 mg; ca. 0.6-2.4 wt.percent; Au: 0.01-0.75 molpercent) was transferred in the reactor. The reactor was pressurized with oxygen to the

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

317/438

2018-03-11 22:07:32


total pressure of 10 atm and placed in an oil bath; then, the solution was intensively stirred at 80-130 °C for the reported time. The reactions were followed by gas chromatography (GC) (Shimadzu 17 instrument, Carbowax 20 M capillary column). At appropriate time intervals, stirring was stopped and after catalyst settling aliquots were taken and analyzed by GC. To ensure correct GC results in solvent-free reactions and in those with high initial substrate concentrations, the aliquots were diluted with methanol before the analysis. The structures of the products were confirmed by GC/MS (Shimadzu QP2010-PLUS instrument, 70 eV). With oxygen, Time= 3h, T= 100 °C , p= 7600.51Torr , Stainless steel reactor, chemoselective reaction Costa, Vinicius V.; Estrada, Miguel; Demidova, Yulia; Prosvirin, Igor; Kriventsov, Vladimir; Cotta, Rafaela F.; Fuentes, Sergio; Simakov, Andrey; Gusevskaya, Elena V.; Journal of Catalysis; vol. 292; (2012); p. 148 - 156 View in Reaxys With Au/γ-Al2O3, oxygen, Time= 3h, T= 59.84 °C , p= 760.051Torr Liu, Peng; Li, Can; Hensen, Emiel J. M.; Chemistry - A European Journal; vol. 18; nb. 38; (2012); p. 12122 12129 View in Reaxys With oxygen, Time= 3h, T= 59.84 °C , p= 760.051Torr Liu, Peng; Li, Can; Hensen, Emiel J. M.; Chemistry - A European Journal; vol. 18; nb. 38; (2012); p. 12122 12129 View in Reaxys With palladium diacetate, sodium carbonate in d(4)-methanol, Time= 24h, T= 40 °C , Inert atmosphere, Green chemistry, chemoselective reaction Wang, Hu; Li, Li; Bai, Xing-Feng; Shang, Jun-Yan; Yang, Ke-Fang; Xu, Li-Wen; Advanced Synthesis and Catalysis; vol. 355; nb. 2-3; (2013); p. 341 - 347 View in Reaxys The reactions were carried out in a stainless steel reactor equipped with a magnetic stirrer. In a typical run, a mixture of benzyl alcohol (2.5 mmol), methanol (2 mL), and the catalyst (10 mg; 1.3 μmol of Au: 0.05 molpercent) was transferred in the reactor. The reactor was pressurized with oxygen to the total pressure of 10 atm and placed in an oil bath; then, the solution was intensively stirred at 110 °C for the reported time. The reactions were followed by gas chromatography (GC) (Shimadzu 17 instrument, Carbowax 20M capillary column). At appropriate time intervals, stirring was stopped and after catalyst settling aliquots were taken and analyzed by GC. The structures of the products were confirmed by GC/MS (Shimadzu QP2010-PLUS instrument, 70 eV). With oxygen, Time= 1h, T= 110 °C , p= 7600.51Torr , Reagent/catalyst, Time Estrada, Miguel; Costa, Vinicius V.; Beloshapkin, Sergey; Fuentes, Sergio; Stoyanov, Evgenii; Gusevskaya, Elena V.; Simakov, Andrey; Applied Catalysis A: General; vol. 473; (2014); p. 96 - 103 View in Reaxys 10 %Chro- Representative Procedure for the Oxidation of Benzyl alcohols to Methylenzoates (2b)[1]with DBDMH: mat., 75 General procedure: DBDMH (20 mmol) was added in portion wise to a mixture of 1b (5 mmol) andmethanol (30 ml). %Chromat. The reaction was kept at room temperature. After the mixture wasstirred for 12h, the methanol was vacuum evaporated. The residue was dissolved byMTBE (30 ml), washed with water (330 ml).The organic extracts was dried byanhydrous MgSO4, filtered, and concentrated under reduce pressure. The residue waspurified by column chromatography (silica gel: petroleum ether/ethyl acetate, 30:1) toafford the product as light yellow solid ( 92percent yield). With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione, Time= 12h, T= 25 °C , chemoselective reaction Li, Zhongzhou; Zhu, Wei; Bao, Jinlong; Zou, Xinzhuo; Synthetic Communications; vol. 44; nb. 8; (2014); p. 1155 - 1164 View in Reaxys 2.6. General procedure for oxidative esterification of benzylicalcohols General procedure: A 50 ml round bottomed flask was charged with heterogeneousPd catalyst 1 (1 molpercent), K2CO3(1.2 equiv.) and methanol (3 ml). Thebase was soluble in the methanol and methanol acted as bothreactant and reaction media for the present transformation. Theresulting flask was sealed with septum, evacuated and backfilledwith oxygen. After that the benzyl alcohol (1.0 equiv.) was added tothe above suspension via syringe. The reaction mixture was stirredat 60C for the time as given in Table 1 in the presence of oxy-gen balloon. After completion,

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

318/438

2018-03-11 22:07:32


the mixture was cooled to roomtemperature and catalyst was recovered by the influence of exter-nal magnet. The crude product was dissolved in ethyl acetate andwashed successively with water to remove the base. The organiclayer was dried over anhydrous MgSO4and concentrated underreduced pressure. The residue so obtained was purified by columnchromatography using eluent ethyl acetate in hexane (20:80) togive the pure desired product. The recovered catalyst was washedwith methanol, dried in vacuum and used for the subsequent runs. With potassium tert-butylate, oxygen, Time= 6h, T= 60 °C , Sealed tube, Catalytic behavior, Reagent/catalyst Verma, Sanny; Verma, Deepak; Sinha, Anil K.; Jain, Suman L.; Applied Catalysis A: General; vol. 489; nb. 1; (2015); p. 17 - 23 View in Reaxys With oxygen, Time= 12h, T= 80 °C , Reagent/catalyst, chemoselective reaction Zhou, Yu-Xiao; Chen, Yu-Zhen; Cao, Lina; Lu, Junling; Jiang, Hai-Long; Chemical Communications; vol. 51; nb. 39; (2015); p. 8292 - 8295 View in Reaxys With oxygen, potassium carbonate, Time= 12h, T= 80 °C , Reagent/catalyst, chemoselective reaction Zhou, Yu-Xiao; Chen, Yu-Zhen; Cao, Lina; Lu, Junling; Jiang, Hai-Long; Chemical Communications; vol. 51; nb. 39; (2015); p. 8292 - 8295 View in Reaxys With oxygen, potassium carbonate, T= 60 °C , Autoclave, Kinetics, Reagent/catalyst Cheng, Tianyuan; Yu, Hao; Peng, Feng; Wang, Hongjuan; Zhang, Bingsen; Su, Dangsheng; Catalysis Science and Technology; vol. 6; nb. 4; (2016); p. 1007 - 1015 View in Reaxys 2.4. General procedure for the selective oxidation of benzylic alcohol General procedure: All oxidation experiments of benzylic alcohol were performed in a 120 mL stainless steel autoclave equipped with the magnetic stirring and a temperature controller. Typical procedure for oxidation of benzyl alcohol is as follows: benzyl alcohol (0.162 g, 1.5 mmol), alcoholic solvent (15 mL), catalyst (0.05 g) and additive (0.05 g) were added into the autoclave. After the reactor was sealed, the pure oxygen was pumped to replace the atmosphere for several times. Then under pressure of 0.3 MPa, the mixture was preheated to 110 °C with magnetic stirring and kept for a certain time. After the autoclave was cooled and the excess gas was released, the as-obtained mixture was analyzed by GC and GC–MS. With oxygen, potassium carbonate, Time= 4h, T= 110 °C , p= 2250.23Torr , Autoclave, Reagent/catalyst Sun, Jinyan; Tong, Xinli; Liu, Zonghui; Liao, Shengyun; Zhuang, Xuli; Xue, Song; Catalysis Communications; vol. 85; (2016); p. 70 - 74 View in Reaxys 85 %Chro- 3.1 : 4.2.1 General procedure for the synthesis of 2 in Table2 mat., 11 General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, PdCl2(CH3CN)2 (0.05mol, 5molper%Chromat. cent), Bi(OTf)3 (0.05mol, 5molpercent), K2CO3 (1mmol) were added. Substrates 1 (1mmol) and MeOH (2mL) were added subsequently. The reaction tube was vacuumed and backfilled with oxygen (3 times). Then the reaction mixture was stirred at 60°C for 3h in the presence of an oxygen balloon. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. Subsequently, the combined organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography with hexane/ethyl acetate to afford the corresponding products 2. With dichloro bis(acetonitrile) palladium(II), bismuth(III) nitrate, oxygen, potassium carbonate, Time= 5h, T= 60 °C , Schlenk technique, Catalytic behavior, Reagent/catalyst, Time Hu, Yongke; Li, Bindong; Tetrahedron; vol. 73; nb. 52; (2017); p. 7301 - 7307 View in Reaxys 43 %Chro- 3.1 : 4.2.1 General procedure for the synthesis of 2 in Table2 mat., 46 General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, PdCl2(CH3CN)2 (0.05mol, 5molper%Chromat. cent), Bi(OTf)3 (0.05mol, 5molpercent), K2CO3 (1mmol) were added. Substrates 1 (1mmol) and MeOH (2mL) were added subsequently. The reaction tube was vacuumed and backfilled with oxygen (3 times). Then the reaction mix-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

319/438

2018-03-11 22:07:32


ture was stirred at 60°C for 3h in the presence of an oxygen balloon. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. Subsequently, the combined organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography with hexane/ethyl acetate to afford the corresponding products 2. With oxygen, palladium diacetate, potassium carbonate, Time= 5h, T= 60 °C , Schlenk technique Hu, Yongke; Li, Bindong; Tetrahedron; vol. 73; nb. 52; (2017); p. 7301 - 7307 View in Reaxys O

H O

HO

O

Rx-ID: 3840152 View in Reaxys 11/435 Yield 4.3 %, 95.7 %

Conditions & References Oxidation of alcohols with the 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl–iodine system. General procedure: A mixture of 10 mL of 0.1 mol/L solution of sodium hydrocarbonate and 0.084 g (0.4 mmol) of compound 1 were charged into a 50 mL flat-bottom flask equipped with a reflux condenser and a magnetic stirrer. 4 mmol of an alcohol dissolved in 10 mL of methylene chloride (alcohol–nitroxyl 1 molar ratio1 : 0.1) was added to the solution, and then 0.4 mmolof an amine was introduced (alcohol–amine 1 : 0.1; 1–amine 1 : 1). 2.0 g (8 mmol) of crystalline iodine was added at vigorous stirring to the two-phase system; the mixture was stirred during 3 h at 20– 25° and then treated with 20percent solution of sodium thiosulfate for elimination of excess iodine. Aqueous and organic layers were separated, and the product was additionally extracted from the aqueous layer with methylene chloride (2×10 mL). The organic phases were combined and analyzed by means of chromatography. With pyridine, 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl, iodine, sodium hydrogencarbonate in dichloromethane, water, Time= 1h, T= 20 - 25 °C Kashparova; Kashparov; Zhukova, I. Yu.; Astakhov; Ilchibaeva; Kagan, E. Sh.; Russian Journal of General Chemistry; vol. 86; nb. 11; (2016); p. 2423 - 2426; Zh. Obshch. Khim.; vol. 86; nb. 11; (2016); p. 1779 - 1783,5 View in Reaxys

14 %, 86 %

With oxygen, caesium carbonate in toluene, Time= 9h, T= 25 °C Kim, Sungjin; Bae, Sang Won; Lee, Jae Sung; Park, Jaiwook; Tetrahedron; vol. 65; nb. 7; (2009); p. 1461 - 1466 View in Reaxys

86 %, 14 %

With Oxone, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, tetrabutylammomium bromide in toluene, Time= 48h, T= 110 °C , Sealed tube, Solvent, Reagent/catalyst Ray, Ritwika; Jana, Rahul Dev; Bhadra, Mayukh; Maiti, Debabrata; Lahiri, Goutam Kumar; Chemistry - A European Journal; vol. 20; nb. 47; (2014); p. 15618 - 15624 View in Reaxys

86 %, 14 %

With Oxone, Pyridine-2,6-dicarboxylic acid, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, tetrabutylammomium bromide, iron(II) acetate in toluene, Time= 48h, T= 110 °C , Sealed tube, Catalytic behavior, Reagent/catalyst, Solvent Ray, Ritwika; Jana, Rahul Dev; Bhadra, Mayukh; Maiti, Debabrata; Lahiri, Goutam Kumar; Chemistry - A European Journal; vol. 20; nb. 47; (2014); p. 15618 - 15624 View in Reaxys

85 %

With tert.-butylhydroperoxide in water, Time= 0.5h, T= 94 °C , p= 760.051Torr Choudhary, Vasant R.; Dumbre, Deepa K.; Applied Catalysis A: General; vol. 375; nb. 2; (2010); p. 252 - 257 View in Reaxys

17 %, 83 %

With oxygen, potassium carbonate in toluene, Time= 15h, T= 110 °C , Reagent/catalyst Vindigni, Floriana; Dughera, Stefano; Armigliato, Francesco; Chiorino, Anna; Monatshefte fur Chemie; vol. 147; nb. 2; (2016); p. 391 - 403 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

320/438

2018-03-11 22:07:32


10 %, 73 %

With bis-triphenylphosphine-palladium(II) chloride, 1,4-bromoiodobenzene, potassium carbonate in tetrahydrofuran, Time= 20h, T= 65 - 70 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst Liu, Chao; Tang, Shan; Lei, Aiwen; Chemical Communications; vol. 49; nb. 13; (2013); p. 1324 - 1326 View in Reaxys

68 %, 20 %

With (1,3-bis-(di-tert-butylphosphinito)cyclohexane)Ir=Cl, Time= 16h, T= 190 °C , Schlenk technique, Reagent/catalyst Polukeev, Alexey V.; Wendt, Ola F.; Organometallics; vol. 36; nb. 3; (2017); p. 639 - 649 View in Reaxys

26 %, 66 %

2.3. Catalytic experiments General procedure: The liquid phase oxidation was carried out in an ACE pressure tube filled with oxygen. Water suspension of Au NPs-rGO composites (8.1 mg in 2 mL), benzyl alcohol (1 mmol) and K2CO3 (3 mmol) were placed in a glass ACE pressure tube (10 mL) with a magnetic stirrer bar. The tube was sealed with a rubber O-ring and threaded Teflon seal under O2, and the entire mixture was vigorously stirred at 130 °C (bath temperature) for 4 h. The reaction mixture was cooled to room temperature and the organic product was extracted with ethyl acetate (3 × 10 mL). The aqueous phase was separated and could be used consecutively for another three times for the oxidation of benzyl alcohols (1st recycle 73percent, 2nd recycle 74percent and 3rd recycle 70percent benzaldehyde was obtained). The upper organic phase was dried and concentrated under reduced pressure. The product was purified by column chromatography. With oxygen, potassium carbonate in water, Time= 4h, T= 160 °C , Sealed tube, Catalytic behavior, Temperature, Time Sharma, Ponchami; Darabdhara, Gitashree; Reddy, Tallapareddy Muralikrishna; Borah, Ashwini; Bezboruah, Pranjal; Gogoi, Pranjal; Hussain, Najrul; Sengupta, Pinaki; Das, Manash R.; Catalysis Communications; vol. 40; (2013); p. 139 - 144 View in Reaxys

12 %

With caesium carbonate in para-xylene, Time= 24h, Reflux, Reagent/catalyst Shapiro, Leora; Avnir, David; ChemCatChem; vol. 9; nb. 5; (2017); p. 816 - 823 View in Reaxys

6 % Chromat., 94 % Chromat.

With 2,4,6-trimethylphenyl bromide, potassium carbonate, triphenylphosphine, palladium diacetate in 1,2-dimethoxyethane, Time= 12h, T= 85 °C , Product distribution Tamaru, Yoshinao; Yamada, Yoshimi; Inoue, Kenji; Yamamoto, Youichi; Yoshida, Zen-ichi; Journal of Organic Chemistry; vol. 48; nb. 8; (1983); p. 1286 - 1292 View in Reaxys

92.1 % Chromat., 1 % Chromat.

With potassium hydroxide, [RuH(PNN)(CO)] in toluene, Time= 4h, T= 115 °C

76.6 % Turnov.

With oxygen, potassium carbonate, titanium oxide-supported gold nanoparticle catalyst, Time= 5h, T= 100 °C , p= 1520.1Torr

Zhang, Jing; Leitus, Gregory; Ben-David, Yehoshoa; Milstein, David; Journal of the American Chemical Society; vol. 127; nb. 31; (2005); p. 10840 - 10841 View in Reaxys

Zheng, Nanfeng; Stucky, Galen D.; Chemical Communications; nb. 37; (2007); p. 3862 - 3864 View in Reaxys With Ag/hydrotalcite in para-xylene, Time= 10h, T= 130 °C Mitsudome, Takato; Mikami, Yusuke; Funai, Hisashi; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Angewandte Chemie - International Edition; vol. 47; nb. 1; (2008); p. 138 - 141 View in Reaxys With hydrotalcite supported Cu nanoparticles in para-xylene, Time= 13h, T= 130 °C , Inert atmosphere Mitsudome, Takato; Mikami, Yusuke; Ebata, Kaori; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Chemical Communications; nb. 39; (2008); p. 4804 - 4806 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

321/438

2018-03-11 22:07:32


With oxygen, potassium carbonate in toluene, Time= 6h, T= 100 °C , p= 2280.15Torr Oliveira, Rafael L.; Kiyohara, Pedro K.; Rossi, Liane M.; Green Chemistry; vol. 12; nb. 1; (2010); p. 144 - 149 View in Reaxys With cesium bicarbonate, oxygen, copper dichloride in toluene, Time= 12h, T= 40 °C Liang, Lei; Rao, Guodong; Sun, Hao-Ling; Zhang, Jun-Long; Advanced Synthesis and Catalysis; vol. 352; nb. 14-15; (2010); p. 2371 - 2377 View in Reaxys With ruthenium trichloride, nitrobenzene, Time= 16h, T= 150 °C , Inert atmosphere Feng, Chao; Liu, Yong; Peng, Shengming; Shuai, Qi; Deng, Guojun; Li, Chao-Jun; Organic Letters; vol. 12; nb. 21; (2010); p. 4888 - 4891 View in Reaxys 69 %Chro- With silver tetrafluoroborate, oxygen, palladium diacetate, potassium carbonate, 1,2-bis[di(t-butyl)phosphinomethmat., 10 yl]benzene in toluene, T= 90 - 100 °C , p= 750.075Torr %Chromat. Gowrisankar, Saravanan; Neumann, Helfried; Beller, Matthias; Angewandte Chemie - International Edition; vol. 50; nb. 22; (2011); p. 5139 - 5143 View in Reaxys With tert.-butylhydroperoxide in acetonitrile, T= 80 °C Behera, Gobinda Chandra; Parida; Applied Catalysis A: General; vol. 413-414; (2012); p. 245 - 253 View in Reaxys With oxygen in toluene, Time= 6h, T= 60 °C , p= 760.051Torr Evangelisti, Claudio; Schiavi, Eleonora; Aronica, Laura Antonella; Caporusso, Anna Maria; Vitulli, Giovanni; Bertinetti, Luca; Martra, Gianmario; Balerna, Antonella; Mobilio, Settimio; Journal of Catalysis; vol. 286; (2012); p. 224 - 236 View in Reaxys 31 %Chro- With Au/CeO2 in toluene, Time= 22h, T= 110 °C mat., 32 %Chromat. Ishida, Tamao; Takamura, Rena; Takei, Takashi; Akita, Tomoki; Haruta, Masatake; Applied Catalysis A: General; vol. 413-414; (2012); p. 261 - 266 View in Reaxys 6 %Spectr., 18 %Spectr.

With ozone, Neat (no solvent) Rodriguez-Reyes, Juan Carlos F.; Friend, Cynthia M.; Madix, Robert J.; Surface Science; vol. 606; nb. 15-16; (2012); p. 1129 - 1134 View in Reaxys Reaction Steps: 2 1: thionyl chloride; pyridine / dichloromethane 2: dimethylsulfoxide-d6 / 35 °C / Irradiation With pyridine, thionyl chloride in dimethylsulfoxide-d6, dichloromethane Grenga, Paolo N.; Stoutenburg, Eric G.; Priefer, Ronny; Tetrahedron Letters; vol. 53; nb. 37; (2012); p. 4933 4937 View in Reaxys

50 %Chromat.

With HRu(1,3-bis(6'-methyl-2'-pyridylimino)isoindolate)(PPh3)2 in toluene, Time= 24h, Inert atmosphere, Schlenk technique, Reflux, chemoselective reaction Tseng, Kuei-Nin T.; Kampf, Jeff W.; Szymczak, Nathaniel K.; Organometallics; vol. 32; nb. 7; (2013); p. 2046 2049 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

322/438

2018-03-11 22:07:32


85 %Chro- With copper(l) iodide, di-tert-butyl peroxide, (E)-N-((Z)-4-((2,6-dimethylphenyl)amino)pent-3-en-2-ylidene)-2,6-dimemat., 9 thylaniline in benzene, Time= 6h, T= 90 °C , Sealed tube, Inert atmosphere, Reagent/catalyst, Solvent %Chromat. Zhu, Yefeng; Wei, Yunyang; European Journal of Organic Chemistry; nb. 21; (2013); p. 4503 - 4508 View in Reaxys 8 %ChroWith di-tert-butyl peroxide, copper diacetate, (E)-N-((Z)-4-((2,6-dimethylphenyl)amino)pent-3-en-2-ylidene)-2,6-dimemat., 65 thylaniline, Time= 6h, T= 90 °C , Sealed tube, Inert atmosphere, Reagent/catalyst, Solvent %Chromat. Zhu, Yefeng; Wei, Yunyang; European Journal of Organic Chemistry; nb. 21; (2013); p. 4503 - 4508 View in Reaxys 3 :A 250 ml three-neck flask equipped with a water separator and a thermometer was charged with 0.21 g of [Ru(1,5-cyclooctadiene)Cl2]2, 0.7 g of 1-methyl-3-n-butylimidazolium chloride, 5 g of potassium hydroxide and 100 g of benzyl alcohol. The mixture was heated under reflux for 20 h with stirring (magnetic stirrer) at atmospheric pressure and an oil bath temperature of 240° C. After the end of the reaction, 10.4percent of unreacted starting material, 4.7percent of benzaldehyde (intermediate of the reaction) and 67.4percent of the carboxylic acid ester (benzyl benzoate; conversion determined by GC area percent) were present in the reaction mixture. The reaction discharge can be worked up as described in example 1. With bis[dichloro-(1,5-cyclooctadiene)ruthenium(2+)], 1-butyl-3-methylimidazolium chloride, potassium hydoxide, Time= 20h, T= 240 °C , p= 760.051Torr Patent; Schaub, Thomas; Rüdenauer, Stefan; Schneider, Daniel; Paciello, Rocco; US2014/24854; (2014); (A1) English View in Reaxys With gold supported on zirconium oxide, oxygen, caesium carbonate in Petroleum ether, Time= 12h, T= 25 °C , p= 760.051Torr , Catalytic behavior, Solvent Wei, Huili; Li, Jingyi; Yu, Jing; Zheng, Jianwei; Su, Haiquan; Wang, Xiaojing; Inorganica Chimica Acta; vol. 427; (2015); p. 33 - 40 View in Reaxys With potassium carbonate in toluene, Time= 5.5h, T= 85 - 90 °C , p= 760.051Torr , Schlenk technique, Inert atmosphere, Sonication, Green chemistry, Reagent/catalyst Wang, Dong; Deraedt, Christophe; Salmon, Lionel; Labrugère, Christine; Etienne, Laetitia; Ruiz, Jaime; Astruc, Didier; Chemistry - A European Journal; vol. 21; nb. 17; (2015); p. 6501 - 6510 View in Reaxys With Pd/TiO2(at)MIL-101, Time= 24h, T= 90 °C , Inert atmosphere Tilgner, Dominic; Friedrich, Martin; Hermannsdörfer, Justus; Kempe, Rhett; ChemCatChem; vol. 7; nb. 23; (2015); p. 3916 - 3922 View in Reaxys With [Rh(PPh3)(trop2NH)][trifluoromethanesulfonate], potassium tert-butylate, dinitrogen monoxide in tetrahydrofuran, T= -78 - 50 °C , p= 750.075Torr , Molecular sieve, Schlenk technique Gianetti, Thomas L.; Annen, Samuel P.; Santiso-Quinones, Gustavo; Reiher, Markus; Driess, Matthias; Grützmacher, Hansjörg; Angewandte Chemie - International Edition; vol. 55; nb. 5; (2016); p. 1854 - 1858; Angew. Chem.; vol. 128; nb. 5; (2015); p. 1886 - 1890,5 View in Reaxys With [Rh(1,3,4,5-tetramethylimidazole-2-ylidene)(trop2NH)][trifluoromethanesulfonate], potassium tert-butylate, dinitrogen monoxide in tetrahydrofuran, toluene, T= -78 - 50 °C , p= 750.075Torr , Molecular sieve, Schlenk technique, Catalytic behavior, Reagent/catalyst, Solvent Gianetti, Thomas L.; Annen, Samuel P.; Santiso-Quinones, Gustavo; Reiher, Markus; Driess, Matthias; Grützmacher, Hansjörg; Angewandte Chemie - International Edition; vol. 55; nb. 5; (2016); p. 1854 - 1858; Angew. Chem.; vol. 128; nb. 5; (2015); p. 1886 - 1890,5 View in Reaxys With oxygen, sodium hydroxide in cyclohexane, Time= 1h, T= 100 °C , p= 4500.45Torr , Solvent

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

323/438

2018-03-11 22:07:32


Ferraz, Camila P.; Garcia, Marco Aurélio S.; Teixeira-Neto, Érico; Rossi, Liane M.; RSC Advances; vol. 6; nb. 30; (2016); p. 25279 - 25285 View in Reaxys 15 %Spectr., 53 %Spectr.

With [{Cu2(5-phenyl-2,8-bis(6′-bipyridinyl)-1,9,10-anthyridine)-(μ-ClO4)2}(PF6)2], dihydrogen peroxide in N,N-dimethyl-formamide, Time= 12h, T= 70 °C , Solvent, Reagent/catalyst Huang, Da-Wei; Liu, Yi-Hung; Peng, Shie-Ming; Liu, Shiuh-Tzung; Organometallics; vol. 35; nb. 2; (2016); p. 151 - 158 View in Reaxys With ceria in para-xylene, Time= 12h, T= 150 °C , p= 760.051Torr , chemoselective reaction Zhang, Zhixin; Wang, Yehong; Wang, Min; Lu, Jianmin; Zhang, Chaofeng; Li, Lihua; Jiang, Jingyang; Wang, Feng; Catalysis Science and Technology; vol. 6; nb. 6; (2016); p. 1693 - 1700 View in Reaxys , Time= 12h, T= 350 °C Kumar, Ashish; Kumar, Vanama Pavan; Srikanth, Amirineni; Vishwanathan, Venkataraman; Chary, Komandur V. R.; Catalysis Letters; vol. 146; nb. 1; (2016); p. 35 - 46 View in Reaxys 2.4. Aerobic oxidation of benzyl alcohol catalyzed byxAu/PDVB-VI-n General procedure: Aerobic oxidation of benzyl alcohol catalyzed by xAu/PDVA-VI-n was performed in a 10 mL flask under atmospheric pressure. In a typical reaction, benzyl alcohol (12.9 L, 0.125 mmol), K2CO3(5.19 mg, 0.0375 mmol), water (2.5 mL) and the requisite amount of xAu/PDVB-VI-n were added into the flask, and then pure O2 was purged into the flask. The mixture was kept at 90 °C for 16 h at the stirring speed of 600 rpm. After the reaction, HCl was added intothe mixture to adjust the pH to the range of 3 ∼ 4, and then the mixture was extracted with ethyl acetate (1.5 mL) and centrifuged to remove the catalyst. The conversion of benzyl alcohol and the yields of products were determined by gas chromatography-mass spectrometer equipped with a HP-5ms column (GC-MS, 7890BGC System-5977MSD, Agilent Technologies). The products were identified by comparison with known authentic standards, and an external standard method was used for the qualitative analysis. With oxygen in water, Time= 16h, T= 90 °C , p= 760.051Torr Wang, Huan; Shi, Yuanyuan; Haruta, Masatake; Huang, Jiahui; Applied Catalysis A: General; vol. 536; (2017); p. 27 - 34 View in Reaxys 2.7 Experimental procedures for alcohol dehydrogenative coupling reactions catalyzed by 1 in the absence of a base and with KOH 200mg of 1 (0.007mmol) was placed in a small round-bottom flask. 21mmol of alcohol was added. In the case of 1hexanol, 400mg (0.014mmol) of 1 was added to 35mmol of alcohol. An applied vacuum degassed the mixture. The mixture was then heated with slow stirring under an inert atmosphere of argon. The reaction mixture was cooled to room temperature and the composite catalyst was separated by filtration. The resulting liquid product mixture was analyzed by GC-MS. Total alcohol conversion and reaction conditions for each alcohol used are summarized in Table1 . With potassium hydoxide, Time= 60h, T= 178 °C , Inert atmosphere, Catalytic behavior Goni, Md Abdul; Rosenberg, Edward; Gobetto, Roberto; Chierotti, Michele; Journal of Organometallic Chemistry; vol. 845; (2017); p. 213 - 228 View in Reaxys

77 %Chromat.

With C36H32Cl2N2O2P2Ru, potassium tert-butylate in toluene, Time= 16h, T= 150 °C , Inert atmosphere, Schlenk technique Sahoo; Jiang; Bruneau; Sharma; Suresh; Roisnel; Dorcet; Achard; Catalysis Science and Technology; vol. 7; nb. 16; (2017); p. 3492 - 3498 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

324/438

2018-03-11 22:07:32


O

H

O

O

HO

O

HO

Rx-ID: 3840158 View in Reaxys 12/435 Yield 22 %

Conditions & References With oxygen, potassium hydoxide in water, Time= 0.166667h, p= 7500.75Torr , Green chemistry Wang, Shuai; Zhao, Qingfei; Wei, Huimin; Wang, Jian-Qiang; Cho, Minhyung; Cho, Hae Sung; Terasaki, Osamu; Wan, Ying; Journal of the American Chemical Society; vol. 135; nb. 32; (2013); p. 11849 - 11860 View in Reaxys With tert.-butylhydroperoxide, aluminum tri-tert-butoxide, Time= 120h, T= 20 °C , various alcohols investigated under different reaction circumstances, Product distribution Dodonov, V. A.; Stepovik, L. P.; Sofronova, S. M.; Mukhina, T. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 58; nb. 7; (1988); p. 1578 - 1583,1406 - 1409 View in Reaxys With oxygen, potassium carbonate, PVP-stabilized 1:3 Au:Pd nanoparticles in water, T= 84.84 °C , p= 760.051Torr , Product distribution, Kinetics, Further Variations: Catalysts, Reagents, Temperatures Hou, Wenbo; Dehm, Nicole A.; Scott, Robert W.J.; Journal of Catalysis; vol. 253; nb. 1; (2008); p. 22 - 27 View in Reaxys With oxygen in toluene, T= 100 °C Wang, Hu; Deng, Shao-Xin; Shen, Zhu-Rui; Wang, Jin-Gui; Ding, Da-Tong; Chen, Tie-Hong; Green Chemistry; vol. 11; nb. 10; (2009); p. 1499 - 1502 View in Reaxys With oxygen, sodium acetate in water, Time= 12h, T= 130 °C , Autoclave Wang, Liang; Meng, Xiangju; Wang, Bin; Chi, Wenyang; Xiao, Feng-Shou; Chemical Communications; vol. 46; nb. 27; (2010); p. 5003 - 5005 View in Reaxys

38 %Spectr., 15 %Spectr., 43 %Spectr.

With oxygen, Time= 4h, T= 80 °C , pH= 9, aq. buffer Saio, Daisuke; Amaya, Toru; Hirao, Toshikazu; Advanced Synthesis and Catalysis; vol. 352; nb. 13; (2010); p. 2177 - 2182 View in Reaxys

With oxygen, Time= 5h, T= 100 °C , neat (no solvent) Wang, Hu; Wang, Jin-Gui; Shen, Zhu-Rui; Liu, Yu-Ping; Ding, Da-Tong; Chen, Tie-Hong; Journal of Catalysis; vol. 275; nb. 1; (2010); p. 140 - 148 View in Reaxys With oxygen, Time= 6h, T= 120 °C , p= 7757.43Torr Lopez-Sanchez, Jose Antonio; Dimitratos, Nikolaos; Glanville, Neil; Kesavan, Lokesh; Hammond, Ceri; Edwards, Jennifer K.; Carley, Albert F.; Kiely, Christopher J.; Hutchings, Graham J.; Applied Catalysis A: General; vol. 391; nb. 1-2; (2011); p. 400 - 406 View in Reaxys With dihydrogen peroxide, Time= 4h, T= 50 °C , Autoclave, neat (no solvent) Wang, Xiaoli; Wu, Gongde; Wei, Wei; Sun, Yuhan; Transition Metal Chemistry; vol. 35; nb. 2; (2010); p. 213 - 220 View in Reaxys With oxygen, T= 59.84 °C , Neat (no solvent), UV-irradiation, Kinetics, Reagent/catalyst, Temperature Feng, Wei; Wu, Guangjun; Li, Landong; Guan, Naijia; Green Chemistry; vol. 13; nb. 11; (2011); p. 3265 - 3272 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

325/438

2018-03-11 22:07:32


With oxygen, potassium carbonate in water, Time= 3h, T= 80 °C , p= 3750.38Torr Guo, Hongfan; Kemell, Marianna; Al-Hunaiti, Afnan; Rautiainen, Sari; Leskelae, Markku; Repo, Timo; Catalysis Communications; vol. 12; nb. 13; (2011); p. 1260 - 1264 View in Reaxys With oxygen in water, Time= 20h, T= 80 °C , p= 760.051Torr Wang, Liang; Zhang, Jian; Meng, Xiangju; Zheng, Dafang; Xiao, Feng-Shou; Catalysis Today; vol. 175; nb. 1; (2011); p. 404 - 410 View in Reaxys With dihydrogen peroxide, Time= 5h, T= 69.84 °C , Solvent Adam, Farook; Ooi, Wan-Ting; Applied Catalysis A: General; vol. 445-446; (2012); p. 252 - 260 View in Reaxys 2.3. Oxidation reaction of benzyl alcohol The oxidation of benzyl alcohol was carried out with O2 in a three-necked flask of 50 mL with a reflux condenser, and the flask was placed in a thermostatic bath with a magnetic stirrer. In a typical experiment, metal nanoparticle colloid (20 mL) was heated at the set temperature with an accuracy of ±0.1 K and bubbled with pure O2 for 60 min. Then, an appropriate amount of benzyl alcohol was added into the reaction mixture, and the oxidation reaction was started under vigorous magnetic stirring by bubbling O2. The reactions were monitored by sampling the reaction mixture (0.5 mL) at fixed intervals. The reaction mixture was immediately quenched with 2 M HCl aqueous solution (0.5 mL) and extracted three times with ethyl acetate (5 mL). The obtained organic layer was dried with Na2SO4 and analyzed by a CP-3800 gas chromatograph with an FID detector using the external standard method. With Au0.9Ag0.1, oxygen, sodium carbonate in water, T= 39.84 °C , p= 760.051Torr , Catalytic behavior Huang, Xuemin; Wang, Xueguang; Wang, Xiaoshu; Wang, Xinxing; Tan, Mingwu; Ding, Weizhong; Lu, Xionggang; Journal of Catalysis; vol. 301; (2013); p. 217 - 226 View in Reaxys 81 %Chromat., 6 %Chromat., 9 %Chromat.

With Au/DNA, oxygen, caesium carbonate in water, Time= 12h, T= 50 °C , Reagent/catalyst Tang, Lin; Guo, Xuefeng; Li, Yunfeng; Zhang, Shuai; Zha, Zhenggen; Wang, Zhiyong; Chemical Communications; vol. 49; nb. 45; (2013); p. 5213 - 5215 View in Reaxys Catalyst reaction General procedure: The oxidation of alcohols was carried out with O2 in a three-necked flask of 50 mL with a reflux condenser with a magnetic stirrer. Typically, 3 mmol of Na2CO3 was firstly dissolved in 30 mL of metal nanoparticle colloid completely. The solution was heated at the set temperature with an accuracy of ± 0.1 K and bubbled with pure O2 (30 mL/min) for 60 min. Then, the desired amount of alcohol was added into the reaction mixture and started the oxidation reaction under vigorous stirring by bubbling O2. The reactions were monitored by sampling the reaction mixture (0.5 mL) at fixed intervals. The reaction mixture was immediately quenched with a 2 M HCl aqueous solution (0.5 mL) and extracted with ethyl acetate (5 mL) for 3 times. The obtained organic layer was dried with Na2SO4 and analyzed by a CP-3800 gas chromatography with FID detector using the external standard method. The overall organic mass balance based on the starting reactants was more than 95percent. With Au0.95Ag0.05, oxygen, sodium carbonate, Time= 1h, T= 39.84 °C , Catalytic behavior, Reagent/catalyst, Temperature Huang, Xuemin; Wang, Xueguang; Tan, Mingwu; Zou, Xiujing; Ding, Weizhong; Lu, Xionggang; Applied Catalysis A: General; vol. 467; (2013); p. 407 - 413 View in Reaxys With oxygen, sodium hydroxide in water, Time= 2h, T= 25 °C , Reagent/catalyst Zhang, Leilei; Wang, Wentao; Wang, Aiqin; Cui, Yitao; Yang, Xiaofeng; Huang, Yanqiang; Liu, Xiaoyan; Liu, Wengang; Son, Jin-Young; Oji, Hiroshi; Zhang, Tao; Green Chemistry; vol. 15; nb. 10; (2013); p. 2680 - 2684 View in Reaxys With oxygen, sodium hydroxide in water, Time= 2h, T= 25 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

326/438

2018-03-11 22:07:32


Zhang, Leilei; Wang, Wentao; Wang, Aiqin; Cui, Yitao; Yang, Xiaofeng; Huang, Yanqiang; Liu, Xiaoyan; Liu, Wengang; Son, Jin-Young; Oji, Hiroshi; Zhang, Tao; Green Chemistry; vol. 15; nb. 10; (2013); p. 2680 - 2684 View in Reaxys Typical oxidation of alcohols General procedure: Into a reaction vessel with a reflux condenser were placed Pd-pol (23.1 mg, Pdpercentw = 2.3), benzyl alcohol (108.1 mg, 1.0 mmol), K2CO3 (138.2 mg, 1.0 mmol) and water (5 mL). The resulting mixture was stirred at 100°C under 1 atm of air. After 6 h, the mixture was cooled down to room temperature and the organic product was extracted with ethyl acetate (3 mL). The water phase was washed with ethyl acetate (2×5 mL) and the organic layers were collected. GLC analysis of the ethyl acetate solution using biphenyl as an internal standard gave a 98percent yield of benzyl aldehyde with >99percent selectivity. With polymer supported palladium, air in water, Time= 16h, T= 100 °C , p= 760.051Torr Dell'Anna, Maria Michela; Mali, Matilda; Mastrorilli, Piero; Cotugno, Pietro; Monopoli, Antonio; Journal of Molecular Catalysis A: Chemical; vol. 386; (2014); p. 114 - 119 View in Reaxys With dihydrogen peroxide, potassium carbonate in water, Time= 6h, Green chemistry Zhang, Mingmei; Sun, Qian; Yan, Zaoxue; Jing, Junjie; Wei, Wei; Jiang, Deli; Xie, Jimin; Chen, Min; Australian Journal of Chemistry; vol. 66; nb. 5; (2013); p. 564 - 571 View in Reaxys 2. Experimental General procedure: The oxidation experiments were carried out in glass liners loaded into a pressurized steel autoclave. For a typical run, 0.97 mmol of benzyl alcohol, 0.38 molpercent Au/Al2O3 (48 mg) and the solvents were measured into the glass liners. Additional base was added as a solid when only organic solvent was used. The autoclave was pressurized with 10 bar oxygen, heated to 100∘C and the mixtures were stirred with magnetic stirring at 1000 rpm. After the reaction the autoclave was depressurized and the mixtures were extracted twice with ethyl acetate. After the first extraction the reaction mixtures were acidified with HCl to transfer benzoate salt to the organic phase as benzoic acid. Centrifuge (3000 rpm, 2 min) was used to separate the phases. The products were analyzed using GC (Agilent 6890N) equipped with a HP-Innowax column and a flame ionization detector. Molar selectivity and conversion were determined using acetophenone as astandard. GC-MS was used to identify the products. With oxygen in water, Time= 2h, T= 100 °C , p= 7500.75Torr , Autoclave, Reagent/catalyst, Solvent Rautiainen, Sari; Simakova, Olga; Guo, Hongfan; Leino, Anne-Riikka; Kordas, Krisztian; Murzin, Dmitry; Leskelae, Markku; Repo, Timo; Applied Catalysis A: General; vol. 485; (2014); p. 202 - 206 View in Reaxys With oxygen in neat (no solvent), T= 120 - 140 °C , p= 7500.75Torr , Autoclave, Reagent/catalyst Hutchings, Graham J.; Catalysis Today; vol. 238; (2014); p. 69 - 73 View in Reaxys With potassium carbonate in toluene, Time= 4.5h, T= 85 - 90 °C , p= 760.051Torr , Schlenk technique, Inert atmosphere, Sonication, Green chemistry Wang, Dong; Deraedt, Christophe; Salmon, Lionel; Labrugère, Christine; Etienne, Laetitia; Ruiz, Jaime; Astruc, Didier; Chemistry - A European Journal; vol. 21; nb. 17; (2015); p. 6501 - 6510 View in Reaxys With oxygen, Time= 0.5h, Irradiation, Wavelength, Reagent/catalyst, Time Cui, Jiabin; Li, Yongjia; Liu, Lei; Chen, Lin; Xu, Jun; Ma, Jingwen; Fang, Gang; Zhu, Enbo; Wu, Hao; Zhao, Lixia; Wang, Leyu; Huang, Yu; Nano Letters; vol. 15; nb. 10; (2015); p. 6295 - 6301 View in Reaxys With C22H17MoN3O7, dihydrogen peroxide, triethylamine in acetonitrile, Time= 5h, T= 80 °C , Catalytic behavior, Reagent/catalyst Maurya, Mannar R.; Saini, Neeraj; Avecilla, Fernando; RSC Advances; vol. 5; nb. 122; (2015); p. 101076 101088 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

327/438

2018-03-11 22:07:32


15 %Spectr., 26 %Spectr., 41 %Spectr.

