Styrene to Ethylbenzene by Asch

Query Query 1. Query

Results

Date

154 reactions in Reaxys

2016-06-28 15h:22m:31s (EST)

Search as: As drawn, No salts, No mixtures, No charges, No radicals

1/96

2016-06-28 15:56:50

Rx-ID: 39021 View in Reaxys 1/154 Yield 20 %, 2 %

Conditions & References With zirconocene dichloride, n-Oct–OTs, n-butyl-magnesium chloride Terao, Jun; Watanabe, Tsunenori; Saito, Koyu; Kambe, Nobuaki; Sonoda, Noboru; Tetrahedron Letters; vol. 39; nb. 50; (1998); p. 9201 - 9204 View in Reaxys With ethanol, sodium Midgley; Henne; Leicester; Journal of the American Chemical Society; vol. 58; (1936); p. 1961 View in Reaxys

Rx-ID: 39024 View in Reaxys 2/154 Yield 100 %

Conditions & References With hydrogen, lt;N,N'-Ethylenebis(salicylideneaminato)gt;p in methanol, Time= 0.316667h, other substrates Kerr, James M.; Suckling, Colin J.; Bamfield, Peter; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1990); p. 887 - 895 View in Reaxys

100 %

With polymeric thiol, hydrogen, palladium on activated charcoal, Time= 1h, var. catalysts, further thiol; poisoning effect of thiols, Product distribution Collman; Kosydar; Bressan; Lamanna; Garrett; Journal of the American Chemical Society; vol. 106; nb. 9; (1984); p. 2569 - 2579 View in Reaxys

100 %

With hydrogen, Pd-1percent Ho in neat (no solvent), Time= 0.00583333h, T= 90 °C , selective hydrogenation; variation of temperature and contact time, Product distribution Parvulescu, V. I.; Parvulescu, V.; Frunza, L.; Grecu, N.; Enache, C.; Angelescu, Em.; Bulletin des Societes Chimiques Belges; vol. 102; nb. 6; (1993); p. 391 - 400 View in Reaxys

100 %

With hydrogen, Pd(salen) in methanol, Time= 0.316667h Kerr, James M.; Suckling, Colin J.; Tetrahedron Letters; vol. 29; nb. 43; (1988); p. 5545 - 5548 View in Reaxys

100 %

With hydrogen, sodium tetrahydroborate, Ni(2-ethylhexanoate)n + NaBH4, Time= 24h, p= 1520Torr , Ambient temperature Collman; Kosydar; Bressan; Lamanna; Garrett; Journal of the American Chemical Society; vol. 106; nb. 9; (1984); p. 2569 - 2579 View in Reaxys

100 %

With {(.eta.6-C6H6)Ru(NCCH3)3}{BF4}2, water, hydrogen in benzene, Time= 4h, T= 90 °C , p= 30400Torr Chan, Wai-Chung; Lau, Chak-Po; Cheng, Lin; Leung, Yin-Shan; Journal of Organometallic Chemistry; vol. 464; nb. 1; (1994); p. 103 - 106 View in Reaxys

100 %

With samarium diiodide, N,N,N',N'',N''-pentamethylethylene triamine, water in tetrahydrofuran, Time= 0.0833333h, T= 20 °C Dahlen, Anders; Hilmersson, Goeran; Tetrahedron Letters; vol. 44; nb. 13; (2003); p. 2661 - 2664

2/96

2016-06-28 15:56:50

View in Reaxys 100 %

With hydrogen, phosphan, palladium(II) acetylacetonate in N,N-dimethyl-formamide, benzene, T= 30 °C , p= 760.051Torr , Product distribution, Further Variations: Catalysts, Reagents, Temperatures Belykh; Skripov; Belonogova; Umanets; Shmidt; Russian Journal of Applied Chemistry; vol. 80; nb. 9; (2007); p. 1523 - 1528 View in Reaxys

100 %

With palladium(II) acetylacetonate, lithium aluminium tetrahydride, hydrogen in benzene, T= 30 °C , p= 760.051Torr , Product distribution Belykh; Titova; Rokhin; Belonogova; Shmidt; Russian Journal of Applied Chemistry; vol. 81; nb. 6; (2008); p. 956 - 964 View in Reaxys

100 %

With hydrogen in N,N-dimethyl-formamide, benzene, T= 30 °C , p= 760.051Torr Belykh; Skripov; Belonogova; Umanets; Schmidt; Kinetics and Catalysis; vol. 51; nb. 1; (2010); p. 42 - 49 View in Reaxys

100 %

10 :Example 10: Transfer hydrogenation of styrene.Pd/ C (5 molpercent) is weighed into a reaction flask. A solvent mixture consisting of ethanol and water (4: 1) and ammonium formate (30 molpercent) is added, the reaction flask is capped with a rubber septa and the mixture is heated (80 °C) for 2 minutes. Formic acid (3 equivalents) and then styrene are added by syringe. The reaction is run for 20 minutes and the reaction is quenched with brine. The product is extracted by DCM and the organic phase is dried by Na2S04. The productethylbenzene was analyzed by NMR and produced in 100percent yield. With formic acid, ammonium formate, 5 palladium on charcoal in ethanol, water, Time= 0.333333h, T= 80 °C Patent; SAMEC, Joseph; LUNDSTEDT, Anna; SAWADJOON, Supaporn; KAT2BIZ AB C/O INTERPARES KONSULT AB; WO2012/121659; (2012); (A1) English View in Reaxys

100 %

C8b : B.5 Series S (Hydrogenation of styrene)#10; B.5 Series 5 (Hydrogenation of styrene) Hydrogenation Procedure (NMR method; 5 molpercent catalyst based on styrene; in-situ formation of the active catalyst, no co-catalyst, no work-up required): in a glove box, a sample of the appropriate metal complex (catalyst) (0.005 mmol) and 500 uL of deuterated solvent [CD2C12 (0.665 g) or C6D5Br (0.748 g)] were combined in a 2 dram vial and transferred to a J- Young tube. Twenty equivalents of Stryene (10.45 mg, 0.100 mmol) were added to the solution and the J- Young tube was sealed. On a schlenk line, the reaction mixture was degassed 3 times using the freeze-pump-thaw method. The sample was then frozen once more in liquid nitrogen and 4 atm of H2 was added. The J- Young tube was sealed again and warmed to room temperature before being placed in an oil bath pre-heated to the appropriate temperature (45°C or 100°C). The sample was refilled with H2 at the 4 h and 8 h time periods. NMR spectra were obtained at appropriate intervals and relative integration of substrate and product peaks were used to determine the percent composition of the mixture. The results of the hydrogenation are summarized in Table 5. Peaks used for Determination of Concentrations: (The number in brackets below represents the relative number of protons represented by each peak - to determine the concentration of each the peak integrations must be normalized) CD2Cl2 [45°C Reactions], C^^Br [lOCfC Reactions] Styrene - 5.80 ppm (1) Ethylbenzene - 1.26 (3) With Wilkinson's catalyst, hydrogen in dichloromethane-d2, Time= 4h, T= 45 °C , p= 3000.3Torr , Sealed tube, Inert atmosphere, Concentration, Reagent/catalyst, Solvent, Temperature, Time Patent; THE GOVERNING COUNCIL OF UNIVERSITY OF TORONTO; LANXESS Deutschland GmbH; MUELLER, Julia Maria; STEPHEN, Douglas; LUND, Clinton; SGRO, Michael; ONG, Christopher; CARIOU, Renan; WO2013/24119; (2013); (A1) English View in Reaxys

100 %

With hydrogen in ethanol, T= 100 °C , p= 30003Torr , Flow reactor, Green chemistry, Pressure, Temperature, Solvent, chemoselective reaction Hudson, Reuben; Hamasaka, Go; Osako, Takao; Yamada, Yoichi M. A.; Li, Chao-Jun; Uozumi, Yasuhiro; Moores, Audrey; Green Chemistry; vol. 15; nb. 8; (2013); p. 2141 - 2148 View in Reaxys

3/96

2016-06-28 15:56:50

100 %

With iron(III) chloride, lithium aluminium tetrahydride, hydrogen in tetrahydrofuran, Time= 6h, T= 18 °C , p= 750.075Torr , Inert atmosphere, Sealed tube Gieshoff, Tim N.; Villa, Matteo; Welther, Alice; Plois, Markus; Chakraborty, Uttam; Wolf, Robert; Jacobi Von Wangelin, Axel; Green Chemistry; vol. 17; nb. 3; (2015); p. 1408 - 1413 View in Reaxys

100 %

With hydrogen, sodium triethylborohydride in tetrahydrofuran, Time= 18h, T= 23 °C , p= 30402Torr , Inert atmosphere, Schlenk technique, Catalytic behavior Manna, Kuntal; Zhang, Teng; Carboni, Michal; Abney, Carter W.; Lin, Wenbin; Journal of the American Chemical Society; vol. 136; nb. 38; (2014); p. 13182 - 13185 View in Reaxys

100 %

With hydrogen in methanol, Time= 0.25h, T= 40 °C , p= 7757.43Torr , Reagent/catalyst, Temperature Sharma, Priti; Singh; RSC Advances; vol. 4; nb. 102; (2014); p. 58467 - 58475 View in Reaxys