With Oxone, [{Cu2(5-phenyl-2,8-bis(6′-bipyridinyl)-1,9,10-anthyridine)-(μ-ClO4)2}(PF6)2] in methanol, Time= 12h, T= 70 °C , Reagent/catalyst, Solvent Huang, Da-Wei; Liu, Yi-Hung; Peng, Shie-Ming; Liu, Shiuh-Tzung; Organometallics; vol. 35; nb. 2; (2016); p. 151 - 158 View in Reaxys With oxygen, potassium carbonate in toluene, Time= 4h, T= 99.84 °C Nozaki, Ai; Tanihara, Yasutomo; Kuwahara, Yasutaka; Ohmichi, Tetsutaro; Mori, Kohsuke; Nagase, Takeshi; Yasuda, Hiroyuki Y.; Calers, Christophe; Louis, Catherine; Yamashita, Hiromi; Journal of Materials Chemistry A; vol. 4; nb. 21; (2016); p. 8458 - 8465 View in Reaxys With potassium carbonate in water, Time= 1h, T= 26.84 °C , p= 760.051Torr , Reagent/catalyst Ishida, Ryo; Arii, Setsuka; Kurashige, Wataru; Yamazoe, Seiji; Koyasu, Kiichirou; Negishi, Yuichi; Tsukuda, Tatsuya; Chinese Journal of Catalysis; vol. 37; nb. 10; (2016); p. 1656 - 1661 View in Reaxys With potassium carbonate in water, Time= 1h, T= 26.84 °C , p= 760.051Torr , Reagent/catalyst Ishida, Ryo; Arii, Setsuka; Kurashige, Wataru; Yamazoe, Seiji; Koyasu, Kiichirou; Negishi, Yuichi; Tsukuda, Tatsuya; Chinese Journal of Catalysis; vol. 37; nb. 10; (2016); p. 1656 - 1661 View in Reaxys 2.4. Aerobic oxidation of benzyl alcohol catalyzed byxAu/PDVB-VI-n General procedure: Aerobic oxidation of benzyl alcohol catalyzed by xAu/PDVA-VI-n was performed in a 10 mL flask under atmospheric pressure. In a typical reaction, benzyl alcohol (12.9 L, 0.125 mmol), K2CO3(5.19 mg, 0.0375 mmol), water (2.5 mL) and the requisite amount of xAu/PDVB-VI-n were added into the flask, and then pure O2 was purged into the flask. The mixture was kept at 90 °C for 16 h at the stirring speed of 600 rpm. After the reaction, HCl was added intothe mixture to adjust the pH to the range of 3 ∼ 4, and then the mixture was extracted with ethyl acetate (1.5 mL) and centrifuged to remove the catalyst. The conversion of benzyl alcohol and the yields of products were determined by gas chromatography-mass spectrometer equipped with a HP-5ms column (GC-MS, 7890BGC System-5977MSD, Agilent Technologies). The products were identified by comparison with known authentic standards, and an external standard method was used for the qualitative analysis. With oxygen, potassium carbonate in water, Time= 16h, T= 90 °C , p= 760.051Torr Wang, Huan; Shi, Yuanyuan; Haruta, Masatake; Huang, Jiahui; Applied Catalysis A: General; vol. 536; (2017); p. 27 - 34 View in Reaxys With oxygen, tungsten(VI) oxide, Time= 8h, T= 24.84 °C , UV-irradiation Ma, Bo; Huang, Erwei; Wu, Guangjun; Dai, Weili; Guan, Naijia; Li, Landong; RSC Advances; vol. 7; nb. 5; (2017); p. 2606 - 2614 View in Reaxys With oxygen, potassium carbonate in water, Time= 6h, T= 30 °C , p= 760.051Torr Yoskamtorn, Tatchamapan; Yamazoe, Seiji; Takahata, Ryo; Nishigaki, Jun-Ichi; Thivasasith, Anawat; Limtrakul, Jumras; Tsukuda, Tatsuya; ACS Catalysis; vol. 4; nb. 10; (2014); p. 3696 - 3700 View in Reaxys

HO

18O

Rx-ID: 9213423 View in Reaxys 13/435 Yield

Conditions & References With (18O)-dimethylsulfoxide, (tetra-n-butylammonium)3[PMo12O40] in various solvent(s), T= 135 °C Khenkin, Alexander M.; Neumann, Ronny; Journal of Organic Chemistry; vol. 67; nb. 20; (2002); p. 7075 - 7079 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

328/438

2018-03-11 22:07:32


With copper dichloride, oxygen-18 in acetonitrile, Time= 1h, T= 25 °C , p= 750.075Torr , Irradiation, Reagent/catalyst, Solvent Meng, Chao; Yang, Kai; Fu, Xianzhi; Yuan, Rusheng; ACS Catalysis; vol. 5; nb. 6; (2015); p. 3760 - 3766 View in Reaxys With C29H33FeN5O2 (18)O(2+)*2CF3O3S(1-) in acetonitrile, Time= 24h Rana, Sujoy; Dey, Aniruddha; Maiti, Debabrata; Chemical Communications; vol. 51; nb. 77; (2015); p. 14469 14472 View in Reaxys With oxygen-18 in acetonitrile, T= 25 °C , Irradiation, Mechanism Li, Hao; Qin, Feng; Yang, Zhiping; Cui, Ximin; Wang, Jianfang; Zhang, Lizhi; Journal of the American Chemical Society; vol. 139; nb. 9; (2017); p. 3513 - 3521 View in Reaxys

H HO

O

Rx-ID: 28588897 View in Reaxys 14/435 Yield

Conditions & References With water, Time= 3h, T= 440 °C , Inert atmosphere, Reactivity, Temperature Wang, Pengyu; Kojima, Hiroyuki; Kobiro, Kazuya; Nakahara, Koichi; Arita, Toshihiko; Kajimoto, Okitsugu; Bulletin of the Chemical Society of Japan; vol. 80; nb. 9; (2007); p. 1828 - 1832 View in Reaxys With oxygen, T= 120 °C , p= 7757.43Torr Dimitratos, Nikolaos; Lopez-Sanchez, Jose Antonio; Morgan, David; Carley, Albert F.; Tiruvalam, Ramchandra; Kiely, Christopher J.; Bethell, Donald; Hutchings, Graham J.; Physical Chemistry Chemical Physics; vol. 11; nb. 25; (2009); p. 5142 - 5153 View in Reaxys With hydrogen, T= 299.84 °C Li, Maoshuai; Wang, Xiaodong; Cárdenas-Lizana, Fernando; Keane, Mark A.; Catalysis Today; vol. 279; (2017) View in Reaxys With oxygen, Time= 1h, T= 120 °C , p= 3000.3Torr , Catalytic behavior Khawaji, Motaz; Chadwick, David; ChemCatChem; vol. 9; nb. 23; (2017); p. 4353 - 4363 View in Reaxys O

H

O

O

HO

HO

Rx-ID: 28664056 View in Reaxys 15/435 Yield

Conditions & References

8 %ChroWith oxygen, Time= 3h, T= 80 °C , p= 3750.38Torr mat., 4 %Chromat. Ishida, Tamao; Nagaoka, Megumi; Akita, Tomoki; Haruta, Masatake; Chemistry - A European Journal; vol. 14; nb. 28; (2008); p. 8456 - 8460 View in Reaxys With triethylsilane, palladium diacetate in methanol, Time= 24h, T= 40 °C , chemoselective reaction Bai, Xing-Feng; Ye, Fei; Zheng, Long-Sheng; Lai, Guo-Qiao; Xia, Chun-Gu; Xu, Li-Wen; Chemical Communications; vol. 48; nb. 68; (2012); p. 8592 - 8594 View in Reaxys 2.4. General procedure for the selective oxidation of benzylic alcohol

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

329/438

2018-03-11 22:07:32


General procedure: All oxidation experiments of benzylic alcohol were performed in a 120 mL stainless steel autoclave equipped with the magnetic stirring and a temperature controller. Typical procedure for oxidation of benzyl alcohol is as follows: benzyl alcohol (0.162 g, 1.5 mmol), alcoholic solvent (15 mL), catalyst (0.05 g) and additive (0.05 g) were added into the autoclave. After the reactor was sealed, the pure oxygen was pumped to replace the atmosphere for several times. Then under pressure of 0.3 MPa, the mixture was preheated to 110 °C with magnetic stirring and kept for a certain time. After the autoclave was cooled and the excess gas was released, the as-obtained mixture was analyzed by GC and GC–MS. With oxygen, Time= 4h, T= 110 °C , p= 2250.23Torr , Autoclave Sun, Jinyan; Tong, Xinli; Liu, Zonghui; Liao, Shengyun; Zhuang, Xuli; Xue, Song; Catalysis Communications; vol. 85; (2016); p. 70 - 74 View in Reaxys With air, palladium nanoparticles hybrid with zirconia/polyvinyl alcoholmembrane, Time= 20.5h, T= 70 °C , p= 7500.75Torr Liguori, Francesca; Moreno-Marrodan, Carmen; Barbaro, Pierluigi; Sawa, Haruo; Applied Catalysis A: General; vol. 530; (2017); p. 217 - 225 View in Reaxys

O

N

O

HO

H O

Rx-ID: 29846321 View in Reaxys 16/435 Yield

Conditions & References With oxygen, oxalic acid, sodium nitrite in dichloromethane, Time= 2h, T= 20 °C , p= 3750.38Torr , Autoclave Sheng, Xuebin; Ma, Hong; Chen, Chen; Gao, Jin; Yin, Guochuan; Xu, Jie; Catalysis Communications; vol. 11; nb. 15; (2010); p. 1189 - 1192 View in Reaxys With silica supported 4-OH-TEMPO/NOx, air in dichloromethane, T= 20 °C , Time Zhang, Hua; Fu, Luoling; Synthetic Communications; vol. 44; nb. 5; (2014); p. 610 - 619 View in Reaxys

6 %Spectr., 94 %Spectr.

With 1,1,1,3',3',3'-hexafluoro-propanol, nitric acid, Time= 24h, T= 20 °C Možina, Štefan; Stavber, Stojan; Iskra, Jernej; European Journal of Organic Chemistry; vol. 2017; nb. 3; (2017); p. 448 - 452 View in Reaxys

H HO

O

Rx-ID: 30451812 View in Reaxys 17/435 Yield

Conditions & References With hydrotalcite-supported gold nanoparticles in para-xylene, Time= 6h, T= 119.84 °C , Inert atmosphere Fang, Wenhao; Chen, Jiashu; Zhang, Qinghong; Deng, Weiping; Wang, Ye; Chemistry - A European Journal; vol. 17; nb. 4; (2011); p. 1247 - 1256 View in Reaxys With oxygen, Time= 1h, T= 120 °C , p= 3000.3Torr Khawaji, Motaz; Chadwick, David; ChemCatChem; vol. 9; nb. 23; (2017); p. 4353 - 4363 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

330/438

2018-03-11 22:07:32


N

HN

HO

H O

Rx-ID: 33900455 View in Reaxys 18/435 Yield 77 %, 81 %

Conditions & References With triphenylphosphine gold (I) chloride, potassium tert-butylate, silver trifluoromethanesulfonate in 1,4-dioxane, T= 100 °C Yang, Hongwei; Mao, Rongfang; Luo, Cuicui; Lu, Chunxu; Cheng, Guangbin; Tetrahedron; vol. 70; nb. 46; (2014); p. 8829 - 8835 View in Reaxys

81 %, 64 %

With C47H38CuIN4P2, potassium tert-butylate in toluene, Reflux, Mechanism Xu, Zhaojun; Wang, Duo-Sheng; Yu, Xiaoli; Yang, Yongchun; Wang, Dawei; Advanced Synthesis and Catalysis; vol. 359; nb. 19; (2017); p. 3332 - 3340 View in Reaxys

61 %, 15 %

With caesium carbonate, Time= 19h, T= 120 °C , p= 750.075Torr , Inert atmosphere, Autoclave Liu, Huihui; Chuah, Gaik-Khuan; Jaenicke, Stephan; Journal of Catalysis; vol. 292; (2012); p. 130 - 137 View in Reaxys

50 %

With [Pd(1,5-cyclooctadiene)Cl(SnCl3)] in o-xylene, Time= 12h, T= 140 °C , Mechanism Mohanty, Anuradha; Roy, Sujit; Tetrahedron Letters; vol. 57; nb. 25; (2016); p. 2749 - 2753 View in Reaxys

43 %, 32 %

With cesiumhydroxide monohydrate in 1,3,5-trimethyl-benzene, Time= 24h, T= 140 °C Wang, Chao; Chen, Changpeng; Han, Jian; Zhang, Jingyu; Yao, Yingming; Zhao, Yingsheng; European Journal of Organic Chemistry; vol. 2015; nb. 13; (2015); p. 2972 - 2977 View in Reaxys With Raney nickel in 5,5-dimethyl-1,3-cyclohexadiene, Reflux Mehta, Astha; Thaker; Londhe; Nandan, Santosh R.; Applied Catalysis A: General; vol. 478; (2014); p. 241 - 251 View in Reaxys With 1,10-Phenanthroline, potassium tert-butylate, nickel dibromide in toluene, Time= 60h, T= 130 °C , chemoselective reaction Vellakkaran, Mari; Singh, Khushboo; Banerjee, Debasis; ACS Catalysis; vol. 7; nb. 12; (2017); p. 8152 - 8158 View in Reaxys O

H HO

O O

Rx-ID: 42735394 View in Reaxys 19/435 Yield

Conditions & References 1.3. General procedurefor the oxidation of benzyl alcohol General procedure: Experiments were carried out in a thermostatedSchlenk vessel equipped with a condenser and stirrer. The solution of benzylalcohol and catalyst in solvent was purified with bubbling nitrogen gas toremove the oxygen. A mixture of benzyl alcohol (1.89×10-3 mol),catalyst (3.16×10-6 mol) and solvent (0.01 L) was stirred in aSchlenk vessel for few minutes at room temperature. The oxidant TBHP (1.58×10-3mol) was then added and the reaction mixture was stirred for the desiredtime. The samples (0.0005 L)were withdrawn periodically from the mixture todetermine the percentage conversion by analyzing them with GC equipped with DBWax (30 mx 0.32 nm ID) using 20 µL of cyclohexanone as an internal standart. With dihydrogen peroxide, Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

331/438

2018-03-11 22:07:32


Aktaş, Ayşe; Acar, Irfan; Saka, Ece Tuǧba; Biyiklioglu, Zekeriya; Journal of Organometallic Chemistry; vol. 815-816; (2016); p. 1 - 7 View in Reaxys With tert.-butylhydroperoxide in N,N-dimethyl-formamide, Time= 3h, T= 50 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst Kamiloğlu, Ayşe Aktaş; Acar, İrfan; Biyiklioglu, Zekeriya; Saka, Ece Tuğba; Journal of Organometallic Chemistry; vol. 828; (2017); p. 59 - 67 View in Reaxys With tert.-butylhydroperoxide in N,N-dimethyl-formamide, Time= 3h, T= 90 °C , Catalytic behavior Aktaş, Ayşe; Acar, İrfan; Saka, Ece Tuğba; Biyiklioglu, Zekeriya; Kantekin, Halit; Journal of Inclusion Phenomena and Macrocyclic Chemistry; vol. 86; nb. 3-4; (2016); p. 183 - 190 View in Reaxys O

HO

H

O

O

HO O

Rx-ID: 42735395 View in Reaxys 20/435 Yield

Conditions & References 1.3. General procedurefor the oxidation of benzyl alcohol General procedure: Experiments were carried out in a thermostatedSchlenk vessel equipped with a condenser and stirrer. The solution of benzylalcohol and catalyst in solvent was purified with bubbling nitrogen gas toremove the oxygen. A mixture of benzyl alcohol (1.89×10-3 mol),catalyst (3.16×10-6 mol) and solvent (0.01 L) was stirred in aSchlenk vessel for few minutes at room temperature. The oxidant TBHP (1.58×10-3mol) was then added and the reaction mixture was stirred for the desiredtime. The samples (0.0005 L)were withdrawn periodically from the mixture todetermine the percentage conversion by analyzing them with GC equipped with DBWax (30 mx 0.32 nm ID) using 20 µL of cyclohexanone as an internal standart. With tert.-butylhydroperoxide, T= 90 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Concentration, Temperature, Reagent/catalyst Aktaş, Ayşe; Acar, Irfan; Saka, Ece Tuǧba; Biyiklioglu, Zekeriya; Journal of Organometallic Chemistry; vol. 815-816; (2016); p. 1 - 7 View in Reaxys With tert.-butylhydroperoxide in N,N-dimethyl-formamide, Time= 3h, T= 50 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Temperature, Reagent/catalyst Kamiloğlu, Ayşe Aktaş; Acar, İrfan; Biyiklioglu, Zekeriya; Saka, Ece Tuğba; Journal of Organometallic Chemistry; vol. 828; (2017); p. 59 - 67 View in Reaxys With tert.-butylhydroperoxide in N,N-dimethyl-formamide, Time= 3h, T= 25 °C , Catalytic behavior, Temperature Aktaş, Ayşe; Acar, İrfan; Saka, Ece Tuğba; Biyiklioglu, Zekeriya; Kantekin, Halit; Journal of Inclusion Phenomena and Macrocyclic Chemistry; vol. 86; nb. 3-4; (2016); p. 183 - 190 View in Reaxys

O

H N

O

H 2N

HO

O

Rx-ID: 43883070 View in Reaxys 21/435 Yield

Conditions & References Stage 1: With α,α,α-trifluorotoluene, cadmium sulfide, Time= 0.5h, p= 750.075Torr , Inert atmosphere, Darkness Stage 2:Time= 4h, T= 50 °C , p= 750.075Torr , Inert atmosphere, Irradiation, Catalytic behavior Ning, Xiaofeng; Meng, Sugang; Fu, Xianliang; Ye, Xiangju; Chen, Shifu; Green Chemistry; vol. 18; nb. 12; (2016); p. 3628 - 3639

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

332/438

2018-03-11 22:07:32


View in Reaxys With CdS on graphitic carbon nitride, Time= 4h, Autoclave, Inert atmosphere, Reagent/catalyst Ye, Xiangju; Dai, Xia; Meng, Sugang; Fu, Xianliang; Chen, Shifu; Chinese Journal of Chemistry; vol. 35; nb. 2; (2017); p. 217 - 225 View in Reaxys

H O

HO

O

O

Rx-ID: 44448557 View in Reaxys 22/435 Yield

Conditions & References

60 %Chromat.

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], C18H17N2O2P in tetrahydrofuran, Time= 24h, T= 150 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst Sahoo; Jiang; Bruneau; Sharma; Suresh; Achard; RSC Advances; vol. 6; nb. 102; (2016); p. 100554 - 100558 View in Reaxys With C36H32Cl2N2O2P2Ru in tetrahydrofuran, Time= 24h, T= 170 °C , Inert atmosphere, Schlenk technique Sahoo; Jiang; Bruneau; Sharma; Suresh; Roisnel; Dorcet; Achard; Catalysis Science and Technology; vol. 7; nb. 16; (2017); p. 3492 - 3498 View in Reaxys

P (v3)

O

(v1) –

HO

(v4) O

Fe(v4) (v6) TB-5 H PO

HP

C –(v6) 2+ Fe (v4) OC-6 P

HO

(v4)

(v3)

H

(v4)

O

(v3)

O

O

(v3)

Rx-ID: 44797700 View in Reaxys 23/435 Yield

Conditions & References in benzene-d6, Time= 18h, T= 20 °C Dauth, Alexander; Gellrich, Urs; Diskin-Posner, Yael; Ben-David, Yehoshoa; Milstein, David; Journal of the American Chemical Society; vol. 139; nb. 7; (2017); p. 2799 - 2807 View in Reaxys O N

O H 2N

HO

H O

Rx-ID: 44974937 View in Reaxys 24/435 Yield

Conditions & References

12 %Chromat., 26 %Chromat., 24 %Chromat.

With potassium hexafluorophosphate, tetralin, C40H37Cl2NP2Ru, Time= 48h, T= 100 °C , Reagent/catalyst

31 %Chromat., 20 %Chromat., 10 %Chromat.

With tetralin, C37H36ClN4PRu, Time= 48h, T= 100 °C , Reagent/catalyst

Stubbs; Firth; Bridge; Berger; Hazlehurst; Boyle; Blacquiere; Dalton Transactions; vol. 46; nb. 3; (2017); p. 647 - 650 View in Reaxys

Stubbs; Firth; Bridge; Berger; Hazlehurst; Boyle; Blacquiere; Dalton Transactions; vol. 46; nb. 3; (2017); p. 647 - 650 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

333/438

2018-03-11 22:07:32


O O

O

N

O

OH

O N

O

H O

HO

O

Rx-ID: 44975725 View in Reaxys 25/435 Yield

Conditions & References With bis(1-methylethyl) 1,2-hydrazinedicarboxylate, 3-benzyl-2',3',4',5'-tetraacetylriboflavin, oxygen, triphenylphosphine in acetonitrile, Time= 24h, T= 25 °C , p= 760.051Torr , Molecular sieve, Irradiation März; Chudoba; Kohout; Cibulka; Organic and Biomolecular Chemistry; vol. 15; nb. 9; (2017); p. 1970 - 1975 View in Reaxys

N

O

H

NH

O

O

O HO

N

Rx-ID: 46128141 View in Reaxys 26/435 Yield

Conditions & References With tert.-butylhydroperoxide, [NiII(2-(2-hydroxylethyl)pyridine)(H2O)4]SO4 in water, Time= 20h, T= 80 °C Mohammad, Akbar; Chandra, Prakash; Ghosh, Topi; Carraro, Mauro; Mobin, Shaikh M.; Inorganic Chemistry; vol. 56; nb. 17; (2017); p. 10596 - 10608 View in Reaxys 2H

2H

2H

2H 2H

O

2H

2H

2H

O

2H 2H

O

O

HO 2H

2H

2H

2H

2H

Rx-ID: 46341188 View in Reaxys 27/435 Yield

Conditions & References With C47H38CuIN4P2, potassium tert-butylate in toluene, Time= 24h, Reflux, Mechanism Xu, Zhaojun; Wang, Duo-Sheng; Yu, Xiaoli; Yang, Yongchun; Wang, Dawei; Advanced Synthesis and Catalysis; vol. 359; nb. 19; (2017); p. 3332 - 3340 View in Reaxys O

O

OH

H HO

O

Rx-ID: 46717910 View in Reaxys 28/435 Yield

Conditions & References With C28H26ClN6Ru(1+)*F6P(1-), sodium isopropylate in toluene, Time= 2.5h, T= 125 °C , Schlenk technique, Inert atmosphere, Sealed tube, Glovebox, Kinetics Shee, Sujan; Paul, Bhaskar; Panja, Dibyajyoti; Roy, Bivas Chandra; Chakrabarti, Kaushik; Ganguli, Kasturi; Das, Ayan; Das, Gourab Kanti; Kundu, Sabuj; Advanced Synthesis and Catalysis; vol. 359; nb. 22; (2017); p. 3888 - 3893 View in Reaxys

OH

HO O

H O O

O

O

Rx-ID: 46733111 View in Reaxys 29/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

334/438

2018-03-11 22:07:32


Yield

Conditions & References

3 %Chromat., 32 %Chromat., 28 %Chromat., 23 %Chromat.

With potassium carbonate in 1,4-dioxane, ethanol, T= 30 °C

5 %Chromat., 41 %Chromat., 6 %Chromat., 14 %Chromat.

With potassium carbonate in 1,4-dioxane, ethanol, T= 30 °C

Kumar, Sandeep; Chaudhary, Abha; Bandna; Bhattacherjee, Dhananjay; Thakur, Vandna; Das, Pralay; New Journal of Chemistry; vol. 41; nb. 9; (2017); p. 3242 - 3245 View in Reaxys

Kumar, Sandeep; Chaudhary, Abha; Bandna; Bhattacherjee, Dhananjay; Thakur, Vandna; Das, Pralay; New Journal of Chemistry; vol. 41; nb. 9; (2017); p. 3242 - 3245 View in Reaxys

H

OH

HO

O

O

Rx-ID: 46733112 View in Reaxys 30/435 Yield

Conditions & References

90 %Chro- With potassium fluoride, oxygen, Time= 24h, T= 60 °C , Catalytic behavior, Reagent/catalyst mat., 8 %Chromat. Kumar, Sandeep; Chaudhary, Abha; Bandna; Bhattacherjee, Dhananjay; Thakur, Vandna; Das, Pralay; New Journal of Chemistry; vol. 41; nb. 9; (2017); p. 3242 - 3245 View in Reaxys

O

OH

E

H

E

HO

O

O

Rx-ID: 46733113 View in Reaxys 31/435 Yield

Conditions & References

25 %Chromat., 16 %Chromat., 50 %

With oxygen, potassium carbonate in 1,4-dioxane, Time= 24h, T= 60 °C , Catalytic behavior, Reagent/catalyst, Solvent Kumar, Sandeep; Chaudhary, Abha; Bandna; Bhattacherjee, Dhananjay; Thakur, Vandna; Das, Pralay; New Journal of Chemistry; vol. 41; nb. 9; (2017); p. 3242 - 3245 View in Reaxys O

H

OH

HO

O

Rx-ID: 46733115 View in Reaxys 32/435 Yield 30 %, 40 %

Conditions & References With oxygen, potassium carbonate in 1,4-dioxane, Time= 48h, T= 80 °C Kumar, Sandeep; Chaudhary, Abha; Bandna; Bhattacherjee, Dhananjay; Thakur, Vandna; Das, Pralay; New Journal of Chemistry; vol. 41; nb. 9; (2017); p. 3242 - 3245 View in Reaxys O Cl

H 2N

H

O

O

HO

N H

H

HO

Rx-ID: 46954609 View in Reaxys 33/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

335/438

2018-03-11 22:07:32


Yield

Conditions & References With tert.-butylhydroperoxide, C80H68Cu6N4O22Si10*2.5C2H6OS, calcium carbonate in acetonitrile, Time= 24h, T= 80 °C , Sealed tube Kulakova, Alena N.; Bilyachenko, Alexey N.; Levitsky, Mikhail M.; Khrustalev, Victor N.; Korlyukov, Alexander A.; Zubavichus, Yan V.; Dorovatovskii, Pavel V.; Lamaty, Frédéric; Bantreil, Xavier; Villemejeanne, Benoît; Martinez, Jean; Shul'Pina, Lidia S.; Shubina, Elena S.; Gutsul, Evgeniy I.; Mikhailov, Igor A.; Ikonnikov, Nikolay S.; Tsareva, Ul'Yana S.; Shul'Pin, Georgiy B.; Inorganic Chemistry; vol. 56; nb. 24; (2017); p. 15026 - 15040 View in Reaxys O

S

HO

S

Z

H

E

O

S

S

O

Rx-ID: 47073309 View in Reaxys 34/435 Yield

Conditions & References

10 %Chromat., 5 %Chromat., 7 %Chromat.

S

With potassium tert-butylate in toluene, Time= 12h, T= 170 °C , Inert atmosphere, Schlenk technique, Sealed tube, Green chemistry, Catalytic behavior, Temperature Li, Jinlei; Liu, Guoliang; Shi, Lijun; Xing, Qi; Li, Fuwei; Green Chemistry; vol. 19; nb. 24; (2017); p. 5782 - 5788 View in Reaxys

S

Z

O

H

E

S

HO

O

Rx-ID: 47073314 View in Reaxys 35/435 Yield 6 %Chromat.

Conditions & References With potassium tert-butylate in toluene, Time= 24h, T= 150 °C , Inert atmosphere, Schlenk technique, Sealed tube, Green chemistry Li, Jinlei; Liu, Guoliang; Shi, Lijun; Xing, Qi; Li, Fuwei; Green Chemistry; vol. 19; nb. 24; (2017); p. 5782 - 5788 View in Reaxys O O

H O

HO

O

Rx-ID: 3840148 View in Reaxys 36/435 Yield

Conditions & References With tetrachloromethane, potassium carbonate, palladium dichloride, Time= 7h, T= 80 °C , Yield given Nagashima, Hideo; Tsuji, Jiro; Chemistry Letters; (1981); p. 1171 - 1172 View in Reaxys With tetrachloromethane, potassium carbonate, palladium dichloride, Time= 7h, T= 80 °C , Yield given. Yields of byproduct given nagashima, Hideo; Sato, Koji; Tsuii, Jiro; Tetrahedron; vol. 41; nb. 23; (1985); p. 5645 - 5651 View in Reaxys With oxygen, Time= 2h, T= 100 °C , p= 3800.26Torr , Neat (no solvent) Evangelisti, Claudio; Schiavi, Eleonora; Aronica, Laura Antonella; Caporusso, Anna Maria; Vitulli, Giovanni; Bertinetti, Luca; Martra, Gianmario; Balerna, Antonella; Mobilio, Settimio; Journal of Catalysis; vol. 286; (2012); p. 224 - 236 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

336/438

2018-03-11 22:07:32


The oxidation reaction was performed in a magnetically stirredthree-neck flask equipped with thermometer and reflux condenser. The reaction in the flask was charged with benzyl alcohol (10 mL) and a prescribed amount of catalyst (0.5 g)was added so that the conversion of benzyl alcohol increased regularly with the amount of the catalyst until BzOH/Fe3BO6ratio at 165 °C. The system was heated at a prescribed temperature (25-150 °C) for a period of 10 h. At higher loadings no furtherincrease in the conversion was noticed. While conversion remained almost constant, the decrease in the selectivity for benzaldehyde was correlated with the increase in the selectivitiesof second generation products (dibenzyl ether and benzaldehyde )from benzaldehyde. Best performance was achievedfor a reaction period of 4-5 h. Benzyl alcohol conversion increased while selectivity for benzaldehyde decreased during the longer reaction time (Fig. 6). With iron orthoborate in neat (no solvent), Time= 10h, T= 110 °C , Temperature, Time Meydan, Engin; Öztürk, Ömer Faruk; Asian Journal of Chemistry; vol. 28; nb. 6; (2016); p. 1325 - 1329 View in Reaxys With hydrogen, potassium carbonate in toluene, Time= 0.5h, T= 49.84 °C , Reagent/catalyst Okumura, Kazu; Synlett; vol. 27; nb. 8; (2016); p. 1223 - 1226; Art.No: ST-2015-U0854-C View in Reaxys O

H

O

O

HO

O

HO

Rx-ID: 5310949 View in Reaxys 37/435 Yield

Conditions & References With BaPb0.6Bi0.1Cu0.3, oxygen, T= 399.85 °C , Oxidation, Product distribution, Further Variations: Catalysts, Temperatures, contact time Sumathi; Johnson; Viswanathan; Varadarajan; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 36; nb. 10; (1997); p. 874 - 878 View in Reaxys With oxygen, BaBiO3, T= 399.85 °C , Product distribution, Further Variations: Temperatures, Catalysts Sumathi; Johnson; Viswanathan; Varadarajan; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 38; nb. 1; (1999); p. 40 - 48 View in Reaxys With oxygen in neat (no solvent), Time= 8h, T= 120 °C , p= 1520.1Torr , Reagent/catalyst Amakawa, Kazuhiko; Kolen'Ko, Yury V.; Villa, Alberto; Schuster, Manfred E.; Csepei, Lenard-Istvan; Weinberg, Gisela; Wrabetz, Sabine; Naumann D'Alnoncourt, Raoul; Girgsdies, Frank; Prati, Laura; Schloegl, Robert; Trunschke, Annette; ACS Catalysis; vol. 3; nb. 6; (2013); p. 1103 - 1113 View in Reaxys With 1 Pd/Sibunit, oxygen in neat (no solvent), T= 120 - 140 °C , p= 7500.75Torr , Autoclave Hutchings, Graham J.; Catalysis Today; vol. 238; (2014); p. 69 - 73 View in Reaxys With oxygen in neat (no solvent), Time= 7h, T= 99.84 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Temperature Kong, Liping; Wang, Chengcheng; Gong, Feilong; Zhu, Weidong; Zhong, Yijun; Ye, Xiangrong; Li, Feng; Catalysis Letters; vol. 146; nb. 7; (2016); p. 1321 - 1330 View in Reaxys O

H

OH

O

HO

O

Rx-ID: 29530602 View in Reaxys 38/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

337/438

2018-03-11 22:07:32


Yield

Conditions & References With oxygen, Time= 3h, T= 85 °C , p= 750.075Torr Yang, Xiaomin; Wang, Xiuna; Qiu, Jieshan; Applied Catalysis A: General; vol. 382; nb. 1; (2010); p. 131 - 137 View in Reaxys 2.4. General procedure for the selective oxidation of benzylic alcohol General procedure: All oxidation experiments of benzylic alcohol were performed in a 120 mL stainless steel autoclave equipped with the magnetic stirring and a temperature controller. Typical procedure for oxidation of benzyl alcohol is as follows: benzyl alcohol (0.162 g, 1.5 mmol), alcoholic solvent (15 mL), catalyst (0.05 g) and additive (0.05 g) were added into the autoclave. After the reactor was sealed, the pure oxygen was pumped to replace the atmosphere for several times. Then under pressure of 0.3 MPa, the mixture was preheated to 110 °C with magnetic stirring and kept for a certain time. After the autoclave was cooled and the excess gas was released, the as-obtained mixture was analyzed by GC and GC–MS. With oxygen, potassium carbonate, Time= 4h, T= 110 °C , p= 2250.23Torr , Autoclave Sun, Jinyan; Tong, Xinli; Liu, Zonghui; Liao, Shengyun; Zhuang, Xuli; Xue, Song; Catalysis Communications; vol. 85; (2016); p. 70 - 74 View in Reaxys

O O

H

N

N HO

O

Rx-ID: 29776539 View in Reaxys 39/435 Yield 87 %Chromat.

Conditions & References With C20H31Cl4IrN4Pd, caesium carbonate, Time= 3h, T= 110 °C , Aerobic conditions Zanardi, Alessandro; Mata, Jose A.; Peris, Eduardo; Chemistry - A European Journal; vol. 16; nb. 34; (2010); p. 10502 - 10506 View in Reaxys With di-tert-butyl peroxide, potassium hydoxide in diethylene glycol dimethyl ether, Time= 24h, T= 140 °C Xiao, Fuhong; Liu, Yong; Tang, Chenglin; Deng, Guo-Jun; Organic Letters; vol. 14; nb. 4; (2012); p. 984 - 987 View in Reaxys

98 %Chromat.

4.2. General procedure for amine General procedure: A mixture of aryl alcohol (1.5mmol), nitrobenzene (1.0mmol), RuCl3·3H2O (3.0molpercent), K2CO3 (1.0mmol) and glycerol (10mmol) was stirred at 130°C for 24h in a sealed tube under a nitrogen atmosphere and then allowed to cool to room temperature. Water (10mL) was added and the aqueous solution extracted with dichloromethane (3×10mL). The combined extracts were dried with anhydrous Na2SO4, the solvent removed and the crude product purified on a short flash chromatography column. With tris(triphenylphosphine)ruthenium(II) chloride, Time= 24h, T= 130 °C , Inert atmosphere, Sealed tube, Reagent/ catalyst Tan, Da-Wei; Li, Hong-Xi; Young, David James; Lang, Jian-Ping; Tetrahedron; vol. 72; nb. 29; (2016); p. 4169 4176 View in Reaxys

HO

H

O

O

HO

Rx-ID: 30025419 View in Reaxys 40/435 Yield

Conditions & References With oxygen, Time= 1h, T= 160 °C , neat (no solvent) Chen, Yuanting; Guo, Zhen; Chen, Tao; Yang, Yanhui; Journal of Catalysis; vol. 275; nb. 1; (2010); p. 11 - 24 View in Reaxys With oxygen, Time= 6h, T= 120 °C , p= 7757.43Torr

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

338/438

2018-03-11 22:07:32


Lopez-Sanchez, Jose Antonio; Dimitratos, Nikolaos; Glanville, Neil; Kesavan, Lokesh; Hammond, Ceri; Edwards, Jennifer K.; Carley, Albert F.; Kiely, Christopher J.; Hutchings, Graham J.; Applied Catalysis A: General; vol. 391; nb. 1-2; (2011); p. 400 - 406 View in Reaxys With oxygen in neat (no solvent), Time= 2.5h, T= 100 °C , p= 4500.45Torr , Autoclave, Reagent/catalyst Silva, Tiago A. G.; Landers, Richard; Rossi, Liane M.; Catalysis Science and Technology; vol. 3; nb. 11; (2013); p. 2993 - 2999 View in Reaxys With oxygen, T= 140 °C , p= 7500.75Torr , Autoclave, Reagent/catalyst Miedziak, Peter J.; Kondrat, Simon A.; Sajjad, Noreen; King, Gavin M.; Douthwaite, Mark; Shaw, Greg; Brett, Gemma L.; Edwards, Jennifer K.; Morgan, David J.; Hussain, Ghulam; Hutchings, Graham J.; Catalysis Science and Technology; vol. 3; nb. 11; (2013); p. 2910 - 2917 View in Reaxys 2.6 General Procedure for Solvent-Free Aerobic Oxidation of Alcohols General procedure: Oxidation of alcohols with palladium nanoparticles supported on PE-HBPE was performed using molecular oxygen in the absence of solvent. For this purpose, 5.0 mg of the catalyst was dispersed in alcohol (5.0 ml) in a three necked round flask with a reflux condenser under stirring. Oxygen flow was bubbled at a flow-rate of 20 ml/min. After the allowed reaction time duration, the catalyst was removed from the mixture, and the products were analyzed using gas chromatography. With oxygen in neat (no solvent), Time= 2h, T= 90 °C , Reagent/catalyst, Overall yield = 80 percent Mahdavi, Hossein; Sahraei, Razieh; Catalysis Letters; vol. 146; nb. 5; (2016); p. 977 - 990 View in Reaxys H 2H

O

O

Rx-ID: 30034453 View in Reaxys 41/435 Yield

Conditions & References With 2CF3O3S(1-)*C12H32Cu2N4O2 (2+) in acetone, T= -30.16 °C , Kinetics Kang, Peng; Bobyr, Elena; Dustman, John; Hodgson, Keith O.; Hedman, Britt; Solomon, Edward I.; Stack, T. Daniel P.; Inorganic Chemistry; vol. 49; nb. 23; (2010); p. 11030 - 11038 View in Reaxys With 1,10-Phenanthroline, 1,2-bis(t-butyloxycarbonyl)hydrazine, oxygen, potassium carbonate, copper(l) chloride in fluorobenzene, T= 27 °C , Reagent/catalyst McCann, Scott D.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 138; nb. 1; (2016); p. 199 206 View in Reaxys H N

HO

O

Rx-ID: 32349303 View in Reaxys 42/435 Yield 9.3 %, 31.2 %

Conditions & References With ammonia, oxygen in toluene, Time= 1h, T= 149.84 °C , p= 22502.3Torr Nie, Renfeng; Shi, Juanjuan; Xia, Shuixin; Shen, Lian; Chen, Ping; Hou, Zhaoyin; Xiao, Feng-Shou; Journal of Materials Chemistry; vol. 22; nb. 35; (2012); p. 18115 - 18118 View in Reaxys

13 %Chro- With manganese(IV) oxide, ammonia, water, oxygen in 1,4-dioxane, Time= 1h, T= 130 °C , p= 1520.1Torr , Automat., 46 clave %Chromat. Yamaguchi, Kazuya; Kobayashi, Hiroaki; Oishi, Takamichi; Mizuno, Noritaka; Angewandte Chemie - International Edition; vol. 51; nb. 2; (2012); p. 544 - 547

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

339/438

2018-03-11 22:07:32


View in Reaxys 22 %Chro- With ammonia, water, oxygen in 1,4-dioxane, Time= 1h, T= 130 °C , p= 2280.15Torr , Autoclave mat., 18 %Chromat. Yamaguchi, Kazuya; Kobayashi, Hiroaki; Oishi, Takamichi; Mizuno, Noritaka; Angewandte Chemie - International Edition; vol. 51; nb. 2; (2012); p. 544 - 547 View in Reaxys 6 %ChroWith ammonium hydroxide, cobalt(II,III) oxide, oxygen in 1,4-dioxane, Time= 1h, T= 130 °C , p= 2280.15Torr , Automat., 57 clave %Chromat. Yamaguchi, Kazuya; Kobayashi, Hiroaki; Wang, Ye; Oishi, Takamichi; Ogasawara, Yoshiyuki; Mizuno, Noritaka; Catalysis Science and Technology; vol. 3; nb. 2; (2013); p. 318 - 327 View in Reaxys 22 %Chro- With ammonium hydroxide, oxygen in 1,4-dioxane, Time= 1h, T= 130 °C , p= 2280.15Torr , Autoclave mat., 18 %Chromat. Yamaguchi, Kazuya; Kobayashi, Hiroaki; Wang, Ye; Oishi, Takamichi; Ogasawara, Yoshiyuki; Mizuno, Noritaka; Catalysis Science and Technology; vol. 3; nb. 2; (2013); p. 318 - 327 View in Reaxys 16 %Chro- With 2,3'-bipyridine, ammonium hydroxide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, copper(ll) bromat., 67 mide in dimethyl sulfoxide, Time= 24h, T= 20 °C , Reagent/catalyst, Solvent, Temperature %Chromat. Yin, Weiyu; Wang, Chengming; Huang, Yong; Organic Letters; vol. 15; nb. 8; (2013); p. 1850 - 1853 View in Reaxys With copper(II) choride dihydrate, ammonium formate, potassium carbonate in neat (no solvent), Time= 24h, T= 125 °C , p= 760.051Torr , Sealed tube, Schlenk technique, Green chemistry, Catalytic behavior, Temperature, Reagent/ catalyst Yadav, Dilip Kumar T.; Bhanage, Bhalchandra M.; European Journal of Organic Chemistry; nb. 23; (2013); p. 5106 - 5110 View in Reaxys 37 %Spectr., 44 %Spectr.

With ammonium hydroxide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [{(MeOH)Cu(OAc)}(μ-k2:k1-2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)acetic acid(-H))]2*0.5H2O, tetraethylammonium iodide, oxygen, potassium carbonate in water, Time= 24h, T= 60 °C , p= 760.051Torr , Reagent/catalyst, Temperature Xie, Jing-Bo; Bao, Jia-Jing; Li, Hong-Xi; Tan, Da-Wei; Li, Hai-Yan; Lang, Jian-Ping; RSC Advances; vol. 4; nb. 96; (2014); p. 54007 - 54017 View in Reaxys

7.4 With [2,2]bipyridinyl, ammonium hydroxide, copper(l) iodide, N,N-dimethyl-(4-(2,2,6,6-tetramethyl-1-oxyl-4-piperidox%Chroyl)butyl)dodecylammonium bromide, oxygen in neat (no solvent), Time= 7h, T= 55 °C , p= 750.075Torr , Green mat., 89.3 chemistry %Chromat. Zhang, Yuecheng; Huang, Rong; Gao, Baosheng; Zhao, Jiquan; Catalysis Letters; vol. 146; nb. 1; (2016); p. 220 - 228 View in Reaxys 83.1 With [2,2]bipyridinyl, ammonium hydroxide, N,N-dimethyl-(4-(2,2,6,6-tetramethyl-1-oxyl-4-piperidoxyl)butyl)dodecy%Chrolammonium bromide, oxygen, copper(ll) bromide in neat (no solvent), Time= 7h, T= 55 °C , p= 750.075Torr , Green mat., 16.7 chemistry %Chromat. Zhang, Yuecheng; Huang, Rong; Gao, Baosheng; Zhao, Jiquan; Catalysis Letters; vol. 146; nb. 1; (2016); p. 220 - 228 View in Reaxys With ammonia, Time= 2h, T= 290 °C , Flow reactor, Temperature Zhang, Yuecheng; Zhao, Xiaofu; Zhang, Hongyu; Yan, Xiang; Zhao, Jiquan; Applied Catalysis A: General; vol. 522; (2016); p. 45 - 53 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

340/438

2018-03-11 22:07:32


HO

HO

O

OH

H O

OH

Rx-ID: 33113668 View in Reaxys 43/435 Yield

Conditions & References

38 %, 40 %, 16 %

With cadmium(II) sulphide in acetonitrile, Time= 24h, T= 20 °C , p= 37.5038Torr , Inert atmosphere, Irradiation Mitkina, Tatiana; Stanglmair, Christoph; Setzer, Wolfgang; Gruber, Michael; Kisch, Horst; Koenig, Burkhard; Organic and Biomolecular Chemistry; vol. 10; nb. 17; (2012); p. 3556 - 3561 View in Reaxys Stage 1: With cadmium sulphide in acetonitrile, Time= 0.00277778h, Schlenk technique, Sonication, Inert atmosphere Stage 2: in acetonitrile, Time= 20h, T= 20 °C , Irradiation, Inert atmosphere, Schlenk technique Chai, Zhigang; Zeng, Ting-Ting; Li, Qi; Lu, Liang-Qiu; Xiao, Wen-Jing; Xu, Dongsheng; Journal of the American Chemical Society; vol. 138; nb. 32; (2016); p. 10128 - 10131 View in Reaxys O

H O

OH

HO

O

Rx-ID: 39966654 View in Reaxys 44/435 Yield

Conditions & References With oxygen, potassium carbonate in n-heptane, Time= 24h, T= 100 °C , chemoselective reaction Zhou, Yu-Xiao; Chen, Yu-Zhen; Cao, Lina; Lu, Junling; Jiang, Hai-Long; Chemical Communications; vol. 51; nb. 39; (2015); p. 8292 - 8295 View in Reaxys 2.4. General procedure for the selective oxidation of benzylic alcohol General procedure: All oxidation experiments of benzylic alcohol were performed in a 120 mL stainless steel autoclave equipped with the magnetic stirring and a temperature controller. Typical procedure for oxidation of benzyl alcohol is as follows: benzyl alcohol (0.162 g, 1.5 mmol), alcoholic solvent (15 mL), catalyst (0.05 g) and additive (0.05 g) were added into the autoclave. After the reactor was sealed, the pure oxygen was pumped to replace the atmosphere for several times. Then under pressure of 0.3 MPa, the mixture was preheated to 110 °C with magnetic stirring and kept for a certain time. After the autoclave was cooled and the excess gas was released, the as-obtained mixture was analyzed by GC and GC–MS. With oxygen, potassium carbonate, Time= 4h, T= 110 °C , p= 2250.23Torr , Autoclave, Reagent/catalyst Sun, Jinyan; Tong, Xinli; Liu, Zonghui; Liao, Shengyun; Zhuang, Xuli; Xue, Song; Catalysis Communications; vol. 85; (2016); p. 70 - 74 View in Reaxys

HO O O

H

O

O

HO

O

Rx-ID: 40194104 View in Reaxys 45/435 Yield

Conditions & References With palladium on activated charcoal, oxygen in m-xylene, T= 70 °C , p= 750.075Torr , Concentration, Pressure, Temperature Savara, Aditya; Chan-Thaw, Carine E.; Rossetti, Ilenia; Villa, Alberto; Prati, Laura; ChemCatChem; vol. 6; nb. 12; (2015); p. 3464 - 3473 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

341/438

2018-03-11 22:07:32


With oxygen in para-xylene, T= 80 °C , p= 750.075Torr , Kinetics, Catalytic behavior, Mechanism, Concentration, Temperature Savara, Aditya; Rossetti, Ilenia; Chan-Thaw, Carine E.; Prati, Laura; Villa, Alberto; ChemCatChem; vol. 8; nb. 15; (2016); p. 2482 - 2491 View in Reaxys

O

O O

HO

O

H

O

O

O

O O

Rx-ID: 42034013 View in Reaxys 46/435 Yield 7 %, 92 %

Conditions & References With dihydrogen peroxide in water, acetonitrile, Time= 16h, T= 80 °C , Catalytic behavior Liu, Kai; Xu, Yanqi; Yao, Zhixiao; Miras, Haralampos N.; Song, Yu-Fei; ChemCatChem; vol. 8; nb. 5; (2016); p. 929 - 937 View in Reaxys N

H N

HO

O

Rx-ID: 42034014 View in Reaxys 47/435 Yield 25 %, 64 %

Conditions & References With dihydrogen peroxide in water, acetonitrile, Time= 24h, T= 80 °C , Catalytic behavior Liu, Kai; Xu, Yanqi; Yao, Zhixiao; Miras, Haralampos N.; Song, Yu-Fei; ChemCatChem; vol. 8; nb. 5; (2016); p. 929 - 937 View in Reaxys H

O N

HO

HO

O

Rx-ID: 42199569 View in Reaxys 48/435 Yield

Conditions & References

7.8 %Chromat., 73 %Chromat., 19.1 %Chromat.

With [2,2]bipyridinyl, ammonium hydroxide, copper(l) iodide, N,N-dimethyl-(4-(2,2,6,6-tetramethyl-1-oxyl-4-piperidoxyl)butyl)dodecylammonium bromide, oxygen in neat (no solvent), Time= 5h, T= 55 °C , p= 750.075Torr , Green chemistry

7.2 %Chromat., 86.2 %Chromat., 6.5 %Chromat.

With [2,2]bipyridinyl, ammonium hydroxide, copper(l) iodide, N,N-dimethyl-(4-(2,2,6,6-tetramethyl-1-oxyl-4-piperidoxyl)butyl)dodecylammonium bromide, oxygen in neat (no solvent), Time= 9.5h, T= 55 °C , p= 750.075Torr , Green chemistry

Zhang, Yuecheng; Huang, Rong; Gao, Baosheng; Zhao, Jiquan; Catalysis Letters; vol. 146; nb. 1; (2016); p. 220 - 228 View in Reaxys

Zhang, Yuecheng; Huang, Rong; Gao, Baosheng; Zhao, Jiquan; Catalysis Letters; vol. 146; nb. 1; (2016); p. 220 - 228 View in Reaxys

O

O

silica-supported Sn catalysts II

N O

O

HO

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

O

342/438

O N O

2018-03-11 22:07:32


O

O

O

N

O

O

O N

O

O

O

O

O

N

N

O

O

O

O N

O

O N

O

H

O

O

O N

O

O

O

N

O

O

O

Rx-ID: 42421641 View in Reaxys 49/435 Yield

Conditions & References in toluene, Time= 16h, T= 100 °C , Kinetics, Reagent/catalyst, Time Beletskiy, Evgeny V.; Hou, Xianliang; Shen, Zhongliang; Gallagher, James R.; Miller, Jeffrey T.; Wu, Yuyang; Li, Tiehu; Kung, Mayfair C.; Kung, Harold H.; Journal of the American Chemical Society; vol. 138; nb. 13; (2016); p. 4294 - 4297 View in Reaxys

HO

O

H

Br

O

Rx-ID: 42642077 View in Reaxys 50/435 Yield

Conditions & References General procedure: To a clean and dry small vial, a solution of substrate 1 (15.0 μmol, 1.0 equivalent) was added using an aqueous cyclodextrin solution (1.0 mL) of the specified concentration in D2O. DBDMH 3 (4.3 mg, 15.0 μmol, 1.0 equivalent) was added to the reaction mixture and sonicated to make sure that the reagents were well suspended. The reaction mixture was heated at 60 °C with occasional shaking to maintain the homogeneity of the solution. After the desired period of time, the 1H NMR spectrum of the reaction mixture was recorded to determine the percent conversion. With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione, water-d2, alpha cyclodextrin, Time= 1h, T= 60 °C , Green chemistry, Catalytic behavior Chaudhuri, Sauradip; Zaki, Hossam; Levine, Mindy; Synthetic Communications; vol. 46; nb. 7; (2016); p. 636 644 View in Reaxys

H 2N

H

N

H

HO

H O

O N H

Rx-ID: 42669866 View in Reaxys 51/435 Yield 32 %Spectr., 9 %Spectr.,

Conditions & References With 1-methyl-1H-imidazole, 4,4'-Dimethoxy-2,2'-bipyridin, 9-azabicyclolt;3.3.1gt;nonane-N-oxyl, oxygen, copper(l) chloride in tetrahydrofuran, Time= 0.5h, T= 20 °C , p= 760.051Torr , Molecular sieve Zultanski, Susan L.; Zhao, Jingyi; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 138; nb. 20; (2016); p. 6416 - 6419

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

343/438

2018-03-11 22:07:32


47 %Spectr.

View in Reaxys

O

H 2N

H

NH

HO

O

Rx-ID: 42669867 View in Reaxys 52/435 Yield 53 %Spectr., 34 %Spectr.

Conditions & References With 1-methyl-1H-imidazole, 4,4'-Dimethoxy-2,2'-bipyridin, 9-azabicyclolt;3.3.1gt;nonane-N-oxyl, oxygen, copper(l) chloride in tetrahydrofuran, Time= 0.5h, T= 20 °C , p= 760.051Torr , Molecular sieve Zultanski, Susan L.; Zhao, Jingyi; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 138; nb. 20; (2016); p. 6416 - 6419 View in Reaxys

HO

H

O

O

Rx-ID: 42975185 View in Reaxys 53/435 Yield

Conditions & References With iododioxobis(triphenylphosphine)rhenium(V), triphenylphosphine in benzene, Time= 92h, T= 150 °C , Sealed tube Kasner, Gabrielle R.; Boucher-Jacobs, Camille; Michael McClain; Nicholas, Kenneth M.; Chemical Communications; vol. 52; nb. 45; (2016); p. 7257 - 7260 View in Reaxys

H

N H

N

HO

O

Rx-ID: 42978112 View in Reaxys 54/435 Yield

Conditions & References With ammonia, Time= 2h, T= 320 °C , Flow reactor Zhang, Yuecheng; Zhao, Xiaofu; Zhang, Hongyu; Yan, Xiang; Zhao, Jiquan; Applied Catalysis A: General; vol. 522; (2016); p. 45 - 53 View in Reaxys

H HO

N

N

N H

O

Rx-ID: 42978113 View in Reaxys 55/435 Yield

Conditions & References With ammonia, Time= 2h, T= 320 °C , Flow reactor Zhang, Yuecheng; Zhao, Xiaofu; Zhang, Hongyu; Yan, Xiang; Zhao, Jiquan; Applied Catalysis A: General; vol. 522; (2016); p. 45 - 53 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

344/438

2018-03-11 22:07:32


H

N H

N

HO

O

Rx-ID: 42978118 View in Reaxys 56/435 Yield

Conditions & References With ammonia, Time= 2h, T= 320 °C , Flow reactor Zhang, Yuecheng; Zhao, Xiaofu; Zhang, Hongyu; Yan, Xiang; Zhao, Jiquan; Applied Catalysis A: General; vol. 522; (2016); p. 45 - 53 View in Reaxys O

O

O

H

O

O

O

HO

HO

O

Rx-ID: 42978827 View in Reaxys 57/435 Yield

Conditions & References With oxygen, potassium carbonate in toluene, Time= 3.5h, T= 100 °C , Reagent/catalyst Cui, Tian-Lu; Ke, Wen-Yu; Zhang, Wen-Bei; Wang, Hong-Hui; Li, Xin-Hao; Chen, Jie-Sheng; Angewandte Chemie - International Edition; vol. 55; nb. 32; (2016); p. 9178 - 9182; Angew. Chem.; vol. 128; (2016); p. 9324 9328,5 View in Reaxys O

OH

H HO

O

Rx-ID: 43015407 View in Reaxys 58/435 Yield Ca. 20 %Spectr., Ca. 20 %Spectr.

Conditions & References 2.3 The controlled reaction of 4 with 2a General procedure: Under nitrogen atmosphere, to a 15-mL Pyrex glass screw-cap tube were added chalcone (5: 1.041 g, 5 mmol), benzyl alcohol (2a: 0.543 g, 5 mmol), K3PO4 (531 mg, 2.5 mmol), and Pt-Sn/γ-Al2O3 (catalyst III: 147 mg, 0.075 mol percent Pt). The resultant mixture was stirred in the sealed tube at 155 °C for 48 h. After cooled to ambient temperature, the catalyst and base were removed by centrifugation. The supernatant was subject to 1H NMR analysis in CDCl3, revealing 20percent conversion for benzylalcohol, and about 20percent yield for both 3a and benzaldehyde. With potassium phosphate, Time= 48h, T= 155 °C , p= 750.075Torr , Inert atmosphere, Sealed tube, Green chemistry Wu, Kaikai; He, Wei; Sun, Chenglin; Yu, Zhengkun; Tetrahedron Letters; vol. 57; nb. 36; (2016); p. 4017 - 4020 View in Reaxys O

H OH

O

HO

O

Rx-ID: 43415385 View in Reaxys 59/435 Yield

Conditions & References 2.4. General procedure for the selective oxidation of benzylic alcohol General procedure: All oxidation experiments of benzylic alcohol were performed in a 120 mL stainless steel autoclave equipped with the magnetic stirring and a temperature controller. Typical procedure for oxidation of benzyl alcohol is as follows: benzyl alcohol (0.162 g, 1.5 mmol), alcoholic solvent (15 mL), catalyst (0.05 g) and additive (0.05 g) were added into the autoclave. After the reactor was sealed, the pure oxygen was pumped to replace the atmosphere for several times. Then under pressure of 0.3 MPa, the mixture was preheated to 110 °C with magnetic stirring and kept for a certain time. After the autoclave was cooled and the excess gas was released, the as-obtained mixture was analyzed by GC and GC–MS.

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

345/438

2018-03-11 22:07:32


With oxygen, potassium carbonate, Time= 4h, T= 110 °C , p= 2250.23Torr , Autoclave Sun, Jinyan; Tong, Xinli; Liu, Zonghui; Liao, Shengyun; Zhuang, Xuli; Xue, Song; Catalysis Communications; vol. 85; (2016); p. 70 - 74 View in Reaxys O

O

H

O

O

O

HO

HO

Rx-ID: 43415386 View in Reaxys 60/435 Yield

Conditions & References 2.4. General procedure for the selective oxidation of benzylic alcohol General procedure: All oxidation experiments of benzylic alcohol were performed in a 120 mL stainless steel autoclave equipped with the magnetic stirring and a temperature controller. Typical procedure for oxidation of benzyl alcohol is as follows: benzyl alcohol (0.162 g, 1.5 mmol), alcoholic solvent (15 mL), catalyst (0.05 g) and additive (0.05 g) were added into the autoclave. After the reactor was sealed, the pure oxygen was pumped to replace the atmosphere for several times. Then under pressure of 0.3 MPa, the mixture was preheated to 110 °C with magnetic stirring and kept for a certain time. After the autoclave was cooled and the excess gas was released, the as-obtained mixture was analyzed by GC and GC–MS. With oxygen, Time= 4h, T= 110 °C , p= 2250.23Torr , Autoclave, Reagent/catalyst Sun, Jinyan; Tong, Xinli; Liu, Zonghui; Liao, Shengyun; Zhuang, Xuli; Xue, Song; Catalysis Communications; vol. 85; (2016); p. 70 - 74 View in Reaxys H

O N

Cl

Cl

HO

O

NH 2

O

Rx-ID: 43883072 View in Reaxys 61/435 Yield

Conditions & References Stage 1: With α,α,α-trifluorotoluene, cadmium sulfide, Time= 0.5h, p= 750.075Torr , Inert atmosphere, Darkness Stage 2:Time= 4h, T= 50 °C , p= 750.075Torr , Inert atmosphere, Irradiation, Catalytic behavior Ning, Xiaofeng; Meng, Sugang; Fu, Xianliang; Ye, Xiangju; Chen, Shifu; Green Chemistry; vol. 18; nb. 12; (2016); p. 3628 - 3639 View in Reaxys O

O

H HO

O

Rx-ID: 44018426 View in Reaxys 62/435 Yield 92.7 %

Conditions & References Catalyst evaluation General procedure: Unless otherwise noted, the reactions were carried out as follows. A mixture of primary alcohol (1.0 mmol), secondary alcohol (0.5 mmol), KOH (2.0 mmol) and catalyst (1.03.0 molpercent) was added to 2 mL H2O in a test tube. The tube was sealed before evacuation and purging with O2 three times. The reaction mixture was vigorously stirred at 60 °C for 6 h under an oxygen balloon. After cooling down to room temperature, the catalyst was separated by filtration and the filtrate was extracted with ethyl acetate (2 × 20.0 mL). The organic layer was dried over anhydrous magnesium sulfate. After adding 100 μL n‐dodecane as the internal standard, the organic mixturewas submitted to GC analysis for conversion and yield determination.The crude product was purified by flash chromatography on a short silica gel (eluent: petroleum ether/ethyl acetate= 10/1, 2/1). With potassium hydoxide in water, Time= 6h, T= 60 °C , p= 750.075Torr , Sealed tube, Green chemistry, Reagent/ catalyst Zhou, Maoxiang; Zhang, Leilei; Miller, Jeffrey T.; Yang, Xiaofeng; Liu, Xiaoyan; Wang, Aiqin; Zhang, Tao; Chinese Journal of Catalysis; vol. 37; nb. 10; (2016); p. 1764 - 1770 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

346/438

2018-03-11 22:07:32


76 %Spectr.

With trans-RuCl(2-(2-pyridyl-6-ol)-1,10-phenanthroline)(PPh3)2PF6, sodium hydroxide in toluene, Time= 1.5h, Reflux, Inert atmosphere, Schlenk technique, Mechanism Chakrabarti, Kaushik; Paul, Bhaskar; Maji, Milan; Roy, Bivas Chandra; Shee, Sujan; Kundu, Sabuj; Organic and Biomolecular Chemistry; vol. 14; nb. 46; (2016); p. 10988 - 10997 View in Reaxys H

HO

HN

H 2N

O

Rx-ID: 44129843 View in Reaxys 63/435 Yield

Conditions & References

19 %Spectr., 14 %Spectr., 46 %Spectr.

With ammonium hydroxide, C36H34N2O2P2Ru, ammonium acetate in ethanol, water, Time= 24.5h, T= 90 °C , Inert atmosphere, Schlenk technique Malan, Frederick P.; Noh, Ji-Hyang; Naganagowda, Gadada; Singleton, Eric; Meijboom, Reinout; Journal of Organometallic Chemistry; vol. 825-826; (2016); p. 139 - 145 View in Reaxys

O

H H 2N

HO

O

S O

Rx-ID: 44252018 View in Reaxys 64/435 Yield

Conditions & References

52 %

With [(tris[2-{N-tetramethylguanidyl}ethyl]amine)CoII–[N-(p-toluenesulfonyl)imino](2-tert-butylsulfonyl)phenyliodinane](OTf)2 in acetone, T= -40 °C , Inert atmosphere, Kinetics, Reagent/catalyst, Time Kundu, Subrata; Chernev, Petko; Engelmann, Xenia; Chung, Chan Siu; Dau, Holger; Bill, Eckhard; England, Jason; Nam, Wonwoo; Ray, Kallol; Dalton Transactions; vol. 45; nb. 37; (2016); p. 14538 - 14543 View in Reaxys

H

O O

HO

O

O

Rx-ID: 44448556 View in Reaxys 65/435 Yield

Conditions & References

85 %Chromat.

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], C18H17N2O2P in tetrahydrofuran, Time= 24h, T= 150 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst Sahoo; Jiang; Bruneau; Sharma; Suresh; Achard; RSC Advances; vol. 6; nb. 102; (2016); p. 100554 - 100558 View in Reaxys

-1 F (v4)

F

B FF

F

H F

F

HO

F

O

N+ N

Rx-ID: 44453817 View in Reaxys 66/435 Yield

Conditions & References With tetrabutylammonium benzoate in dimethylsulfoxide-d6 Fabre, Indira; Perego, Luca Alessandro; Bergès, Julien; Ciofini, Ilaria; Grimaud, Laurence; Taillefer, Marc; European Journal of Organic Chemistry; vol. 2016; nb. 35; (2016); p. 5887 - 5896

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

347/438

2018-03-11 22:07:32


View in Reaxys

H 2H

O

O

Rx-ID: 44516945 View in Reaxys 67/435 Yield

Conditions & References With bis(tetrabutylammonium) hexamolybdate, isopropyl alcohol, Time= 3h, T= 220 °C , Microwave irradiation Larsen, Daniel B.; Petersen, Allan R.; Dethlefsen, Johannes R.; Teshome, Ayele; Fristrup, Peter; Chemistry - A European Journal; vol. 22; nb. 46; (2016); p. 16621 - 16631 View in Reaxys

2H

2H

2H

2H

2H

2H

2H

O

HO

2H

2H

2

H

Rx-ID: 44516946 View in Reaxys 68/435 Yield

Conditions & References With bis(tetrabutylammonium) hexamolybdate, isopropyl alcohol, Time= 3h, T= 220 °C , Microwave irradiation Larsen, Daniel B.; Petersen, Allan R.; Dethlefsen, Johannes R.; Teshome, Ayele; Fristrup, Peter; Chemistry - A European Journal; vol. 22; nb. 46; (2016); p. 16621 - 16631 View in Reaxys

H HO

O

Rx-ID: 44516947 View in Reaxys 69/435 Yield

Conditions & References With bis(tetrabutylammonium) hexamolybdate, isopropyl alcohol, Time= 2h, T= 240 °C , Microwave irradiation, Temperature Larsen, Daniel B.; Petersen, Allan R.; Dethlefsen, Johannes R.; Teshome, Ayele; Fristrup, Peter; Chemistry - A European Journal; vol. 22; nb. 46; (2016); p. 16621 - 16631 View in Reaxys O

H HO

HO

O

Rx-ID: 44633209 View in Reaxys 70/435 Yield

Conditions & References Reaction Steps: 2 1: oxygen; potassium hydoxide / water / 6 h / 60 °C / 750.08 Torr / Sealed tube; Green chemistry 2: potassium hydoxide / water / 6 h / 60 °C / 750.08 Torr / Sealed tube; Green chemistry With oxygen, potassium hydoxide in water Zhou, Maoxiang; Zhang, Leilei; Miller, Jeffrey T.; Yang, Xiaofeng; Liu, Xiaoyan; Wang, Aiqin; Zhang, Tao; Chinese Journal of Catalysis; vol. 37; nb. 10; (2016); p. 1764 - 1770 View in Reaxys 2H

2H

2

H

HO 2H

2H 2

H

2H

O 2H

2H 2H

Rx-ID: 2117815 View in Reaxys 71/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

348/438

2018-03-11 22:07:32


Yield 94 %

Conditions & References With pyridinium chlorochromate in dichloromethane, Time= 2h, Ambient temperature Fleming, Paul E.; Mocek, Ursula; Floss, Heinz G.; Journal of the American Chemical Society; vol. 115; nb. 2; (1993); p. 805 - 807 View in Reaxys

84 %

With pyridinium chlorochromate in dichloromethane, Time= 1h, T= 20 °C Bialecki, Jason B.; Ruzicka, Josef; Attygalle, Athula B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 50; nb. 8; (2007); p. 711 - 715 View in Reaxys

80 %

With manganese(IV) oxide in benzene, Time= 15h, Reflux, Inert atmosphere Takahashi, Masayuki; Micalizio, Glenn C.; Chemical Communications; vol. 46; nb. 19; (2010); p. 3336 - 3338 View in Reaxys With dipyridinium dichromate, Oxidation Yamataka, Hiroshi; Sasaki, Daizo; Kuwatani, Yoshiyuki; Mishima, Masaaki; Tsuno, Yuho; Journal of the American Chemical Society; vol. 119; nb. 42; (1997); p. 9975 - 9979 View in Reaxys With dipyridinium dichromate Yamataka, Hiroshi; Shimizu, Makoto; Mishima, Masaaki; Bulletin of the Chemical Society of Japan; vol. 75; nb. 1; (2002); p. 127 - 129 View in Reaxys With pyridinium chlorochromate in dichloromethane, Time= 1h, T= 20 °C Li, Long; Zhou, Bo; Wang, Yong-Heng; Shu, Chao; Pan, Yi-Fei; Lu, Xin; Ye, Long-Wu; Angewandte Chemie International Edition; vol. 54; nb. 28; (2015); p. 8245 - 8249; Angew. Chem.; vol. 54; (2015); p. 8245 - 8249,4 View in Reaxys

H

N

H 2N

HO

O

Rx-ID: 28714100 View in Reaxys 72/435 Yield 95 %

Conditions & References With Au/HAP, oxygen, Time= 5h, T= 100 °C , chemoselective reaction Sun, Hao; Su, Fang-Zheng; Ni, Ji; Cao, Yong; He, He-Yong; Fan, Kang-Nian; Angewandte Chemie, International Edition; vol. 48; nb. 24; (2009); p. 4390 - 4393 View in Reaxys

97 %Chromat., 136 μmol

With TiO2 loading Pt(0.3) nanoparticles, Time= 12h, T= 24.84 °C , p= 760.051Torr , UV-irradiation, Inert atmosphere Shiraishi, Yasuhiro; Ikeda, Makoto; Tsukamoto, Daijiro; Tanaka, Shunsuke; Hirai, Takayuki; Chemical Communications; vol. 47; nb. 16; (2011); p. 4811 - 4813 View in Reaxys

39 %Chro- With Au/MgO in toluene, Time= 22h, T= 110 °C , p= 760.051Torr , Inert atmosphere mat., 19 %Chromat. Ishida, Tamao; Takamura, Rena; Takei, Takashi; Akita, Tomoki; Haruta, Masatake; Applied Catalysis A: General; vol. 413-414; (2012); p. 261 - 266 View in Reaxys 2.4. General procedure for the synthesis of imines from alcohols and amines General procedure: In a typical reaction, the catalyst was weighed into a screw-capped glass pressure vessel containing a stir bar. The required amounts of alcohol (0.5 mmol) and amine (0.6 mmol), pre-dissolved in solvent (2 mL), were added and the vessel was filled with oxygen, sealed, and heated to the desired temperature in an oil bath with stirring. The products of the reaction were analyzed by gas chromatography (GC, Agilent 7890A) and GC-mass spectrometry (MS, Agilent 7890A/5975C).

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

349/438

2018-03-11 22:07:32


With cerium(IV) oxide, oxygen in para-xylene, Time= 12h, T= 60 °C , Catalytic behavior, Solvent Zhang, Zhixin; Wang, Yehong; Wang, Min; Lü, Jianmin; Li, Lihua; Zhang, Zhe; Li, Mingrun; Jiang, Jingyang; Wang, Feng; Chinese Journal of Catalysis; vol. 36; nb. 9; (2015); p. 1623 - 1630 View in Reaxys

18O

H 18O

Rx-ID: 28828043 View in Reaxys 73/435 Yield

Conditions & References With platinum doped titanium oxide, oxygen in benzotrifluoride, Time= 4h, T= 20 °C , p= 750.075Torr , Irradiation, Inert atmosphere Zhang, Miao; Wang, Qi; Chen, Chuncheng; Ma, Wanhong; Zhao, Jincai; Zang, Ling; Angewandte Chemie, International Edition; vol. 48; nb. 33; (2009); p. 6081 - 6084; Angewandte Chemie; vol. 121; nb. 33; (2009); p. 6197 6200 View in Reaxys With oxygen, titanium(IV) oxide in acetonitrile, Time= 1h, T= 25 °C , Irradiation, Molecular sieve, Reagent/catalyst, Solvent Meng, Chao; Yang, Kai; Fu, Xianzhi; Yuan, Rusheng; ACS Catalysis; vol. 5; nb. 6; (2015); p. 3760 - 3766 View in Reaxys H

H 18O

O

Rx-ID: 28828044 View in Reaxys 74/435 Yield

Conditions & References With oxygen, titanium(IV) oxide in benzotrifluoride, Time= 4h, T= 20 °C , p= 750.075Torr , Irradiation Zhang, Miao; Wang, Qi; Chen, Chuncheng; Ma, Wanhong; Zhao, Jincai; Zang, Ling; Angewandte Chemie, International Edition; vol. 48; nb. 33; (2009); p. 6081 - 6084; Angewandte Chemie; vol. 121; nb. 33; (2009); p. 6197 6200 View in Reaxys With Oxone in water, Time= 21h, T= 50 °C , Inert atmosphere, chemoselective reaction Wu, Shang; Ma, Hengchang; Lei, Ziqiang; Synlett; nb. 18; (2010); p. 2818 - 2822 View in Reaxys With oxygen, copper dichloride in acetonitrile, Time= 1h, T= 25 °C , Irradiation, Reagent/catalyst Meng, Chao; Yang, Kai; Fu, Xianzhi; Yuan, Rusheng; ACS Catalysis; vol. 5; nb. 6; (2015); p. 3760 - 3766 View in Reaxys O

O S

O H 2N

O

H

NH

S

HO

O

Rx-ID: 29116973 View in Reaxys 75/435 Yield 95 %, 25 %

Conditions & References With potassium hydoxide, Time= 10h, T= 130 °C , Inert atmosphere Li, Qiang-Qiang; Xiao, Zu-Feng; Yao, Chuan-Zhi; Zheng, Hong-Xing; Kang, Yan-Biao; Organic Letters; vol. 17; nb. 21; (2015); p. 5328 - 5331 View in Reaxys With copper diacetate, potassium carbonate, Time= 12h, T= 150 °C Cui, Xinjiang; Shi, Feng; Tse, Man Kin; Goerdes, Dirk; Thurow, Kerstin; Beller, Matthias; Deng, Youquan; Advanced Synthesis and Catalysis; vol. 351; nb. 17; (2009); p. 2949 - 2958

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

350/438

2018-03-11 22:07:32


View in Reaxys O

O

O

O

S

S

N

H

NH

HO

O

Rx-ID: 29379039 View in Reaxys 76/435 Yield 98 %Spectr., 98 %Chromat.

Conditions & References With [(Cp*Ir)2(μ-NTs)2], potassium tert-butylate in toluene, Time= 17h, Inert atmosphere, Reflux Zhu, Mingwen; Fujita, Ken-Ichi; Yamaguchi, Ryohei; Organic Letters; vol. 12; nb. 6; (2010); p. 1336 - 1339 View in Reaxys With potassium carbonate, Time= 6h, T= 100 °C , Inert atmosphere, Sealed tube Xu, Qing; Li, Qiang; Zhu, Xiaogang; Chen, Jianhui; Advanced Synthesis and Catalysis; vol. 355; nb. 1; (2013); p. 73 - 80 View in Reaxys With potassium hydoxide, Time= 25h, T= 130 °C , Inert atmosphere, Mechanism Li, Qiang-Qiang; Xiao, Zu-Feng; Yao, Chuan-Zhi; Zheng, Hong-Xing; Kang, Yan-Biao; Organic Letters; vol. 17; nb. 21; (2015); p. 5328 - 5331 View in Reaxys O

H O

HO

O

Rx-ID: 30785765 View in Reaxys 77/435 Yield

Conditions & References With oxygen, T= 120 °C , p= 7757.43Torr Dimitratos, Nikolaos; Lopez-Sanchez, Jose Antonio; Morgan, David; Carley, Albert F.; Tiruvalam, Ramchandra; Kiely, Christopher J.; Bethell, Donald; Hutchings, Graham J.; Physical Chemistry Chemical Physics; vol. 11; nb. 25; (2009); p. 5142 - 5153 View in Reaxys With oxygen in neat (no solvent), T= 120 - 140 °C , p= 7500.75Torr , Autoclave, Reagent/catalyst Hutchings, Graham J.; Catalysis Today; vol. 238; (2014); p. 69 - 73 View in Reaxys With oxygen in cyclohexane, T= 80 °C , p= 1520.1Torr , Catalytic behavior Chan-Thaw, Carine E.; Villa, Alberto; Veith, Gabriel M.; Prati, Laura; ChemCatChem; vol. 7; nb. 8; (2015); p. 1338 - 1346 View in Reaxys 2.3. Catalytic performance General procedure: Solvent-free aerobic oxidation of benzyl alcohol using molecular O2 was carried out in a batchtype reactor under mild conditions. 5 ml benzyl alcohol and 20 mg catalyst were added into a 25 ml three-necked glass flask equipped with a reflux condenser. Prior to reaction, the system was first charged with O2 by bubbling ultrahigh purity O2 at a flow rate of 15 ml min1 for 20 min to remove air. Under the continuous flow of O2, the reactor was immersed into a silicon oil bath at 90 °C to initiate the reaction. During the reaction, the mixture was vigorously stirred at a rateof 1250 rpm to exclude any mass transfer limitation [60]. Finally,the reaction products were analyzed using a Shimadzu GC-2014 gas chromatograph equipped with an Rtx-1 capillary column and an auto-injector. With oxygen in neat (no solvent), Time= 6h, T= 90 °C , Catalytic behavior, Reagent/catalyst, chemoselective reaction Wang, Hengwei; Wang, Chunlei; Yan, Huan; Yi, Hong; Lu, Junling; Journal of Catalysis; vol. 324; (2015); p. 59 68

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

351/438

2018-03-11 22:07:32


View in Reaxys O

H O

HO

O

Rx-ID: 30785766 View in Reaxys 78/435 Yield

Conditions & References With oxygen, T= 120 °C , p= 7757.43Torr Dimitratos, Nikolaos; Lopez-Sanchez, Jose Antonio; Morgan, David; Carley, Albert F.; Tiruvalam, Ramchandra; Kiely, Christopher J.; Bethell, Donald; Hutchings, Graham J.; Physical Chemistry Chemical Physics; vol. 11; nb. 25; (2009); p. 5142 - 5153 View in Reaxys With oxygen in neat (no solvent), Time= 5h, T= 120 °C , p= 760.051Torr , Catalytic behavior Nepak, Devadutta; Srinivas, Darbha; RSC Advances; vol. 5; nb. 59; (2015); p. 47740 - 47748 View in Reaxys

2H

2H

2H 2

H

O

O

Rx-ID: 33276208 View in Reaxys 79/435 Yield

Conditions & References With Dess-Martin periodane in dichloromethane, Time= 2h, T= 20 °C Albaladejo, Maria Jose; Alonso, Francisco; Moglie, Yanina; Yus, Miguel; European Journal of Organic Chemistry; nb. 16; (2012); p. 3093 - 3104 View in Reaxys With sodium acetate, pyridinium chlorochromate in dichloromethane, Time= 3h, Molecular sieve Zheng, Hong-Xing; Xiao, Zu-Feng; Yao, Chuan-Zhi; Li, Qiang-Qiang; Ning, Xiao-Shan; Kang, Yan-Biao; Tang, Yong; Organic Letters; vol. 17; nb. 24; (2015); p. 6102 - 6105 View in Reaxys O

H

O

O

O

HO

HO

HO

Rx-ID: 33846439 View in Reaxys 80/435 Yield

Conditions & References

30 %Chro- With dihydrogen peroxide, trifluoroacetic acid, zinc dibromide, Time= 16h, T= 20 °C mat., 32 %Chromat. Wu, Xiao-Feng; Chemistry - A European Journal; vol. 18; nb. 29; (2012); p. 8912 - 8915 View in Reaxys With oxygen, Time= 10h, T= 110 °C , p= 7600.51Torr , Catalytic behavior, Time Smolentseva, Elena; Costa, Vinícius V.; Cotta, Rafaela F.; Simakova, Olga; Beloshapkin, Sergey; Gusevskaya, Elena V.; Simakov, Andrey; ChemCatChem; vol. 7; nb. 6; (2015); p. 1011 - 1017 View in Reaxys 16 %Chromat., 21 %Chromat., 12 %Chromat.