100 %

With hydrogen in neat (no solvent), Time= 5h, T= 30 °C , Flow reactor, Catalytic behavior Kobayashi, Shu; Okumura, Mikiko; Akatsuka, Yuichi; Miyamura, Hiroyuki; Ueno, Masaharu; Oyamada, Hidekazu; ChemCatChem; vol. 7; nb. 24; (2015); p. 4025 - 4029 View in Reaxys

100 %

General procedure: In a typical experiment, complex 1 (6.1 mg, 10 tmol) and H[BAr’4].(Et2O)2 (10.1 mg, 10 tmol) were dissolved in tetrahydrofuran (“THF”, 2.0 mL) in a 100 mL thick-walled glass vessel equipped with a TEFLON stopcock and a stir bat The substrate (0.5 mmol) to be hydrogenated was added and then hexamethylbenzene (ca. 32 mg, 0.2 mmol) was added as an internal standard. The reaction vessel was degassed by freeze-pump-thaw, 1 atm of hydrogen gas was admitted, and the vessel was sealed. The resulting solution was stirred at 25°C. for the indicated reaction time. At the end of the reaction time, the reaction vessel was opened under air, the reaction mixture was diluted with dichloromethane, and the yield was determined by GC analysis (integration against the internal standard). Product identities were verified by GC-MS analysis and comparison to authentic samples. With tetrakis[3,5-bis(trifluoromethyl)phenyl]boric acid bis(diethyl ether) complex, (bis[(2-dicyclohexylphosphino)ethyl]amine)cobalt(II)(CH2SiMe3), hydrogen in tetrahydrofuran, Time= 24h, T= 25 °C , p= 760.051Torr , Reagent/catalyst Patent; LOS ALAMOS NATIONAL SECURITY, LLC; Vasudevan, Kalyan V.; Zhang, Guoqi; Hanson, Susan K.; US2015/336862; (2015); (A1) English View in Reaxys

99 %

With water, zinc, chloro(1,5-cyclooctadiene)rhodium(I) dimer in 1,4-dioxane, Time= 20h, T= 90 °C Sato, Takashi; Watanabe, Shoji; Kiuchi, Hiroyoshi; Oi, Shuichi; Inoue, Yoshio; Tetrahedron Letters; vol. 47; nb. 44; (2006); p. 7703 - 7705 View in Reaxys

99 %

With sodium tetrahydroborate, 1 mol Pd/C, acetic acid in isopropyl alcohol, Time= 0.25h, T= 20 °C Tran, Anthony T.; Huynh, Vincent A.; Friz, Emily M.; Whitney, Sara K.; Cordes, David B.; Tetrahedron Letters; vol. 50; nb. 16; (2009); p. 1817 - 1819 View in Reaxys

99 %

With hydrogen in methanol, Time= 1.5h, T= 30 °C , p= 7500.75Torr Huang, Xin; Wu, Hao; Liao, Xuepin; Shi, Bi; Catalysis Communications; vol. 11; nb. 5; (2010); p. 487 - 492 View in Reaxys

99 %

With iron(III) chloride hexahydrate, hydrazine hydrate in ethanol, Time= 14h, T= 20 °C Lamani, Manjunath; Ravikumara, Guralamata S.; Prabhu, Kandikere Ramaiah; Advanced Synthesis and Catalysis; vol. 354; nb. 8; (2012); p. 1437 - 1442 View in Reaxys

4/96

2016-06-28 15:56:50

> 99 %

With bis-triphenylphosphine-palladium(II) chloride, Triethoxysilane, (Z)-N,N-diisopropyl-2-styrylbenzamide in tetrahydrofuran, T= 65 °C , Inert atmosphere, chemoselective reaction Bai, Xing-Feng; Xu, Li-Wen; Zheng, Long-Sheng; Jiang, Jian-Xiong; Lai, Guo-Qiao; Shang, Jun-Yan; Chemistry - A European Journal; vol. 18; nb. 26; (2012); p. 8174 - 8179 View in Reaxys

99 %

With hydrogen, nitrobenzene in 1,4-dioxane, Time= 10h, T= 20 °C , Solvent Huang, Lei; Luo, Pingfei; Pei, Weige; Liu, Xiaoyun; Wang, Yong; Wang, Jun; Xing, Weihong; Huang, Jun; Advanced Synthesis and Catalysis; vol. 354; nb. 14-15; (2012); p. 2689 - 2694 View in Reaxys

> 99 %

With 0.42C23H20N4O4*2Cl(1-)*Zn(2+)*10.16H2O*0.58Pd(2+)*0.58C23H20N4O4 (1-), hydrogen in tetrahydrofuran, Time= 1h, T= 20 °C , p= 760.051Torr Kong, Guo-Qiang; Ou, Sha; Zou, Chao; Wu, Chuan-De; Journal of the American Chemical Society; vol. 134; nb. 48; (2012); p. 19851 - 19857 View in Reaxys

> 99 %

With hydrogen in n-heptane, Time= 0.166667h, T= 30 °C , Pressure, Time Peng, Li; Zhang, Jianling; Li, Jianshen; Han, Buxing; Xue, Zhimin; Yang, Guanying; Angewandte Chemie - International Edition; vol. 52; nb. 6; (2013); p. 1792 - 1795; Angew. Chem.; vol. 125; nb. 6; (2013); p. 1836 - 1839,4 View in Reaxys

> 99 %

in methanol, Time= 0.5h, T= 24.84 °C , UV-irradiation, Catalytic behavior, Quantum yield, Reagent/catalyst, Solvent Imamura, Kazuya; Okubo, Yuki; Ito, Tomohiko; Tanaka, Atsuhiro; Hashimoto, Keiji; Kominami, Hiroshi; RSC Advances; vol. 4; nb. 38; (2014); p. 19883 - 19886 View in Reaxys

> 99 %

With hydrogen in isopropyl alcohol, Time= 20h, T= 40 °C , p= 750.075Torr , Schlenk technique, Inert atmosphere Dehe, Daniel; Wang, Lei; Müller, Melanie K.; Dörr, Gunder; Zhou, Zhou; Klupp-Taylor, Robin N.; Sun, Yu; Ernst, Stefan; Hartmann, Martin; Bauer, Matthias; Thiel, Werner R.; ChemCatChem; vol. 7; nb. 1; (2015); p. 127 - 136 View in Reaxys

> 99 %

With hydrogen, Time= 3h, T= 20 °C , Catalytic behavior, Reagent/catalyst Mitsudome, Takato; Yamamoto, Masaaki; Maeno, Zen; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Journal of the American Chemical Society; vol. 137; nb. 42; (2015); p. 13452 - 13455 View in Reaxys

99 %

With hydrogen in ethanol, Time= 5h, T= 60 °C , p= 3000.3Torr Gole, Bappaditya; Sanyal, Udishnu; Banerjee, Rahul; Mukherjee, Partha Sarathi; Inorganic Chemistry; vol. 55; nb. 5; (2016); p. 2345 - 2354 View in Reaxys

> 99 %

With hydrogen in hexane, Time= 1h, T= 20 °C , p= 750.075Torr , Green chemistry Martina, Katia; Baricco, Francesca; Caporaso, Marina; Berlier, Gloria; Cravotto, Giancarlo; ChemCatChem; vol. 8; nb. 6; (2016); p. 1176 - 1184 View in Reaxys

98 %

With methanol, ytterbium in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 18h, Ambient temperature Hou, Zhaomin; Taniguchi, Hiroshi; Fujiwara, Yuzo; Chemistry Letters; (1987); p. 305 - 308 View in Reaxys

98 %

With poly(p-aminostyrene)-palladium(II), hydrogen in N,N-dimethyl-formamide, T= 25 °C , p= 760Torr Mukherjee, Debkumar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 42; nb. 2; (2003); p. 346 - 352

5/96

2016-06-28 15:56:50

View in Reaxys 98 %

With Rh on carbon, iron(II) acetate in tetrahydrofuran, Time= 16h, T= 20 °C Akao, Atsushi; Sato, Kimihiko; Nonoyama, Nobuaki; Mase, Toshiaki; Yasuda, Nobuyoshi; Tetrahedron Letters; vol. 47; nb. 6; (2006); p. 969 - 972 View in Reaxys

98 %

With hydrogen in methanol, Time= 2h, T= 20 °C , p= 2068.65Torr Polshettiwar, Vivek; Nadagouda, Mallikarjuna N.; Varma, Rajender S.; Chemical Communications; nb. 47; (2008); p. 6318 - 6320 View in Reaxys

> 98 %

With hydrogen in toluene, T= 79.84 °C , p= 15001.5Torr , Kinetics, Reagent/catalyst Betti, Carolina; Badano, Juan; MacCarrone, M. Juliana; Mazzieri, Vanina; Vera, Carlos; Quiroga, Monica; Applied Catalysis A: General; vol. 435-436; (2012); p. 181 - 186 View in Reaxys