With oxygen, Time= 2h, T= 184.84 °C , p= 750.075Torr , Autoclave Deng, Weiping; Zhang, Hongxi; Wu, Xuejiao; Li, Rongsheng; Zhang, Qinghong; Wang, Ye; Green Chemistry; vol. 17; nb. 11; (2015); p. 5009 - 5018 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

352/438

2018-03-11 22:07:32


O

H

O

O

HO

O

HO

O

Rx-ID: 37474767 View in Reaxys 81/435 Yield

Conditions & References The reactions were carried out in a stainless steel reactor equipped with a magnetic stirrer. In a typical run, a mixture of benzyl alcohol (2.5 mmol), methanol (2 mL), and the catalyst (10 mg; 1.3 μmol of Au: 0.05 molpercent) was transferred in the reactor. The reactor was pressurized with oxygen to the total pressure of 10 atm and placed in an oil bath; then, the solution was intensively stirred at 110 °C for the reported time. The reactions were followed by gas chromatography (GC) (Shimadzu 17 instrument, Carbowax 20M capillary column). At appropriate time intervals, stirring was stopped and after catalyst settling aliquots were taken and analyzed by GC. The structures of the products were confirmed by GC/MS (Shimadzu QP2010-PLUS instrument, 70 eV). With oxygen, Time= 4h, T= 110 °C , p= 7600.51Torr , Reagent/catalyst, Time Estrada, Miguel; Costa, Vinicius V.; Beloshapkin, Sergey; Fuentes, Sergio; Stoyanov, Evgenii; Gusevskaya, Elena V.; Simakov, Andrey; Applied Catalysis A: General; vol. 473; (2014); p. 96 - 103 View in Reaxys With oxygen, Time= 10h, T= 110 °C , p= 7600.51Torr , Catalytic behavior, Time Smolentseva, Elena; Costa, Vinícius V.; Cotta, Rafaela F.; Simakova, Olga; Beloshapkin, Sergey; Gusevskaya, Elena V.; Simakov, Andrey; ChemCatChem; vol. 7; nb. 6; (2015); p. 1011 - 1017 View in Reaxys

O

H

N

N

H 2N

HO

O

O

Rx-ID: 38790859 View in Reaxys 82/435 Yield 28 %

Conditions & References With titanium(IV) oxide in water, Time= 4h, T= 24.84 °C , Sealed tube, UV-irradiation, Inert atmosphere, Reagent/ catalyst Selvam, Kaliyamoorthy; Sakamoto, Hirokatsu; Shiraishi, Yasuhiro; Hirai, Takayuki; New Journal of Chemistry; vol. 39; nb. 4; (2015); p. 2467 - 2473 View in Reaxys

22.1 μmol, 121.2 μmol, 19.2 μmol

in acetonitrile, Time= 12h, T= 24.84 °C , Irradiation, Catalytic behavior, Quantum yield, Reagent/catalyst, Wavelength Higashimoto, Shinya; Nakai, Yuta; Azuma, Masashi; Takahashi, Masanari; Sakata, Yoshihisa; RSC Advances; vol. 4; nb. 71; (2014); p. 37662 - 37668 View in Reaxys O O

H

O

O

HO

HO

O

O

O

Rx-ID: 39565254 View in Reaxys 83/435 Yield

Conditions & References With oxygen, Time= 10h, T= 110 °C , p= 7600.51Torr , Catalytic behavior, Reagent/catalyst, Time Smolentseva, Elena; Costa, Vinícius V.; Cotta, Rafaela F.; Simakova, Olga; Beloshapkin, Sergey; Gusevskaya, Elena V.; Simakov, Andrey; ChemCatChem; vol. 7; nb. 6; (2015); p. 1011 - 1017 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

353/438

2018-03-11 22:07:32


O

HN

N

H

N

HO

O

O

Rx-ID: 39814906 View in Reaxys 84/435 Yield

Conditions & References

56 %, 30 %

in water, Time= 4h, T= 24.84 °C , Sealed tube, UV-irradiation, Inert atmosphere, Reagent/catalyst Selvam, Kaliyamoorthy; Sakamoto, Hirokatsu; Shiraishi, Yasuhiro; Hirai, Takayuki; New Journal of Chemistry; vol. 39; nb. 4; (2015); p. 2467 - 2473 View in Reaxys

O

HN

N

H

N

H 2N

HO

O

O

Rx-ID: 39814907 View in Reaxys 85/435 Yield

Conditions & References

8 %, 8 %

With silver-deposited TiO2 in water, Time= 4h, T= 24.84 °C , Sealed tube, UV-irradiation, Inert atmosphere Selvam, Kaliyamoorthy; Sakamoto, Hirokatsu; Shiraishi, Yasuhiro; Hirai, Takayuki; New Journal of Chemistry; vol. 39; nb. 4; (2015); p. 2467 - 2473 View in Reaxys

O

H

HN

N HO

O

O

Rx-ID: 39814908 View in Reaxys 86/435 Yield

Conditions & References

96 %

in water, Time= 4h, T= 24.84 °C , Sealed tube, UV-irradiation, Inert atmosphere Selvam, Kaliyamoorthy; Sakamoto, Hirokatsu; Shiraishi, Yasuhiro; Hirai, Takayuki; New Journal of Chemistry; vol. 39; nb. 4; (2015); p. 2467 - 2473 View in Reaxys

NiAl-LDH/RGO supported Au catalyst

HO O

H

O

O

HO

O

Rx-ID: 39895442 View in Reaxys 87/435 Yield

Conditions & References With oxygen, Time= 10h, T= 140 °C , p= 1500.15Torr , Autoclave, Catalytic behavior, Reagent/catalyst Miao; Feng; Jin; He; Liu; Du; Zhang; Li; RSC Advances; vol. 5; nb. 45; (2015); p. 36066 - 36074 View in Reaxys H

HO

HO

O

Rx-ID: 40385927 View in Reaxys 88/435 Yield

Conditions & References With Co-CoO(at)N-doped porous carbon, Time= 12h, T= 80 °C , Reagent/catalyst, chemoselective reaction Zhou, Yu-Xiao; Chen, Yu-Zhen; Cao, Lina; Lu, Junling; Jiang, Hai-Long; Chemical Communications; vol. 51; nb. 39; (2015); p. 8292 - 8295 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

354/438

2018-03-11 22:07:32


H HO

OH

O

Rx-ID: 40663645 View in Reaxys 89/435 Yield

Conditions & References

87 %

General procedures for the synthesis of benzaldehydes General procedure: The benzyl alcohols substrates (1a–1p) (0.2mmol), FeCl3·6H2O (0.002mmol, 5.4mg) and triphenylmethanol 2 (0.2mmol, 52mg) were mixed in a dried vessel. Then the reaction was irradiated under the microwave at 55°C for 1h. The crude mixture was purified by a flash column chromatography to afford the benzaldehydes (4a– 4p). With iron(III) chloride hexahydrate, T= 55 °C , Microwave irradiation, Catalytic behavior, Reagent/catalyst, Temperature Wang, Xiaoyu; Du, Chuan; Shi, Hui; Pang, Yadong; Jin, Shengfei; Hou, Yuqian; Wang, Yanshi; Peng, Xiaoshi; Xiao, Jianyong; Liu, Yang; Liu, Yongxiang; Cheng, Maosheng; Tetrahedron; vol. 71; nb. 38; (2015); p. 6744 6748 View in Reaxys 2H

H

2H

HO

O

O

HO

Rx-ID: 40744588 View in Reaxys 90/435 Yield

Conditions & References With iron(II) perchlorate monohydrate, ozone, acetonitrile, Kinetics Bataineh, Hajem; Pestovsky, Oleg; Bakac, Andreja; ACS Catalysis; vol. 5; nb. 3; (2015); p. 1629 - 1637 View in Reaxys 2H

OH

H

O

2H

O

HO

Rx-ID: 40744589 View in Reaxys 91/435 Yield

Conditions & References With iron(II) perchlorate monohydrate, ozone, acetonitrile, Kinetics Bataineh, Hajem; Pestovsky, Oleg; Bakac, Andreja; ACS Catalysis; vol. 5; nb. 3; (2015); p. 1629 - 1637 View in Reaxys H

2

H

HO

HO

O

O

Rx-ID: 40744590 View in Reaxys 92/435 Yield

Conditions & References With iron(II) perchlorate monohydrate, ozone, acetonitrile, Kinetics Bataineh, Hajem; Pestovsky, Oleg; Bakac, Andreja; ACS Catalysis; vol. 5; nb. 3; (2015); p. 1629 - 1637 View in Reaxys

2H 2H

2H

OH

H

2H 2H2H

2H

HO

O

O

Rx-ID: 40744591 View in Reaxys 93/435 Yield

Conditions & References With iron(II) perchlorate monohydrate, ozone, acetonitrile, Kinetics Bataineh, Hajem; Pestovsky, Oleg; Bakac, Andreja; ACS Catalysis; vol. 5; nb. 3; (2015); p. 1629 - 1637

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

355/438

2018-03-11 22:07:32


View in Reaxys H

OH

O

HO

O

O

Rx-ID: 40744593 View in Reaxys 94/435 Yield

Conditions & References With iron(II) perchlorate monohydrate, ozone, acetonitrile, Kinetics Bataineh, Hajem; Pestovsky, Oleg; Bakac, Andreja; ACS Catalysis; vol. 5; nb. 3; (2015); p. 1629 - 1637 View in Reaxys H O

HO

HO

O

Rx-ID: 40744596 View in Reaxys 95/435 Yield

Conditions & References With iron(II) perchlorate monohydrate, ozone, acetonitrile, Kinetics Bataineh, Hajem; Pestovsky, Oleg; Bakac, Andreja; ACS Catalysis; vol. 5; nb. 3; (2015); p. 1629 - 1637 View in Reaxys H

OH

HO

O

O

Rx-ID: 40744597 View in Reaxys 96/435 Yield

Conditions & References With iron(II) perchlorate monohydrate, ozone, acetonitrile, Kinetics Bataineh, Hajem; Pestovsky, Oleg; Bakac, Andreja; ACS Catalysis; vol. 5; nb. 3; (2015); p. 1629 - 1637 View in Reaxys O

H

O N

O

HO

O

O N

Rx-ID: 40759007 View in Reaxys 97/435 Yield 19 %, 58 %

Conditions & References Stage 1: With oxygen, potassium carbonate in toluene, Time= 24.5h, T= 89.84 °C , Schlenk technique Stage 2: in toluene, Schlenk technique, Knoevenagel Condensation Horiuchi, Yu; Do Van, Dang; Yonezawa, Yusuke; Saito, Masakazu; Dohshi, Satoru; Kim, Tae-Ho; Matsuoka, Masaya; RSC Advances; vol. 5; nb. 89; (2015); p. 72653 - 72658 View in Reaxys

H 2N

HS

HO

N

H

S

O

Rx-ID: 40863015 View in Reaxys 98/435 Yield

Conditions & References

25 %, 6 With sodium t-butanolate in toluene, Time= 24h, T= 100 °C , Schlenk technique, Sealed tube, Green chemistry, %Chromat. Concentration Shi, Xinkang; Guo, Junmei; Liu, Jianping; Ye, Mingde; Xu, Qing; Chemistry - A European Journal; vol. 21; nb. 28; (2015); p. 9988 - 9993 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

356/438

2018-03-11 22:07:32


(v3)

O

H

O

Cu

(v4)

O

HO

O

(v3)

Cu

O

O

O

Rx-ID: 40865979 View in Reaxys 99/435 Yield

Conditions & References T= 170 °C Staniuk, Malwina; Zindel, Daniel; Van Beek, Wouter; Hirsch, Ofer; Kränzlin, Niklaus; Niederberger, Markus; Koziej, Dorota; CrystEngComm; vol. 17; nb. 36; (2015); p. 6962 - 6971 View in Reaxys

(v3)

O (v4)

H

O

Cu

O

HO

O

(v3)

Cu 2O

O

O

O

Rx-ID: 40865980 View in Reaxys 100/435 Yield

Conditions & References T= 140 °C Staniuk, Malwina; Zindel, Daniel; Van Beek, Wouter; Hirsch, Ofer; Kränzlin, Niklaus; Niederberger, Markus; Koziej, Dorota; CrystEngComm; vol. 17; nb. 36; (2015); p. 6962 - 6971 View in Reaxys O

H 2N O

HS

HO

N

H

S

O

E

Rx-ID: 41111829 View in Reaxys 101/435 Yield 5.4 %, 16.8%, 28.6 %

Conditions & References Stage 1: With oxygen in dodecane, toluene, Time= 9h, T= 84.84 °C Stage 2:Time= 7h, T= 99.84 °C Stage 3: in toluene, Time= 2h, T= 109.84 °C Srivastava, Rajendra; Sarmah, Bhaskar; Satpati, Biswarup; RSC Advances; vol. 5; nb. 33; (2015); p. 25998 26006 View in Reaxys

NH

H H 2N O

HO

O

O

Rx-ID: 41111834 View in Reaxys 102/435 Yield 75.1 %, 6.7 %

Conditions & References Stage 1: With oxygen in dodecane, toluene, Time= 9h, T= 84.84 °C Stage 2:Time= 7h, T= 29.84 °C Srivastava, Rajendra; Sarmah, Bhaskar; Satpati, Biswarup; RSC Advances; vol. 5; nb. 33; (2015); p. 25998 26006 View in Reaxys

18.9 %, 35.7 %

Stage 1: With oxygen in dodecane, toluene, Time= 9h, T= 84.84 °C Stage 2:Time= 7h, T= 29.84 °C Srivastava, Rajendra; Sarmah, Bhaskar; Satpati, Biswarup; RSC Advances; vol. 5; nb. 33; (2015); p. 25998 26006

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

357/438

2018-03-11 22:07:32


View in Reaxys O

H O

HO

E

O

Rx-ID: 41111835 View in Reaxys 103/435 Yield

Conditions & References

7.8 %, 73.6%

Stage 1: With oxygen in dodecane, toluene, Time= 9h, T= 84.84 °C Stage 2:Time= 7h, T= 99.84 °C Srivastava, Rajendra; Sarmah, Bhaskar; Satpati, Biswarup; RSC Advances; vol. 5; nb. 33; (2015); p. 25998 26006 View in Reaxys

45.9 %, 9.4 %

Stage 1: With oxygen in dodecane, toluene, Time= 9h, T= 84.84 °C Stage 2:Time= 7h, T= 99.84 °C Srivastava, Rajendra; Sarmah, Bhaskar; Satpati, Biswarup; RSC Advances; vol. 5; nb. 33; (2015); p. 25998 26006 View in Reaxys O

O S

H

N

HO

O

Rx-ID: 41286878 View in Reaxys 104/435 Yield

Conditions & References Time= 25h, T= 130 °C , Inert atmosphere, Mechanism Li, Qiang-Qiang; Xiao, Zu-Feng; Yao, Chuan-Zhi; Zheng, Hong-Xing; Kang, Yan-Biao; Organic Letters; vol. 17; nb. 21; (2015); p. 5328 - 5331 View in Reaxys H

O

O

HO

HO

O

Rx-ID: 41451056 View in Reaxys 105/435 Yield

Conditions & References With silver doped crystalline titania in acetonitrile, Time= 48h, p= 750.075Torr , UV-irradiation, Reagent/catalyst, Concentration, Time Wang, Liujie; Zhang, Xiaoliang; Yang, Longhua; Wang, Chao; Wang, Hongming; Catalysis Science and Technology; vol. 5; nb. 10; (2015); p. 4800 - 4805 View in Reaxys OH

O

O

H O

HO

O

Rx-ID: 36931389 View in Reaxys 106/435 Yield 49 %

Conditions & References With potassium hydoxide in toluene, Time= 16h, T= 135 °C , Sealed tube, Inert atmosphere, Schlenk technique Xu, Qing; Chen, Jianhui; Tian, Haiwen; Yuan, Xueqin; Li, Shuangyan; Zhou, Chongkuan; Liu, Jianping; Angewandte Chemie - International Edition; vol. 53; nb. 1; (2014); p. 225 - 229; Angew. Chem.; vol. 126; nb. 1; (2014); p. 229 - 233,5 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

358/438

2018-03-11 22:07:32


1

N

N

2

(v4)

Cl

Cl

(v4)

(v4)

Cu

N

N

O

O

H

(v4) (v4)

(v4)

Cu 2+ O– O–

HO

O

(v2)

(v2)

-1 F

F

Sb

F

F

F (v6)

F

Rx-ID: 37210344 View in Reaxys 107/435 Yield

Conditions & References in dichloromethane, T= 19.84 °C , Kinetics Asami, Kazutaka; Takashina, Akiko; Kobayashi, Misato; Iwatsuki, Satoshi; Yajima, Tatsuo; Kochem, Amelie; Van Gastel, Maurice; Tani, Fumito; Kohzuma, Takamitsu; Thomas, Fabrice; Shimazaki, Yuichi; Dalton Transactions; vol. 43; nb. 5; (2014); p. 2283 - 2293 View in Reaxys 1

N

0.5

(v4)

Cl

Cl

O

O

N (v4)

(v4)

Cu

O

N

N

O

HO

O

H

(v4) (v4)

(v4)

Cu 2+ O– O–

O

O

(v2)

(v2)

-1 F F

F Sb F

F (v6)

F

Rx-ID: 37210345 View in Reaxys 108/435 Yield

Conditions & References in dichloromethane, T= 19.84 °C , Kinetics Asami, Kazutaka; Takashina, Akiko; Kobayashi, Misato; Iwatsuki, Satoshi; Yajima, Tatsuo; Kochem, Amelie; Van Gastel, Maurice; Tani, Fumito; Kohzuma, Takamitsu; Thomas, Fabrice; Shimazaki, Yuichi; Dalton Transactions; vol. 43; nb. 5; (2014); p. 2283 - 2293 View in Reaxys 1 O

O

O

O

-1 N

(v4)

O

N (v4)

Cu

(v4)

O

F F

F Sb F

F F

N

N

(v6)

(v4)

HO

H

(v4) (v4)

Cu 2+

O–

(v2)

O– (v2)

O

Rx-ID: 37210346 View in Reaxys 109/435 Yield

Conditions & References in dichloromethane, T= 19.84 °C , Kinetics Asami, Kazutaka; Takashina, Akiko; Kobayashi, Misato; Iwatsuki, Satoshi; Yajima, Tatsuo; Kochem, Amelie; Van Gastel, Maurice; Tani, Fumito; Kohzuma, Takamitsu; Thomas, Fabrice; Shimazaki, Yuichi; Dalton Transactions; vol. 43; nb. 5; (2014); p. 2283 - 2293 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

359/438

2018-03-11 22:07:32


N

H

HO

O N

Rx-ID: 37276867 View in Reaxys 110/435 Yield

Conditions & References

91 %, 2 %

With Zr-MOF-NH2 in para-xylene, Time= 48h, T= 89.84 °C , Irradiation, Knoevenagel Condensation Toyao, Takashi; Saito, Masakazu; Horiuchi, Yu; Matsuoka, Masaya; Catalysis Science and Technology; vol. 4; nb. 3; (2014); p. 625 - 628 View in Reaxys N

N

H

N

HO

O N

Rx-ID: 37276868 View in Reaxys 111/435 Yield 1 %, 89 %

Conditions & References With Zr-MOF-NH2 in para-xylene, Time= 48h, T= 24.84 °C , Irradiation, Knoevenagel Condensation Toyao, Takashi; Saito, Masakazu; Horiuchi, Yu; Matsuoka, Masaya; Catalysis Science and Technology; vol. 4; nb. 3; (2014); p. 625 - 628 View in Reaxys Cl

H HO

O

Rx-ID: 37276879 View in Reaxys 112/435 Yield 90 %

Conditions & References With iron(III) chloride hexahydrate in toluene, T= 80 °C Zhang, Houcai; Liu, Ruiting; Zhou, Xigeng; Science China Chemistry; vol. 57; nb. 2; (2014); p. 282 - 288 View in Reaxys H

2H

O

HO

O

Rx-ID: 37403176 View in Reaxys 113/435 Yield

Conditions & References With tert.-butylhydroperoxide, [Fe(N-(2-pyridylmethyl)iminodiethanolate)(NO3)]2(NO3)2*2CH3OH in acetonitrile, Time= 24h, T= 50 °C , Kinetics, Reagent/catalyst Shin, Jong Won; Bae, Jeong Mi; Kim, Cheal; Min, Kil Sik; Dalton Transactions; vol. 43; nb. 10; (2014); p. 3999 4008 View in Reaxys

H C

O

O

E

HO

O

O

Rx-ID: 37926886 View in Reaxys 114/435 Yield

Conditions & References

11 %, 57 % With oxygen, copper(II) acetate monohydrate, palladium dichloride in dimethyl sulfoxide, Time= 14h, T= 80 °C , Schlenk technique Wang, Lu; Wang, Yanxia; Liu, Chao; Lei, Aiwen; Angewandte Chemie - International Edition; vol. 53; nb. 22; (2014); p. 5657 - 5661; Angew. Chem.; vol. 126; nb. 22; (2014); p. 5763 - 5767,5 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

360/438

2018-03-11 22:07:32


Cl

H 2N

H N

HO

Cl

O

Rx-ID: 37949858 View in Reaxys 115/435 Yield

Conditions & References With oxygen in toluene, Time= 24h, T= 80 °C , Green chemistry, Overall yield = 76 percentChromat. Chen, Bo; Li, Jun; Dai, Wen; Wang, Lianyue; Gao, Shuang; Green Chemistry; vol. 16; nb. 6; (2014); p. 3328 3334 View in Reaxys

N

NH 2

H N

N

HO

O

Rx-ID: 37949859 View in Reaxys 116/435 Yield

Conditions & References With oxygen in toluene, Time= 24h, T= 80 °C , Green chemistry, Overall yield = 28 percentChromat. Chen, Bo; Li, Jun; Dai, Wen; Wang, Lianyue; Gao, Shuang; Green Chemistry; vol. 16; nb. 6; (2014); p. 3328 3334 View in Reaxys

O

N

NH 2

H

O

HO

O

Rx-ID: 38086772 View in Reaxys 117/435 Yield

Conditions & References General procedure: General procedure for N-alkylation of amines with alcoholsusing Al-MS With Aluminium grafted mesoporous silica (Al-MCM-41) in neat (no solvent), Time= 17h, T= 180 - 200 °C , Green chemistry Tayade, Kamlesh N.; Mishra, Manish; Munusamy; Somani, Rajesh S.; Journal of Molecular Catalysis A: Chemical; vol. 390; (2014); p. 91 - 96 View in Reaxys O

H

O N

N

NH 2

O

HO

N

O

O

Rx-ID: 38086773 View in Reaxys 118/435 Yield

Conditions & References General procedure: General procedure for N-alkylation of amines with alcoholsusing Al-MS With Aluminium grafted mesoporous silica (Al-MCM-41) in neat (no solvent), Time= 17h, T= 180 - 200 °C , Green chemistry Tayade, Kamlesh N.; Mishra, Manish; Munusamy; Somani, Rajesh S.; Journal of Molecular Catalysis A: Chemical; vol. 390; (2014); p. 91 - 96 View in Reaxys O

O H 2N

O

S

N

S

O

O

S

O

H

NH

HO

O

Rx-ID: 38086774 View in Reaxys 119/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

361/438

2018-03-11 22:07:32


Yield

Conditions & References General procedure: General procedure for N-alkylation of amines with alcoholsusing Al-MS With Aluminium grafted mesoporous silica (Al-MCM-41) in neat (no solvent), Time= 17h, T= 180 - 220 °C , Green chemistry Tayade, Kamlesh N.; Mishra, Manish; Munusamy; Somani, Rajesh S.; Journal of Molecular Catalysis A: Chemical; vol. 390; (2014); p. 91 - 96 View in Reaxys

3

O

9 Fe 3+ H 2O O N

HO

O–

H

O

O

HO

Rx-ID: 38398433 View in Reaxys 120/435 Yield

Conditions & References

41 %

Oxidation of phenylmethanol Oxidation of phenylmethanol Phenylmethanol (1.08 g, 10 mmol) was mixed with Mn(NO3)2*H2O (0.06 g, 0.2 mmol) and Fe(NO3)3*9H2O (0.08 g, 0.3 mmol) according to the general procedure. Standard workup gave 0.50 g (41percent) of benzoic acid and 0.41 g (39percent) of benzaldehyde. Patent; University of Tennessee Research Foundation; Bozell, Joseph J.; Chatterjee, Sabornie; US2014/249300; (2014); (A1) English View in Reaxys

H HO

OH

O HO

O

O

Rx-ID: 46451556 View in Reaxys 121/435 Yield

Conditions & References

59.7 With 5-palladium/activated carbon, oxygen in cyclohexane, Time= 22h, T= 90 °C , p= 750.075Torr %Chromat., 40.3 Li, Xinle; Guo, Zhiyong; Xiao, Chaoxian; Goh, Tian Wei; Tesfagaber, Daniel; Huang, Wenyu; ACS Catalysis; %Chromat. vol. 4; nb. 10; (2014); p. 3490 - 3497 View in Reaxys 45.9 With oxygen in cyclohexane, Time= 22h, T= 90 °C , p= 750.075Torr %Chromat., 54.1 Li, Xinle; Guo, Zhiyong; Xiao, Chaoxian; Goh, Tian Wei; Tesfagaber, Daniel; Huang, Wenyu; ACS Catalysis; %Chromat. vol. 4; nb. 10; (2014); p. 3490 - 3497 View in Reaxys O

HO

HO

OH

O HO

H O

O

O

Rx-ID: 46451557 View in Reaxys 122/435 Yield 59.2 %Chromat., 30.6 %Chromat., 6.2 %Chromat.

Conditions & References With oxygen, Time= 3h, T= 90 °C , p= 750.075Torr Li, Xinle; Guo, Zhiyong; Xiao, Chaoxian; Goh, Tian Wei; Tesfagaber, Daniel; Huang, Wenyu; ACS Catalysis; vol. 4; nb. 10; (2014); p. 3490 - 3497 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

362/438

2018-03-11 22:07:32


HO

H

O

O

HO

Rx-ID: 9213424 View in Reaxys 123/435 Yield 70.2 %, 21.8 %, 6.1 %, 1.9 %

Conditions & References With oxygen, Pd561(1,10-phenanthroline)60(OAc)180 giant cluster, Time= 2h, T= 60 °C , p= 760.051Torr , Product distribution, Kinetics, Further Variations: Reagents, Temperatures, Pressures Kovtun, Grigory; Kameneva, Tatiana; Hladyi, Serhy; Starchevsky, Mykhailo; Pazdersky, Yury; Stolarov, Igor; Vargaftik, Michael; Moiseev, Ilya; Advanced Synthesis and Catalysis; vol. 344; nb. 9; (2002); p. 957 - 964 View in Reaxys With oxygen, Pd561phen60(OAc)180, Time= 2h, T= 60 °C , p= 760Torr , oxidation, Product distribution, Kinetics, Further Variations: Solvents Hladyi, Serhiy S.; Starchevsky, Mykhailo K.; Pazdersky, Yuriy A.; Vargaftik, Michael N.; Moiseev, Ilya I.; Mendeleev Communications; vol. 12; nb. 2; (2002); p. 45 - 46 View in Reaxys With oxygen in neat (no solvent), T= 120 °C , p= 7500.75Torr , Autoclave, Reagent/catalyst Pritchard, James; Piccinini, Marco; Tiruvalam, Ramchandra; He, Quian; Dimitratos, Nikolaos; Lopez-Sanchez, Jose A.; Morgan, David J.; Carley, Albert F.; Edwards, Jennifer K.; Kiely, Christopher J.; Hutchings, Graham J.; Catalysis Science and Technology; vol. 3; nb. 2; (2013); p. 308 - 317 View in Reaxys H

HO

HO

O

O

Rx-ID: 29532719 View in Reaxys 124/435 Yield 99 %, 15 %

Conditions & References With potassium carbonate in toluene, Time= 8h, T= 20 °C Layek, Keya; Maheswaran; Arundhathi; Kantam, M. Lakshmi; Bhargava, Suresh K.; Advanced Synthesis and Catalysis; vol. 353; nb. 4; (2011); p. 606 - 616 View in Reaxys

87 %, < 10 %

With iodosylbenzene sulfate, β‐cyclodextrin in water, Time= 2h, T= 60 °C , chemoselective reaction Zhu, Chenjie; Wei, Yunyang; Catalysis Letters; vol. 141; nb. 4; (2011); p. 582 - 586 View in Reaxys

85 %, 14 %

With periodic acid in water, Time= 1h, T= 27 °C , chemoselective reaction Ganesamoorthy; Muthu Tamizh; Shanmugasundaram; Karvembu; Tetrahedron Letters; vol. 54; nb. 51; (2013); p. 7035 - 7039 View in Reaxys

83 %, 13 %

With periodic acid in water, Time= 12h, T= 27 °C , chemoselective reaction Babu, S. Ganesh; Priyadarsini, P. Aruna; Karvembu; Applied Catalysis A: General; vol. 392; nb. 1-2; (2011); p. 218 - 224 View in Reaxys

85 %Chro- With oxygen in o-xylene, Time= 1h, T= 90 °C , Flow conditions mat., 14 %Chromat. Yasu-eda, Takashi; Kitamura, Susumu; Ikenaga, Na-oki; Miyake, Takanori; Suzuki, Toshimitsu; Journal of Molecular Catalysis A: Chemical; vol. 323; nb. 1-2; (2010); p. 7 - 15 View in Reaxys With [2,2]bipyridinyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, sodium methylate, copper(ll) bromide in water, acetonitrile, Time= 0.5h, T= 30 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

363/438

2018-03-11 22:07:32


Mase, Nobuyuki; Mizumori, Tomoya; Tatemoto, Yuji; Chemical Communications; vol. 47; nb. 7; (2011); p. 2086 2088 View in Reaxys With oxygen in toluene, T= 79.84 °C Yoshida, Akihiro; Takahashi, Youichi; Ikeda, Tsuyoshi; Azemoto, Kazuki; Naito, Shuichi; Catalysis Today; vol. 164; nb. 1; (2011); p. 332 - 335 View in Reaxys With oxygen in toluene, Time= 8h, T= 20 °C , chemoselective reaction Singha, Sudarshan; Sahoo, Mitarani; Parida; Dalton Transactions; vol. 40; nb. 44; (2011); p. 11838 - 11844 View in Reaxys

HN

H 2N

N

HO

H O

Rx-ID: 30696727 View in Reaxys 125/435 Yield

Conditions & References

5 %Chromat., 84 %Chromat., 86 μmol

With TiO2 loading Pt(0.1) nanoparticles, Time= 12h, T= 24.84 °C , p= 760.051Torr , UV-irradiation, Inert atmosphere Shiraishi, Yasuhiro; Ikeda, Makoto; Tsukamoto, Daijiro; Tanaka, Shunsuke; Hirai, Takayuki; Chemical Communications; vol. 47; nb. 16; (2011); p. 4811 - 4813 View in Reaxys in toluene, Time= 7h, T= 130 °C , p= 37503.8Torr , Continuous flow recycle reactor, Kinetics Zotova, Natalia; Roberts, Felicity J.; Kelsall, Geoffrey H.; Jessiman, Alan S.; Hellgardt, Klaus; Hii, King Kuok Mimi; Green Chemistry; vol. 14; nb. 1; (2012); p. 226 - 232 View in Reaxys

27 %Chromat., 24 %Chromat., 49 %Chromat.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in neat (no solvent), Time= 10h, T= 100 °C , chemoselective reaction Sharma, Rakesh K.; Monga, Yukti; Puri, Aditi; Gaba, Garima; Green Chemistry; vol. 15; nb. 10; (2013); p. 2800 2809 View in Reaxys O

O

O

O

S

S

N

H

NH HO

O

Rx-ID: 32164863 View in Reaxys 126/435 Yield 68 %Spectr., 74 %Spectr.

Conditions & References With manganese(IV) oxide, potassium carbonate, Time= 8h, T= 100 °C , Inert atmosphere Yu, Xiaochun; Liu, Chuanzhi; Jiang, Lan; Xu, Qing; Organic Letters; vol. 13; nb. 23; (2011); p. 6184 - 6187 View in Reaxys

45 %Chro- With palladium diacetate, potassium carbonate in neat (no solvent), T= 100 °C , Inert atmosphere mat., 69 %Chromat. View in Reaxys With potassium carbonate, Time= 8h, T= 100 °C , Inert atmosphere Xu, Qing; Li, Qiang; Zhu, Xiaogang; Chen, Jianhui; Advanced Synthesis and Catalysis; vol. 355; nb. 1; (2013); p. 73 - 80 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

364/438

2018-03-11 22:07:32


H 2N

H

O

O

N

HO

Rx-ID: 32349301 View in Reaxys 127/435 Yield

Conditions & References

9 %, 37.5 %, 6.5 %

With manganese(II) chloride tetrahydrate, ammonia, oxygen in water, Time= 1h, T= 149.84 °C , p= 22502.3Torr Nie, Renfeng; Shi, Juanjuan; Xia, Shuixin; Shen, Lian; Chen, Ping; Hou, Zhaoyin; Xiao, Feng-Shou; Journal of Materials Chemistry; vol. 22; nb. 35; (2012); p. 18115 - 18118 View in Reaxys

10 %Chromat., 17 %Chromat., 52 %Chromat. 10 %Chromat., 17 %Chromat., 52 %Chromat.

With ammonia, water, oxygen in water, Time= 1h, T= 130 °C , p= 2280.15Torr , Autoclave Yamaguchi, Kazuya; Kobayashi, Hiroaki; Oishi, Takamichi; Mizuno, Noritaka; Angewandte Chemie - International Edition; vol. 51; nb. 2; (2012); p. 544 - 547 View in Reaxys With ammonium hydroxide, cryptomelane, oxygen in water, Time= 1h, T= 130 °C , p= 2280.15Torr , Autoclave, Green chemistry Yamaguchi, Kazuya; Kobayashi, Hiroaki; Wang, Ye; Oishi, Takamichi; Ogasawara, Yoshiyuki; Mizuno, Noritaka; Catalysis Science and Technology; vol. 3; nb. 2; (2013); p. 318 - 327 View in Reaxys

H

N H 2N

HO

O

Rx-ID: 34302761 View in Reaxys 128/435 Yield

Conditions & References

45 %Chromat., Ca. 10 %

With Iron(III) nitrate nonahydrate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in toluene, Time= 24h, T= 80 °C , Green chemistry, Temperature Zhang, Erlei; Tian, Haiwen; Xu, Sendong; Yu, Xiaochun; Xu, Qing; Organic Letters; vol. 15; nb. 11; (2013); p. 2704 - 2707 View in Reaxys

100 With [2,2]bipyridinyl, copper(l) iodide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in acetonitrile, Time= 12h, T= %Chro25 °C mat., Ca. 9 %Chromat. View in Reaxys O

H

O

O

HO

O

HO

Rx-ID: 34975007 View in Reaxys 129/435 Yield

Conditions & References With oxygen in neat (no solvent), T= 120 °C , p= 7500.75Torr , Autoclave, Reagent/catalyst Pritchard, James; Piccinini, Marco; Tiruvalam, Ramchandra; He, Quian; Dimitratos, Nikolaos; Lopez-Sanchez, Jose A.; Morgan, David J.; Carley, Albert F.; Edwards, Jennifer K.; Kiely, Christopher J.; Hutchings, Graham J.; Catalysis Science and Technology; vol. 3; nb. 2; (2013); p. 308 - 317 View in Reaxys 2H

2H

2H

2H

2H

HN

2H

2H

2H

2H

2H

O

HO 2H

2H

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

2H

2

2H

365/438

2

H

2H

H

H N

N 2H

2H 2H 2H

2H

2018-03-11 22:07:32


2H

2H

2

2

H

2

H

2

H

N

2H

2

H

2H

H

2

H

2

H

N

2

H

2

H

H

2H

2H

HN

N

N

2

N

N

2

H

2H

2

2H

2

H

H

H

H N

H

2H

2 2

2

H

2

H

H 2H

2

H

H N

2

2

2H 2

H

H

2H

2H

2H

2H

2

H

Rx-ID: 35001172 View in Reaxys 130/435 Yield

Conditions & References With NiCuFeO(x) in 5,5-dimethyl-1,3-cyclohexadiene, Time= 12h, Inert atmosphere, Sealed tube, Reflux Cui, Xinjiang; Dai, Xingchao; Deng, Youquan; Shi, Feng; Chemistry - A European Journal; vol. 19; nb. 11; (2013); p. 3665 - 3675 View in Reaxys H HO

O

Rx-ID: 35029177 View in Reaxys 131/435 Yield

Conditions & References

69 %

With C29H54IrN3P2, Time= 48h, T= 120 °C , Inert atmosphere Guo, Le; Liu, Yinghua; Yao, Wubing; Leng, Xuebing; Huang, Zheng; Organic Letters; vol. 15; nb. 5; (2013); p. 1144 - 1147 View in Reaxys

HO

H

O

O

HO

air

O

HO

Rx-ID: 35038334 View in Reaxys 132/435 Yield

Conditions & References With C48H45Cu4N16O14, potassium carbonate in water, acetonitrile, T= 50 °C , Reagent/catalyst, Overall yield = 82.5 percent Kopylovich, Maximilian N.; Mizar, Archana; Guedes Da Silva, M. Fatima C.; Mac Leod, Tatiana C. O.; Mahmudov, Kamran T.; Pombeiro, Armando J. L.; Chemistry - A European Journal; vol. 19; nb. 2; (2013); p. 588 - 600 View in Reaxys H

air HO

O

Rx-ID: 35038335 View in Reaxys 133/435 Yield

Conditions & References

82.3 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, C48H45Cu4N16O14, potassium carbonate in water, acetonitrile, T= 50 °C , Reagent/catalyst, chemoselective reaction Kopylovich, Maximilian N.; Mizar, Archana; Guedes Da Silva, M. Fatima C.; Mac Leod, Tatiana C. O.; Mahmudov, Kamran T.; Pombeiro, Armando J. L.; Chemistry - A European Journal; vol. 19; nb. 2; (2013); p. 588 - 600 View in Reaxys O

OH

H HO

O

Rx-ID: 35061701 View in Reaxys 134/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

366/438

2018-03-11 22:07:32


Yield

Conditions & References With potassium hydoxide, Time= 16h, T= 135 °C , Inert atmosphere, Schlenk technique Xu, Qing; Chen, Jianhui; Liu, Quan; Advanced Synthesis and Catalysis; vol. 355; nb. 4; (2013); p. 697 - 704 View in Reaxys H Cl

Cl HO

O

O

HO

Rx-ID: 35061702 View in Reaxys 135/435 Yield

Conditions & References With potassium hydoxide, Time= 8h, T= 135 °C , Inert atmosphere, Schlenk technique Xu, Qing; Chen, Jianhui; Liu, Quan; Advanced Synthesis and Catalysis; vol. 355; nb. 4; (2013); p. 697 - 704 View in Reaxys H

HO

HO

O

Rx-ID: 35071444 View in Reaxys 136/435 Yield

Conditions & References

85 %

With oxygen in toluene, Time= 5h, T= 110 °C Kamimura, Akio; Nozaki, Yuichiro; Nishiyama, Mai; Nakayama, Masaharu; RSC Advances; vol. 3; nb. 2; (2013); p. 468 - 472 View in Reaxys O

H HO

HO

O

Rx-ID: 35071445 View in Reaxys 137/435 Yield

Conditions & References

18 %, 54 %

With oxygen in toluene, Time= 7h, T= 110 °C Kamimura, Akio; Nozaki, Yuichiro; Nishiyama, Mai; Nakayama, Masaharu; RSC Advances; vol. 3; nb. 2; (2013); p. 468 - 472 View in Reaxys

H

Cl

HO

O

Rx-ID: 35309409 View in Reaxys 138/435 Yield

Conditions & References Reaction Steps: 2 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 24 h / 25 °C 2: iodine / neat (no solvent) / 20 h / 85 °C With iodine, 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane Jereb, Marjan; Vrazic, Dejan; Organic and Biomolecular Chemistry; vol. 11; nb. 12; (2013); p. 1978 - 1999 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

367/438

2018-03-11 22:07:32


HO

O

NH 2

N

H O

N

HO

O

F F

F

Rx-ID: 35483256 View in Reaxys 139/435 Yield

Conditions & References

20 %

in chloroform, Time= 10h, Reflux Perrone, Serena; Rosato, Francesca; Salomone, Antonio; Troisi, Luigino; Tetrahedron; vol. 69; nb. 19; (2013); p. 3878 - 3884 View in Reaxys

O

NH 2

N+

N

O HO

O

OH

P

O O

P

OH O

N O

O HO

HO

OH

NH 2

OH OH

OH N

O

O

P

O

P

N O O

O

O O

HO

OH

NH 2

H

N N

N

N

N

O

NH 2 OH

HO

Rx-ID: 35927400 View in Reaxys 140/435 Yield

Conditions & References With 5'-CCGCGTTGGAATTCCTTTCTTATATTCTGCATGCG-3' in aq. buffer, T= 4 °C , pH= 7, Kinetics Nagel, Zachary D.; Cun, Shujian; Klinman, Judith P.; Journal of Biological Chemistry; vol. 288; nb. 20; (2013); p. 14087 - 14097 View in Reaxys OH

H O

HO

O

Rx-ID: 36088474 View in Reaxys 141/435 Yield

Conditions & References With ZnAlPO4 nanoparticles Sreenivasulu, Peta; Nandan, Devaki; Sreedhar; Viswanadham, Nagabhatla; RSC Advances; vol. 3; nb. 33; (2013); p. 13651 - 13654 View in Reaxys

O

O

H

O

HO

O

Rx-ID: 36298194 View in Reaxys 142/435 Yield 15 %Chromat.

Conditions & References With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in n-heptane, o-xylene, T= 140 °C , p= 18751.9Torr Obermayer, David; Balu, Alina M.; Romero, Antonio A.; Goessler, Walter; Luque, Rafael; Kappe, C. Oliver; Green Chemistry; vol. 15; nb. 6; (2013); p. 1530 - 1537 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

368/438

2018-03-11 22:07:32


2H

2

2H

2

H

H

2H

2H 2

O

HO

H

2H

Rx-ID: 36371999 View in Reaxys 143/435 Yield

Conditions & References With water, palladium diacetate, sodium 3-(diphenylphosphanyl)benzenesulfonate, Time= 16h, T= 120 °C , Sealed tube Hikawa, Hidemasa; Matsuda, Naoya; Suzuki, Hideharu; Yokoyama, Yuusaku; Azumaya, Isao; Advanced Synthesis and Catalysis; vol. 355; nb. 11-12; (2013); p. 2308 - 2320 View in Reaxys

HO

HO

O

H

O

O

O

HO

Rx-ID: 36380772 View in Reaxys 144/435 Yield

Conditions & References Aerobic Photooxidation; Benzoic Acid (2a); Typical Procedurefor Method A General procedure: A solution of benzyl alcohol (1a; 32 mg, 0.3 mmol), 2-Cl-AQN (5.8mg, 0.024 mmol), and K2CO3 (2.1 mg, 0.015 mmol, 0.05 equiv) in anhyd EtOAc (1 mL) in a Pyrex test tube under an air atmosphere was stirred and irradiated externally with four 22 W fluorescent lamps for 15 h. The reaction mixture was extracted with 10percent aq NaHCO3 (30 mL), acidified with aq 2 N HCl, and extracted with Et2O (3 × 20 mL). Evaporation of the solvent from the combined organic layers provided benzoic acid (2a) as a colorless solid; yield: 35.3 mg (96percent); Method B, 36.1 mg (99percent); colorless solid With 2-chloroanthracene-9,10-dione, oxygen, potassium carbonate in ethyl acetate, Irradiation, Reagent/catalyst Shimada, Yoshiko; Hattori, Kasumi; Tada, Norihiro; Miura, Tsuyoshi; Itoh, Akichika; Synthesis (Germany); vol. 45; nb. 19; (2013); p. 2684 - 2688; Art.No: 1669 View in Reaxys O

H

O

O

HO

O

HO

Rx-ID: 36557474 View in Reaxys 145/435 Yield

Conditions & References With oxygen in neat (no solvent), Time= 4h, T= 140 °C , p= 750.075Torr , Catalytic behavior, Reagent/catalyst, Time Feng, Junting; Ma, Chao; Miedziak, Peter J.; Edwards, Jennifer K.; Brett, Gemma L.; Li, Dianqing; Du, Yiyun; Morgan, David J.; Hutchings, Graham J.; Dalton Transactions; vol. 42; nb. 40; (2013); p. 14498 - 14508 View in Reaxys

H 2N

H 2N

HO

H

NH

O

N

Rx-ID: 36689095 View in Reaxys 146/435 Yield

Conditions & References

6 %ChroWith [2,2]bipyridinyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper(l) chloride, T= 20 °C , Green chemistry mat., 52 %Chromat. Yu, Jiatao; Xu, Jian; Lu, Ming; Applied Organometallic Chemistry; vol. 27; nb. 10; (2013); p. 606 - 610 View in Reaxys H OH

HO

HO

O

Rx-ID: 38590119 View in Reaxys 147/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

369/438

2018-03-11 22:07:32


Yield

Conditions & References

85 %Chromat.

2.4. Typical procedure for oxidation of alcohols In a typical reaction, to a mixture of benzyl alcohol (1 mmol, 108 mg) and hybrid compound1-POM(Zn) (0.05 mmol) in acetonitrile (3 mL), aqueous H2O2 30percent (1 mL) wasadded. The reaction mixture was stirred in a preheated oil bath at reflux and the progressof the reaction was monitored by TLC or GC. After completion of the reaction, the mixturewas cooled to room temperature and the catalyst was filtered, washed with n-hexane,and dried at room temperature to recover the catalyst. The solvent was evaporated and thepure product was obtained by chromatography on a short column of silica gel. With C21H33N3O6*3H(1+)*(PW11ZnO39)(5-), dihydrogen peroxide in acetonitrile, Time= 4.5h, Reflux Nadealian, Zahra; Mirkhani, Valiollah; Yadollahi, Bahram; Moghadam, Majid; Tangestaninejad, Shahram; Mohammadpoor-Baltork, Iraj; Journal of Coordination Chemistry; vol. 66; nb. 7; (2013); p. 1264 - 1275 View in Reaxys

NE

N

H N

S

S

HO

O

NH

Rx-ID: 32307052 View in Reaxys 148/435 Yield 96 %, 96 %Spectr.

Conditions & References With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], sodium hydroxide, Time= 12h, T= 150 °C , Inert atmosphere Li, Feng; Shan, Haixia; Chen, Lin; Kang, Qikai; Zou, Po; Chemical Communications; vol. 48; nb. 4; (2012); p. 603 - 605 View in Reaxys

H

HO HO

O

O

Rx-ID: 32439514 View in Reaxys 149/435 Yield

Conditions & References With oxygen, 2,3-dicyano-5,6-dichloro-p-benzoquinone, sodium nitrite in dichloromethane, acetic acid, Time= 2h, T= 20 °C Wang, Lianyue; Li, Jun; Yang, Hua; Lv, Ying; Gao, Shuang; Journal of Organic Chemistry; vol. 77; nb. 1; (2012); p. 790 - 794 View in Reaxys H

O

HO

HO

O

Rx-ID: 32439518 View in Reaxys 150/435 Yield

Conditions & References With oxygen, 2,3-dicyano-5,6-dichloro-p-benzoquinone, sodium nitrite in dichloromethane, acetic acid, Time= 10h, T= 20 °C Wang, Lianyue; Li, Jun; Yang, Hua; Lv, Ying; Gao, Shuang; Journal of Organic Chemistry; vol. 77; nb. 1; (2012); p. 790 - 794 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

370/438

2018-03-11 22:07:32


H

HN

H 2N

HO

O

Rx-ID: 32696205 View in Reaxys 151/435 Yield

Conditions & References in toluene, Time= 4h, T= 150 °C , p= 37503.8Torr , Continuous flow recycle reactor, Kinetics Zotova, Natalia; Roberts, Felicity J.; Kelsall, Geoffrey H.; Jessiman, Alan S.; Hellgardt, Klaus; Hii, King Kuok Mimi; Green Chemistry; vol. 14; nb. 1; (2012); p. 226 - 232 View in Reaxys

H 2N

HO O HN

H

N

O

O

Rx-ID: 32759946 View in Reaxys 152/435 Yield

Conditions & References

10 %Chromat., 17 %Chromat., 17 %Chromat., 20 %Chromat.

With Au/CeO2 in toluene, Time= 22h, T= 110 °C , p= 760.051Torr , Inert atmosphere Ishida, Tamao; Takamura, Rena; Takei, Takashi; Akita, Tomoki; Haruta, Masatake; Applied Catalysis A: General; vol. 413-414; (2012); p. 261 - 266 View in Reaxys

O N HO

O

O

O

O

H

N

O NH

N N

O

Rx-ID: 32784593 View in Reaxys 153/435 Yield

Conditions & References With bis(1-methyl-1-phenylethyl)peroxide, potassium hydoxide in chlorobenzene, Time= 24h, T= 140 °C Xiao, Fuhong; Liu, Yong; Tang, Chenglin; Deng, Guo-Jun; Organic Letters; vol. 14; nb. 4; (2012); p. 984 - 987 View in Reaxys O

O

O HO

O

H O

N

NH

O

Rx-ID: 32784594 View in Reaxys 154/435 Yield 70 %

Conditions & References With di-tert-butyl peroxide, potassium hydoxide in chlorobenzene, Time= 24h, T= 140 °C Xiao, Fuhong; Liu, Yong; Tang, Chenglin; Deng, Guo-Jun; Organic Letters; vol. 14; nb. 4; (2012); p. 984 - 987 View in Reaxys O

O O

N

O

N HO

H O

Rx-ID: 32784595 View in Reaxys 155/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

371/438

2018-03-11 22:07:32


Yield

Conditions & References With di-tert-butyl peroxide, potassium hydoxide in N,N-dimethyl-formamide, Time= 24h, T= 140 °C Xiao, Fuhong; Liu, Yong; Tang, Chenglin; Deng, Guo-Jun; Organic Letters; vol. 14; nb. 4; (2012); p. 984 - 987 View in Reaxys

O HO

O

O

H

N

N

N N

O

Rx-ID: 32784596 View in Reaxys 156/435 Yield

Conditions & References With oxygen, potassium hydoxide in chlorobenzene, Time= 24h, T= 140 °C Xiao, Fuhong; Liu, Yong; Tang, Chenglin; Deng, Guo-Jun; Organic Letters; vol. 14; nb. 4; (2012); p. 984 - 987 View in Reaxys

O

O

H

N

N HO

O

N

O

Rx-ID: 32784597 View in Reaxys 157/435 Yield

Conditions & References With potassium hydoxide in chlorobenzene, Time= 24h, T= 140 °C Xiao, Fuhong; Liu, Yong; Tang, Chenglin; Deng, Guo-Jun; Organic Letters; vol. 14; nb. 4; (2012); p. 984 - 987 View in Reaxys HO

HO

H O

OH

Rx-ID: 33113669 View in Reaxys 158/435 Yield

Conditions & References

17 %, 83 %

With cadmium(II) sulphide in acetonitrile, Time= 24h, T= 20 °C , p= 37.5038Torr , Inert atmosphere, Irradiation Mitkina, Tatiana; Stanglmair, Christoph; Setzer, Wolfgang; Gruber, Michael; Kisch, Horst; Koenig, Burkhard; Organic and Biomolecular Chemistry; vol. 10; nb. 17; (2012); p. 3556 - 3561 View in Reaxys

H

N

N

HO

O

Rx-ID: 33342117 View in Reaxys 159/435 Yield

Conditions & References

14 %Chromat., 8 %Chromat., 34 %Chromat.

With nickel(II) oxide, ammonia, oxygen in toluene, Time= 4h, T= 100 °C , p= 10126Torr , Autoclave Ishida, Tamao; Watanabe, Hiroto; Takei, Takashi; Hamasaki, Akiyuki; Tokunaga, Makoto; Haruta, Masatake; Applied Catalysis A: General; vol. 425-426; (2012); p. 85 - 90 View in Reaxys

O

O

HO

O

O

O

H O

Rx-ID: 33593910 View in Reaxys 160/435 Yield

Conditions & References With ozone, Neat (no solvent)

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

372/438

2018-03-11 22:07:32


Rodriguez-Reyes, Juan Carlos F.; Friend, Cynthia M.; Madix, Robert J.; Surface Science; vol. 606; nb. 15-16; (2012); p. 1129 - 1134 View in Reaxys H 2N

H

O

O

HO

Rx-ID: 33673883 View in Reaxys 161/435 Yield

Conditions & References

75 %Chro- With iron(III) chloride, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, hydroxylamine hydrochloride, iodine, potassimat., 10 um carbonate in 1,2-dichloro-ethane, Time= 12h, T= 90 °C %Chromat. Das, Rima; Chakraborty, Debashis; Catalysis Communications; vol. 26; (2012); p. 48 - 53 View in Reaxys H HO

O

HO

N

Rx-ID: 33673884 View in Reaxys 162/435 Yield

Conditions & References

72 %Chro- With iron(III) chloride, hydroxylamine hydrochloride, iodine, potassium carbonate, potassium iodide in 1,2-dichloromat., 25 ethane, Time= 12h, T= 90 °C %Chromat. Das, Rima; Chakraborty, Debashis; Catalysis Communications; vol. 26; (2012); p. 48 - 53 View in Reaxys H OH

O

HO

O

Rx-ID: 33835003 View in Reaxys 163/435 Yield 20 %, 80 %

Conditions & References With 3-(3-(1,2-dicarboxyethylamino)-3-oxopropyl)-1-methyl-1H-imidazol-3-ium bromide, dihydrogen peroxide, Time= 0.25h, T= 25 °C , Neat (no solvent), chemoselective reaction Karthikeyan, Parasuraman; Arunrao, Aswar Sachin; Narayan, Muskawar Prashant; Kumar, Sythana Suresh; Kumar, S. Senthil; Bhagat, Pundlik Rambhau; Journal of Molecular Liquids; vol. 173; (2012); p. 180 - 183 View in Reaxys

H

O

SiH

HO

Si

HO

O

O

O

Rx-ID: 33864169 View in Reaxys 164/435 Yield

Conditions & References With palladium diacetate, sodium carbonate in methanol, Time= 24h, T= 40 °C , chemoselective reaction Bai, Xing-Feng; Ye, Fei; Zheng, Long-Sheng; Lai, Guo-Qiao; Xia, Chun-Gu; Xu, Li-Wen; Chemical Communications; vol. 48; nb. 68; (2012); p. 8592 - 8594 View in Reaxys

N

NH 2

HO

H O

Rx-ID: 34029449 View in Reaxys 165/435 Yield

Conditions & References With oxygen in toluene, Time= 1h, T= 59.84 °C , p= 760.051Torr Liu, Peng; Li, Can; Hensen, Emiel J. M.; Chemistry - A European Journal; vol. 18; nb. 38; (2012); p. 12122 12129 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

373/438

2018-03-11 22:07:32


H NH 2

HO

N

O

Rx-ID: 34029450 View in Reaxys 166/435 Yield

Conditions & References With oxygen in toluene, Time= 5h, T= 59.84 °C , p= 760.051Torr Liu, Peng; Li, Can; Hensen, Emiel J. M.; Chemistry - A European Journal; vol. 18; nb. 38; (2012); p. 12122 12129 View in Reaxys

H

O

HO

HO

Cl

O

Rx-ID: 34033762 View in Reaxys 167/435 Yield

Conditions & References

53 %, 11 %, 30 %

With tetrachloromethane, bis(acetylacetonate)oxovanadium, triethylamine, Time= 20h, T= 175 °C , Autoclave, Inert atmosphere Khusnutdinov; Bayguzina; Gallyamova; Dzhemilev; Petroleum Chemistry; vol. 52; nb. 4; (2012); p. 261 - 266 View in Reaxys H

HO

H 2N

O

Rx-ID: 34065450 View in Reaxys 168/435 Yield

Conditions & References

13 %Chro- With L-alanin, L-alanine dehydrogenase, ω-transaminase from Chromobacterium violaceum, alcohol dehydrogenmat., 87 ase from Bacillus stearothermophilus, pyridoxal 5'-phosphate, NAD, ammonium chloride, sodium hydroxide in water, %Chromat. Time= 24h, T= 20 °C , pH= 8.5, Enzymatic reaction Sattler, Johann H.; Fuchs, Michael; Tauber, Katharina; Mutti, Francesco G.; Faber, Kurt; Pfeffer, Jan; Haas, Thomas; Kroutil, Wolfgang; Angewandte Chemie - International Edition; vol. 51; nb. 36; (2012); p. 9156 - 9159; Angew. Chem.; vol. 124; nb. 36; (2012); p. 9290 - 9293 View in Reaxys O S

S

HO

H O

Rx-ID: 34233502 View in Reaxys 169/435 Yield 95 %, 83 %

Conditions & References General procedure: In a typical experiment, to a solution of HReO4 (5.0 mol percent) in toluene (3 mL) was added the 4-methylphenyl sulfoxide (1.0 mmol) and the alcohol (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Tables 1–3) and the progress of the reactions was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford the carbonyl compounds and 4-methylphenyl sulfide, which are all known compounds. With per-rhenic acid in toluene, Time= 17h, Reflux View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

374/438

2018-03-11 22:07:32


N (v4) Cu 2+O(v2) N SP-4 O– (v2)

(v4)

F

N (v4) Cu 2+OH(v3) N SP-4 O– (v2)

H

(v4) (v4)

F Sb–FF F

2H

F

O

O

Rx-ID: 34450101 View in Reaxys 170/435 Yield

Conditions & References in dichloromethane, T= 19.84 °C , Kinetics Asami, Kazutaka; Tsukidate, Kazuaki; Iwatsuki, Satoshi; Tani, Fumito; Karasawa, Satoru; Chiang, Linus; Storr, Tim; Thomas, Fabrice; Shimazaki, Yuichi; Inorganic Chemistry; vol. 51; nb. 22; (2012); p. 12450 - 12461 View in Reaxys

2H

N (v4) Cu 2+O(v2) N SP-4 O– (v2)

2H

F

(v4)

2H

N (v4) Cu 2+OH(v3) N SP-4 O– (v2)

(v4) (v4)

F Sb–FF F O

F

HO

Rx-ID: 34450102 View in Reaxys 171/435 Yield

Conditions & References in dichloromethane, T= 19.84 °C , Kinetics Asami, Kazutaka; Tsukidate, Kazuaki; Iwatsuki, Satoshi; Tani, Fumito; Karasawa, Satoru; Chiang, Linus; Storr, Tim; Thomas, Fabrice; Shimazaki, Yuichi; Inorganic Chemistry; vol. 51; nb. 22; (2012); p. 12450 - 12461 View in Reaxys

N (v4) Cu 2+O(v2) N SP-4 O– (v2)

(v4)

F

N (v4) Cu 2+OH(v3) N SP-4 O– (v2)

H

(v4) (v4)

F Sb–FF F

HO

F

O

Rx-ID: 34450106 View in Reaxys 172/435 Yield

Conditions & References in dichloromethane, T= 19.84 °C , Kinetics, Temperature Asami, Kazutaka; Tsukidate, Kazuaki; Iwatsuki, Satoshi; Tani, Fumito; Karasawa, Satoru; Chiang, Linus; Storr, Tim; Thomas, Fabrice; Shimazaki, Yuichi; Inorganic Chemistry; vol. 51; nb. 22; (2012); p. 12450 - 12461 View in Reaxys O

H

N

N HO

O

N

O

Rx-ID: 34542452 View in Reaxys 173/435 Yield

Conditions & References With Rh(trop2N)(PPh3) Annen, Samuel P.; Gruetzmacher, Hansjoerg; Dalton Transactions; vol. 41; nb. 46; (2012); p. 14137 - 14145 View in Reaxys

O

E

HO

O HO

H

HO

E

O

Rx-ID: 30205423 View in Reaxys 174/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

375/438

2018-03-11 22:07:32


Yield

Conditions & References With hydrogen in toluene, Time= 4h, T= 150 °C , p= 7500.75Torr , Autoclave, chemoselective reaction Hong, Yong-Chun; Sun, Ke-Qiang; Zhang, Gui-Rong; Zhong, Ru-Yi; Xu, Bo-Qing; Chemical Communications; vol. 47; nb. 4; (2011); p. 1300 - 1302 View in Reaxys

E

O

H

O HO

E

HO

O

Rx-ID: 30205424 View in Reaxys 175/435 Yield

Conditions & References With hydrogen in toluene, Time= 4h, T= 150 °C , p= 7500.75Torr , Autoclave, chemoselective reaction Hong, Yong-Chun; Sun, Ke-Qiang; Zhang, Gui-Rong; Zhong, Ru-Yi; Xu, Bo-Qing; Chemical Communications; vol. 47; nb. 4; (2011); p. 1300 - 1302 View in Reaxys

E

HO

H

E

O HO

O

Rx-ID: 30520424 View in Reaxys 176/435 Yield

Conditions & References

15 %, 99 %

With potassium carbonate in toluene, Time= 12h, T= 20 °C Layek, Keya; Maheswaran; Arundhathi; Kantam, M. Lakshmi; Bhargava, Suresh K.; Advanced Synthesis and Catalysis; vol. 353; nb. 4; (2011); p. 606 - 616 View in Reaxys

2H

2H

2H

O

2H

2H

N O

HO 2H

2H 2H 2H

2H

2H

2H

2H

O 2

H

H

2H 2 H

2H

2H

2H

2H

2H

2H 2H

2H 2H

2

2H

2H

H N

2H

2H

2H

N

2H 2H 2H

2H

N 2H 2H 2H

2H

2H

Rx-ID: 30977215 View in Reaxys 177/435 Yield

Conditions & References With Au/Fe2O3, Time= 2h, T= 160 °C , Inert atmosphere, chemoselective reaction Peng, Qiling; Zhang, Yan; Shi, Feng; Deng, Youquan; Chemical Communications; vol. 47; nb. 22; (2011); p. 6476 - 6478 View in Reaxys 2H

2H

2H

2H 2H

2H

2H

2H

N 2H

N O

HO

2H

2H

2H

O

2H 2H

O 2

2H

H 2N

H

2

2H

H

2H

Rx-ID: 30977216 View in Reaxys 178/435 Yield

Conditions & References With Au/Fe2O3, Time= 1h, T= 160 °C , Inert atmosphere, chemoselective reaction

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

376/438

2018-03-11 22:07:32


Peng, Qiling; Zhang, Yan; Shi, Feng; Deng, Youquan; Chemical Communications; vol. 47; nb. 22; (2011); p. 6476 - 6478 View in Reaxys O

OH

H O

O

HO

O

Rx-ID: 31388253 View in Reaxys 179/435 Yield

Conditions & References With ruthenium trichloride, potassium carbonate, Time= 24h, T= 120 °C Liu, Chuanzhi; Liao, Shiheng; Li, Qiang; Feng, Sunlin; Sun, Qing; Yu, Xiaochun; Xu, Qing; Journal of Organic Chemistry; vol. 76; nb. 14; (2011); p. 5759 - 5773 View in Reaxys HO

OH HO

HO

OH

HO

HO

HO

H

O

OH

O

O

OH

O HO

O

Rx-ID: 31545592 View in Reaxys 180/435 Yield

Conditions & References With water, oxygen, Time= 5h, T= 24.84 °C , p= 760.051Torr , Sonication, Irradiation Tsukamoto, Daijiro; Ikeda, Makoto; Shiraishi, Yasuhiro; Hara, Takayoshi; Ichikuni, Nobuyuki; Tanaka, Shunsuke; Hirai, Takayuki; Chemistry - A European Journal; vol. 17; nb. 35; (2011); p. 9816 - 9824 View in Reaxys H O

O OH

HO

O

O

Rx-ID: 32331831 View in Reaxys 181/435 Yield

Conditions & References

10 %Chro- With tetra‐n‐butyl‐ammonium oxone, meso-tetraphenylporphyrin iron(III) chloride in water, Time= 0.0833333h, Air mat., 68 %Chromat. Rezaeifard, Abdolreza; Jafarpour, Maasoumeh; Naeimi, Atena; Catalysis Communications; vol. 16; nb. 1; (2011); p. 240 - 244 View in Reaxys

H Si

Si N H

HO

Si O

O

Rx-ID: 33208404 View in Reaxys 182/435 Yield 12 %, 64 %

Conditions & References With Br3 (1-)*C12H24KO6 in dichloromethane Zolfigol; Kolvari; Koukabi; Salehzadeh; Chehardoli; Tidmarsh; Niknamd; Journal of the Iranian Chemical Society; vol. 8; nb. 2; (2011); p. 484 - 494 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

377/438

2018-03-11 22:07:32


-1 F

O

(v4)

F

B FF

O+

H HO

O

Rx-ID: 37065323 View in Reaxys 183/435 Yield

Conditions & References in acetonitrile, T= 60 °C , Kinetics Lu, Yun; Bradshaw, Joshua; Zhao, Yu; Kuester, William; Kabotso, Daniel; Journal of Physical Organic Chemistry; vol. 24; nb. 12; (2011); p. 1172 - 1178 View in Reaxys

H

OH 2H

2H

H

O

O

Rx-ID: 2061602 View in Reaxys 184/435 Yield 74 %, 30 %

Conditions & References With oxalyl dichloride, dimethyl sulfoxide, triethylamine in dichloromethane, Time= 0.25h, T= -60 °C , isotope effects Marx, Michael; Tidwell, Thomas T.; Journal of Organic Chemistry; vol. 49; (1984); p. 788 - 793 View in Reaxys With chloroperoxidase from the fungus Caldariomyces fumago, dihydrogen peroxide in [D3]acetonitrile, water, T= 25 °C , pH= 6.0, Oxidation, Kinetics Baciocchi, Enrico; Lanzalunga, Osvaldo; Manduchi, Laura; Chemical Communications; nb. 17; (1999); p. 1715 1716 View in Reaxys With carbon dioxide, oxygen, tetrapropylammonium perruthennate, T= 75 °C , p= 165013Torr , Kinetics Campestrini, Sandro; Carraro, Massimo; Ciriminna, Rosaria; Pagliaro, Mario; Tonellato, Umberto; Advanced Synthesis and Catalysis; vol. 347; nb. 6; (2005); p. 825 - 832 View in Reaxys With 2CF3O3S(1-)*C12H32Cu2N4O2 (2+) in acetone, T= -30.16 °C Kang, Peng; Bobyr, Elena; Dustman, John; Hodgson, Keith O.; Hedman, Britt; Solomon, Edward I.; Stack, T. Daniel P.; Inorganic Chemistry; vol. 49; nb. 23; (2010); p. 11030 - 11038 View in Reaxys With oxygen in 2,3,4-trifluorotoluene, Time= 3h, T= 100 °C , p= 6000.6Torr , UV-irradiation, Autoclave Su, Fangzheng; Mathew, Smitha C.; Lipner, Grzegorz; Fu, Xianzhi; Antonietti, Markus; Blechert, Siegfried; Wang, Xinchen; Journal of the American Chemical Society; vol. 132; nb. 46; (2010); p. 16299 - 16301 View in Reaxys Stage 1: With oxalyl dichloride, dimethyl sulfoxide in dichloromethane, Time= 0.533333h, T= -78 °C , Swern oxidation Stage 2: With triethylamine in dichloromethane, Time= 0.666667h, T= -78 °C , Swern oxidation Giagou, Thomas; Meyer, Matthew P.; Journal of Organic Chemistry; vol. 75; nb. 23; (2010); p. 8088 - 8099 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

378/438

2018-03-11 22:07:32


F O

O

F O F

F

O

F F

F

HO

H

O F

O

F

Rx-ID: 10230349 View in Reaxys 185/435 Yield

Conditions & References With dimethyl sulfoxide, triethylamine in dichloromethane, T= -20 °C , Swern oxidation, Product distribution, Further Variations: Temperatures Kawaguchi, Tatsuya; Miyata, Hiroyuki; Ataka, Kikuo; Mae, Kazuhiro; Yoshida, Jun-Ichi; Angewandte Chemie International Edition; vol. 44; nb. 16; (2005); p. 2413 - 2416 View in Reaxys With dimethyl sulfoxide, N-ethyl-N,N-diisopropylamine in dichloromethane, T= 70 °C , Automated microreactor, Large scale reaction Nieuwland, Pieter J.; Koch, Kaspar; Van Harskamp, Noud; Wehrens, Ron; Van Hest, Jan C. M.; Rutjes, Floris P. J. T.; Chemistry - An Asian Journal; vol. 5; nb. 4; (2010); p. 799 - 805 View in Reaxys 18; 5; 37; 38; 39 :In the production of benzaldehyde from benzyl alcohol by the method of the present invention, the steps (1), (2) and (3) were carried out using the following reactor.Step (1) A microreactor (manufactured by IMM GmbH, Single Mixer Ver. 2, Inlay: Ag plating, fine liquid introducing channel width: 40 μm) was used. To each of two introduction channels for a sulfoxide-containing liquid and an activating agent-containing liquid for the sulfoxide compound, a SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected, and each channel was connected to a liquid supply source through the SUS tube.Step (2) A microreactor (the same as the microreactor for step (1)) was used. A reaction product liquid-discharging channel of the microreactor of the step (1) was connected to a reaction product solution-introducing channel of the microreactor of the step (2) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm), and then an alcohol supply source was connected to an alcohol-introducing channel of a microreactor for the step (2) through a SUS tube (inner diameter: 1.0 mm, length: 20 cm).Step (3) A microreactor (the same as the microreactor for step (1)) was used. A reaction product solution-discharging channel of a microreactor of the step (2) was connected to a reaction product solution-introducing channel for the step (3) through a connecting SUS tube (inner diameter: 1.0 mm, length: 10 cm). Also, a basic compound-introducing channel of a microreactor for the step (3) was connected to a basic compound supply source through a SUS tube (inner diameter: 1.0 mm, length: 20 cm) and then a reaction product solution-discharging SUS tube (inner diameter: 1.0 mm, length: 20 cm) was connected to a reaction product solution-discharging channel. The microreactors for the steps (1), (2) and (3) and the SUS tubes connected thereto were dipped in a constant low-temperature bath set at a constant temperature of -20°C. To the end of the SUS tube for discharging a reaction product solution of the microreactor for the step (3), a SUS tube (inner diameter: 1.0 mm, length: 100 cm) was connected through a connecting tube (inner diameter: 1 mm, length: 50 cm) made of PTFE (polytetrafluoroethylene), and then only the connecting tube was dipped in a water bath at a temperature of 30°C. By using a gas-tight syringe, a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/liter and a trifluoroacetic anhydride (TFAA)/methylene chloride solution having a concentration of 2.4 mol/liter were respectively fed into the microreactor for the step (1) at a flow rate of 1.0 ml/min. Immediately after the reaction mixture solution was retained for 2.4 seconds, the reaction product solution was fed into the microreactor for the step (2) and, at the same time, a benzyl alcohol/methylene chloride solution having a concentration of 1.0 mol/liter was fed into the microreactor for the step (2) at a flow rate of 2.0 ml/min. Immediately after the reaction mixture solution was retained for 1.2 seconds, the reaction product solution was fed into the microreactor for the step (3) and, at the same time, a triethylamine/methylene chloride solution having a concentration of 1.5 mol/liter was fed at a flow rate of 4.0 ml/min. After the above reaction operation was carried out for 4 minutes, the reaction product solution was discharged from the microreactor for the step (3) and was collected in a sample bottle, containing an internal standard substance, for one minute. The amount of TFAA employed in the step (1) was 1.2 equivalents, the reaction temperature of the step (1) was -20°C, and the reaction time was 2.4 seconds. The contents of the collected compounds in the reaction product solution were determined by a gas chromatograph internal standard method. The results are shown below. Benzaldehyde 88percent Benzyl trifluoroacetate 8percent Benzyl alcohol 3percent; Comparative Example 5 (Batch Synthesis Comparative Example) In an argon gas atmosphere, 1 ml of a dimethyl sulfoxide/methylene chloride solution having a concentration of 4 mol/liter was charged in a Schrenk tube having an inner volume of 30 ml and then cooled to a temperature of -23°C. While stirring this solution using a magnetic stirrer, 1 ml of a trifluoroacetic anhydride/methylene chloride solution having a concentration of 2.4 mol/liter was added dropwise to the solution at an addition rate of 0.1 ml/min, followed by mixing. After the completion of the dropwise addition and mixing, the resultant mixture solution was stirred at the above temperature for 10 minutes. To this mixed solution, 2 ml of a benzyl alcohol/methylene chloride solution having a concentration of 1.0 mol/liter was added dropwise at an addition rate of 0.2 ml/min, followed by mixing. After the completion of the drop-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

379/438

2018-03-11 22:07:32


wise addition and mixing, the resultant mixture solution was stirred at the above temperature for 10 minutes. To the resulting mixed solution, 4 ml of a triethylamine/methylene chloride solution having a concentration of 1.5 mol/liter was added dropwise at an addition rate of 0.4 ml/min, followed by mixing. After the completion of the dropwise addition and mixing, the temperature of the resultant mixture solution was returned to room temperature and an internal standard agent was added thereinto, and then the contents of the compounds in the mixed solution were measured by a gas chromatograph internal standard method. The measurement results are shown below. Benzaldehyde 39percent Benzyl trifluoroacetate 40percent Benzyl alcohol 20percent; Examples 31 to 39 (Example of synthesis of decanal, 2-octanone or benzaldehyde from decanol, 2-octanol or benzyl alcohol by using Single Mixer manufactured by IMM GmbH under the conditions of a reaction temperature of -10 to 20°C and a reaction time of 0.01 seconds) In each of Examples 31 to 39, SUS tubes were connected to three Single Mixers Ver. 2 (Inlay: made of Ag plating, fine liquid introducing channel width: 40 μm) manufactured by IMM GmbH (Germany) to constitute a reaction apparatus. A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to each of two reaction reagent inlets of the first unit and then a reaction solution outlet of the first unit was connected to one of two reaction reagent inlets of the second unit through a SUS tube (inner diameter = 0.1 mm, length = 3.2 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the second unit and then the reaction solution outlet of the second unit was connected to one of two reaction reagent inlets of the third unit through a SUS tube (inner diameter = 1.0 mm, length = 10 cm). A SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to the other reaction reagent inlet of the third unit and then a SUS tube (inner diameter = 1.0 mm, length = 20 cm) was connected to a reaction solution outlet of the third unit. The upper portion of the present apparatus was dipped in a constant low-temperature water bath at a predetermined temperature described in Table 1. Furthermore, a SUS tube (inner diameter = 1.0 mm, length = 100 cm) was connected to the outlet of the apparatus through a PTFE connecting tube (inner diameter = 1.0 mm, length = 50 cm). Only this connecting tube was dipped in a water bath at 30°C. By using a gas-tight syringe manufactured by Hamilton Co., a dimethyl sulfoxide/methylene chloride solution having a concentration of 4.0 mol/L and a trifluoroacetic anhydride/methylene chloride solution having a concentration of 2.4 mol/L were respectively fed through two inlets of the first unit at a rate of 1.0 mL/min (step 1), and then the reaction product solution of the first unit was rapidly fed into one of two inlets of the second unit from the reaction solution outlet of the first unit and a reactant/methylene chloride solution having a concentration of 1.0 mol/L was fed through the other inlet of the second unit at a rate of 2.0 mL/min (step 2). The reaction product solution was rapidly fed into one of two inlets of the third unit through the reaction solution outlet of the second unit, and then a triethylamine/ methylene chloride solution having a concentration of 1.4 mol/L was fed through the other inlet of the third unit at a rate of 4.0 mL/min (step 3). After feeding the solution for 4 minutes, the reaction solution produced in the third unit was sampled into sample bottle containing an internal standard substance through the outlet of the third unit. The yield of the product was determined by a GC internal standard method. The Reactant (starting compound) fed into the second unit and the target reaction product obtained from the third unit are as follows.Examples 31 to 33 Starting substance:Decanol Target reaction product:Decanal Examples 34 to 36 Starting substance:2-octanol Target reaction product:2-octanone Examples 37 to 39 Starting substance:Benzyl alcohol Target reaction product:Benzaldehyde The reaction results are shown in Table 1. Table 1 Example No. Starting Substance Reaction temperature (°C) Yield (percent) Product TFA ester MTM ether Non-reacted starting substance 31 Decanol -1066*1 20*4 7*7 7 32 Decanol 066*1 21*4 6*7 6 33 Decanol 2068*1 21*6*7 4 34 2-octanol -1078*2 3*5 4*8 10 35 2-octanol 078*2 3*5 4*8 9 36 2-octanol 2078*2 2*5 3*8 12 37 Benzyl alcohol -1079*3 15*6 Uncalculated 1 38 Benzyl alcohol 078*3 14*6 Uncalculated 0 39 Benzyl alcohol 2075*3 16*6 Uncalculated 0(Note) *1: Decanal *2: 2-octanone *3: Benzaldehyde *4: Decyl trifluoroacetate *5: Octyl trifluoroacetate *6: Benzyl trifluoroacetate *7: Decyl methylthiomethyl ether *8: Octyl methylthiomethyl ether Stage 1: With dimethyl sulfoxide in dichloromethane, Time= 2.77778E-06 - 0.166667h, T= -23 - 20 °C , Swern Oxidation Stage 2: in dichloromethane, Time= 2.77778E-06 - 0.166667h, T= -23 - 20 °C , Swern Oxidation Stage 3: With triethylamine in dichloromethane, Time= 0.0666667h, T= -23 - 20 °C , Swern Oxidation, Product distribution / selectivity Patent; Ube Industries, Ltd.; EP1710223; (2006); (A1) English View in Reaxys

2H

2H

2H

O

O

2H 2H

E

S N

HO 2H

2H

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

380/438

2018-03-11 22:07:32


2

H

2

H

2

2H

H O N H

2H

2H

O S

2H

2H

O 2H

2H

S

O

H

H O

2H

O 2H

2

H N

2H

Rx-ID: 28856687 View in Reaxys 186/435 Yield

Conditions & References With air, copper diacetate, potassium carbonate, Time= 3h, T= 150 °C , Mechanism Shi, Feng; Tse, Man Kin; Cui, Xinjiang; Goerdes, Dirk; Michalik, Dirk; Thurow, Kerstin; Deng, Youquan; Beller, Matthias; Angewandte Chemie - International Edition; vol. 48; nb. 32; (2009); p. 5912 - 5915 View in Reaxys With potassium carbonate, iron(II) chloride, Time= 10h, T= 135 °C , Inert atmosphere, Mechanism Cui, Xinjiang; Shi, Feng; Zhang, Yan; Deng, Youquan; Tetrahedron Letters; vol. 51; nb. 15; (2010); p. 2048 2051 View in Reaxys

HO

O HO

H

O

O

HO

O HO

Rx-ID: 29351745 View in Reaxys 187/435 Yield

Conditions & References

73 %, 58 %

With sodium tetrahydroborate, 1 Pd/C, water, oxygen, potassium carbonate in methanol, Time= 12h, T= 20 °C An, Gwangil; Ahn, Hyunseok; De Castro, Kathlia A.; Rhee, Hakjune; Synthesis; nb. 3; (2010); p. 477 - 485; Art.No: F19009SS View in Reaxys

H

HO HO

O

Rx-ID: 29351746 View in Reaxys 188/435 Yield

Conditions & References

92 %

With sodium tetrahydroborate, 1 Pd/C, water, oxygen, potassium carbonate in methanol, Time= 0.333333h, T= 20 °C An, Gwangil; Ahn, Hyunseok; De Castro, Kathlia A.; Rhee, Hakjune; Synthesis; nb. 3; (2010); p. 477 - 485; Art.No: F19009SS View in Reaxys O

C

O

O

Na +

I

H

O

O–

O

O

O

Rx-ID: 29384206 View in Reaxys 189/435 Yield

Conditions & References With bis-triphenylphosphine-palladium(II) chloride, benzyl alcohol, T= 60 °C , Kinetics Hu, Yanhe; Liu, Jing; Lu, Zhixin; Luo, Xiancai; Zhang, Heng; Lan, Yu; Lei, Aiwen; Journal of the American Chemical Society; vol. 132; nb. 9; (2010); p. 3153 - 3158 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

381/438

2018-03-11 22:07:32


O

O

O O

S

N–

Cl

O

H

N

Na +

S

H 2N

HO

O

S O

Rx-ID: 29622722 View in Reaxys 190/435 Yield

Conditions & References

90 %, 5 %, Stage 1: With saccharin, lithium bromide in dichloromethane, Time= 3h, T= 20 °C 6% Stage 2: in dichloromethane, Molecular sieve, Reflux Patel, Rajesh; Srivastava, Vishnu P.; Yadav, La Dhar S.; Advanced Synthesis and Catalysis; vol. 352; nb. 10; (2010); p. 1610 - 1614 View in Reaxys 35 %, 62 %, 63 %

Stage 1: With saccharin, potassium bromide in dichloromethane, Time= 3h, T= 20 °C Stage 2: in dichloromethane, Molecular sieve, Reflux Patel, Rajesh; Srivastava, Vishnu P.; Yadav, La Dhar S.; Advanced Synthesis and Catalysis; vol. 352; nb. 10; (2010); p. 1610 - 1614 View in Reaxys

O O

H 2N

N–

Cl

O

H Na +

S

HO

O

S O

Rx-ID: 29622723 View in Reaxys 191/435 Yield 53 %, 56 %

Conditions & References Stage 1: With saccharin in dichloromethane, Time= 3h, T= 20 °C Stage 2: in dichloromethane, Molecular sieve, Reflux Patel, Rajesh; Srivastava, Vishnu P.; Yadav, La Dhar S.; Advanced Synthesis and Catalysis; vol. 352; nb. 10; (2010); p. 1610 - 1614 View in Reaxys

O N

N

O

H

O

HO

O

O

Rx-ID: 29776533 View in Reaxys 192/435 Yield 75 %Chromat.