98%

With Rh(2-o-oxyphenyl-4-amino-6-ethoxy-1,3,5-triazene)(CO)2, hydrogen in N,N-dimethyl-formamide, toluene, T= 25 °C , p= 0Torr , High pressure, Autoclave, Reagent/catalyst, Temperature Sagar, Priyanka; Sharma, Varsha; Kumar, Rohit; Journal of the Indian Chemical Society; vol. 89; nb. 2; (2012); p. 139 - 145 View in Reaxys

97 %

With ammonium chloride in methanol, Electrochemical reaction Santana, Diogo S.; Lima, Marcio V. F.; Daniel, Jorge R. R.; Navarro, Marcelo; Tetrahedron Letters; vol. 44; nb. 25; (2003); p. 4725 - 4727 View in Reaxys

97 %

With formic acid in methanol, water, Time= 12h, T= 100 °C , Green chemistry, chemoselective reaction Qureshi, Ziyauddin S.; Sarawade, Pradip B.; Albert, Matthias; D'Elia, Valerio; Hedhili, Mohamed N.; Köhler, Klaus; Basset, Jean-Marie; ChemCatChem; vol. 7; nb. 4; (2015); p. 635 - 642 View in Reaxys

96.4 %

With hydrogen in dichloromethane, Time= 5h, T= 50 °C , p= 15001.5Torr , Reagent/catalyst Gonzalez De Rivera, Ferran; Angurell, Inmaculada; Rossell, Marta D.; Erni, Rolf; Llorca, Jordi; Divins, Nuria J.; Muller, Guillermo; Seco, Miquel; Rossell, Oriol; Chemistry - A European Journal; vol. 19; nb. 36; (2013); p. 11963 - 11974 View in Reaxys

96 %

With hydrogen in water, ethyl acetate, Time= 1.2h, T= 40 °C , p= 2625.26Torr Huang, Jianping; Yang, Hengquan; Chemical Communications; vol. 51; nb. 34; (2015); p. 7333 - 7336 View in Reaxys

95.1 %

With hydrogen, (Bu4N)4lt;Pt2(P2O5H2)4gt; in isopropyl alcohol, Time= 10h, T= 26 - 67 °C , p= 31464Torr , E(excit), ΔH(excit.), ΔS(excit.); effect of substrate and catalyst concentration, pressure of hydrogen; other substrates, Kinetics, Mechanism, Thermodynamic data Lin, Jinyan; Pittman Jr., Charles U.; Journal of Organometallic Chemistry; vol. 512; nb. 1-2; (1996); p. 69 - 78 View in Reaxys

95 %

With hydrogen, Rhodium chloride tri(triphenylphosphine-meta-trisulfonate) in water, Time= 40h, Ambient temperature Larpent, Chantal; Dabard, Renee; Patin, Henri; Tetrahedron Letters; vol. 28; nb. 22; (1987); p. 2507 - 2510 View in Reaxys

95 %

With hydrogen, Pd-polymethylhydrosiloxane nanocomposite in benzene, Time= 4h, T= 20 °C Chauhan, Bhanu P. S.; Rathore, Jitendra S.; Bandoo, Tariq; Journal of the American Chemical Society; vol. 126; nb. 27; (2004); p. 8493 - 8500

6/96

2016-06-28 15:56:50

View in Reaxys 95 %

15 With dihydrogen peroxide, acetic acid, hydrazine in water, Time= 20.5h, T= 50 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; JP2005/350427; (2005); (A) Japanese View in Reaxys

95 %

With C28H18Co(1-)*K(1+)*2C4H10O2, hydrogen in toluene, Time= 3h, T= 20 °C , p= 750.075Torr , Kinetics, Catalytic behavior, Reagent/catalyst, Pressure, Temperature, Solvent, chemoselective reaction Gaertner, Dominik; Welther, Alice; Rad, Babak Rezaei; Wolf, Robert; Von Wangelin, Axel Jacobi; Angewandte Chemie - International Edition; vol. 53; nb. 14; (2014); p. 3722 - 3726; Angew. Chem.; vol. 126; nb. 14; (2014); p. 3796 - 3800,5 View in Reaxys

95 %

With ammonium hydroxide, hydrazine hydrate in ethanol, Time= 0.5h, T= 60 °C , Catalytic behavior, Reagent/catalyst Datta, Kasibhatta Josena; Datta, Kasibhatta Kumara Ramanatha; Gawande, Manoj B.; Ranc, Vaclav; pe, Klra; Malgras, Victor; Yamauchi, Yusuke; Varma, Rajender S.; Zboril, Radek; Chemistry - A European Journal; vol. 22; nb. 5; (2016); p. 1577 - 1581 View in Reaxys

94 %

With hydrogen in ethanol, Time= 0.5h, T= 20 °C , p= 760.051Torr , chemoselective reaction Kantam, Mannepalli Lakshmi; Kishore, Ramineni; Yadav, Jagjit; Sudhakar, Medak; Venugopal, Akula; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 663 - 669 View in Reaxys

93 %

With ammonium formate, PdMCM-41 in methanol, Time= 3h, T= 69.84 °C Selvam, Parasuraman; Sonavane, Sachin U.; Mohapatra, Susanta K.; Jayaram, Radha V.; Tetrahedron Letters; vol. 45; nb. 15; (2004); p. 3071 - 3075 View in Reaxys

92 %

With sodium tetrahydroborate, aluminium trichloride in tetrahydrofuran, Time= 2h, Heating Ono, Aoi; Suzuki, Nobuko; Kamimura, Junko; Synthesis; nb. 8; (1987); p. 736 - 738 View in Reaxys

92 %

With palladium on activated charcoal, hydrogen in N,N-dimethyl-formamide, T= 25 °C , p= 760.051Torr Islam, Sk. Manirul; Mondal, Sanchita; Mondal, Paromita; Roy, Anupam Singha; Salam, Noor; Paul, Sumantra; Mobarak, Manir; Transition Metal Chemistry; vol. 36; nb. 7; (2011); p. 699 - 706 View in Reaxys

92 %

2.6. General procedure for the hydrogenation of different unsaturated compounds General procedure: In a typical reaction, 0.015 g of catalyst and 2 mmol of the reactant were taken in 10 mL of ethanol under hydrogen atmosphere. The reaction was monitored by thin-layer chromatography (TLC). After complete disappearance of the starting material, the catalyst was separated by simple filtration and the solvent was removed under reduced pressure to obtain the pure product. With hydrogen in ethanol, Time= 1h, T= 20 °C , p= 760.051Torr , chemoselective reaction Lakshmi, Kantam M.; Parsharamulu; Manorama; Journal of Molecular Catalysis A: Chemical; vol. 365; (2012); p. 115 - 119 View in Reaxys

91 %

With sodium hydrogen telluride in ethanol, Time= 2.5h, Heating, other styrenes Barton, Derek H. R.; Bohe, Luis; Lusinchi, Xavier; Tetrahedron; vol. 46; nb. 15; (1990); p. 5273 - 5284 View in Reaxys

91 %

With sodium hydrogen telluride in ethanol, Time= 2.5h, Heating

7/96

2016-06-28 15:56:50

Barton, Derek H. R.; Bohe, Luis; Lusinchi, Xavier; Tetrahedron; vol. 46; nb. 15; (1990); p. 5273 - 5284 View in Reaxys 91 %

With hydrogen, sodium triethylborohydride in tetrahydrofuran, Time= 30h, T= 23 °C , p= 30003Torr , Autoclave, Reagent/catalyst Zhang, Teng; Manna, Kuntal; Lin, Wenbin; Journal of the American Chemical Society; vol. 138; nb. 9; (2016); p. 3241 - 3249 View in Reaxys

90 %

3 With sodium bromate, acetic acid, hydrazine in water, Time= 5h, T= 60 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; JP2005/350427; (2005); (A) Japanese View in Reaxys

90 %

Hydrogenation catalysis using Pd-G1 General procedure for hydrogenation: Substrate to be hydrogenated was taken in a 100 mL RB flask containing PdG1 (5.0 mg) and ethyl acetate (15 mL). Hydrogen atmosphere for the reaction was provided by connecting a hydrogen filled bladder to the reaction vessel using a glass connector so that there will be always a slight positive pressure of hydrogen (hydrogen pressure was approximately 1.04 atm). After the specified time, ethyl acetate was removed in a rotavapour and the products were extracted into ether. The ether extract was passed through a pad of silica to remove suspended impurities. Ether was then removed to get the pure products. With hydrogen in ethyl acetate, Time= 4h, p= 790.453Torr Ratheesh Kumar, Venugopal K.; Gopidas, Karical R.; Tetrahedron Letters; vol. 52; nb. 24; (2011); p. 3102 - 3105 View in Reaxys

88 %

With [ReBr2(NO)(.eta.(2)-H2)(P(C6H11)3)2], dimethylamine borane, hydrogen, Time= 3h, T= 90 °C , p= 7500.75Torr , Autoclave Jiang, Yanfeng; Hess, Jeannine; Fox, Thomas; Berke, Heinz; Journal of the American Chemical Society; vol. 132; nb. 51; (2010); p. 18233 - 18247 View in Reaxys