Conditions & References With C20H31Cl4IrN4Pd, caesium carbonate, Time= 3h, T= 110 °C , Aerobic conditions Zanardi, Alessandro; Mata, Jose A.; Peris, Eduardo; Chemistry - A European Journal; vol. 16; nb. 34; (2010); p. 10502 - 10506 View in Reaxys

H

O

N

N O

HO

O

Rx-ID: 29776536 View in Reaxys 193/435 Yield 83 %Chromat.

Conditions & References With C15H21Cl4N5Pd2, C25H41Cl4Ir2N3, caesium carbonate, Time= 3h, T= 110 °C , Aerobic conditions Zanardi, Alessandro; Mata, Jose A.; Peris, Eduardo; Chemistry - A European Journal; vol. 16; nb. 34; (2010); p. 10502 - 10506 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

382/438

2018-03-11 22:07:32


OH

H Br HO

O

Rx-ID: 29802398 View in Reaxys 194/435 Yield

Conditions & References

55 %Chro- With potassium nitrate, tin(ll) chloride in water, Time= 4h, T= 25 °C , Electrochemical reaction mat., 12.5 %Chromat. Zhang, Li; Zha, Zhenggen; Zhang, Zhenlei; Li, Yunfeng; Wang, Zhiyong; Chemical Communications; vol. 46; nb. 38; (2010); p. 7196 - 7198 View in Reaxys 15.7 With potassium nitrate, tin(ll) chloride in water, Time= 4h, T= 25 °C , Electrochemical reaction %Chromat., 19.5 Zhang, Li; Zha, Zhenggen; Zhang, Zhenlei; Li, Yunfeng; Wang, Zhiyong; Chemical Communications; vol. 46; nb. %Chromat. 38; (2010); p. 7196 - 7198 View in Reaxys

16O

H 18O

Rx-ID: 29845303 View in Reaxys 195/435 Yield

Conditions & References With aluminum (III) chloride, Oxone, ice, Inert atmosphere Wu, Shang; Ma, Hengchang; Lei, Ziqiang; Tetrahedron; vol. 66; nb. 45; (2010); p. 8641 - 8647 View in Reaxys

O N HO

O

O

H

HN

O

N

O

Rx-ID: 29906841 View in Reaxys 196/435 Yield

Conditions & References With ruthenium trichloride, 2,2'-bis-(diphenylphosphino)-1,1'- binaphthyl, Time= 16h, T= 150 °C , Inert atmosphere Feng, Chao; Liu, Yong; Peng, Shengming; Shuai, Qi; Deng, Guojun; Li, Chao-Jun; Organic Letters; vol. 12; nb. 21; (2010); p. 4888 - 4891 View in Reaxys With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II), 1,3-bis(mesityl)imidazolium chloride, Time= 16h, T= 150 °C , Inert atmosphere Feng, Chao; Liu, Yong; Peng, Shengming; Shuai, Qi; Deng, Guojun; Li, Chao-Jun; Organic Letters; vol. 12; nb. 21; (2010); p. 4888 - 4891 View in Reaxys

O N O

HO

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

383/438

2018-03-11 22:07:32


O O

N

O

N

H O

Rx-ID: 29906842 View in Reaxys 197/435 Yield

Conditions & References With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II), 1,3-bis(mesityl)imidazolium chloride, Time= 16h, T= 150 °C , Inert atmosphere Feng, Chao; Liu, Yong; Peng, Shengming; Shuai, Qi; Deng, Guojun; Li, Chao-Jun; Organic Letters; vol. 12; nb. 21; (2010); p. 4888 - 4891 View in Reaxys

O N HO

O

O

H

O

O

N

O

Rx-ID: 29906843 View in Reaxys 198/435 Yield

Conditions & References With [RhCl2(p-cymene)]2, 1,3-bis(mesityl)imidazolium chloride, Time= 16h, T= 150 °C , Inert atmosphere Feng, Chao; Liu, Yong; Peng, Shengming; Shuai, Qi; Deng, Guojun; Li, Chao-Jun; Organic Letters; vol. 12; nb. 21; (2010); p. 4888 - 4891 View in Reaxys

O HO

O

H

O

N

N

O

Rx-ID: 29906844 View in Reaxys 199/435 Yield

Conditions & References With ruthenium trichloride, triphenylphosphine, Time= 16h, T= 150 °C , Inert atmosphere Feng, Chao; Liu, Yong; Peng, Shengming; Shuai, Qi; Deng, Guojun; Li, Chao-Jun; Organic Letters; vol. 12; nb. 21; (2010); p. 4888 - 4891 View in Reaxys With ruthenium trichloride, 1,3-bis(mesityl)imidazolium chloride, Time= 16h, T= 150 °C , Inert atmosphere Feng, Chao; Liu, Yong; Peng, Shengming; Shuai, Qi; Deng, Guojun; Li, Chao-Jun; Organic Letters; vol. 12; nb. 21; (2010); p. 4888 - 4891 View in Reaxys

O

O

H O

N O

HO

N

O

Rx-ID: 29906845 View in Reaxys 200/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

384/438

2018-03-11 22:07:32


Yield

Conditions & References

88 %

With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II), 1,3-bis(mesityl)imidazolium chloride, Time= 16h, T= 150 °C , Inert atmosphere Feng, Chao; Liu, Yong; Peng, Shengming; Shuai, Qi; Deng, Guojun; Li, Chao-Jun; Organic Letters; vol. 12; nb. 21; (2010); p. 4888 - 4891 View in Reaxys With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II), 1,3-bis(mesityl)imidazolium chloride, Time= 16h, T= 150 °C , Inert atmosphere Feng, Chao; Liu, Yong; Peng, Shengming; Shuai, Qi; Deng, Guojun; Li, Chao-Jun; Organic Letters; vol. 12; nb. 21; (2010); p. 4888 - 4891 View in Reaxys O

O

H

HN

N

O

HO

O

O

Rx-ID: 29906846 View in Reaxys 201/435 Yield

Conditions & References With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II), 1,3-bis(mesityl)imidazolium chloride in 5,5-dimethyl-1,3-cyclohexadiene, Time= 16h, T= 150 °C , Inert atmosphere Feng, Chao; Liu, Yong; Peng, Shengming; Shuai, Qi; Deng, Guojun; Li, Chao-Jun; Organic Letters; vol. 12; nb. 21; (2010); p. 4888 - 4891 View in Reaxys H 18O

H 18O

O

Rx-ID: 30031599 View in Reaxys 202/435 Yield

Conditions & References With Oxone, [18O]water, Time= 21h, T= 50 °C , Inert atmosphere, chemoselective reaction Wu, Shang; Ma, Hengchang; Lei, Ziqiang; Synlett; nb. 18; (2010); p. 2818 - 2822 View in Reaxys

18O

HO

O

18O

H 18O

H 18O

Rx-ID: 31661254 View in Reaxys 203/435 Yield

Conditions & References With hydrogen (18)O-peroxide, Agrocybe aegerita aromatic peroxygenase in acetonitrile, pH= 7, aq. phosphate buffer, Enzymatic reaction Kinne, Matthias; Zeisig, Christian; Ullrich, Rene; Kayser, Gernot; Hammel, Kenneth E.; Hofrichter, Martin; Biochemical and Biophysical Research Communications; vol. 397; nb. 1; (2010); p. 18 - 21 View in Reaxys O

2H

2H

HO

2H

2

H

Rx-ID: 31662939 View in Reaxys 204/435 Yield

Conditions & References With tripropylammonium fluorochromate in dimethyl sulfoxide, T= 24.84 °C , Kinetics, Temperature Mansoor, S. Sheik; Shafi, S. Syed; Journal of Molecular Liquids; vol. 155; nb. 2-3; (2010); p. 85 - 90 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

385/438

2018-03-11 22:07:32


O O HO

N

N

H N

O

O

O

O

O N H

H O

O

Rx-ID: 28409865 View in Reaxys 205/435 Yield

Conditions & References

90 %

With zinc dibromide in toluene, Time= 1.5h, Reflux Cao, Hai Thuong; Gree, Rene; Tetrahedron Letters; vol. 50; nb. 13; (2009); p. 1493 - 1494 View in Reaxys

18O

H 18O

HO

Rx-ID: 28891574 View in Reaxys 206/435 Yield

Conditions & References With C36H40Cu2N6 (18)O2 (2+) in acetone, T= -70 °C Matsumoto, Takahiro; Ohkubo, Kei; Honda, Kaoru; Yazawa, Akiko; Furutachi, Hideki; Fujinami, Shuhei; Fukuzumi, Shunichi; Suzuki, Masatatsu; Journal of the American Chemical Society; vol. 131; nb. 26; (2009); p. 9258 - 9267 View in Reaxys

N

N

HO

H N

N

H

O

O

Rx-ID: 28901269 View in Reaxys 207/435 Yield

Conditions & References

7 %, 71 Stage 1: With sodium azide, (Dichloroiodo)benzene in acetonitrile, Time= 24h, T= 0 °C %Chromat. Stage 2:Time= 8h, T= 80 °C Li, Xiao-Qiang; Wang, Wei-Kun; Zhang, Chi; Advanced Synthesis and Catalysis; vol. 351; nb. 14-15; (2009); p. 2342 - 2350 View in Reaxys H

OH

OH HO

HO

O

O

Rx-ID: 28927773 View in Reaxys 208/435 Yield

Conditions & References

99 %, 11 % With air, potassium carbonate, Time= 12h, T= 20 °C Lakshmi Kantam; Arundhathi; Likhar, Pravin R.; Damodara; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2633 - 2637 View in Reaxys

H

O

HO

O

O

Rx-ID: 28937020 View in Reaxys 209/435 Yield

Conditions & References With Janibacter terrae DSM 13953 cells in water, Time= 5h, T= 30 °C , pH= 7.5, aq. phosphate buffer, Enzymatic reaction Orbegozo, Thomas; Lavandera, Ivan; Fabian, Walter M.F.; Mautner, Barbara; de Vries, Johannes G.; Kroutil, Wolfgang; Tetrahedron; vol. 65; nb. 34; (2009); p. 6805 - 6809 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

386/438

2018-03-11 22:07:32


O

O

2H

2H

2

S

H

NH

2H

2

H

HO 2H

2H

2H

O

2H

2H

2H

O

2H

2H

2H

S

N

2H

2H

2H

2H

O N H

O S

H O

2H 2H

Rx-ID: 29116962 View in Reaxys 210/435 Yield

Conditions & References With copper diacetate, potassium carbonate, Time= 12h, T= 150 °C Cui, Xinjiang; Shi, Feng; Tse, Man Kin; Goerdes, Dirk; Thurow, Kerstin; Beller, Matthias; Deng, Youquan; Advanced Synthesis and Catalysis; vol. 351; nb. 17; (2009); p. 2949 - 2958 View in Reaxys With Ru/Fe3O4, potassium carbonate, Time= 15h, T= 150 °C Shi, Feng; Tse, Man Kin; Zhou, Shaolin; Pohl, Marga-Martina; Radnik, Joerg; et al.; Journal of the American Chemical Society; vol. 131; (2009); p. 1775 - 1779 View in Reaxys

2H

2H

2H

E

2H

2

2H

H

O

O

2H

H

2H

2H

S

2H

O S

2H

2H

O 2H

H

H N O

2

H

O S

2

H

O

2

H N

N

2H

O S

H

2

2H

2H

2H

2H

2

O O

O N H

N

HO 2H

2H

2

S

2H

2H

H

O

2

H

Rx-ID: 29116965 View in Reaxys 211/435 Yield

Conditions & References With copper diacetate, potassium carbonate, Time= 3h, T= 150 °C Cui, Xinjiang; Shi, Feng; Tse, Man Kin; Goerdes, Dirk; Thurow, Kerstin; Beller, Matthias; Deng, Youquan; Advanced Synthesis and Catalysis; vol. 351; nb. 17; (2009); p. 2949 - 2958 View in Reaxys O

O E

O

O

S

S

N

H

NH

HO

O

Rx-ID: 29116966 View in Reaxys 212/435 Yield

Conditions & References With copper diacetate, potassium carbonate, Time= 3h, T= 150 °C Cui, Xinjiang; Shi, Feng; Tse, Man Kin; Goerdes, Dirk; Thurow, Kerstin; Beller, Matthias; Deng, Youquan; Advanced Synthesis and Catalysis; vol. 351; nb. 17; (2009); p. 2949 - 2958 View in Reaxys O

H 2N

S O

HO

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

387/438

2018-03-11 22:07:32


O

O

O

O

O

O

O

S

E

NH

S

H

N

O

Rx-ID: 29116969 View in Reaxys 213/435 Yield

Conditions & References With copper diacetate, Time= 12h, T= 150 °C Cui, Xinjiang; Shi, Feng; Tse, Man Kin; Goerdes, Dirk; Thurow, Kerstin; Beller, Matthias; Deng, Youquan; Advanced Synthesis and Catalysis; vol. 351; nb. 17; (2009); p. 2949 - 2958 View in Reaxys O

H 2N

S

HO

O

O

O

O

O

S

O

E

NH

S

H

N

O

Rx-ID: 29116970 View in Reaxys 214/435 Yield

Conditions & References With copper diacetate, sodium carbonate, Time= 12h, T= 150 °C Cui, Xinjiang; Shi, Feng; Tse, Man Kin; Goerdes, Dirk; Thurow, Kerstin; Beller, Matthias; Deng, Youquan; Advanced Synthesis and Catalysis; vol. 351; nb. 17; (2009); p. 2949 - 2958 View in Reaxys O

O O H 2N

S

O

S

HO

O

H

NH

O

Rx-ID: 29116971 View in Reaxys 215/435 Yield

Conditions & References With copper diacetate, potassium carbonate, Time= 12h, T= 150 °C Cui, Xinjiang; Shi, Feng; Tse, Man Kin; Goerdes, Dirk; Thurow, Kerstin; Beller, Matthias; Deng, Youquan; Advanced Synthesis and Catalysis; vol. 351; nb. 17; (2009); p. 2949 - 2958 View in Reaxys

O

HO

H

O

O

Rx-ID: 29326700 View in Reaxys 216/435 Yield 14 %Chromat., 64 %Chromat., 20 %Chromat.

Conditions & References With Mo2N nanoparticle, Time= 20h, T= 150 °C Yao, Weitang; Makowski, Philippe; Giordano, Cristina; Goettmann, Frederic; Chemistry - A European Journal; vol. 15; nb. 44; (2009); p. 11999 - 12004 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

388/438

2018-03-11 22:07:32


H O F

HO

O

Rx-ID: 30138421 View in Reaxys 217/435 Yield 31 %Spectr., 12 %Spectr.

Conditions & References With difluoro[4-(trifluoromethyl)phenyl]-λ3-bromane in diethyl ether, Time= 3h, T= 20 °C , Inert atmosphere Ochiai, Masahito; Yoshimura, Akira; Miyamoto, Kazunori; Tetrahedron Letters; vol. 50; nb. 33; (2009); p. 4792 4795 View in Reaxys H O

HO

O

O

Rx-ID: 4504936 View in Reaxys 218/435 Yield

Conditions & References With sodium oxide, oxygen, Cu-NaZSM-5 zeolite, T= 573 - 673 °C , influence of alkali-metal additives, percentage of Cu ion exchanged, alakli-metal/Cu atomic ratio on the gas-phase catalytic oxidation; further additives, Product distribution Genta, Minoru; Nishiyama, Satoru; Tsuruya, Shigeru; Masai, Mitsuo; Journal of the Chemical Society - Faraday Transactions; vol. 92; nb. 7; (1996); p. 1267 - 1275 View in Reaxys With oxygen, sodium, silica gel, copper, T= 299.9 °C , further alkali metals: Li, K, Rb, Cs, Product distribution Arai, Masahide; Nishiyama, Satoru; Tsuruya, Shigeru; Masai, Mitsuo; Journal of the Chemical Society - Faraday Transactions; vol. 92; nb. 14; (1996); p. 2631 - 2636 View in Reaxys With CeL-NaZSM-5, oxygen, T= 399.85 °C , other reagents, temperatrures, Product distribution Kanada, Arihiro; Idaka, Nao; Nishiyama, Satoru; Tsuruya, Shigeru; Masai, Mitsuo; Physical Chemistry Chemical Physics; vol. 1; nb. 2; (1999); p. 373 - 381 View in Reaxys With oxygen, titanium(IV) oxide in water, Time= 8.4h, Irradiation Augugliaro, Vincenzo; Caronna, Tullio; Loddo, Vittorio; Marci, Giuseppe; Palmisano, Giovanni; Palmisano, Leonardo; Yurdakal, Sedat; Chemistry - A European Journal; vol. 14; nb. 15; (2008); p. 4640 - 4646 View in Reaxys O

NH 2

N

O

HO

E

H O

Rx-ID: 25930858 View in Reaxys 219/435 Yield

Conditions & References With KMn8O16*nH2O in acetonitrile, Time= 12h, T= 80 °C Sithambaram, Shanthakumar; Kumar, Ranjit; Son, Young-Chan; Suib, Steven L.; Journal of Catalysis; vol. 253; nb. 2; (2008); p. 269 - 277 View in Reaxys

N

NH 2

H

E

HO

O

Rx-ID: 25930859 View in Reaxys 220/435 Yield

Conditions & References With KMn8O16*nH2O in octanol, Time= 12h, T= 125 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

389/438

2018-03-11 22:07:32


Sithambaram, Shanthakumar; Kumar, Ranjit; Son, Young-Chan; Suib, Steven L.; Journal of Catalysis; vol. 253; nb. 2; (2008); p. 269 - 277 View in Reaxys O

H O

HO

O

Rx-ID: 26033476 View in Reaxys 221/435 Yield

Conditions & References With gold-palladium nanoparticles, T= 160 °C , p= 7500.75Torr , Further byproducts. Lopez-Sanchez, Jose Antonio; Dimitratos, Nikolaos; Miedziak, Peter; Ntainjua, Edwin; Edwards, Jennifer K.; Morgan, David; Carley, Albert F.; Tiruvalam, Ramchandra; Kiely, Christopher J.; Hutchings, Graham J.; Physical Chemistry Chemical Physics; vol. 10; nb. 14; (2008); p. 1921 - 1930 View in Reaxys H O

HO

HO

O

Rx-ID: 26050922 View in Reaxys 222/435 Yield

Conditions & References

27 %, 59 %

With Amberlite IRA-120, urea-hydrogen peroxide, 1-n-butyl-3-methylimidazolim bromide, Time= 0.5h, T= 70 °C Bhati, Nishi; Sarma, Kuladip; Goswami, Amrit; Chemistry Letters; vol. 37; nb. 5; (2008); p. 496 - 497 View in Reaxys

2H

H

2H

OH 2H

H

2H

O

HO

HO

O

Rx-ID: 28249425 View in Reaxys 223/435 Yield

Conditions & References With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], oxygen, triethylamine in toluene, T= 80 °C , p= 760.051Torr , Kinetics Jiang, Bi; Feng, Yuee; Ison, Elon A.; Journal of the American Chemical Society; vol. 130; nb. 44; (2008); p. 14462 - 14464 View in Reaxys

O

O Cl

O

H

OO

H

H

HO

NH 2

N H

O

Rx-ID: 28322067 View in Reaxys 224/435 Yield 46 %, 15 %

Conditions & References With tert.-butylhydroperoxide, potassium iodide in water, Time= 15h, T= 80 °C Rajender Reddy; Uma Maheswari; Venkateshwar; Lakshmi Kantam; European Journal of Organic Chemistry; nb. 21; (2008); p. 3619 - 3622 View in Reaxys

HO

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

390/438

2018-03-11 22:07:32


HO

HO

H O

O

OH

O

O

OH

O

OH

HO

O

O

O

Rx-ID: 28323917 View in Reaxys 225/435 Yield

Conditions & References With oxygen, titanium(IV) oxide in water, Irradiation Augugliaro, Vincenzo; Caronna, Tullio; Loddo, Vittorio; Marci, Giuseppe; Palmisano, Giovanni; Palmisano, Leonardo; Yurdakal, Sedat; Chemistry - A European Journal; vol. 14; nb. 15; (2008); p. 4640 - 4646 View in Reaxys O H 13 2 C

H 13 2 C

N

O

O

HO

O H 13C

13C

O

HO

Rx-ID: 10506896 View in Reaxys 226/435 Yield

Conditions & References With ammonium cerium(IV) nitrate, 1-ethyl-3-methylimidazolium triflate, Time= 6h, T= 100 °C Mehdi, Hasan; Bodor, Andrea; Lantos, Diana; Horvath, Istvan T.; De Vos, Dirk E.; Binnemans, Koen; Journal of Organic Chemistry; vol. 72; nb. 2; (2007); p. 517 - 524 View in Reaxys

O

HO

N

O

O

H

O

O

HO

Rx-ID: 10549403 View in Reaxys 227/435 Yield

Conditions & References With ammonium cerium(IV) nitrate, 1-ethyl-3-methylimidazolium triflate, Time= 6h, T= 100 °C Mehdi, Hasan; Bodor, Andrea; Lantos, Diana; Horvath, Istvan T.; De Vos, Dirk E.; Binnemans, Koen; Journal of Organic Chemistry; vol. 72; nb. 2; (2007); p. 517 - 524 View in Reaxys H

HO

Br

O

Rx-ID: 11044833 View in Reaxys 228/435 Yield 34 %, 60 %

Conditions & References With N-Bromosuccinimide, water in 1,4-dioxane, Time= 1h, T= 70 °C Adimurthy, Subbarayappa; Patoliya, Paresh U.; Synthetic Communications; vol. 37; nb. 9; (2007); p. 1571 - 1577 View in Reaxys OH

OH

H HO

HO

O

Rx-ID: 25672453 View in Reaxys 229/435 Yield

Conditions & References 2 :Example 2.A packed bed reactor was loaded with 5 cubic centimeters (cc) of magnesium carbonate pellets, having an average particle size of 1000 micrometers to 1400 micrometers. This catalyst was calcined in-situ for 16 to 22 hours at 390° C at a rate of 0.2 to 5°C/min under 0.06 to 0.24 (10) g of nitrogen/hr/g of catalyst. All the reactions were performed under atmospheric pressure. After calcination, the temperature was increased from 3900C to 475°C within two hours under nitrogen atmosphere. After 15 minutes of attaining this temperature, a feed mixture was introduced at 0.12 cc/min. The feed contained 16.21 wt.percent phenol, 74.48 wt.percent benzylalcohol, and 9.31 wt.per-

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

391/438

2018-03-11 22:07:32


cent water (4:1 molar ratio of benzylalcohol to phenol). The benzylation reaction was carried out under isothermal condition for a period of 24 hours. The yields of reaction products such as ortho benzylphenol, 2,6 dibenzylphenol, benzaldehyde and unconverted phenols and benzylalcohol were monitored over the period of 20 hours. The conversion measured was based on area percent peaks reported by gas chromatography. The results were shown in Table 1. EPO <DP n="11"/> With water, magnesium carbonate; calcined at 390°C; heated up to 475°C, Time= 24h, T= 475 °C , p= 760.051Torr Patent; GENERAL ELECTRIC COMPANY; WO2007/27375; (2007); (A2) English View in Reaxys

O

OH

O

HO

O

H

O

O

HO

Rx-ID: 2885099 View in Reaxys 230/435 Yield

Conditions & References

5.54 %, 83.6 %, 9.42 %

With oxygen, zirconium-cobalt-manganese, sodium bromide, T= 75 °C , atmospheric pressure, Product distribution, Kinetics, Further Variations: Catalysts, Temperatures, addition of water Partenheimer, Walt; Advanced Synthesis and Catalysis; vol. 348; nb. 4-5; (2006); p. 559 - 568 View in Reaxys

3.8 %, 80 %, 4.6 %

With zirconium tetraacetate, sodium bromide, Co(II)-Mn(II) acetate, Time= 1.66667h, T= 75 °C , Kinetics Partenheimer, Walt; Grushin, Vladimir V.; Advanced Synthesis and Catalysis; vol. 343; nb. 1; (2001); p. 102 - 111 View in Reaxys

96 % Chromat., 2 % Chromat., 2 % Chromat.

With ammonium nitrate in sulfuric acid, T= 20 °C , var. ratio of reactants, Product distribution, Mechanism Rodkin, M. A.; Shtern, M. M.; Cheprakov, A. V.; Makhon'kov, D. I.; Merdaleishvili, R. E.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 3; (1988); p. 434 - 440; Zhurnal Organicheskoi Khimii; vol. 24; nb. 3; (1988); p. 488 - 495 View in Reaxys

O

O O

O

P N

N

O

H

E

HO

O

N

O

Rx-ID: 9213396 View in Reaxys 231/435 Yield

Conditions & References

11 %, 11 %, 47 %

With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,3-bis-(diphenylphosphino)propane, caesium carbonate in toluene, Time= 72h, T= 150 °C , indirect Wittig reaction Edwards, Michael G.; Williams, Jonathan M.J.; Angewandte Chemie - International Edition; vol. 41; nb. 24; (2002); p. 4740 - 4743 View in Reaxys

47 %

With 1,3-bis-(diphenylphosphino)propane, caesium carbonate, bis(1,5-cyclooctadiene)diiridium(I) dichloride in toluene, Time= 72h, T= 150 °C Black, Phillip J.; Edwards, Michael G.; Williams, Jonathan M. J.; European Journal of Organic Chemistry; nb. 19; (2006); p. 4367 - 4378 View in Reaxys N

N

H Z

HO

O

Rx-ID: 10445803 View in Reaxys 232/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

392/438

2018-03-11 22:07:32


Yield

Conditions & References

98 % Chromat.

With ruthenium-grafted hydrotalcite in toluene, Time= 20h, T= 180 °C Motokura, Ken; Fujita, Noriaki; Mori, Kohsuke; Mizugaki, Tomoo; Ebitani, Kohki; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Chemistry - A European Journal; vol. 12; nb. 32; (2006); p. 8228 - 8239 View in Reaxys

H P

HO

O

N

N

N

Rx-ID: 10545084 View in Reaxys 233/435 Yield

Conditions & References With bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride in toluene, Product distribution, Further Variations: Catalysts Black, Phillip J.; Edwards, Michael G.; Williams, Jonathan M. J.; European Journal of Organic Chemistry; nb. 19; (2006); p. 4367 - 4378 View in Reaxys H

O HO

O

HO

O

Cl

O

Rx-ID: 10549339 View in Reaxys 234/435 Yield

Conditions & References With tetrachloromethane, hexacarbonyl molybdenum, T= 160 °C , Product distribution Khusnutdinov; Shchadneva; Burangulova; Muslimov; Dzhemilev; Russian Journal of Organic Chemistry; vol. 42; nb. 11; (2006); p. 1615 - 1621 View in Reaxys

O

O

O

N N

HO

O

H

N

O O

Rx-ID: 10549345 View in Reaxys 235/435 Yield

Conditions & References

31 %

With 1,3-bis-(diphenylphosphino)propane, caesium carbonate, bis(1,5-cyclooctadiene)diiridium(I) dichloride in toluene, Time= 72h, T= 150 °C , Wadsworth-Emmons reaction Black, Phillip. J.; Cami-Kobeci, Gerta; Edwards, Michael G.; Slatford, Paul A.; Whittlesey, Michael K.; Williams, Jonathan M. J.; Organic and Biomolecular Chemistry; vol. 4; nb. 1; (2006); p. 116 - 125 View in Reaxys

O P O

HO

O

O

O

H O

O

O

E

O

Rx-ID: 10549402 View in Reaxys 236/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

393/438

2018-03-11 22:07:32


Yield 54 %

Conditions & References With 1,3-bis-(diphenylphosphino)propane, caesium carbonate, bis(1,5-cyclooctadiene)diiridium(I) dichloride in toluene, Time= 72h, T= 150 °C Black, Phillip J.; Edwards, Michael G.; Williams, Jonathan M. J.; European Journal of Organic Chemistry; nb. 19; (2006); p. 4367 - 4378 View in Reaxys

H HO

O

O

O

Rx-ID: 23744435 View in Reaxys 237/435 Yield 20.5 %Chromat., 1.6 %Chromat.

Conditions & References 4 :In the same manner as in Example 4, the operation was conducted, except that 0.43 g (4 mmols) of benzyl alcohol was used in place of m-methoxybenzyl alcohol and 1 ml (17.4 mmols) of acetic acid was used in place of 2 ml of acetic acid, and also 1 ml of water and 0.14 g (1.35 mmols) of sodium chlorate was used in place of sodium bromate. With respect to the components in the reaction solution, an area ratio as determined by gas chromatography of the intended benzaldehyde was 1.6percent, that of benzyl alcohol was 77.9percent and that of benzyl acetate was 20.5percent. Example 4 (An embodiment of the invention described in the above embodiment [1]): Production of benzaldehyde In the same manner as in Example 3, the operation was conducted, except that 0.43 g (4 mmols) of benzyl alcohol was used in place of m-methoxybenzyl alcohol and 0.39 g (2 mmols) of sodium bromite trihydrate was used in place of sodium bromate, and also the mixture was stirred at 50°C for 4 hours. With respect to the components in the reaction solution, the intended benzaldehyde was produced in an area ratio, as determined by gas chromatography, of 93.5percent.Example 3 (An embodiment of the invention described in the above embodiment [1]): Production of mmethoxybenzaldehyde In a 15 ml test tube type reaction vessel equipped with a magnetic stirrer and a reflux condenser, 0.55 g (4 mmols) of m-methoxybenzyl alcohol, 0.18 g (1.2 mmols) of sodium bromate and 2 ml (34.8 mmols) of acetic acid were charged, and then the resultant mixture was stirred at 90°C for 1.5 hours. Along with the progress of the reaction, a small amount of bromine was produced. After the completion of the reaction, bromine completely disappeared. With sodium chlorate, acetic acid in water, Time= 4h, T= 50 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1661877; (2006); (A1) English View in Reaxys

O

HO

H O

Rx-ID: 817414 View in Reaxys 238/435 Yield

Conditions & References

56 %, 9 %, With HY-100 zeolite in tetrachloromethane, Time= 1h, T= 78 °C , Product distribution 9% Climent, Maria J.; Corma, Avelino; Garcia, Hermenegildo; Iborra, Sara; Primo, Jaime; Recueil des Travaux Chimiques des Pays-Bas; vol. 110; nb. 6; (1991); p. 275 - 278 View in Reaxys 30 %, 3 %, With methyltrioxorhenium(VII) in benzene, Time= 48h, Ambient temperature, dehydration, amination and dispropor3% tionation of various alcohols catalyzed by methylrhenium trioxide; direct formation of symmetric and unsymmetric ethers from alcohols; possible mechanism of catalytic reactions, Product distribution Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 61; nb. 1; (1996); p. 324 - 328 View in Reaxys 30 %, 3 %, With methyltrioxorhenium(VII) in benzene, Time= 48h, Ambient temperature 3% Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 61; nb. 1; (1996); p. 324 - 328 View in Reaxys T= 340 °C , Leiten ueber Aluminiumoxyd

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

394/438

2018-03-11 22:07:32


Adkins; Folkers; Journal of the American Chemical Society; vol. 53; (1931); p. 1422 View in Reaxys T= 210 - 215 °C , im Glasrohr Lachman; Journal of the American Chemical Society; vol. 45; (1923); p. 2359 View in Reaxys With (CO)4(palladium)4(acetate)4, Time= 2h, T= 60 °C , Title compound not separated from byproducts Stolarov; Dobrokhotova; Kryukova; Kozitsyna; Gekhman; Vargaftik; Moiseev; Russian Chemical Bulletin; vol. 54; nb. 3; (2005); p. 803 - 806 View in Reaxys O

H O

HO

Br

O

Rx-ID: 9815636 View in Reaxys 239/435 Yield

Conditions & References With 2,2,6,6-tetramethyl-piperidine-N-oxyl, air, 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione, sodium nitrite in dichloromethane, Time= 1h, p= 3000.24Torr , Heating, Product distribution, Further Variations: Solvents, Pressures, Reagents, reaction times Liu, Renhua; Dong, Chunyan; Liang, Xinmiao; Wang, Xiujuan; Hu, Xinquan; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 729 - 731 View in Reaxys

H

O

HO

Br

O

Rx-ID: 9900408 View in Reaxys 240/435 Yield

Conditions & References With bromine, triethyl phosphite, Time= 3h Iranpoor, Nasser; Firouzabadi, Habib; Jamalian, Arezu; Kazemi, Foad; Tetrahedron; vol. 61; nb. 23; (2005); p. 5699 - 5704 View in Reaxys 2H

2H

2H

2H 2H 13 13 C C 2H

2H

2H

13CH

13C 13C

13CH

O

O 2H

2H

2H

2H

Rx-ID: 9997409 View in Reaxys 241/435 Yield

Conditions & References With dipyridinium dichromate Torizawa, Takuya; Ono, Akira Mei; Terauchi, Tsutomu; Kainosho, Masatsune; Journal of the American Chemical Society; vol. 127; nb. 36; (2005); p. 12620 - 12626 View in Reaxys 2H

2H

2H

2H 13 13 C C 2H

2H

2H 13C 2H 13C

O 2H

13C 13C

2H 13C

O

2H

2H 13C

2

H

2

H

Rx-ID: 9998346 View in Reaxys 242/435 Yield

Conditions & References With dipyridinium dichromate

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

395/438

2018-03-11 22:07:32


Torizawa, Takuya; Ono, Akira Mei; Terauchi, Tsutomu; Kainosho, Masatsune; Journal of the American Chemical Society; vol. 127; nb. 36; (2005); p. 12620 - 12626 View in Reaxys O

H

NH

O

H 2N

N

HO

Rx-ID: 23488048 View in Reaxys 243/435 Yield

Conditions & References 3 :An operation was conducted in the same manner as in Example 8 except that 25percent aqueous ammonia was replaced by 0.35 g (4.5 mmol) of 40percent methylamine. The reaction mixture contained, as components, 12.4percent (in terms of areal ratio of gas chromatography) of intended benzonitrile, 32.1percent of N-methylbenzamide (a by-product) and 45.7percent of benzaldehyde used as a raw material. With sodium bromate, acetic acid in water, Time= 15h, T= 90 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1555257; (2005); (A1) English View in Reaxys

2H

2H

2H

13CH

13C

O

O

Rx-ID: 9347974 View in Reaxys 244/435 Yield

Conditions & References With MnO4 Hill, Alison M.; Thompson, Betty L.; Harris, Jonathan P.; Segret, Roger; Chemical Communications; nb. 12; (2003); p. 1358 - 1359 View in Reaxys H 14C 14C

H 14C

HO

H 14C 14CH

14CH

14C

14CH 14CH

O

14CH

H 14C 14CH

Rx-ID: 9350985 View in Reaxys 245/435 Yield

Conditions & References With horse liver alcohol dehydrogenase, NAD, sodium cacodylate, hydrazine carboxamide in methanol, T= 3 °C , pH= 7.0, Enzymatic reaction, Enzyme kinetics Tsai, Shiou-Chuan; Klinman, Judith P.; Bioorganic Chemistry; vol. 31; nb. 2; (2003); p. 172 - 190 View in Reaxys

H

S

H 2N

NH

HO

O

Rx-ID: 9084414 View in Reaxys 246/435 Yield

Conditions & References

95 % Spectr.

With N-(tert-butyl)benzenesulfinimidoyl chloride, 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane, Time= 0.5h, T= -78 °C Matsuo, Jun-Ichi; Iida, Daisuke; Tatani, Kazuya; Mukaiyama, Teruaki; Bulletin of the Chemical Society of Japan; vol. 75; nb. 2; (2002); p. 223 - 234 View in Reaxys

O

O

O

O

P

O

HO

E

H O

O

Rx-ID: 9207212 View in Reaxys 247/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

396/438

2018-03-11 22:07:32


Yield

Conditions & References

51 %, 3 %, With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,3-bis-(diphenylphosphino)propane, caesium carbonate in tol21 % uene, Time= 72h, T= 150 °C , indirect Wittig reaction Edwards, Michael G.; Williams, Jonathan M.J.; Angewandte Chemie - International Edition; vol. 41; nb. 24; (2002); p. 4740 - 4743 View in Reaxys

H P

HO

E

N

O

N

N

Rx-ID: 9210441 View in Reaxys 248/435 Yield

Conditions & References

7 %, 7 %, 56 %

With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,3-bis-(diphenylphosphino)propane, caesium carbonate in toluene, Time= 72h, T= 150 °C , indirect Wittig reaction Edwards, Michael G.; Williams, Jonathan M.J.; Angewandte Chemie - International Edition; vol. 41; nb. 24; (2002); p. 4740 - 4743 View in Reaxys

O

O

O P

O

O

HO

O

O

H

E

O

O

O

Rx-ID: 9213390 View in Reaxys 249/435 Yield

Conditions & References

14 % Spectr., 28 % Spectr., 18 % Spectr.

With 1,3-bis-(diphenylphosphino)propane, caesium carbonate, 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2a]pyrimidine, bis(1,5-cyclooctadiene)diiridium(I) dichloride in toluene, Time= 72h, T= 150 °C , indirect Horner-Wadsworth-Emmons reaction, Product distribution, Further Variations: Catalysts, Reagents Edwards, Michael G.; Williams, Jonathan M.J.; Angewandte Chemie - International Edition; vol. 41; nb. 24; (2002); p. 4740 - 4743 View in Reaxys

O P O

HO

O E

O

H O

O

O

Rx-ID: 9213392 View in Reaxys 250/435 Yield 12 %, 71 %, 5 %

Conditions & References With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,3-bis-(diphenylphosphino)propane, caesium carbonate in toluene, Time= 72h, T= 150 °C , indirect Wittig reaction Edwards, Michael G.; Williams, Jonathan M.J.; Angewandte Chemie - International Edition; vol. 41; nb. 24; (2002); p. 4740 - 4743

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

397/438

2018-03-11 22:07:32


View in Reaxys

O

O

H

O

O

P

O

O

HO

E

O

Rx-ID: 9213410 View in Reaxys 251/435 Yield

Conditions & References

54 %, 4 %, With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,3-bis-(diphenylphosphino)propane, caesium carbonate in tol20 % uene, Time= 72h, T= 150 °C , indirect Wittig reaction Edwards, Michael G.; Williams, Jonathan M.J.; Angewandte Chemie - International Edition; vol. 41; nb. 24; (2002); p. 4740 - 4743 View in Reaxys

O

H

Br–

O

HO

N+

O

Rx-ID: 9345544 View in Reaxys 252/435 Yield

Conditions & References

51 %, 4 % Chromat.

With palladium dichloride, Time= 6h, T= 120 °C Ganchegui, Benjamin; Bouquillon, Sandrine; Henin, Francoise; Muzart, Jacques; Tetrahedron Letters; vol. 43; nb. 37; (2002); p. 6641 - 6644 View in Reaxys O

H O

HO

Cl

O

Rx-ID: 9345597 View in Reaxys 253/435 Yield

Conditions & References

12 % Chromat., 73 % Chromat., 15 % Chromat.

H

With tetrachloromethane, bis(acetylacetonate)oxovanadium, Time= 3h, T= 150 °C Khusnutdinov; Shchadneva; Baiguzina; Lavrentieva; Dzhemilev; Russian Chemical Bulletin; vol. 51; nb. 11; (2002); p. 2074 - 2079 View in Reaxys

OH 2H

H O

Rx-ID: 8813207 View in Reaxys 254/435 Yield

Conditions & References With 3,3-dimethyldioxirane in acetone, T= 0 °C , Kinetics Angelis, Yiannis S.; Hatzakis, Nikos S.; Smonou, Ioulia; Orfanopoulos, Michael; Tetrahedron Letters; vol. 42; nb. 22; (2001); p. 3753 - 3756 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

398/438

2018-03-11 22:07:32


O O

H

I

O

O

O

HO

O

Rx-ID: 8824475 View in Reaxys 255/435 Yield

Conditions & References

33 % Chromat., 13 % Chromat.

Stage 1: With oxygen, tetraethylammonium perchlorate in acetonitrile, Time= 1h, T= 20 °C , Electrochemical reaction Stage 2:Time= 24h, T= 20 °C , Further stages. Casadei, Maria Antonietta; European Journal of Organic Chemistry; nb. 9; (2001); p. 1689 - 1693 View in Reaxys O

H

I

O

HO

O

Rx-ID: 8824476 View in Reaxys 256/435 Yield 22 % Chromat., 62 % Chromat.

Conditions & References Stage 1: With carbon dioxide, oxygen, tetraethylammonium perchlorate in acetonitrile, Time= 24h, T= 20 °C , Electrochemical reaction Stage 2:Time= 24h, T= 20 °C , Further stages. Casadei, Maria Antonietta; European Journal of Organic Chemistry; nb. 9; (2001); p. 1689 - 1693 View in Reaxys

H O

O

HO

O

Rx-ID: 8839040 View in Reaxys 257/435 Yield

Conditions & References With oxygen, NaY, T= 399.85 °C , Product distribution, Further Variations: Catalysts, Temperatures Tsuruya; Idaka; Nishiyama; Physical Chemistry Chemical Physics; vol. 3; nb. 10; (2001); p. 1918 - 1924 View in Reaxys O

H O

N

HO

O

Rx-ID: 8904240 View in Reaxys 258/435 Yield

Conditions & References With HMnO4*H3N, Time= 2h, Product distribution, Further Variations: Temperatures, time Kotai, Laszlo; Kazinczy, Bela; Keszler, Agnes; Holly, Sandor; Gacs, Istvan; Banerji, Kalyan K.; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 56; nb. 8; (2001); p. 823 - 825 View in Reaxys

HO HO

OH HO

HO

OH

H O

HO

Rx-ID: 8967028 View in Reaxys 259/435 Yield

Conditions & References With water, dinitrogen monoxide, T= 20 °C , pH= 6, Radiolysis, Kinetics Steenken, Steen; Ramaraj, Ramasamy; Journal of the Chemical Society. Perkin Transactions 2; nb. 9; (2001); p. 1613 - 1619

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

399/438

2018-03-11 22:07:32


View in Reaxys

H HO

HO

O

Rx-ID: 9155022 View in Reaxys 260/435 Yield

Conditions & References With gallium sulphate, copper, zinc, T= 300 °C , Product distribution, Further Variations: Catalysts, Temperatures Gavankar, Swati R.; Darshane; Journal of the Indian Chemical Society; vol. 78; nb. 3; (2001); p. 115 - 118 View in Reaxys

H 14 2 C

H 14C

HO

O

Rx-ID: 4823004 View in Reaxys 261/435 Yield 84 %

Conditions & References With manganese(IV) oxide in pentane, Time= 5h, T= 40 °C , Oxidation Le, Diem Duy; Zhang, Yinsheng; Chien, David H.; Moravek, Josef; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 43; nb. 11; (2000); p. 1119 - 1125 View in Reaxys

80 %

With ammonium cerium(IV) nitrate, acetic acid in water, Time= 1.5h, T= 70 °C Azim, Elmostafa; Dupuy, Jean Michel; Lepage, Francis; Veyre, Annie; Madelmont, Jean Claude; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 39; nb. 11; (1997); p. 907 - 914 View in Reaxys

12 mmol

With dipyridinium dichromate in dichloromethane, Time= 18.5h, Oxidation Woo, Peter W. K.; Hartman, Jon; Huang, Yun; Nanninga, Thomas; Bauman, Kelvin; Butler, Donald E.; Rubin, John R.; Lee, Helen T.; Huang, Che C.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 42; nb. 2; (1999); p. 121 - 127 View in Reaxys

H

O HO

O

O

O

Rx-ID: 8664375 View in Reaxys 262/435 Yield 87 %, 3 %

Conditions & References With 2,4,6-trimethyl-pyridine, Bromotrichloromethane, T= 60 °C , Alkylation Barks; Gilbert; Parsons; Upeandran; Tetrahedron Letters; vol. 41; nb. 32; (2000); p. 6249 - 6252 View in Reaxys N

N

N

N

N

N

H HO

O

H 2N

O

Rx-ID: 8734451 View in Reaxys 263/435 Yield 21 % Chromat., 70 %

Conditions & References Time= 20h, T= 20 °C , Irradiation Ito, Yoshikatsu; Nakabayashi, Hironari; Ohba, Shigeru; Hosomi, Hiroyuki; Tetrahedron; vol. 56; nb. 37; (2000); p. 7139 - 7152

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

400/438

2018-03-11 22:07:32


View in Reaxys O

OH

O

O

HO

O

N

O

H NH

N O

HO

O O

NH

O

O

O O

O

O

O

Rx-ID: 10330914 View in Reaxys 264/435 Yield

Conditions & References in acetonitrile, T= 24.84 °C , Irradiation, reduction; oxidation, Kinetics, Quantum yield Fukuzumi, Shunichi; Itoh, Shinobu; Komori, Takashi; Suenobu, Tomoyoshi; Ishida, Akito; Fujitsuka, Mamoru; Ito, Osamu; Journal of the American Chemical Society; vol. 122; nb. 35; (2000); p. 8435 - 8443 View in Reaxys

O

H

OH

O

HO

O

O

Rx-ID: 5104377 View in Reaxys 265/435 Yield

Conditions & References

68 %, 32 %

With dihydrogen peroxide, methyltrioxorhenium(VII), sodium chloride, Time= 10h, Ambient temperature Espenson; Zhu; Zauche; Journal of Organic Chemistry; vol. 64; nb. 4; (1999); p. 1191 - 1196 View in Reaxys

H 13C H 13 2 C HO

13C

13CH

H 13C

13CH

H 13C

H 13C

13CH

O

13C

H 13C

13CH 13CH 13CH

Rx-ID: 5227035 View in Reaxys 266/435 Yield

Conditions & References With pyridinium chlorochromate in dichloromethane, Time= 1.5h, Heating, Oxidation Woo, Peter W. K.; Hartman, Jon; Hicks, James; Hayes, Roger; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 42; nb. 2; (1999); p. 135 - 145 View in Reaxys

2H

H

H

OH

O

Rx-ID: 5268432 View in Reaxys 267/435 Yield

Conditions & References With chloroperoxidase from the fungus Caldariomyces fumago, dihydrogen peroxide in [D3]acetonitrile, water, T= 25 °C , pH= 6.0, Oxidation, Kinetics Baciocchi, Enrico; Lanzalunga, Osvaldo; Manduchi, Laura; Chemical Communications; nb. 17; (1999); p. 1715 1716 View in Reaxys

H

OH 2H

2H

O

Rx-ID: 5268929 View in Reaxys 268/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

401/438

2018-03-11 22:07:32


Yield

Conditions & References With chloroperoxidase from the fungus Caldariomyces fumago, dihydrogen peroxide in [D3]acetonitrile, water, T= 25 °C , pH= 6.0, Oxidation, Kinetics Baciocchi, Enrico; Lanzalunga, Osvaldo; Manduchi, Laura; Chemical Communications; nb. 17; (1999); p. 1715 1716 View in Reaxys

N S N

O

Cu 2+ S

(v1)

N

HO N

N

H

Cu +

OH

O

N

O N

O–

O

Rx-ID: 27175071 View in Reaxys 269/435 Yield

Conditions & References in acetonitrile Itoh, Shinobu; Taki, Masayasu; Takayama, Shigehisa; Nagatomo, Shigenori; Kitagawa, Teizo; Sakurada, Norio; Arakawa, Ryuichi; Fukuzumi, Shunichi; Angewandte Chemie - International Edition; vol. 38; nb. 18; (1999); p. 2774 - 2776 ; (from Gmelin) View in Reaxys

O

H

O O

Bi

O

Bi

HO

HO

O

Rx-ID: 4975001 View in Reaxys 270/435 Yield

Conditions & References Time= 30h, T= 10 - 15 °C , Product distribution Zinov'eva; Dolganova; Dodonov; Prezhbog; Russian Chemical Bulletin; vol. 47; nb. 4; (1998); p. 659 - 662 View in Reaxys HO

HO

O

OH

H O

OH

O

O

Rx-ID: 5043403 View in Reaxys 271/435 Yield 1 %, 1 %, 60 %, 4 %

Conditions & References With air, 2,2'-thiobis(2,4-di-tert-butylphenol), triethylamine, copper(l) chloride in tetrahydrofuran, Time= 12h, T= 20 °C Chaudhuri, Phalguni; Hess, Martina; Floerke, Ulrich; Wieghardt, Karl; Angewandte Chemie - International Edition; vol. 37; nb. 16; (1998); p. 2217 - 2220 View in Reaxys H HC

HC

HO

O

Rx-ID: 5135223 View in Reaxys 272/435 Yield

Conditions & References ΔE(excit.), ΔH, other olefins, other ketyl radicals, Thermodynamic data

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

402/438

2018-03-11 22:07:32


Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys

H

C HC HO

O

Rx-ID: 5136524 View in Reaxys 273/435 Yield

Conditions & References ΔE(excit.), ΔH, other olefins, other ketyl radicals, Thermodynamic data Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys H O

HC

H 2C

OH

HO

O

Rx-ID: 5137524 View in Reaxys 274/435 Yield

Conditions & References ΔE(excit.), ΔH, other ketyl radicals, other carbonyl compounds, Thermodynamic data, Mechanism Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys O

OH

H

C HC HO

O

Rx-ID: 5138203 View in Reaxys 275/435 Yield

Conditions & References ΔE(excit.), ΔH, other ketyl radicals, other carbonyl compounds, Thermodynamic data, Mechanism Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys

H C H

HC HO

O

Rx-ID: 5140473 View in Reaxys 276/435 Yield

Conditions & References ΔE(excit.), ΔH, other olefins, other ketyl radicals, Thermodynamic data Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys

E

H

H C

HC HO

O

Rx-ID: 5141001 View in Reaxys 277/435 Yield

Conditions & References ΔE(excit.), ΔH, other olefins, other ketyl radicals, Thermodynamic data Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys H HC HO

CH 2

O

Rx-ID: 5141398 View in Reaxys 278/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

403/438

2018-03-11 22:07:32


Yield

Conditions & References ΔE(excit.), ΔH, other olefins, other ketyl radicals, Thermodynamic data Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys H

HC HO

O

Rx-ID: 5144140 View in Reaxys 279/435 Yield

Conditions & References With oxygen, ΔH, other ketyl radicals, Thermodynamic data, Rate constant Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys

O

HC HO

C H

H

OH

O

Rx-ID: 5153522 View in Reaxys 280/435 Yield

Conditions & References ΔE(excit.), ΔH, other ketyl radicals, other carbonyl compounds, Thermodynamic data, Mechanism Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys H

HC HO

C O

HO

O

Rx-ID: 5157932 View in Reaxys 281/435 Yield

Conditions & References ΔE(excit.), ΔH, other ketyl radicals, other carbonyl compounds, Thermodynamic data, Mechanism Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys O C

HC

OH

HO

H O

Rx-ID: 5159473 View in Reaxys 282/435 Yield

Conditions & References ΔE(excit.), ΔH, other ketyl radicals, other carbonyl compounds, Thermodynamic data, Mechanism Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys H C

HC HO

O

Rx-ID: 5162750 View in Reaxys 283/435 Yield

Conditions & References ΔE(excit.), ΔH, other olefins, other ketyl radicals, Thermodynamic data Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

404/438

2018-03-11 22:07:32


O

O

H HC HO

O

C O

OH

Rx-ID: 5163038 View in Reaxys 284/435 Yield

Conditions & References ΔE(excit.), ΔH, other ketyl radicals, other carbonyl compounds, Thermodynamic data, Mechanism Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys

H HC

C H

HO

O

Rx-ID: 5182239 View in Reaxys 285/435 Yield

Conditions & References ΔE(excit.), ΔH, other ketyl radicals, Thermodynamic data Denisov; Russian Chemical Bulletin; vol. 47; nb. 11; (1998); p. 2110 - 2116 View in Reaxys O

H O

HO

HO

O

Rx-ID: 36555121 View in Reaxys 286/435 Yield 9 %, 40 %

Conditions & References With dihydrogen peroxide, bromine in dichloromethane, water, Time= 24h, T= 20 °C Amati, Alessandro; Dosualdo, Gabriele; Zhao, Lihua; Bravo, Anna; Fontana, Francesca; Minisci, Francesco; Bjorsvik, Hans-Rene; Organic Process Research and Development; vol. 2; nb. 4; (1998); p. 261 - 269 View in Reaxys H

HO

CO2

O

Rx-ID: 6211672 View in Reaxys 287/435 Yield

Conditions & References With oxygen, NaZSM-5 Cu supported zeolite, T= 296.9 - 366.9 °C , gas-phase oxidation; the influence of temperature, method of supporting Cu on the NaZSM-5 zeolite, the supported amount of Cu, the addition of alkali method to the Cu supported NaZSM-5 zeolites prepared by different methods on the catalytic activity, Product distribution Sueto, Souichi; Nishiyama, Satoru; Tsuruya, Shigeru; Masai, Mitsuo; Journal of the Chemical Society - Faraday Transactions; vol. 93; nb. 4; (1997); p. 659 - 664 View in Reaxys O HO

H

N

N

Na + O–

O N H

Rx-ID: 4569714 View in Reaxys 288/435 Yield

Conditions & References Yield given. Multistep reaction. Yields of byproduct given Halfen, Jason A.; Young, Victor G.; Tolman, William B.; Angewandte Chemie; vol. 108; nb. 15; (1996); p. 1832 1835

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

405/438

2018-03-11 22:07:32


View in Reaxys

H HO

O

Rx-ID: 4601801 View in Reaxys 289/435 Yield

Conditions & References With Montmorillonite, ferric nitrate, T= 60 °C , further metal salts on montmorillonite: FeCl3, Cu(NO3)2; further supports: alumina, silica; further solvents: hexane, toluene; effect of reaction atmosphere, of iron nitrate content on surface, and of reaction time, Product distribution, Rate constant Cseril, Tivadar; Bekassy, Sandor; Figueras, Francois; Bulletin de la Societe Chimique de France; vol. 133; nb. 6; (1996); p. 547 - 552 View in Reaxys

O

HO

O

H

O

O

HO

Rx-ID: 4601803 View in Reaxys 290/435 Yield

Conditions & References With 3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane, Time= 24h, T= 60 °C , Product distribution, Mechanism Bravo, Anna; Bjorsvik, Hans-Rene; Fontana, Francesca; Minisci, Francesco; Serri, Anna; Journal of Organic Chemistry; vol. 61; nb. 26; (1996); p. 9409 - 9416 View in Reaxys N

Br

Br H

Br

H

(v3)

O HO

Rx-ID: 4374014 View in Reaxys 291/435 Yield

Conditions & References in acetic acid, T= 19.9 °C , ΔH(excit.), ΔS(excit.), ΔG(excit.), var. temp., Rate constant, Kinetics, Thermodynamic data Suri, Deepa; Banerji, Kalyan K.; Kothari, Seema; Journal of Chemical Research, Miniprint; nb. 7; (1995); p. 1734 1758 View in Reaxys N

Br

Br H

Br 2H

(v3) 2H 2H

O

HO

Rx-ID: 4374364 View in Reaxys 292/435 Yield

Conditions & References in acetic acid, T= 19.9 °C , ΔH(excit.), ΔS(excit.), ΔG(excit.), var. temp., Rate constant, Kinetics, Thermodynamic data Suri, Deepa; Banerji, Kalyan K.; Kothari, Seema; Journal of Chemical Research, Miniprint; nb. 7; (1995); p. 1734 1758 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

406/438

2018-03-11 22:07:32


HO

H

O

O

HO

Rx-ID: 3840159 View in Reaxys 293/435 Yield

Conditions & References With Cu(II)(bpy)2(OCH2Ph)2, oxygen in acetonitrile, Time= 0.25h, p= 760Torr , other primary, secondary alcohols and reagents; var. conditions, Rate constant, Product distribution Liu, Xiu; Qiu, Aimin; Sawyer, Donald T.; Journal of the American Chemical Society; vol. 115; nb. 8; (1993); p. 3239 - 3243 View in Reaxys H O

O

HO

O

Rx-ID: 3840145 View in Reaxys 294/435 Yield

Conditions & References With manganese(IV) oxide in tetrahydrofuran, T= 45 °C , Rate constant Constantinides, Ioannis; Macomber, Roger S.; Journal of Organic Chemistry; vol. 57; nb. 22; (1992); p. 6063 6067 View in Reaxys OH

H O

HO

O

Rx-ID: 3840156 View in Reaxys 295/435 Yield

Conditions & References With Zn1-xCuxMnFeO4, T= 199.9 °C , other spinels, x = 0.2, 0.4, 0.6, 0.8, 1.0, other temperatures, Product distribution Dube, Gulabshankar R.; Darshane, Vishnu S.; Journal of the Chemical Society, Faraday Transactions; vol. 88; nb. 9; (1992); p. 1299 - 1304 View in Reaxys

O–

2 O

O

2

Cl OO

H O

(v3)

(v4)

N

N

(v4)Ru 2+(v4) (v7) N

N

(v4)

(v4)

N

HO (v4)

P

H

H

N

(v4) Ru 2+(v4) N (v4) (v6) N (v4)

O– Cl O OO

O

P

Rx-ID: 26487299 View in Reaxys 296/435 Yield >99

Conditions & References in water, Kinetics, 25°C, pH 2.0, 3 h, reaction monitored by UV-spectroscopy;; organic product extd. with pentane, complex identified by UV-spectroscopy, organic product by g.c.-m.s. Marmion, Mary E.; Takeuchi, Kenneth J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1988); p. 2385 - 2392 ; (from Gmelin) View in Reaxys

>99

With NaNO3/HNO3 buffer in water, Kinetics, ratio Ru-complex : alc.= 1 : 50, at 25°C under N2, pH = 2.00; sepn. by gas chromy. (FID), yield of benzaldehyde 80-95 percent Muller, James G.; Acquaye, John Henry; Takeuchi, Kenneth J.; Inorganic Chemistry; vol. 31; (1992); p. 4552 4557 ; (from Gmelin) View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

407/438

2018-03-11 22:07:32


>99

in dichloromethane, 25°C, 3 h, reaction monitored by UV-spectroscopy;; pptn. of Ru-complex by addn of pentane, complex identified by UV-spectroscopy, organic product by g.c.-m.s. Marmion, Mary E.; Takeuchi, Kenneth J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1988); p. 2385 - 2392 ; (from Gmelin) View in Reaxys

>99

in dichloromethane, Kinetics, ratio Ru-complex : alc.= 1 : 50, at 25°C under N2; sepn. by gas chromy. (FID), yield of benzaldehyde 80-95 percent Muller, James G.; Acquaye, John Henry; Takeuchi, Kenneth J.; Inorganic Chemistry; vol. 31; (1992); p. 4552 4557 ; (from Gmelin) View in Reaxys

2

O–

2

Cl O OO

O (v4)

N (v4) N(v4) Ru 2+ (v4)N N (v7) (v4)

HO

P

O– Cl O OO

(v3) OH 2 (v4) N (v4) N(v4) Ru 2+ (v4)N N (v6) (v4)

H O

P

Rx-ID: 26906652 View in Reaxys 297/435 Yield

Conditions & References

>99

in dichloromethane, Kinetics, ratio Ru-complex : alc.= 1 : 50, at 25°C under N2; sepn. by gas chromy. (FID), yield of benzaldehyde 80-95 percent Muller, James G.; Acquaye, John Henry; Takeuchi, Kenneth J.; Inorganic Chemistry; vol. 31; (1992); p. 4552 4557 ; (from Gmelin) View in Reaxys

>99

With NaNO3/HNO3 buffer in water, Kinetics, ratio Ru-complex : alc.= 1 : 50, at 25°C under N2, pH = 2.00; sepn. by gas chromy. (FID), yield of benzaldehyde 80-95 percent Muller, James G.; Acquaye, John Henry; Takeuchi, Kenneth J.; Inorganic Chemistry; vol. 31; (1992); p. 4552 4557 ; (from Gmelin) View in Reaxys

2

O–

2

Cl O OO

O (v4)

N (v4) N(v4) Ru 2+ (v4)N N (v7) (v4)

HO

P

F

H O

P

F

F

F

O– Cl O OO

(v3) OH 2 (v4) N (v4) N(v4) Ru 2+ (v4)N N (v6) (v4)

F F

Rx-ID: 26906653 View in Reaxys 298/435 Yield >99

Conditions & References in dichloromethane, Kinetics, ratio Ru-complex : alc.= 1 : 50, at 25°C under N2; sepn. by gas chromy. (FID), yield of benzaldehyde 80-95 percent Muller, James G.; Acquaye, John Henry; Takeuchi, Kenneth J.; Inorganic Chemistry; vol. 31; (1992); p. 4552 4557 ; (from Gmelin) View in Reaxys

>99

With NaNO3/HNO3 buffer in water, Kinetics, ratio Ru-complex : alc.= 1 : 50, at 25°C under N2, pH = 2.00; sepn. by gas chromy. (FID), yield of benzaldehyde 80-95 percent Muller, James G.; Acquaye, John Henry; Takeuchi, Kenneth J.; Inorganic Chemistry; vol. 31; (1992); p. 4552 4557 ; (from Gmelin) View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

408/438

2018-03-11 22:07:32


O–

2 O (v4)

P

(v4)

HO F

F F F

F F

Cl O OO

(v3) OH 2 (v4) N (v4) N (v4) 2+ (v4) N Ru (v6)N

N (v4) N (v4) 2+ (v4) N Ru (v7)N (v4)

O–

2

Cl O OO

P

O F

F F F

F

H

F

F

F

F

F F

F

Rx-ID: 26906654 View in Reaxys 299/435 Yield

Conditions & References

>99

in dichloromethane, Kinetics, ratio Ru-complex : alc.= 1 : 50, at 25°C under N2; sepn. by gas chromy. (FID), yield of benzaldehyde 80-95 percent Muller, James G.; Acquaye, John Henry; Takeuchi, Kenneth J.; Inorganic Chemistry; vol. 31; (1992); p. 4552 4557 ; (from Gmelin) View in Reaxys

>99

With NaNO3/HNO3 buffer in water, Kinetics, ratio Ru-complex : alc.= 1 : 50, at 25°C under N2, pH = 2.00; sepn. by gas chromy. (FID), yield of benzaldehyde 80-95 percent Muller, James G.; Acquaye, John Henry; Takeuchi, Kenneth J.; Inorganic Chemistry; vol. 31; (1992); p. 4552 4557 ; (from Gmelin) View in Reaxys O–

2 O

O

(v3) OH 2 (v4) N (v4) N (v4) Ru 2+ (v4) N (v6)N

(v4)

N (v4) N (v4) Ru 2+ (v4) N (v7)N (v4)

P

(v4)

HO O

O

O–

2

Cl OO

O

Cl OO

H

P

O O

O

O

O

Rx-ID: 26906655 View in Reaxys 300/435 Yield

Conditions & References

>99

in dichloromethane, Kinetics, ratio Ru-complex : alc.= 1 : 50, at 25°C under N2; sepn. by gas chromy. (FID), yield of benzaldehyde 80-95 percent Muller, James G.; Acquaye, John Henry; Takeuchi, Kenneth J.; Inorganic Chemistry; vol. 31; (1992); p. 4552 4557 ; (from Gmelin) View in Reaxys

>99

With NaNO3/HNO3 buffer in water, Kinetics, ratio Ru-complex : alc.= 1 : 50, at 25°C under N2, pH = 2.00; sepn. by gas chromy. (FID), yield of benzaldehyde 80-95 percent Muller, James G.; Acquaye, John Henry; Takeuchi, Kenneth J.; Inorganic Chemistry; vol. 31; (1992); p. 4552 4557 ; (from Gmelin) View in Reaxys O–

2 O

O

(v3)

OH 2

(v4)

N (v4) N (v4) Ru 2+ N (v4) N (v7) (v4)

P

O–

2

Cl OO

N (v4) N (v4) Ru 2+ (v4)N (v4) N

O

Cl OO

H

(v6)

(v4)

HO

F F F

P

O

F F F F

F

F

F

F

F

Rx-ID: 26906656 View in Reaxys 301/435 Yield >99

Conditions & References in dichloromethane, Kinetics, ratio Ru-complex : alc.= 1 : 50, at 25°C under N2; sepn. by gas chromy. (FID), yield of benzaldehyde 80-95 percent

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

409/438

2018-03-11 22:07:32


Muller, James G.; Acquaye, John Henry; Takeuchi, Kenneth J.; Inorganic Chemistry; vol. 31; (1992); p. 4552 4557 ; (from Gmelin) View in Reaxys >99

With NaNO3/HNO3 buffer in water, Kinetics, ratio Ru-complex : alc.= 1 : 50, at 25°C under N2, pH = 2.00; sepn. by gas chromy. (FID), yield of benzaldehyde 80-95 percent Muller, James G.; Acquaye, John Henry; Takeuchi, Kenneth J.; Inorganic Chemistry; vol. 31; (1992); p. 4552 4557 ; (from Gmelin) View in Reaxys

2H

H

2H

O

HO

Rx-ID: 2063920 View in Reaxys 302/435 Yield

Conditions & References With lt;Ru(VI)(dmbipy)2O2gt;lt;ClO4gt;2 in acetonitrile, Time= 4h, T= 298 °C , Rate constant Che, Chi-Ming; Leung, Wai-Ho; Li, Chi-Keung; Poon, Chung-Kwong; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 3; (1991); p. 379 - 384 View in Reaxys O

H O

O

HO

O

Rx-ID: 2897155 View in Reaxys 303/435 Yield

Conditions & References

92 %, 3 %

With N,N,N,N,N,N-hexamethylphosphoric triamide, bromine, sodium hydrogencarbonate in dichloromethane, water Al Neirabeyeh, Mamdouh; Pujol, M. Dolors; Tetrahedron Letters; vol. 31; nb. 16; (1990); p. 2273 - 2276 View in Reaxys

E

HO

H

O

O

Rx-ID: 3840154 View in Reaxys 304/435 Yield

Conditions & References With hydrogen, iron(II,III) oxide, vanadia, T= 250 °C , p= 405.03Torr , Product distribution Glebov, L. S.; Shuikin, A. N.; Kliger, G. A.; Mikaya, A. I.; Zaikin, V. G.; et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 39; nb. 4.2; (1990); p. 814 - 817; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 4; (1990); p. 907 - 910 View in Reaxys

O O

N O

(v4) N–

H

O

O

HO

Co O OSP-4

HO

Na +

Rx-ID: 26812563 View in Reaxys 305/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

410/438

2018-03-11 22:07:32


Yield

Conditions & References

0 %, 0 %

in benzyl alcohol, Irradiation (UV/VIS); photolysis of Co-complex in benzylalcohol; HPLC Lee, Gyu-Hwan; Larson, James L.; Perkins, Thomas A.; Schanze, Kirk S.; Inorganic Chemistry; vol. 29; (1990); p. 2015 - 2017 ; (from Gmelin) View in Reaxys N

N

H HO

O

N

N

Rx-ID: 3838530 View in Reaxys 306/435 Yield

Conditions & References

68 %

in acetonitrile, T= 17 °C , Irradiation Sulpizio, Ada; Albini, Angelo; d'Alessandro, Nicola; Fasani, Elisa; Pietra, Silvio; Journal of the American Chemical Society; vol. 111; nb. 15; (1989); p. 5773 - 5777 View in Reaxys O H + N

O

N H

N

H O

O

HO

NH

O O O

O

O

O O

Rx-ID: 3840155 View in Reaxys 307/435 Yield

Conditions & References With 7,8-dimethyl-10-(tetra-O-acetyl-D-arabinitol-1-yl)-10H-benzo[g]pteridine-2,4-dione, perchloric acid in acetonitrile, T= 24.9 °C , Irradiation Fukuzumi, Shunichi; Tanii, Kumiko; Tanaka, Toshio; Chemistry Letters; (1989); p. 35 - 38 View in Reaxys

HO

HO

HO

O OH

O

H

O

O

HO

Rx-ID: 3840157 View in Reaxys 308/435 Yield

Conditions & References Time= 12h, T= 20 °C , Irradiation, effect of irradiation time, Product distribution Hansen, Sissel H.; Sydnes, Leiv K.; Acta Chemica Scandinavica; vol. 43; nb. 4; (1989); p. 395 - 398 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

411/438

2018-03-11 22:07:32


(v3) O N(v3) O(v3) (v4) Co +O O O O O Co (v4) Co(v6) (v6) (v3) N N OO O (v3) (v4) O

F

(v3) O (v3) (v6)O

F

–F

FP F

H F

O

HO

O

O

Rx-ID: 26374791 View in Reaxys 309/435 Yield

Conditions & References

4 %, 75 %

With dimethyl terephthalate in chlorobenzene, in a thickwall glass ampule, after filled with the substances evacuated, filled with argon three times, sealed under vacuum, shaked in a oil bath at 150°C for 17 h, cooled; gas chromatography Sumner, Charles E. Jr.; Steinmetz, Guy R.; Inorganic Chemistry; vol. 28; (1989); p. 4290 - 4294 ; (from Gmelin) View in Reaxys

(v3)

NO

(v3) (v3) (v4) OOCo O (v6) O (v3)O(v3) O (v6)O (v6)+O Co Co (v4) O N (v4) O (v3)

N

(v3)

F

O H

H

F –F FP F F

O

HO

O

O

Rx-ID: 26381898 View in Reaxys 310/435 Yield

Conditions & References

4 %, 82 %

With dimethyl terephthalate in chlorobenzene, in a thickwall glass ampule, after filled with the substances evacuated, filled with argon three times, sealed under vacuum, shaked in a oil bath at 150°C for 17 h, cooled; gas chromatography Sumner, Charles E. Jr.; Steinmetz, Guy R.; Inorganic Chemistry; vol. 28; (1989); p. 4290 - 4294 ; (from Gmelin) View in Reaxys

O

HO

O

H

O

O

HO

Rx-ID: 30673672 View in Reaxys 311/435 Yield

Conditions & References Reaction Steps: 2 1: acetonitrile 2: dimethyl terephthalate / chlorobenzene With dimethyl terephthalate in chlorobenzene, acetonitrile Sumner, Charles E. Jr.; Steinmetz, Guy R.; Inorganic Chemistry; vol. 28; (1989); p. 4290 - 4294 View in Reaxys

N

HO O

N

N

H

N

N

O O

N

N

O

N

Rx-ID: 1736027 View in Reaxys 312/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

412/438

2018-03-11 22:07:32


Yield

Conditions & References Time= 3h, T= 200 °C , Further byproducts given Brown, Jonathan W.; Clack, Dennis W.; Wilson, David A.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1988); p. 117 - 122 View in Reaxys

Cl

N+

Cl

Cl –

O

Cl

O

HO

H

N

N

Cl

O

Rx-ID: 3298733 View in Reaxys 313/435 Yield

Conditions & References With sodium hydroxide in water, T= 75 - 80 °C , catalytically active organic phase analysis, Product distribution Shavanov, S. S.; Tolstikov, G. A.; Shutenkova, T. V.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 37; (1988); p. 1612 - 1616; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 8; (1988); p. 1806 - 1811 View in Reaxys

H HO

Ph3Bi

HO

O

Rx-ID: 6218224 View in Reaxys 314/435 Yield

Conditions & References With (C6H5)3Bilt;OOC(CH3)3gt;2, Yield given. Yields of byproduct given Dodonov, V. A.; Zinov'eva, T. I.; Osadchaya, N. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 58; nb. 3; (1988); p. 712,630 - 631 View in Reaxys

2

(v4)

O– Cl O OO (v4)

P

(v4) N (v4)

N (v4) N O Ru 2+ O N OC-6(v6)(v4) P

(v1)

HO

P

N O N (v4) Ru +(v4) N (v4)N OC-6 (v6) (v4) O P

(v4)

(v1)

H

O–

Cl O OO

H( 1+)

O

(v4)

Rx-ID: 26487292 View in Reaxys 315/435 Yield

Conditions & References in water, Kinetics, pH = 6.8; kinetics measured by UV-Vis spectrophotometry, product distribution determined by GC Leising, Randolph A.; Takeuchi, Kenneth J.; Journal of the American Chemical Society; vol. 110; nb. 12; (1988); p. 4079 - 4080 ; (from Gmelin) View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

413/438

2018-03-11 22:07:32


O–

2 O

O

Cl OO

H

N

(v4)Ru 2+(v4) (v7) N

N

N

H

(v4) Ru 2+(v4) N (v4) (v6) N

N

HO (v4)

As

H

N

(v4)

(v4)

Cl O OO

O

(v3)

(v4)

O–

2

(v4)

O

As

Rx-ID: 26487294 View in Reaxys 316/435 Yield

Conditions & References

>99

in water, Kinetics, 25°C, 3 h, pH 2, reaction monitored by UV-spectroscopy;; separation by addn of pentane, complex identified by UV-spectroscopy, organic product by g.c.-m.s. Marmion, Mary E.; Takeuchi, Kenneth J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1988); p. 2385 - 2392 ; (from Gmelin) View in Reaxys O–

2 O N (v4)Ru 2+(v4) (v7) N

(v4)

N

2

Cl O OO H (v3)

N

H

(v4)

HO (v4)

O

N 2+ N (v4)Ru (v4) N (v6) N (v4)

N

(v4)

H

O– Cl O OO

As

O

N

(v4)

Rx-ID: 26487295 View in Reaxys 317/435 Yield

Conditions & References

>99

in dichloromethane, acetonitrile, Kinetics, 25°C, 3 h, reaction monitored by UV-spectroscopy;; separation by addn of pentane, complex identified by UV-spectroscopy, organic product by g.c.-m.s. Marmion, Mary E.; Takeuchi, Kenneth J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1988); p. 2385 - 2392 ; (from Gmelin) View in Reaxys

O–

2 O

O

Cl OO

H (v3)

N (v4) N (v4)Ru 2+ (v4) N (v4) (v7) N (v4)

O–

2 O

Cl O OO

H

H

N 2+ N N (v4)Ru (v4) (v4) (v6) N

(v4)

HO

P

(v4)

O

P

Rx-ID: 26487296 View in Reaxys 318/435 Yield

Conditions & References

>99

in water, Kinetics, 25°C, pH 2.0, 3 h, reaction monitored by UV-spectroscopy;; extn. of organic product with pentane, complex identified by UV-spectroscopy, organic product by g.c.-m.s. Marmion, Mary E.; Takeuchi, Kenneth J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1988); p. 2385 - 2392 ; (from Gmelin) View in Reaxys

O–

2 O

O

2

Cl OO

H (v3)

(v4)

N

N

(v4)Ru 2+ (v4) N (v4) (v7) N

(v4)

N

(v4)

N

HO

P

H O

N (v4)Ru 2+ (v4) N (v6) N (v4)

(v4)

O– Cl O OO

H O

N

Rx-ID: 26487297 View in Reaxys 319/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

414/438

2018-03-11 22:07:32


Yield

Conditions & References

>99

in dichloromethane, acetonitrile, Kinetics, 25°C, 2.0, 3 h, reaction monitored by UV-spectroscopy;; separation by addn. of pentane, complex identified by UV-spectroscopy, organic product by g.c.-m.s. Marmion, Mary E.; Takeuchi, Kenneth J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1988); p. 2385 - 2392 ; (from Gmelin) View in Reaxys O–

2 O

H

N (v4)Ru 2+(v4) (v7) N

(v4)

N

2

Cl O OO (v3)

N

N 2+ N (v4)Ru (v4) N (v6) N (v4)

N

(v4)

H

(v4)

HO (v4)

H O

O– Cl O OO

P

(v4)

O

N

Rx-ID: 26487300 View in Reaxys 320/435 Yield

Conditions & References

>99

in dichloromethane, acetonitrile, Kinetics, 25°C, 3 h, reaction monitored by UV-spectroscopy;; separation by addn. of pentane, complex identified by UV-spectroscopy, organic product by g.c.-m.s. Marmion, Mary E.; Takeuchi, Kenneth J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1988); p. 2385 - 2392 ; (from Gmelin) View in Reaxys

O

O

HO

O

O

H

O

O

Rx-ID: 3838448 View in Reaxys 321/435 Yield

Conditions & References

20 % Chromat., 60 % Chromat.

With dihydridotetrakis(triphenylphosphine)ruthenium in toluene, Time= 10h, Heating Minami, Ichiro; Tsuji, Jiro; Tetrahedron; vol. 43; nb. 17; (1987); p. 3903 - 3916 View in Reaxys

HO

O

H

O

O

Rx-ID: 3840143 View in Reaxys 322/435 Yield

Conditions & References

20 % Chromat., 60 % Chromat.

(v5) (v5)H(v5)(v5)H – CH H (v4) (v10) Fe 3+

With allyl methyl carbonate, dihydridotetrakis(triphenylphosphine)ruthenium in toluene, Time= 10h, Heating Minami, Ichiro; Tsuji, Jiro; Tetrahedron; vol. 43; nb. 17; (1987); p. 3903 - 3916 View in Reaxys

-1

H

(v5) H – H CH H (v5)(v5) H (v4)

F

(v5)(v5) (v5)H H (v5) – CH H (v4) 2+ (v10) Fe

H

F

F P (v6) F F F

HO

(v5)

(v5) H – H CH H (v5)(v5) H (v4)

H O

(v5)

Rx-ID: 26152903 View in Reaxys 323/435 Yield 85 %, 40 %

Conditions & References in acetonitrile, Irradiation (UV/VIS); under argon; FcPF6 and benzylalcohol are dissolved in MeCN and irradiated (>300 nm) for 1 h; detn. of ferrocene by UV-Vis spectroscopy Divisia-Blohorn, B.; Paltrier, M.; Inorganica Chimica Acta; vol. 131; (1987); p. 65 - 68 ; (from Gmelin) View in Reaxys

75 %

in acetonitrile, Irradiation (UV/VIS); under argon; FcPF6 and benzylalcohol are dissolved in MeCN and irradiated (>300 nm) for 21 h; detn. of ferrocene by UV-Vis spectroscopy

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

415/438

2018-03-11 22:07:32


Divisia-Blohorn, B.; Paltrier, M.; Inorganica Chimica Acta; vol. 131; (1987); p. 65 - 68 ; (from Gmelin) View in Reaxys H I HO

HO

O

Rx-ID: 3840151 View in Reaxys 324/435 Yield

Conditions & References

14 %, 70 %

With periodic acid in 1,4-dioxane, water, T= 100 °C , other substrates, Mechanism Bhatt, M. V.; Hosur, B. M.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 1004 - 1005 View in Reaxys

14 %, 70 %

With periodic acid in 1,4-dioxane, water, T= 100 °C Bhatt, M. V.; Hosur, B. M.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 1004 - 1005 View in Reaxys

O

H

O

Si O

O

HO

O

O

Rx-ID: 3838950 View in Reaxys 325/435 Yield

Conditions & References

7% Spectr., 72 % Spectr.