87 %

With tributylphosphine, carbon monoxide, hydrogen, cobalt(II) acetate in methanol, T= 80 °C , p= 60004.8Torr , Irradiation Mirbach, Manfred J.; Topalsavoglu, Nicholaos; Phu, Tuyet Nhu; Mirbach, Marlis F.; Saus, Alfons; Angewandte Chemie; vol. 93; nb. 4; (1981); p. 391 - 397 View in Reaxys

87.6 %

With p-tolylstibane in benzene, Time= 1h, T= 80 °C Breunig; Probst; Journal of Organometallic Chemistry; vol. 571; nb. 2; (1998); p. 297 - 303 View in Reaxys

82 %

With hydrazine hydrate, Ni(0) nanoparticles/K-10 Montmorillonite clay in ethanol, Time= 8h, T= 70 °C , Product distribution, Further Variations: Solvents, Reagents, Catalysts, Temperatures, time Dhakshinamoorthy, Amarajothi; Pitchumani, Kasi; Tetrahedron Letters; vol. 49; nb. 11; (2008); p. 1818 - 1823 View in Reaxys

81 %

With hydrogen, palladium diacetate in ethanol, T= 20 °C Hussain, Najrul; Borah, Ashwini; Darabdhara, Gitashree; Gogoi, Pranjal; Azhagan, Vedi Kuyil; Shelke, Manjusha V.; Das, Manash R.; New Journal of Chemistry; vol. 39; nb. 8; (2015); p. 6631 - 6641 View in Reaxys

80 %

With bismuth(III) chloride, sodium tetrahydroborate in ethanol, Time= 5h, selective reduction of aromatic olefins; other aromatic olefins, var. time Ren, Ping-Da; Pan, Shi-Feng; Dong, Ting-Wei; Wu, Shi-Hui; Synthetic Communications; vol. 26; nb. 4; (1996); p. 763 - 767

8/96

2016-06-28 15:56:50

View in Reaxys 75 %

With hydrogen, sodium methylate, nickel in methanol, hydrogen generated in situ electrochemically on Raney nickel electrode Chiba; Okimoto; Nagai; Takata; Bulletin of the Chemical Society of Japan; vol. 56; nb. 3; (1983); p. 719 - 723 View in Reaxys

74 %

With octylated silica, hydrogen, cetyltrimethylammonim bromide, Rh(cod)(PPh3)2PF6, Time= 4h, T= 80 °C , p= 10343Torr Abu-Reziq, Raed; Blum, Jochanan; Avnir, David; Chemistry - A European Journal; vol. 10; nb. 4; (2004); p. 958 962 View in Reaxys

70.1 %

With methanesulfonic acid, Pt(C2H4)(1,3-bis(diphenylphosphino)butane), hydrogen in toluene, Time= 22h, T= 25 °C , p= 60800Torr , var. Pt catalyst, cocatalysts, solvents, temp. and pressure, Product distribution, Kinetics, Mechanism Matteoli, U.; Scrivanti, A.; Paganelli, S.; Journal of Organometallic Chemistry; vol. 476; nb. 2; (1994); p. 145 - 152 View in Reaxys

65 %

With methanol, sodium tetrahydroborate, cobalt(II) chloride in tetrahydrofuran, CoCl2 - NaBH4 - CH3OH, 0 deg C, 1 h, then alkene, room temp., 3 h Satyanarayana, N.; Periasamy, M.; Tetrahedron Letters; vol. 25; nb. 23; (1984); p. 2501 - 2504 View in Reaxys

65 %

With formic acid, [Ru(PPh3)2(CH3CN)3Cl][BPh4], Time= 6h, T= 100 °C Naskar, Sipra; Bhattacharjee, Manish; Tetrahedron Letters; vol. 48; nb. 3; (2007); p. 465 - 467 View in Reaxys

62 %

With nickel(II) nitrate hexahydrate, hydrazine hydrate, sodium hydroxide in isopropyl alcohol, Time= 8h, T= 60 °C Popov; Mokhov; Nebykov; Russian Journal of General Chemistry; vol. 84; nb. 3; (2014); p. 444 - 448; Zh. Obshch. Khim.; vol. 84; nb. 3; (2014); p. 385 - 390,6 View in Reaxys

60 %

With [bis(cyclopentadienyl)zirconium(IV)(PCy2)][(methyl)(pentafluorophenyl)3borate], hydrogen, Time= 2h, T= 20 °C , Glovebox, Schlenk technique Normand, Adrien T.; Daniliuc, Constantin G.; Wibbeling, Birgit; Kehr, Gerald; Le Gendre, Pierre; Erker, Gerhard; Journal of the American Chemical Society; vol. 137; nb. 33; (2015); p. 10796 - 10808 View in Reaxys

Ca. 50 %

With [(η5-pentamethylcyclopentadienyl)IrIIIbis-(κC-1,3-dimethylimidazol-2-ylidene)Cl]BF4, potassium hydoxide in isopropyl alcohol, Time= 5h, T= 60 °C , Reagent/catalyst Campos, Jesus; Hintermair, Ulrich; Brewster, Timothy P.; Takase, Michael K.; Crabtree, Robert H.; ACS Catalysis; vol. 4; nb. 3; (2014); p. 973 - 985 View in Reaxys

48 %

With hydrogen in hexane, Time= 6h, T= 24.84 °C , p= 750.075Torr Boutros, Maya; Denicourt-Nowicki, Audrey; Roucoux, Alain; Gengembre, Leon; Beaunier, Patricia; Gedeon, Antoine; Launay, Franck; Chemical Communications; nb. 25; (2008); p. 2920 - 2922 View in Reaxys

16 %

With hydrazine hydrate in ethanol, Time= 24h, Reflux Chen, Hao; Wang, Jianmin; Hong, Xuechuan; Zhou, Hai-Bing; Dong, Chune; Canadian Journal of Chemistry; vol. 90; nb. 9; (2012); p. 758 - 761 View in Reaxys Hydrogenation

9/96

2016-06-28 15:56:50

Komatsu; Mitsui; Recueil des Travaux Chimiques des Pays-Bas; vol. 57; (1938); p. 586,587, 589 View in Reaxys With hydrogen, lt;Rh(NBD)(PPh3)2gt;lt;ClO4gt; in diethylene glycol dimethyl ether, water, Time= 1h, T= 30 °C , p= 735.5Torr , influence of the phosphorus ligands in cationic rhodium complexes on its catalytic activity for hydrogenation of the olefinic bond, Product distribution Fujitsu, Hiroshi; Matsumura, Eiichi; Takeshita, Kenjiro; Mochida, Isao; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2650 - 2655 View in Reaxys With hydrogen, OsHCl(CO)(PMe-t-Bu2)2 in isopropyl alcohol, T= 23 °C , p= 760Torr , Kinetics, Rate constant Andriollo, Antida; Esteruelas, Miguel A.; Meyer, Uwe; Oro, Luis A.; Sanchez-Delgado, Roberto A.; et al.; Journal of the American Chemical Society; vol. 111; nb. 19; (1989); p. 7431 - 7437 View in Reaxys With hydrogen, magnesium hydroxide, rhodium in ethanol, T= 30 °C , further catalysts, Rate constant Nakao, Yukimichi; Kaeriyama, Kyoji; Chemistry Letters; (1983); p. 949 - 950 View in Reaxys With hydrogen, monoaluminum phosphate, silica gel, platinum in methanol, T= 27 °C , p= 3750.3Torr , initial reduction rate was determined Aramendia, M. A.; Borau, V.; Jimenez, C.; Marinas, J. M.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 110; nb. 1; (1982); p. 97 - 101 View in Reaxys With hydrogen, lt;Rh(μ-Cl)(CO)2(dpm)2gt;(1+) (2.0E-3 M) in methanol, T= 22 °C , p= 760Torr , further catalysts, Mechanism Sanger, Alan R.; Canadian Journal of Chemistry; vol. 60; (1982); p. 1363 - 1367 View in Reaxys 88.5 % Chromat.

With hydrogen, B(2,75) in benzene, Time= 23h, T= 25 °C , catalist, temperature, Product distribution Brzezinska, Zofia C.; Cullen, William R.; Strukul, Giorgio; Canadian Journal of Chemistry; vol. 58; (1980); p. 750 - 754 View in Reaxys With hydrogen, OsH3Cl(CO)(PiPr3)2 in benzene, Time= 2h, T= 60 °C , p= 750.06Torr , effect of use of var. solvents and var. times, Product distribution Esteruelas, Miguel A.; Sola, Eduardo; Oro, Luis A.; Meyer, Uwe; Werner, Helmut; Angewandte Chemie; vol. 100; nb. 11; (1988); p. 1621 - 1622 View in Reaxys

96 % Chromat.

With hydrogen, (o-OC6H4CH3)3PRuCl(PPh3)2, Time= 3.5h, T= 165 °C , p= 4137.2Torr , other catalysts, Product distribution Lewis,L.N.; Journal of the American Chemical Society; vol. 108; (1986); p. 743 View in Reaxys With hydrogen, lt;lt;Pri2P(CH2)3PPrigt;Rhgt;2(μ-H)2 in toluene, T= 30 °C , p= 760Torr , other catalysts, Rate constant, Mechanism Fryzuk, Michael D.; Piers, Warren E.; Einstein, Frederick W. B.; Jones, Terry; Canadian Journal of Chemistry; vol. 67; (1989); p. 883 - 896 View in Reaxys With H2-dmbipy(2+), water, edetate disodium, platinum, Time= 20h, Irradiation, different catalysts, Mechanism Tan, Chee-Kai; Newberry, Vincent; Webb, Thomas R.; McAuliffe, Charles A.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1987); p. 1299 - 1304 View in Reaxys

10/96

2016-06-28 15:56:50

With hydrogen, aluminum oxide, nickel in methanol, T= 19.9 - 59.9 °C , p= 3075.2Torr , further catalysts; Ea, ln A, ΔH(excit.), ΔS(excit.); solvent effect, Thermodynamic data, Mechanism Bautista, Felipa M.; Campelo, Juan M.; Garcia, Angel; Guardeno, Rafael; Luna, Diego; Marinas, Jose M.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1989); p. 493 - 498 View in Reaxys With hydrogen, Co(acac)2-(+)-PPh2(neomenthyl)-AlEt3 in toluene, T= 20 °C , p= 760Torr , other catalyst, Product distribution, Rate constant Nindakova, L. O.; Pavlov, V. A.; Shmidt, F. K.; Klabunovskii, E. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; (1982); p. 1847 - 1851; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 9; (1982); p. 2094 - 2099 View in Reaxys With potassium hydroxide, isopropyl alcohol, immobilized rhodium, T= 82.4 °C , Rate constant Dovganyuk, V. F.; Isaeva, V. I.; Sharf, V. Z.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 37; nb. 6; (1988); p. 1074 - 1078; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 6; (1988); p. 1223 - 1228 View in Reaxys With hydrogen, palladium in diethyl ether, T= 25 °C , diff. alkenes and alkines Fowley, Lissa A.; Michos, Demetrius; Luo, Xiao-Liang; Crabtree, Robert H.; Tetrahedron Letters; vol. 34; nb. 19; (1993); p. 3075 - 3078 View in Reaxys With hydrogen, lt;Rh(NO)(PPh3)2(p-benzoquinone)gt; in toluene, T= 60 °C , p= 760Torr , hydrogenation, other pressure Cenini, Sergio; Ugo, Renato; Porta, Francesca; Gazzetta Chimica Italiana; vol. 111; nb. 7/8; (1981); p. 293 - 298 View in Reaxys 4090 % Turnov.

With Pt(PPh3)(SMe2)Cl2, hydrogen, tin(ll) chloride in acetone, Time= 2h, T= 60 °C , p= 31028.9Torr , var. platinum(II) complexes and SnCl2*2H2O concentrations, Product distribution Clark, Howard C.; Billard, Claude; Wong, Chun S.; Journal of Organometallic Chemistry; vol. 190; nb. 4; (1980); p. C105 - C116 View in Reaxys With di-μ-chlorobis(norbornadiene)dirhodium(I), ethanol, hydrogen, ethyl-diphenyl-phosphane, T= 50 °C , p= 750.06Torr , other olefins and primary alcohols; catalyst deactivation via decarbonylation of primary alcohols, Mechanism Kollar, Laszlo; Toeroes, Szilard; Heil, Balint; Marko, Laszlo; Journal of Organometallic Chemistry; vol. 192; nb. 2; (1980); p. 253 - 256 View in Reaxys With hydridotetracarbonylcobalt, carbon monoxide in dichloromethane, T= 0 °C , Rate constant Roth, Jerome A.; Wiseman, Paul; Ruszala, Lois; Journal of Organometallic Chemistry; vol. 240; nb. 3; (1982); p. 271 - 276 View in Reaxys With n-butyllithium, hydrogen, bis(cyclopentadienyl)titanium dichloride, Time= 3h, with various titanium complexes, at various times, Rate constant Booth, B. L.; Ofunne, G. C.; Stacey, C.; Tait, P. J. T.; Journal of Organometallic Chemistry; vol. 315; (1986); p. 143 - 156 View in Reaxys With bis(cyclopentadienyl)titanium dichloride, tert-butylmagnesium chloride, hydrogen in diethyl ether, T= 25 °C , p= 760Torr , other alkene, other catalyst system with var. Grignard or organolithium reagents

11/96

2016-06-28 15:56:50

Bergbreiter, David E.; Parsons, Gregory L.; Journal of Organometallic Chemistry; vol. 208; nb. 1; (1981); p. 47 54 View in Reaxys With hydrogen, pumice-supported Pd in tetrahydrofuran, T= 25 °C , p= 760Torr , E(a), var. temp., other catalyst, var. time, Thermodynamic data, Rate constant Duca, Dario; Liotta, Leonarda F.; Deganello, Giulio; Journal of Catalysis; vol. 154; nb. 1; (1995); p. 69 - 79 View in Reaxys With {(RuCl(1,4-bis(diphenylphosphino)butane)(.mu.-Cl))2}, hydrogen in DME, T= 30 °C , p= 785Torr , rate of hydrogenation, Mechanism Joshi, Ajey M.; MacFarlane, Kenneth S.; James, Brian R.; Journal of Organometallic Chemistry; vol. 488; nb. 1-2; (1995); p. 161 - 168 View in Reaxys With cobalt(III) acetylacetonate, (Bu3PhCH2N2PdCl4, hydrogen, triphenylphosphine in chloroform, water, T= 25 °C , homogeneous hydrogenation, other reaction partners, solvents Nindakova; Shmidt; Dmitrieva; Verkhozin; Russian Journal of Organic Chemistry; vol. 33; nb. 1; (1997); p. 11 - 16 View in Reaxys With nickel, T= 25 °C , p= 24271.8Torr , Hydrogenation Sasa; Yuki Gosei Kagaku Kyokaishi; vol. 12; (1954); p. 24; ; (1957); p. 2779 View in Reaxys With nickel, T= 203 °C , p= 735.5Torr , Hydrogenation Hata et al.; Bulletin of the Chemical Society of Japan; vol. 31; (1958); p. 775 View in Reaxys With aluminum nickel, T= 160 °C , Hydrogenation Borunowa et al.; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 1409,1410; engl. Ausg. S. 1383, 1384 View in Reaxys With ethanol, rhenium-catalyst, T= 135 °C , p= 88260.9Torr , Hydrogenation Broadbent et al.; Journal of the American Chemical Society; vol. 76; (1954); p. 1519,1521 View in Reaxys With hydrogen iodide, T= 280 °C Berthelot; Bulletin de la Societe Chimique de France; vol. <2> 9; (1868); p. 277; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1867); p. 349 View in Reaxys With ethanol, sodium Klages; Keil; Chemische Berichte; vol. 36; (1903); p. 1635 View in Reaxys With hydrogen, platinum Willstaetter; King; Chemische Berichte; vol. 46; (1913); p. 535 View in Reaxys With sodium ammonium, ammonia Lebeau; Picon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 157; (1913); p. 223 View in Reaxys With ethanol, rhenium-catalyst, T= 110 °C , p= 117681Torr , Hydrogenation Broadbent et al.; Journal of Organic Chemistry; vol. 24; (1959); p. 1847,1852

12/96

2016-06-28 15:56:50

View in Reaxys 100 % Spectr.

With sodium hydrogen telluride in ethanol, Time= 2.5h, Heating Barton, Derek H. R.; Bohe, Luis; Lusinchi, Xavier; Tetrahedron Letters; vol. 28; nb. 52; (1987); p. 6609 - 6612 View in Reaxys With NiCRASi in DME, Time= 1h, T= 45 °C , Yield given Fort, Y; Vanderesse, R; Caubere, P; Tetrahedron Letters; vol. 27; nb. 45; (1986); p. 5487 - 5490 View in Reaxys With hydrogenchloride, water, n-propylmagnesium bromide, Yield given. Multistep reaction Sato, Fumie; Ishikawa, Hiroaki; Sato, Masao; Tetrahedron Letters; vol. 21; nb. 4; (1980); p. 365 - 368 View in Reaxys With C/poly PPV2+-Pd electrodes in methanol, water, Ambient temperature, electrolysis at pH=1, Yield given Coche, Liliane; Ehui, Bernadette; Limosin, Daniele; Moutet, Jean-Claude; Journal of Organic Chemistry; vol. 55; nb. 23; (1990); p. 5905 - 5910 View in Reaxys With hydrogen, magnesium hydroxide, nickel boride Nakao, Yukimichi; Chemistry Letters; (1982); p. 997 - 998 View in Reaxys With sodium tetrahydroborate, boron trifluoride diethyl etherate, propionic acid, 1.) diglyme, 1 h, RT; 2.) diglyme, 140 deg C, 2 h, Yield given. Multistep reaction Brown, Herbert C.; Murray, Kenneth J.; Tetrahedron; vol. 42; nb. 20; (1986); p. 5497 - 5504 View in Reaxys With hydrogen, lt;Rh(NBD)(PPh3)2gt;lt;ClO4gt; in diethylene glycol dimethyl ether, water, Time= 1h, T= 30 °C , p= 735.5Torr Fujitsu, Hiroshi; Matsumura, Eiichi; Takeshita, Kenjiro; Mochida, Isao; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2650 - 2655 View in Reaxys With hydrogen, 2.0E-3 M lt;Rh(μ-Cl)(CO)2(dpm)2gt;(1+) in methanol, T= 22 °C , p= 760Torr Sanger, Alan R.; Canadian Journal of Chemistry; vol. 60; (1982); p. 1363 - 1367 View in Reaxys

96 % Chromat.