With diethyl ether, iodosylbenzene, boron trifluoride in 1,4-dioxane, Time= 0.5h, Ambient temperature Ochiai, Masahito; Fujita, Eiichi; Arimoto, Masao; Yamaguchi, Hideo; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 1; (1985); p. 41 - 47 View in Reaxys

O O

O

H

O Bi

O

HO

O

O

Rx-ID: 3839218 View in Reaxys 326/435 Yield

Conditions & References in toluene, Time= 22h, T= 80 °C , Yield given. Yields of byproduct given Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 1; (1985); p. 73 - 80,63 - 68 View in Reaxys H S

HO

O

Rx-ID: 3840144 View in Reaxys 327/435 Yield 57.4 %

Conditions & References With air, antimonypentachloride, dimethyl sulfoxide in nitromethane, Time= 3h, T= 60 °C , Product distribution Yamamoto, Jiro; Ito, Satoshi; Tsuboi, Takashi; Tsuboi, Toshiaki; Tsukihara, Kumiko; Bulletin of the Chemical Society of Japan; vol. 58; nb. 2; (1985); p. 470 - 472 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

416/438

2018-03-11 22:07:32


H O

HO

O

O

Rx-ID: 3840160 View in Reaxys 328/435 Yield

Conditions & References With triphenylbismuth(V) diacetate in toluene, Time= 22h, T= 80 °C , Yield given. Yields of byproduct given Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 1; (1985); p. 73 - 80,63 - 68 View in Reaxys

2H 2H

2H

2H

2H

O

HO

Rx-ID: 2818063 View in Reaxys 329/435 Yield

Conditions & References With silver carbonate Smith, John R. Lindsay; Nee, Michael W.; Noar, J. Barry; Bruice, Thomas C.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 2; (1984); p. 255 - 260 View in Reaxys

H HO

O

Rx-ID: 3537475 View in Reaxys 330/435 Yield

Conditions & References With dipotassium peroxodisulfate in water, Time= 0.5h, T= 80 °C , var. ratio of reac. partners, Product distribution, Mechanism Eberhardt, Manfred K.; Tetrahedron Letters; vol. 25; nb. 34; (1984); p. 3663 - 3666 View in Reaxys H

HO

O

HO

O

Rx-ID: 3838185 View in Reaxys 331/435 Yield 98 %

Conditions & References With Cr(OAc)3 impregnated NafionR 511 in chlorobenzene, benzene, Time= 6h, T= 85 °C Kanemoto, Sigekazu; Saimoto, Hiroyuki; Oshima, Koichiro; Nozaki, Hitosi; Tetrahedron Letters; vol. 25; nb. 31; (1984); p. 3317 - 3320 View in Reaxys H

nickel HO

oxygen O

Rx-ID: 19144777 View in Reaxys 332/435 Yield

Conditions & References Reaction Steps: 2 1: Fe(II), H2O / acetonitrile 2: Fe(II), H2O2 / acetonitrile With water, dihydrogen peroxide, iron(II) in acetonitrile Sugimoto, Hiroshi; Sawyer, Donald T.; Journal of the American Chemical Society; vol. 106; nb. 15; (1984); p. 4283 - 4285 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

417/438

2018-03-11 22:07:32


H Si

Si Cl

HO

Si O

O

Rx-ID: 3838211 View in Reaxys 333/435 Yield

Conditions & References With chromium(VI) oxide, Multistep reaction, var. alcohols, oximes and disulfides, Product distribution Aizpurua, J. M.; Palomo, Claudio; Tetrahedron Letters; vol. 24; nb. 40; (1983); p. 4367 - 4370 View in Reaxys

F

F

F

F

F

F

F

OH

HO

F

F F

F F

F F

F

F

F

H F

F

F

F

F

F F

O

HO

Rx-ID: 3838363 View in Reaxys 334/435 Yield

Conditions & References

28 % Turnov., 18 % Turnov., 46 % Turnov., 11 % Turnov.

Time= 72h, T= 240 °C Haszeldine, Robert N.; Raynor, Clive M.; Tipping, Anthony E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1983); p. 2801 - 2806 View in Reaxys

N

O

N

H O

HO

O

Rx-ID: 3840109 View in Reaxys 335/435 Yield

Conditions & References Time= 0.333333h, T= 10 °C , Irradiation, Yield given. Yields of byproduct given Tomioka, Hideo; Nakamura, Hiroyuki; Izawa, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 19; (1983); p. 1070 - 1071 View in Reaxys H

water HO

O

Rx-ID: 6221071 View in Reaxys 336/435 Yield

Conditions & References

6 %, 6 % Turnov.

Time= 72h, T= 240 °C Haszeldine, Robert N.; Raynor, Clive M.; Tipping, Anthony E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1983); p. 2801 - 2806 View in Reaxys O

O

H

N

N Cs +

N

N

O

HO

N

O

N–

O

Rx-ID: 3480667 View in Reaxys 337/435 Yield

Conditions & References With cesium hydroxide, 2,4-dimethyl-6-tert-butylphenol in water, N,N-dimethyl-formamide, Rate constant

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

418/438

2018-03-11 22:07:32


Shinkai, Seiji; Kuroda, Hideo; Manabe, Osamu; Tetrahedron Letters; vol. 23; nb. 13; (1982); p. 1357 - 1360 View in Reaxys

C

O

HO

O O

H I

O

Rx-ID: 3838546 View in Reaxys 338/435 Yield

Conditions & References With lt;Ru(CO)3gt;2, hydrogen iodide, hydrogen, Time= 3h, T= 220 °C , var. benzyl compounds; or benzaldehyd; other reagents, temp.,times, Product distribution, Mechanism Hardin, Simon G.; Turney, Terence W.; Australian Journal of Chemistry; vol. 35; nb. 8; (1982); p. 1599 - 1608 View in Reaxys HO

O

O

OH

H HO

HO

O

Rx-ID: 3838593 View in Reaxys 339/435 Yield

Conditions & References in dichloromethane, Time= 18h, T= 60 - 70 °C , Yield given. Yields of byproduct given Balsells, R. Erra; Frasca, A. R.; Tetrahedron; vol. 38; nb. 16; (1982); p. 2525 - 2538 View in Reaxys in dichloromethane, Time= 18h, T= 60 - 70 °C , thermal stability Balsells, R. Erra; Frasca, A. R.; Tetrahedron; vol. 38; nb. 16; (1982); p. 2525 - 2538 View in Reaxys

O

N

O

H N

O

NH

O

H

NH

HO

O

O

O

Rx-ID: 3838857 View in Reaxys 340/435 Yield

Conditions & References Time= 10h, T= 90 °C , Product distribution Yoneda, Fumio; Hirayama, Ryiochi; Yamashita, Machiko; Journal of Heterocyclic Chemistry; vol. 19; (1982); p. 301 - 304 View in Reaxys

O

N

O

O

H N

N

O

H

N

HO O

O O

Rx-ID: 3838860 View in Reaxys 341/435 Yield

Conditions & References Time= 10h, T= 90 °C , Product distribution Yoneda, Fumio; Hirayama, Ryiochi; Yamashita, Machiko; Journal of Heterocyclic Chemistry; vol. 19; (1982); p. 301 - 304 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

419/438

2018-03-11 22:07:32


Cl

O

N

O

Cl

H N

O

O

N

H

N

HO

O

O

O

Rx-ID: 3838862 View in Reaxys 342/435 Yield

Conditions & References Time= 10h, T= 90 °C , Product distribution Yoneda, Fumio; Hirayama, Ryiochi; Yamashita, Machiko; Journal of Heterocyclic Chemistry; vol. 19; (1982); p. 301 - 304 View in Reaxys

O

N

O

H N

O

N

O

H

N

HO

O

O

O

Rx-ID: 3839074 View in Reaxys 343/435 Yield

Conditions & References Time= 10h, T= 90 °C , Product distribution Yoneda, Fumio; Hirayama, Ryiochi; Yamashita, Machiko; Journal of Heterocyclic Chemistry; vol. 19; (1982); p. 301 - 304 View in Reaxys

O

N

O

H N

O

N

O

H

N

HO

O

O

O

Rx-ID: 3839075 View in Reaxys 344/435 Yield

Conditions & References Time= 10h, T= 90 °C , Product distribution Yoneda, Fumio; Hirayama, Ryiochi; Yamashita, Machiko; Journal of Heterocyclic Chemistry; vol. 19; (1982); p. 301 - 304 View in Reaxys

O

N

O N

Cl

H N

O

O

Cl

HO

H

N

O

O

O

Rx-ID: 3839080 View in Reaxys 345/435 Yield

Conditions & References Time= 10h, T= 90 °C , Product distribution Yoneda, Fumio; Hirayama, Ryiochi; Yamashita, Machiko; Journal of Heterocyclic Chemistry; vol. 19; (1982); p. 301 - 304 View in Reaxys

O

N

O

O

H N

O

H N O

N

HO

O

O

Rx-ID: 3839085 View in Reaxys 346/435 Yield

Conditions & References Time= 10h, T= 90 °C , Product distribution

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

420/438

2018-03-11 22:07:32


Yoneda, Fumio; Hirayama, Ryiochi; Yamashita, Machiko; Journal of Heterocyclic Chemistry; vol. 19; (1982); p. 301 - 304 View in Reaxys

O

N

O

O

H N

O

H N

Cl

N

Cl

HO

O

O

O

Rx-ID: 3839094 View in Reaxys 347/435 Yield

Conditions & References Time= 10h, T= 90 °C , Product distribution Yoneda, Fumio; Hirayama, Ryiochi; Yamashita, Machiko; Journal of Heterocyclic Chemistry; vol. 19; (1982); p. 301 - 304 View in Reaxys

O

O N

H N

HO Cl

O

N

O

O

Cl

O

N H

O

Rx-ID: 3839095 View in Reaxys 348/435 Yield

Conditions & References Time= 10h, T= 90 °C , Product distribution Yoneda, Fumio; Hirayama, Ryiochi; Yamashita, Machiko; Journal of Heterocyclic Chemistry; vol. 19; (1982); p. 301 - 304 View in Reaxys N

N

N

N

HO

H O

Rx-ID: 3840146 View in Reaxys 349/435 Yield

Conditions & References With ethenetetracarbonitrile in ethyl acetate, Heating, Product distribution Nasakin, O. E.; Petrov, G. N.; Alekseev, V. V.; Promonenkov, V. K.; Sukhobokov, A. v.; J. Appl. Chem. USSR (Engl. Transl.); vol. 55; nb. 6; (1982); p. 1399 - 1402,1286 - 1289 View in Reaxys

O

HO

HO HO

H

HO

H

H

H

O

H

O

H

H

OH

O

H

O H

O

racemate

Rx-ID: 3840149 View in Reaxys 350/435 Yield

Conditions & References in dichloromethane, Time= 18h, T= 60 - 70 °C , Irradiation, without solvent, other reaction time and further light sources, Product distribution, Mechanism

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

421/438

2018-03-11 22:07:32


Balsells, R. Erra; Frasca, A. R.; Tetrahedron; vol. 38; nb. 16; (1982); p. 2525 - 2538 View in Reaxys

H

O

O

O

H

H

HO

H

O

O

H

O

Rx-ID: 3840150 View in Reaxys 351/435 Yield

Conditions & References in dichloromethane, Time= 18h, T= 60 - 70 °C , Irradiation, Yield given. Further byproducts given. Yields of byproduct given Balsells, R. Erra; Frasca, A. R.; Tetrahedron; vol. 38; nb. 16; (1982); p. 2525 - 2538 View in Reaxys Cl

H

H

H 2N

HO

O

Rx-ID: 3840153 View in Reaxys 352/435 Yield

Conditions & References

82 %, 20 % Chromat.

With N,N-dichloro-t-butylamine in tetrachloromethane, Time= 1h, T= 20 °C , Irradiation, Product distribution Ogata, Yoshiro; Kimura, Makoto; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1982); p. 947 - 950 View in Reaxys OH +

+HC

C+

N

OH

N +HO

HO

Rx-ID: 2987189 View in Reaxys 353/435 Yield

Conditions & References T= 24.9 °C , ΔG0, Thermodynamic data Bromilow, J.; Abboud, J. L. M.; Lebrilla, C. B.; Taft, R. W.; Scorrano, G.; Lucchini V.; Journal of the American Chemical Society; vol. 103; nb. 18; (1981); p. 5448 - 5453 View in Reaxys H O+

H O+

+

HC

N

N

+HO

HO

Rx-ID: 2988987 View in Reaxys 354/435 Yield

Conditions & References T= 24.9 °C , ΔG0, Thermodynamic data Bromilow, J.; Abboud, J. L. M.; Lebrilla, C. B.; Taft, R. W.; Scorrano, G.; Lucchini V.; Journal of the American Chemical Society; vol. 103; nb. 18; (1981); p. 5448 - 5453 View in Reaxys O

O

H

O

HO

O

O

O

HO

Rx-ID: 3744744 View in Reaxys 355/435 Yield

Conditions & References T= 140 °C

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

422/438

2018-03-11 22:07:32


Moreno-Manas, M.; Trius, A.; Tetrahedron; vol. 37; nb. 17; (1981); p. 3009 - 3016 View in Reaxys O O

O

H

O

HO

O

O

O

Rx-ID: 3744745 View in Reaxys 356/435 Yield

Conditions & References

8 %, 10 %, With palladium(II) acetylacetonate, triphenylphosphine, Time= 48h, T= 140 °C 32 % Moreno-Manas, M.; Trius, A.; Tetrahedron; vol. 37; nb. 17; (1981); p. 3009 - 3016 View in Reaxys

F

F

F

N

F

F

F F

O

F

F

F

N

HO

(v1)

F

F F

OH

FO

F

N

H

O

F

O F

F

Rx-ID: 3838563 View in Reaxys 357/435 Yield

Conditions & References

59 %, 64 %, 35 %

Time= 0.0333333h, T= 20 °C , analogous reactions of other benzyl derivatives (PhCH2CN, PhCH2Cl, and PhCH2N3); various reactant ratio, Mechanism, Product distribution Banks, Ronald E.; Birchall, J. Michael; Haszeldine, Robert N.; Hughes, Raymond A.; Nona, Shmaiel N.; Stephens, Christopher W.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 455 - 456 View in Reaxys

H N+

OH

I–

N

HO

OH

O

Rx-ID: 3839131 View in Reaxys 358/435 Yield

Conditions & References With potassium tert-butylate, Time= 8h, T= 80 °C , other alcohol, Product distribution, Mechanism Shinkai, Seiji; Hamada, Hisatake; Kuroda, Hideo; Manabe, Osamu; Journal of Organic Chemistry; vol. 46; nb. 11; (1981); p. 2333 - 2338 View in Reaxys

S

N

O

S

N

N

O

H

N

HO

O O

O

Rx-ID: 3840113 View in Reaxys 359/435 Yield 90 %

Conditions & References With potassium tert-butylate, Time= 2h, T= 80 °C , in the dark, Product distribution Yoneda, Fumio; Tsukuda, Kinshiro; Kawazoe, Michiko; Sone, Atsuko; Koshiro, Akira; Journal of Heterocyclic Chemistry; vol. 18; (1981); p. 1329 - 1334 View in Reaxys

F

F

F

N

F

F

HO

F

OH

F F

FO N

H

O

F

O F

F

Rx-ID: 3840147 View in Reaxys 360/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

423/438

2018-03-11 22:07:32


Yield

Conditions & References

59 %, 64 %, 35 %

With bis-trifluoromethyl-aminooxyl, Time= 0.0333333h, T= 20 °C Banks, Ronald E.; Birchall, J. Michael; Haszeldine, Robert N.; Hughes, Raymond A.; Nona, Shmaiel N.; Stephens, Christopher W.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 455 - 456 View in Reaxys

H HO

O

O

O

Rx-ID: 4293139 View in Reaxys 361/435 Yield

Conditions & References With tris(triphenylphosphine)ruthenium(II) chloride in various solvent(s), T= 170 - 190 °C , var. reactants and reaction partner, Kinetics, Mechanism Speier, Gabor; Marko, Laszlo; Journal of Organometallic Chemistry; vol. 210; nb. 2; (1981); p. 253 - 262 View in Reaxys

2H

2H

2H

deuterium oxyde HO

O

Rx-ID: 7453117 View in Reaxys 362/435 Yield

Conditions & References With d,oxyde de cuivre, Time= 6h, T= 176 °C , Heating, in liquid phase Berthon, Bruno; Forestiere, Alain; Leleu, Gerard; Sillion, Bernard; Tetrahedron Letters; vol. 22; nb. 41; (1981); p. 4073 - 4076 View in Reaxys With copper(II) oxide, Time= 6h, T= 176 °C Berthon, Bruno; Forestiere, Alain; Leleu, Gerard; Sillion, Bernard; Tetrahedron Letters; vol. 22; nb. 41; (1981); p. 4073 - 4076 View in Reaxys H

O

O N+ N

N

HO

O

N

HC

C

O

O

Rx-ID: 1797297 View in Reaxys 363/435 Yield

Conditions & References in water, Rate constant Packer, John E.; Heigway, Christopher J.; Miller, Helen M.; Dobson, Brian C.; Australian Journal of Chemistry; vol. 33; nb. 5; (1980); p. 965 - 977 View in Reaxys H

O

N+ N

HC

O

C

HO

O

Rx-ID: 1834986 View in Reaxys 364/435 Yield

Conditions & References in water, Rate constant Packer, John E.; Heigway, Christopher J.; Miller, Helen M.; Dobson, Brian C.; Australian Journal of Chemistry; vol. 33; nb. 5; (1980); p. 965 - 977 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

424/438

2018-03-11 22:07:32


H N

N+

C

HC HO

O

Rx-ID: 1842106 View in Reaxys 365/435 Yield

Conditions & References in water, Rate constant Packer, John E.; Heigway, Christopher J.; Miller, Helen M.; Dobson, Brian C.; Australian Journal of Chemistry; vol. 33; nb. 5; (1980); p. 965 - 977 View in Reaxys H

N

N+

Cl

Cl

HC

C

HO

O

Rx-ID: 1975149 View in Reaxys 366/435 Yield

Conditions & References in water, Rate constant Packer, John E.; Heigway, Christopher J.; Miller, Helen M.; Dobson, Brian C.; Australian Journal of Chemistry; vol. 33; nb. 5; (1980); p. 965 - 977 View in Reaxys H

N

N+

N

N

HC

C

HO

O

Rx-ID: 1975314 View in Reaxys 367/435 Yield

Conditions & References in water, Rate constant Packer, John E.; Heigway, Christopher J.; Miller, Helen M.; Dobson, Brian C.; Australian Journal of Chemistry; vol. 33; nb. 5; (1980); p. 965 - 977 View in Reaxys O

H HO

HO

O

Rx-ID: 2343179 View in Reaxys 368/435 Yield

Conditions & References

76 % Chromat.

With tin(IV) ethoxide in toluene, Time= 20h, T= 110 °C Casiraghi, Giovanni; Casnati, Giuseppe; Sartori, Giovanni; Zanafredi, Girolamo T.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 407 - 411 View in Reaxys O

O N

N

H N

N

O

N

HO

O

N H

O

Rx-ID: 3127441 View in Reaxys 369/435 Yield 296 %

Conditions & References With potassium carbonate, Time= 5h, T= 90 °C , Product distribution Yoneda, Fumio; Tsukuda, Kinshiro; Shinozuka, Kazuo; Hirayama, Fumitoshi; Uekama, Kaneto; Koshiro, Akira; Chemical and Pharmaceutical Bulletin; vol. 28; nb. 10; (1980); p. 3049 - 3056 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

425/438

2018-03-11 22:07:32


N

N

O

N

H N

O

H N

N

HO

O O

O

Rx-ID: 3135468 View in Reaxys 370/435 Yield

Conditions & References

128 % Chromat.

With potassium carbonate, Time= 10h, T= 90 °C , oxidation of benzyl alcohol and benzylamine by various 5-deazaflavins as oxido-reductive catalyst Yoneda; Mori; Ono; et al.; Chemical and Pharmaceutical Bulletin; vol. 28; nb. 12; (1980); p. 3514 - 3520 View in Reaxys O

O N

N

N

N

H

O

HO

N

N H

O

O

Cl

Cl

Rx-ID: 3150970 View in Reaxys 371/435 Yield

Conditions & References

199 %

Time= 5h, T= 90 °C , Rate constant Yoneda, Fumio; Tsukuda, Kinshiro; Shinozuka, Kazuo; Hirayama, Fumitoshi; Uekama, Kaneto; Koshiro, Akira; Chemical and Pharmaceutical Bulletin; vol. 28; nb. 10; (1980); p. 3049 - 3056 View in Reaxys

2H

2H

H

O

O

2H

HO

HO

Rx-ID: 3838609 View in Reaxys 372/435 Yield

Conditions & References With lithium perchlorate in acetonitrile, competitive anodic oxidation; isotope effect, Product distribution Boyd, Jean W.; Schmalzl, Paul W.; Miller, Larry L.; Journal of the American Chemical Society; vol. 102; nb. 11; (1980); p. 3856 - 3862 View in Reaxys O N N

O N

HN O

N

H HO

N O

O

Rx-ID: 3839421 View in Reaxys 373/435 Yield 51 %

Conditions & References With air, potassium carbonate, Time= 10h, T= 90 °C , further alcohol or amine, further 2H-pyrido<1',2':1,6>pyrido<2,3-d>pyrimidine-2,4(3H)dione ("bent 5-deazaflavin"), Product distribution Yoneda, Fumio; Ono, Masami; Kira, Keiko; Tanaka, Hisako; Sakuma, Yoshiharu; Chemistry Letters; (1980); p. 817 - 820 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

426/438

2018-03-11 22:07:32


O

O N

N

H Cl

N

N

Cl

O

HO

N

N H

O

O

Rx-ID: 3839502 View in Reaxys 374/435 Yield

Conditions & References

399 %

Time= 5h, T= 90 °C , Product distribution Yoneda, Fumio; Tsukuda, Kinshiro; Shinozuka, Kazuo; Hirayama, Fumitoshi; Uekama, Kaneto; Koshiro, Akira; Chemical and Pharmaceutical Bulletin; vol. 28; nb. 10; (1980); p. 3049 - 3056 View in Reaxys O

O Cl

Cl

N

N

H N

N

N

O

HO

N H

O

O

Rx-ID: 3839633 View in Reaxys 375/435 Yield

Conditions & References

214 %

Time= 5h, T= 90 °C , Product distribution Yoneda, Fumio; Tsukuda, Kinshiro; Shinozuka, Kazuo; Hirayama, Fumitoshi; Uekama, Kaneto; Koshiro, Akira; Chemical and Pharmaceutical Bulletin; vol. 28; nb. 10; (1980); p. 3049 - 3056 View in Reaxys

HO

H

O

WO3

O

Rx-ID: 5819711 View in Reaxys 376/435 Yield

Conditions & References T= 140 °C Mastagli; de Fournas; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 248; (1959); p. 1352 View in Reaxys

O

H

OH

HO

O O

O

Rx-ID: 642903 View in Reaxys 377/435 Yield

Conditions & References T= 450 °C , Leiten ueber einen Chrom-Mangan-Katalysator Jakowlew; Popa; Zhurnal Obshchei Khimii; vol. 28; (1958); p. 2475; engl. Ausg. S. 2510 View in Reaxys H

copper HO

O

Rx-ID: 5819624 View in Reaxys 378/435 Yield

Conditions & References T= 229 - 236 °C , Rate constant Balandin; Teteni; Doklady Akademii Nauk SSSR; vol. 113; (1957); p. 1090; Doklady Physical Chemistry; 112-117<1957>235

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

427/438

2018-03-11 22:07:32


View in Reaxys O

H

Br

N N

HO

HO

Br

O

O

Rx-ID: 146477 View in Reaxys 379/435 Yield

Conditions & References T= 25 °C , Rate constant Orazi; Corral; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 42; (1954); p. 139,145 View in Reaxys

O

H Br

N

HO

HO

N Br

O

O

Rx-ID: 154499 View in Reaxys 380/435 Yield

Conditions & References T= 25 °C , Kinetics Orazi; Corral; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 42; (1954); p. 139,145 View in Reaxys H

OH O

Cl OO

iron (3+)

HO

O

Rx-ID: 5819630 View in Reaxys 381/435 Yield

Conditions & References T= 25 °C , UV-Licht (λ: 365 nm).Irradiation, Kinetics Bates; Uri; Journal of the American Chemical Society; vol. 75; (1953); p. 2754,2756 View in Reaxys O

O

H N

Br

H

O

H

NH

HO O

O O

Rx-ID: 5673499 View in Reaxys 382/435 Yield

Conditions & References T= 90 °C BARAKAT; MOUSA; The Journal of pharmacy and pharmacology; vol. 4; nb. 2; (1952); p. 115 - 117 View in Reaxys

O

cationen-exchanger HO

H O

Rx-ID: 5819709 View in Reaxys 383/435 Yield

Conditions & References T= 150 °C Mastagli et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 232; (1951); p. 1848 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

428/438

2018-03-11 22:07:32


H

O

cationen-exchanger HO

O

Rx-ID: 5957242 View in Reaxys 384/435 Yield

Conditions & References T= 275 - 290 °C Mastagli et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 232; (1951); p. 1848 View in Reaxys O

Br

H

Br

HO

H

O

O

HO

O

KBrO3

Br

Rx-ID: 5958068 View in Reaxys 385/435 Yield

Conditions & References T= 50 - 80 °C Farkas; Schaechter; Journal of the American Chemical Society; vol. 71; (1949); p. 2828; ; (1948); p. 7313 View in Reaxys H

aqueous Mg(OBr)2 HO

O

Rx-ID: 5819616 View in Reaxys 386/435 Yield

Conditions & References Metayer; Roumens; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 225; (1947); p. 1324 View in Reaxys H

aqueous NaOBr HO

O

Rx-ID: 5819617 View in Reaxys 387/435 Yield

Conditions & References Palfray; Metayer; Panouse; Bulletin de la Societe Chimique de France; (1947); p. 766,770 View in Reaxys Panouse; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 223; (1946); p. 745 View in Reaxys H

copper / magnesium pumice stone-catalyst HO

O

H2 Rx-ID: 6214137 View in Reaxys 388/435

Yield

Conditions & References T= 200 - 300 °C , Equilibrium constant Cubberley; Mueller; Journal of the American Chemical Society; vol. 68; (1946); p. 1150 View in Reaxys H

O

O

HO

air HO

Rx-ID: 5958026 View in Reaxys 389/435 Yield

Conditions & References T= 300 - 350 °C , Leiten ueber einen Kupfer-Silber-Bimsstein-Katalysator Davies; Hodgson; Journal of the Chemical Society; (1943); p. 281

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

429/438

2018-03-11 22:07:32


View in Reaxys H

TeO2

HO

O

Rx-ID: 5819688 View in Reaxys 390/435 Yield

Conditions & References Fisher; Eisner; Journal of Organic Chemistry; vol. 6; (1941); p. 169,172 View in Reaxys

aluminium benzylate

O O

HO

O

H

O

O O

OH

O

Rx-ID: 5958737 View in Reaxys 391/435 Yield

Conditions & References Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 147; (1936); p. 211,225 View in Reaxys

calcium-benzylate

O O

HO

O

H

O

O O

OH

O

Rx-ID: 5958738 View in Reaxys 392/435 Yield

Conditions & References Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 147; (1936); p. 211,225 View in Reaxys

magnesium benzylate

O O

HO

O

H

O

O O

OH

O

Rx-ID: 5958739 View in Reaxys 393/435 Yield

Conditions & References Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 147; (1936); p. 211,225 View in Reaxys

zinc benzylate

O O

HO

O

H

O

O O

OH

O

Rx-ID: 5958740 View in Reaxys 394/435 Yield

Conditions & References Meerwein; Journal fuer Praktische Chemie (Leipzig); vol. <2> 147; (1936); p. 211,225 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

430/438

2018-03-11 22:07:32


HO

OH

H

O

O

HO

H 2N 2

O

carbon monoxide HO

Rx-ID: 6211162 View in Reaxys 395/435 Yield

Conditions & References T= 400 °C , Leiten ueber MoO3/Bimsstein Rubinschtein; Lukaschina; ; nb. 6; (1936); p. 299,303; Chem. Zentralbl.; vol. 109; nb. I; (1938); p. 3608 View in Reaxys

nickel-anodes

H

O

O

HO

alkaline aqueous benzenesulfonate

HO

Rx-ID: 5958045 View in Reaxys 396/435 Yield

Conditions & References T= 70 °C McKee; Heard; ; vol. 65; (1934); p. 301,316 View in Reaxys H

OH HO

S OO

NaN3

HO

O H 2N

HO

O

Rx-ID: 5958115 View in Reaxys 397/435 Yield

Conditions & References Franklin; Journal of the American Chemical Society; vol. 56; (1934); p. 568,571 View in Reaxys H

–N

N

N

Na +

H 2N

HO

O

Rx-ID: 26082447 View in Reaxys 398/435 Yield

Conditions & References in water, byproducts: benzoic acid Franklin, E. C.; Journal of the American Chemical Society; vol. 56; (1934); p. 570 ; (from Gmelin) View in Reaxys in water, byproducts: benzoic acid vol. N: MVol.2; 1.3, page 294 - 301 ; (from Gmelin) View in Reaxys

–O

O

4

O

H

OH

Pb4+

HO

O

Rx-ID: 642901 View in Reaxys 399/435 Yield

Conditions & References T= 80 °C Criegee; Kraft; Rank; Justus Liebigs Annalen der Chemie; vol. 507; (1933); p. 159,167 View in Reaxys

–O

4

H

O Pb4+

HO

O

Rx-ID: 817361 View in Reaxys 400/435 Yield

Conditions & References T= 80 °C Criegee; Kraft; Rank; Justus Liebigs Annalen der Chemie; vol. 507; (1933); p. 159,167

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

431/438

2018-03-11 22:07:32


View in Reaxys H

O Se

O

HO

O

Rx-ID: 5819610 View in Reaxys 401/435 Yield

Conditions & References Astin; Newman; Riley; Journal of the Chemical Society; (1933); p. 393 View in Reaxys H

O

O

HO

alkaline aqueous KOBr HO

Rx-ID: 5958028 View in Reaxys 402/435 Yield

Conditions & References Straus; Kuehnel; Chemische Berichte; vol. 66; (1933); p. 1834,1839 View in Reaxys H

O

alkaline aqueous KOCl HO

HO

O

Rx-ID: 5958029 View in Reaxys 403/435 Yield

Conditions & References Straus; Kuehnel; Chemische Berichte; vol. 66; (1933); p. 1834,1839 View in Reaxys H

carbon monoxide

C

HO

O

Rx-ID: 6211159 View in Reaxys 404/435 Yield

Conditions & References T= 300 °C , Leiten ueber Aktivkohle Zelinsky; Gawerdowskaja; Chemische Berichte; vol. 64; (1931); p. 435 View in Reaxys Bahr; Chemische Berichte; vol. 64; (1931); p. 2258,2262 View in Reaxys O

O

N

O

O

N

H

oxygen

O

HO

O

O

Rx-ID: 5819660 View in Reaxys 405/435 Yield

Conditions & References T= 135 - 145 °C Patent; I. G. Farbenind.; DE539476; (1929); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 782 View in Reaxys H

air

O

vanadium (V)-oxide pumice stone

HO

O

HO

Rx-ID: 5958055 View in Reaxys 406/435 Yield

Conditions & References T= 400 - 480 °C Schorygin; Kisber; Smoljanikowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 2; p. 150; Chem. Zentralbl.; vol. 100; nb. II; (1929); p. 730 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

432/438

2018-03-11 22:07:32


H

nitrogen oxides

alkalibenzylate

HO

O

Rx-ID: 5819656 View in Reaxys 407/435 Yield

Conditions & References Wieland; Chemische Berichte; vol. 61; (1928); p. 2383 View in Reaxys H

air

zinc oxide pumice stone

HO

O

Rx-ID: 5819695 View in Reaxys 408/435 Yield

Conditions & References T= 330 °C , unter vermindertem Druck Ottensooser; Bulletin de la Societe Chimique de France; vol. <4> 41; (1927); p. 324 View in Reaxys

N

+ 2 O Na

–O

O–

H HO

O

Rx-ID: 42860 View in Reaxys 409/435 Yield

Conditions & References Zetzsche; Zala; Helvetica Chimica Acta; vol. 9; (1926); p. 288 View in Reaxys

O

O

O

N

N

O

+ 2 O Na

–O

O–

H HO

O

Rx-ID: 816899 View in Reaxys 410/435 Yield

Conditions & References Zetzsche; Zala; Helvetica Chimica Acta; vol. 9; (1926); p. 288 View in Reaxys

O

HO

aluminium benzylate HO

H O

Rx-ID: 5819706 View in Reaxys 411/435 Yield

Conditions & References unter vermindertem Druck Ponndorf; Angewandte Chemie; vol. 39; (1926); p. 140 View in Reaxys H

O

O

HO

copper HO

Rx-ID: 5958149 View in Reaxys 412/435 Yield

Conditions & References T= 230 - 330 °C Hara; Memoirs of the College of Science, Kyoto Imperial University; vol. <A> 9; p. 409; Chem. Zentralbl.; vol. 97; nb. II; (1926); p. 2658 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

433/438

2018-03-11 22:07:32


Cl

Cl

O

O N O

Cl

H

O

O

HO

N O

HO

Rx-ID: 5958025 View in Reaxys 413/435 Yield

Conditions & References Bass; Johnson; Journal of the American Chemical Society; vol. 46; (1924); p. 460 View in Reaxys NH 2

H 2N

O

H

O

O

N H

O

HO

O

Rx-ID: 638096 View in Reaxys 414/435 Yield

Conditions & References Electrolysis Schaum; Chemische Berichte; vol. 56; (1923); p. 2461 View in Reaxys With platinum electrode, Electrolysis Schaum; Chemische Berichte; vol. 56; (1923); p. 2461 View in Reaxys NH 2

H 2N

O

H

O

platinum electrodeene HO

O

N H

O

O

Rx-ID: 5819719 View in Reaxys 415/435 Yield

Conditions & References Electrolysis Schaum; Chemische Berichte; vol. 56; (1923); p. 2461 View in Reaxys

Cl

Cl

Cl

Cl

palladium-barium sulfate HO

H

O

O

Rx-ID: 5819710 View in Reaxys 416/435 Yield

Conditions & References Rosenmund; Zetzsche; Chemische Berichte; vol. 54; (1921); p. 2036 View in Reaxys

air

copper

HO

O

H

O

O

HO

Rx-ID: 5958064 View in Reaxys 417/435 Yield

Conditions & References Verb. 5: Chinolin Rosenmund; Zetzsche; Chemische Berichte; vol. 54; (1921); p. 1094 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

434/438

2018-03-11 22:07:32


oxygen

copper

HO

O

H

O

O

HO

Rx-ID: 5958065 View in Reaxys 418/435 Yield

Conditions & References Verb. 5: Chinolin Rosenmund; Zetzsche; Chemische Berichte; vol. 54; (1921); p. 1094 View in Reaxys

O HO

HO

H O

OH

HO

OH

Rx-ID: 816931 View in Reaxys 419/435 Yield

Conditions & References Sonnenlicht Cohen; Recueil des Travaux Chimiques des Pays-Bas; vol. 39; (1920); p. 244 View in Reaxys Ciamician; Silber; Chemische Berichte; vol. 36; (1903); p. 1576; Gazzetta Chimica Italiana; vol. 34 II; (1904); p. 133 View in Reaxys H

air

silver-asbestos

HO

O

Rx-ID: 5819674 View in Reaxys 420/435 Yield

Conditions & References T= 300 °C Moureu; Mignonac; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 260; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 171; (1920); p. 652 View in Reaxys H

silver-asbestos

oxygen

HO

O

Rx-ID: 5819675 View in Reaxys 421/435 Yield

Conditions & References T= 320 - 330 °C , p= 30 - 40Torr Moureu; Mignonac; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 171; (1920); p. 652; Bulletin de la Societe Chimique de France; vol. <4>29; (1921); p. 100 View in Reaxys

sulfur

S

HO

H

O

O

HO

Rx-ID: 5958069 View in Reaxys 422/435

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

435/438

2018-03-11 22:07:32


Yield

Conditions & References T= 180 °C Szperl; Wierusz-Kowalski; Chem. Zentralbl.; vol. 89; nb. I; (1918); p. 909 View in Reaxys Cl

Cl Al

Cl

O

Cl

Cl

H

Cl

HO

O

Rx-ID: 5819612 View in Reaxys 423/435 Yield

Conditions & References Frankforter; Kritchevsky; Journal of the American Chemical Society; vol. 36; (1914); p. 1518 View in Reaxys H

palladium black HO

O

Rx-ID: 5819663 View in Reaxys 424/435 Yield

Conditions & References in einer CO2-Atmosphaere Wieland; Chemische Berichte; vol. 45; (1912); p. 493 View in Reaxys

H

N H

H

H

HO

N H

O

Rx-ID: 6208231 View in Reaxys 425/435 Yield

Conditions & References T= 380 °C , beim Leiten ueber ThO2 Mailhe; Chemiker-Zeitung, Chemische Apparatur; vol. 34; (1910); p. 1184 View in Reaxys Sabatier; Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 153; (1911); p. 162 View in Reaxys

H

hydrogen

iron

H

O

H

HO

O

Rx-ID: 5957267 View in Reaxys 426/435 Yield

Conditions & References T= 350 - 360 °C Ipatjew; Chemische Berichte; vol. 41; (1908); p. 991; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 40; (1908); p. 492; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 1098 View in Reaxys H

hydrogen HO

O

Rx-ID: 6214844 View in Reaxys 427/435 Yield

Conditions & References T= 400 °C , im eisernen Rohr Ipatjew; Chemische Berichte; vol. 41; (1908); p. 991; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 40; (1908); p. 492; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 1098 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

436/438

2018-03-11 22:07:32


H N

N+

HO

O HO

Rx-ID: 816953 View in Reaxys 428/435 Yield

Conditions & References beim Behandeln von Benzoldiazoniumchlorid Hantzsch; Vock; Chemische Berichte; vol. 36; (1903); p. 2062 View in Reaxys H

copper HO

hydrogen O

Rx-ID: 6214845 View in Reaxys 429/435 Yield

Conditions & References T= 300 °C Sabatier; Senderens; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 136; (1903); p. 984 View in Reaxys

copper HO

H

HO

OH O

O

H 2N 2

hydrogen

carbon monoxide Rx-ID: 6214950 View in Reaxys 430/435

Yield

Conditions & References T= 380 °C Sabatier; Senderens; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 136; (1903); p. 984 View in Reaxys O

O

HO

O

H O

OH

Rx-ID: 734530 View in Reaxys 431/435 Yield

Conditions & References Knoevenagel; Arndts; Chemische Berichte; vol. 35; (1902); p. 1989 View in Reaxys

H HO

O

C O

hydrogen Rx-ID: 6215001 View in Reaxys 432/435

Yield

Conditions & References T= 800 - 820 °C , in kupfernen Roehren Ipatjew; Chemische Berichte; vol. 35; (1902); p. 1061;; Chemische Berichte; vol. 36; (1903); p. 1997,1998 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

437/438

2018-03-11 22:07:32


H 2N HO

OH

O

O

O

O

O

H O O

HO

N

O

O

Rx-ID: 817138 View in Reaxys 433/435 Yield

Conditions & References Wegscheider; Monatshefte fuer Chemie; vol. 21; (1900); p. 627; Monatshefte fuer Chemie; vol. 23; (1902); p. 410 View in Reaxys O H 2N

nitrate urea

N

HO

H O

Rx-ID: 5819715 View in Reaxys 434/435 Yield

Conditions & References T= 100 °C Campisi; Amato; Chemische Berichte; vol. 4; (1871); p. 412 View in Reaxys H

O N O

OH

HO

O

Rx-ID: 5819611 View in Reaxys 435/435 Yield

Conditions & References Cannizzaro; Justus Liebigs Annalen der Chemie; vol. 88; (1853); p. 130 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

438/438

2018-03-11 22:07:32


Turn static files into dynamic content formats.

Create a flipbook
Issuu converts static files into: digital portfolios, online yearbooks, online catalogs, digital photo albums and more. Sign up and create your flipbook.