With hydrogen, (o-OC6H4CH3)3PRuCl(PPh3)2, Time= 3.5h, T= 165 °C , p= 4137.2Torr Lewis,L.N.; Journal of the American Chemical Society; vol. 108; (1986); p. 743 View in Reaxys With hydrogen, lt;lt;Pri2P(CH2)2PPrigt;Rhgt;2(μ-H)2 in toluene, T= 30 °C , p= 760Torr , Yield given Fryzuk, Michael D.; Piers, Warren E.; Einstein, Frederick W. B.; Jones, Terry; Canadian Journal of Chemistry; vol. 67; (1989); p. 883 - 896 View in Reaxys With sodium tetrahydroborate, aluminium trichloride in tetrahydrofuran, Time= 2h, Heating, Yield given Ono, Aoi; Maruyama, Tamiko; Suzuki, Nobuko; Synthetic Communications; vol. 17; nb. 8; (1987); p. 1001 - 1006 View in Reaxys With hydrogen, triphenylphosphine, lt;closo-3,3-(PPh3)2-3-H-3,1,2-RhC2B9H11gt; in tetrahydrofuran, T= 40.8 °C Behnken, Paul E.; Belmont, James A.; Busby, David C.; Delaney, Mark S.; King, Roswell E.; et al.; Journal of the American Chemical Society; vol. 106; (1984); p. 3011 - 3025 View in Reaxys

13/96

2016-06-28 15:56:50

99 % Chromat.

With hydrogen, palladium in diethyl ether, T= 25 °C Fowley, Lissa A.; Michos, Demetrius; Luo, Xiao-Liang; Crabtree, Robert H.; Tetrahedron Letters; vol. 34; nb. 19; (1993); p. 3075 - 3078 View in Reaxys With hydrogen, lt;(η5-C5H5)2ZrH(CH2PPh2)gt;300 in tetrahydrofuran, Time= 1h, T= 80 °C , p= 30002.4Torr , Yield given Choukroun, Robert; Basso-Bert, Mario; Gervais, Daniele; Journal of the Chemical Society, Chemical Communications; nb. 17; (1986); p. 1317 - 1319 View in Reaxys With carbon monoxide, hydrogen, tricarbonylbis(triphenylphosphine)ruthenium(0) in benzene-d6, Irradiation Gordon, Edward M.; Eisenberg, Richard; Journal of Organometallic Chemistry; vol. 306; (1986); p. C53 - C57 View in Reaxys With hydrogen, Pd(2-diphenylphosphino)benzaldehyde benzoylhydrazonato(CH3CO2) in methanol, Time= 24h, T= 25 °C , p= 760Torr , Yield given Bacchi, Alessia; Carcelli, Mauro; Costa, Mirco; Pelagatti, Paolo; Pelizzi, Corrado; Pelizzi, Giancarlo; Gazzetta Chimica Italiana; vol. 124; nb. 10; (1994); p. 429 - 436 View in Reaxys With hydrogen, lt;W2(OCH2tBu)6(py)2gt;, T= 23 °C , p= 2280Torr Barry, Jane T.; Chisholm, Malcolm H.; Journal of the Chemical Society, Chemical Communications; nb. 15; (1995); p. 1599 - 1600 View in Reaxys

98 % Chromat.

With LiH-NICRA in tetrahydrofuran, Time= 4h Fort, Yves; Tetrahedron Letters; vol. 36; nb. 34; (1995); p. 6051 - 6054 View in Reaxys With potassium hydroxide, hydrogen, electrolysis: Pt counter electrode, Hg-HgO-KOH reference electrode, 10 mA, Yield given Inoue, Hiroshi; Abe, Toshiyuki; Iwakura, Chiaki; Chemical Communications; nb. 1; (1996); p. 55 - 56 View in Reaxys With hydrogen, lt;fulvalene(Cr2(CO)6)gt; in tetrahydrofuran McGovern, Patricia A.; Peter; Vollhardt; Chemical Communications; nb. 13; (1996); p. 1593 - 1594 View in Reaxys With acetato(phenyl 2-pyridyl ketone thiosemicarbazonato)palladium(II), hydrogen, Time= 48h, T= 30 °C Pelagatti, Paolo; Venturini, Andrea; Leporati, Andrea; Carcelli, Mauro; Costa, Mirco; Bacchi, Alessia; Pelizzi, Giancarlo; Pelizzi, Corrado; Journal of the Chemical Society - Dalton Transactions; nb. 16; (1998); p. 2715 - 2721 View in Reaxys

100 % Chromat.

With Amberlite IRA-400, borohydride form, copper(II) sulfate in methanol, Time= 1h, T= 20 °C , Reduction Sim, Tae Bo; Yoon, Nung Min; Bulletin of the Chemical Society of Japan; vol. 70; nb. 5; (1997); p. 1101 - 1107 View in Reaxys With parahydrogen, [Rh(COD)(1,4-bis(diphenylphosphino)butane)]BF4 in acetone, other styrene derivatives, Rate constant, Mechanism Huebler, Patrick; Giernoth, Ralf; Kuemmerle, Guenther; Bargon, Joachim; Journal of the American Chemical Society; vol. 121; nb. 22; (1999); p. 5311 - 5318 View in Reaxys With hydrogen, Montmorillonite, palladium in toluene, T= 29.85 °C , Catalytic hydrogenation, Kinetics, Further Variations: Catalysts

14/96

2016-06-28 15:56:50

Kiraly, Zoltan; Veisz, Bernadett; Mastalir, Agnes; Razga, Zsolt; Dekany, Imre; Chemical Communications; nb. 19; (1999); p. 1925 - 1926 View in Reaxys With hydrogen, triphenylphosphine, bis(ethylene)rhodium(I) chloride dimer in hexane, toluene, Time= 1h, T= 63.5 °C , Catalytic hydrogenation, Kinetics, Further Variations: Reagents, Solvents, Temperatures Hope, Eric G.; Kemmitt, Ray D.W.; Paige, Danny R.; Stuart, Alison M.; Journal of Fluorine Chemistry; vol. 99; nb. 2; (1999); p. 197 - 200 View in Reaxys 94 % Chromat.

With aluminum oxide, sodium tetrahydroborate, nickel dichloride in hexane, Time= 3h, T= 30 °C , Hydrogenation, Product distribution, Further Variations: Reagents Yakabe; Hirano; Morimoto; Tetrahedron Letters; vol. 41; nb. 35; (2000); p. 6795 - 6798 View in Reaxys

90 % Chromat.

With aluminum oxide, sodium tetrahydroborate, nickel dichloride in hexane, Time= 3h, T= 30 °C , Catalytic hydrogenation Yakabe; Hirano; Morimoto; Tetrahedron Letters; vol. 41; nb. 35; (2000); p. 6795 - 6798 View in Reaxys

72 % Chromat.

With potassium fluoride, polymethylhydrosiloxane, bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran, Time= 24h, T= 70 °C Maleczka Jr., Robert E.; Rahaim Jr., Ronald J.; Teixeira, Robson R.; Tetrahedron Letters; vol. 43; nb. 39; (2002); p. 7087 - 7090 View in Reaxys With dibromobis(triphenylphosphine)nickel(II), diphenylphosphane in benzene-d6, Time= 48h, T= 20 °C Kazankova; Shulyupin; Borisenko; Beletskaya; Russian Journal of Organic Chemistry; vol. 38; nb. 10; (2002); p. 1479 - 1484 View in Reaxys With acetylacetonatodicarbonylrhodium(l), o,o'-dimethylene(tri-p-cresyl)bicyclophosphite, hydrogen, sodium tetrahydroborate in N,N-dimethyl-formamide, T= 49.85 °C , atmospheric pressure, Product distribution, Further Variations: Reagents Kudryavtsev; Teleshev; Nifant'ev; Linert; Russian Chemical Bulletin; vol. 52; nb. 12; (2003); p. 2740 - 2746 View in Reaxys With hydrogen, [PdCl(4-Me-BPI)] in tetrahydrofuran, Time= 8.33333h, T= 25 °C , p= 750.06Torr , Product distribution, Further Variations: Solvents, reaction times Siggelkow, Bettina; Meder, Markus B.; Galka, Christian H.; Gade, Lutz H.; European Journal of Inorganic Chemistry; nb. 17; (2004); p. 3424 - 3435 View in Reaxys With hydrogen, Pd147(o-phenanthroline)32O60(OC(O)tBu)30, T= 20 °C , Kinetics, Further Variations: Catalysts Stolyarov; Gaugash; Kryukova; Kochubei; Vargaftik; Moiseev; Russian Chemical Bulletin; vol. 53; nb. 6; (2004); p. 1194 - 1199 View in Reaxys

98 % Chromat.

With hydrogen, (iPrPDI)Fe(N2)2 in toluene, Time= 0.266667h, T= 22 °C , p= 760Torr Bart, Suzanne C.; Lobkovsky, Emil; Chirik, Paul J.; Journal of the American Chemical Society; vol. 126; nb. 42; (2004); p. 13794 - 13807 View in Reaxys With hydrogen, palladium(II) acetylacetonate, phenylphosphane in N,N-dimethyl-formamide, T= 30 °C , p= 760Torr , Product distribution, Further Variations: catalyst composition Belykh; Goremyka; Shmidt; Russian Journal of Applied Chemistry; vol. 77; nb. 5; (2004); p. 770 - 774 View in Reaxys

15/96

2016-06-28 15:56:50

With hydrogen, triethylamine, {[bis(2-diPhphosphinoxynaphthalen-1-yl)methane]-Rh(COD)}BF4 in tetrahydrofuran, Time= 3h, T= 25 °C , p= 5171.48Torr Punji, Benudhar; Mague, Joel T.; Balakrishna, Maravanji S.; Dalton Transactions; vol. 6; nb. 10; (2006); p. 1322 1330 View in Reaxys With [Ir2(μ-H)(μ-Pz)2H2(OSO2CF3)(NCMe)(PiPr3)2] in 1,2-dichloro-ethane, Time= 1.5h, T= 59.85 °C , p= 750.06Torr Martin, Marta; Sola, Eduardo; Tejero, Santiago; Lopez, Jose A.; Oro, Luis A.; Chemistry - A European Journal; vol. 12; nb. 15; (2006); p. 4057 - 4068 View in Reaxys 100 % Spectr.

With hydrogen, [Rh(PyP)(COD)]BPh4 in tetrahydrofuran, Time= 0.583333h, T= 55 °C , p= 6205.78Torr , Product distribution, Further Variations: Catalysts, reaction times Messerle, Barbara A.; Page, Michael J.; Turner, Peter; Dalton Transactions; nb. 32; (2006); p. 3927 - 3933 View in Reaxys With silicon sesquioxide, perfluoro-1,3-dimethylcyclohexane, hydrogen, tris(4-tridecafluoro-n-hexylphenyl)phosphine, bis(ethylene)rhodium(I) chloride dimer in toluene, Time= 1h, T= 63.5 °C , p= 760Torr , Product distribution, Further Variations: Reagents, silica porosity, without support, amount of reagent Hope, Eric G.; Sherrington, James; Stuart, Alison M.; Advanced Synthesis and Catalysis; vol. 348; nb. 12-13; (2006); p. 1635 - 1639 View in Reaxys With hydrogen, [RuCl(C10H14)-2,6-C5H3N{CH2OP(-OC10H6)S(C10H6O-)}2-P,P][Cl] in tetrahydrofuran, T= 80 °C , p= 3040Torr , Product distribution, Further Variations: reaction time Punji, Benudhar; Balakrishna, Maravanji S.; Journal of Organometallic Chemistry; vol. 692; nb. 8; (2007); p. 1683 - 1689 View in Reaxys With hydrogen, 4-hexadecylaniline stabilized Pt nanoparticles in cyclohexane, T= 79.84 °C , p= 10343.2Torr Mandal, Saikat; Selvakannan; Roy, Debdut; Chaudhari, Raghunath V.; Sastry, Murali; Chemical Communications; nb. 24; (2002); p. 3002 - 3003 View in Reaxys With hydrogen, palladium, Time= 4h, p= 258581Torr Yeung; Lee C.T.; Johnston; Crooks; Chemical Communications; nb. 21; (2001); p. 2290 - 2291 View in Reaxys With 1,3-bis-(diphenylphosphino)propane, caesium carbonate, isopropyl alcohol, bis(1,5-cyclooctadiene)diiridium(I) dichloride in toluene, Time= 4h, T= 80 °C Sakaguchi; Yamaga; Ishii; Journal of Organic Chemistry; vol. 66; nb. 13; (2001); p. 4710 - 4712 View in Reaxys With carbon dioxide, fluorous reverse-phase silica, hydrogen, [RhCl{P(C6H4-p-CH2CH2(CF2)6F)3}3] in cyclohexane, T= 40 °C , p= 67506.8Torr Ablan, Christopher D.; Hallett, Jason P.; West, Kevin N.; Jones, Rebecca S.; Eckert, Charles A.; Liotta, Charles L.; Jessop, Philip G.; Chemical Communications; nb. 24; (2003); p. 2972 - 2973 View in Reaxys

100 % Chromat.

With hydrogen, triethylaluminum, palladium(II) acetylacetonate in hexane, toluene, T= 30 °C , p= 760.051Torr , Product distribution, Further Variations: Reagents Belykh; Titova; Umanets; Shmidt; Russian Journal of Applied Chemistry; vol. 79; nb. 8; (2006); p. 1271 - 1277 View in Reaxys With hydrogen, ruthenium, Time= 10h, T= 20 °C , p= 750.075Torr

16/96

2016-06-28 15:56:50

Nowicki, Audrey; Zhang, Yong; Leger, Bastien; Rolland, Jean-Paul; Bricout, Herve; Monflier, Eric; Roucoux, Alain; Chemical Communications; nb. 3; (2006); p. 296 - 298 View in Reaxys 100 % Chromat.

With hydrogen, triethylamine, cis-[Rh(COD){κ2-P,O-Ph2PC6H4OC6H4PPh2=NP(O)(OPh)2}][OTf] in tetrahydrofuran, Time= 1.33333h, T= 20 °C , p= 3040.2Torr , Kinetics Venkateswaran, Ramalingam; Balakrishna, Maravanji S.; Mobin, Shaikh M.; European Journal of Inorganic Chemistry; nb. 13; (2007); p. 1930 - 1938 View in Reaxys 3 With sodium hypochlorite, acetic acid, hydrazine in water, Time= 5h, T= 10 - 60 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; JP2005/350427; (2005); (A) Japanese View in Reaxys 19 With sodium bromate, montmorillonite K-10, hydrazine, tetrabutylammomium bromide in water, acetonitrile, Time= 19h, T= 40 - 55 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; JP2005/350427; (2005); (A) Japanese View in Reaxys 20 With sodium bromate, acetic acid, hydrazine in water, acetonitrile, Time= 14.5h, T= 60 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; JP2005/350427; (2005); (A) Japanese View in Reaxys 18 With sodium bromate, propionic acid, hydrazine in water, Time= 3.5h, T= 60 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; JP2005/350427; (2005); (A) Japanese View in Reaxys 17 With sodium bromate, phosphoric acid, hydrazine, tetrabutylammomium bromide in water, acetonitrile, Time= 6.5h, T= 60 - 70 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; JP2005/350427; (2005); (A) Japanese View in Reaxys 1 With dihydrogen peroxide, acetic acid, hydrazine, copper(l) chloride in water, Time= 5h, T= 0 - 10 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; JP2005/350427; (2005); (A) Japanese View in Reaxys 2 With sodium chlorate, acetic acid, hydrazine in water, Time= 3.5h, T= 60 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; JP2005/350427; (2005); (A) Japanese View in Reaxys 3 : EXAMPLE 3 EXAMPLE 3

17/96

2016-06-28 15:56:50

Toluene (5 ml) and a cyclometallated complex of formula XVII (0.011 gms, 0.011 mmol) were combined in a 90 ml thick walled glass bottle. Styrene (1 ml, 8.75 mmol) was added to the solution and the bottle was sealed. The bottle was then pressurized with hydrogen (80 psi) and heated to 165° with stirring for 31/2 hours. After cooling, the solution was analyzed by gas chromatography, which showed a 96percent conversion to ethyl benzene. With hydrogen in toluene Patent; General Electric Company; US4645849; (1987); (A1) English View in Reaxys 100 % Chromat.

With hydrogen, [Rh(COD)(κ3-triphos)]PF6 in tetrahydrofuran, Time= 10h, T= 50 °C , p= 750.075Torr , Kinetics, Further Variations: Catalysts, Reagents Chaplin, Adrian B.; Dyson, Paul J.; European Journal of Inorganic Chemistry; nb. 31; (2007); p. 4973 - 4979 View in Reaxys With hydrogen, Methylated β-cyclodextrin in water, Time= 11h, T= 20 °C , p= 750.075Torr Denicourt-Nowicki, Audrey; Ponchel, Anne; Monflier, Eric; Roucoux, Alain; Dalton Transactions; nb. 48; (2007); p. 5714 - 5719 View in Reaxys With hydrogen, palladium nanoparticles embedded in polysiloxane matrix, T= 120 °C , p= 600.06Torr , Kinetics Trapp, Oliver; Weber, Sven K.; Bauch, Sabrina; Hofstadt, Werner; Angewandte Chemie - International Edition; vol. 46; nb. 38; (2007); p. 7307 - 7310 View in Reaxys

100 % Turnov.

With hydrogen, poly(diallyldimethylammonium Cl)-supported, [Pt30(CO)60]2- in water, Time= 12h, T= 26.84 °C , p= 37503.8Torr Maity, Prasenjit; Basu, Susmit; Bhaduri, Sumit; Lahiri, Goutam Kumar; Advanced Synthesis and Catalysis; vol. 349; nb. 11-12; (2007); p. 1955 - 1962 View in Reaxys With hydrogen, palladium in isopropyl alcohol, Time= 0.0833333h, T= 20 °C , p= 760.051Torr Chun, Yu Sung; Shin, Ju Yeon; Song, Choong Eui; Lee, Sang-Gi; Chemical Communications; nb. 8; (2008); p. 942 - 944 View in Reaxys With air, hydrazine hydrate in ethanol, Time= 4h, T= 25 °C Smit, Christian; Fraaije, Marco W.; Minnaard, Adriaan J.; Journal of Organic Chemistry; vol. 73; nb. 23; (2008); p. 9482 - 9485 View in Reaxys With COD-rhodium(I) complex in silver, hydrogen in 1,2-dichloro-ethane, Time= 24h, T= 80 °C , p= 10343.2Torr Yosef, Itzik; Abu-Reziq, Raed; Avnir, David; Journal of the American Chemical Society; vol. 130; nb. 36; (2008); p. 11880 - 11882 View in Reaxys With hydrogen, Time= 4h, T= 40 °C , p= 3800.26Torr , Autoclave Wu, Lei; Li, Zhi-Wei; Zhang, Feng; He, Yan-Mei; Fan, Qing-Hua; Advanced Synthesis and Catalysis; vol. 350; nb. 6; (2008); p. 846 - 862 View in Reaxys With hydrogen, Time= 7h, T= 34.84 °C , p= 760.051Torr Henschel, Antje; Gedrich, Kristina; Kraehnert, Ralph; Kaskel, Stefan; Chemical Communications; nb. 35; (2008); p. 4192 - 4194 View in Reaxys

18/96

2016-06-28 15:56:50

With C32H56CaN2O2Si2, hydrogen in benzene, Time= 15h, T= 20 °C , p= 7500.75Torr , Inert atmosphere, Autoclave Spielmann, Jan; Buch, Frank; Harder, Sjoerd; Angewandte Chemie - International Edition; vol. 47; nb. 49; (2008); p. 9434 - 9438 View in Reaxys 27 %Chromat.

With chloro(1,5-cyclooctadiene)rhodium(I) dimer, carbon monoxide, hydrogen, sodium 3-(diphenylphosphanyl)benzenesulfonate in tetrahydrofuran, 1,2-dichloro-ethane, Time= 14h, T= 80 °C , p= 43729.4Torr Hamza, Khalil; Schumann, Herbert; Blum, Jochanan; European Journal of Organic Chemistry; nb. 10; (2009); p. 1502 - 1505 View in Reaxys

100 With hydrogen, [BMMIM][PF6], p= 750.075Torr , Autoclave %Chromat. Hu, Yu; Yu, Yinyin; Hou, Zhenshan; Li, Huan; Zhao, Xiuge; Feng, Bo; Advanced Synthesis and Catalysis; vol. 350; nb. 13; (2008); p. 2077 - 2085 View in Reaxys 100 With hydrogen, HEA16Cl, randomly methylated β-cyclodextrin in water, Time= 1.2h, T= 20 °C , p= 750.075Torr %Chromat. Hubert, Claudie; Denicourt-Nowicki, Audrey; Roucoux, Alain; Landy, David; Leger, Bastien; Crowyn, Gregory; Monflier, Eric; Chemical Communications; nb. 10; (2009); p. 1228 - 1230 View in Reaxys With hydrogen in methanol, T= 20 °C , p= 760.051Torr , Darkness Nakamula, Ikuse; Yamanoi, Yoshinori; Yonezawa, Tetsu; Imaoka, Takane; Yamamoto, Kimihisa; Nishihara, Hiroshi; Chemical Communications; nb. 44; (2008); p. 5716 - 5718 View in Reaxys With hydrogen in water, Time= 2h, T= 35 °C , p= 760.051Torr Lan, Yang; Zhang, Minchao; Zhang, Wangqing; Yang, Li; Chemistry - A European Journal; vol. 15; nb. 15; (2009); p. 3670 - 3673 View in Reaxys 81 %Chromat.

With Basolite® A100, ammonia, hydrazine hydrate in acetonitrile, Time= 24h, T= 25 °C , chemoselective reaction Dhakshinamoorthy, Amarajothi; Alvaro, Mercedes; Garcia, Hermenegildo; Advanced Synthesis and Catalysis; vol. 351; nb. 14-15; (2009); p. 2271 - 2276 View in Reaxys With 5-palladium/activated carbon, glycerol, Time= 5h, T= 70 °C Wolfson, Adi; Dlugy, Christina; Shotland, Yoram; Tavor, Dorith; Tetrahedron Letters; vol. 50; nb. 43; (2009); p. 5951 - 5953 View in Reaxys With Mo(CO)3(NCMe)(PPh3)2, hydrogen, Time= 8h, T= 99.84 °C , p= 45603.1Torr Baricelli, Pablo J.; Melean, Luis G.; Ricardes, Santiago; Guanipa, Victor; Rodriguez, Mariandry; Romero, Carlos; Pardey, Alvaro J.; Moya, Sergio; Rosales, Merlin; Journal of Organometallic Chemistry; vol. 694; nb. 21; (2009); p. 3381 - 3385 View in Reaxys With hydrogen in methanol, chloroform, T= 25 °C , p= 760.051Torr Orneias, Catia; Diallo, Abdouk; Ruiz, Jaime; Astmc, Didier; Advanced Synthesis and Catalysis; vol. 351; nb. 13; (2009); p. 2147 - 2154 View in Reaxys With hydrogen in dichloromethane, T= 100 °C , p= 20252Torr Craythorne, Steven J.; Lorenzini, Kris Anderson Fabio; McCausland, Christina; Smith, Emily F.; Licence, Peter; Marr, Andrew C.; Marr, Patricia C.; Chemistry - A European Journal; vol. 15; nb. 29; (2009); p. 7094 - 7100

19/96

2016-06-28 15:56:50

View in Reaxys 86 %Chromat.

With [Tp(Me2)RhH(SPh)(MeCN)], hydrogen in tetrahydrofuran, Time= 10h, T= 50 °C , p= 760.051Torr Misumi, Yoshiyuki; Seino, Hidetake; Mizobe, Yasushi; Journal of the American Chemical Society; vol. 131; nb. 41; (2009); p. 14636 - 14637 View in Reaxys With oxygen, 5-ethyl-3-methyllumiflavin perchlorate, hydrazine hydrate in acetonitrile, Time= 8h, T= 30 °C , p= 760.051Torr Imada, Yasushi; Kitagawa, Takahiro; Ohno, Takashi; Iida, Hiroki; Naota, Takeshi; Organic Letters; vol. 12; nb. 1; (2010); p. 32 - 35 View in Reaxys

98 %Spectr.

With iododioxobis(triphenylphosphine)rhenium(V), Dimethylphenylsilane, Time= 26h, T= 45 °C , neat (no solvent) de Noronha, Rita G.; Romao, Carlos C.; Fernandes, Ana C.; Tetrahedron Letters; vol. 51; nb. 7; (2010); p. 1048 1051 View in Reaxys

> 99 With hydrogen, Time= 0.5h, T= 60 °C , p= 15001.5Torr %Chromat. Tao, Ranting; Miao, Shiding; Liu, Zhimin; Xie, Yun; Han, Buxing; An, Guimin; Ding, Kunlun; Green Chemistry; vol. 11; nb. 1; (2009); p. 96 - 101 View in Reaxys With bis(triphenylphosphane)(4,5-diazafluorene)dihydridorhodium(III) chloride - dichloromethane (1/0.125), hydrogen in methanol, Time= 27h, T= 20 °C , p= 760.051Torr Jiang, Huiling; Stepowska, Elzbieta; Song, Datong; European Journal of Inorganic Chemistry; nb. 14; (2009); p. 2083 - 2089 View in Reaxys With sodium tetrahydroborate, bis(acetylacetonato)palladium(II) in ethanol, N,N-dimethyl-formamide, T= 30 °C , p= 760.051Torr Titova; Belykh; Belonogova; Shmidt; Russian Journal of Applied Chemistry; vol. 82; nb. 11; (2009); p. 1978 1985 View in Reaxys With C16H22N4Rh, hydrogen in tetrahydrofuran, T= 27 °C , p= 2585.81Torr Page, Michael J.; Wagler, Joerg; Messerle, Barbara A.; Dalton Transactions; nb. 35; (2009); p. 7029 - 7038 View in Reaxys With Ph2P(CH2CH2O)16CH3, hydrogen, rhodium in water, butan-1-ol, Time= 1h, T= 60 °C , p= 7500.75Torr , Autoclave Li, Kaoxue; Wang, Yanhua; Jiang, Jingyang; Jin, Zilin; Catalysis Communications; vol. 11; nb. 6; (2010); p. 542 546 View in Reaxys > 99 With hydrogen in methanol, Time= 4h, p= 760.051Torr %Chromat. Park, Young Kwan; Choi, Sang Beom; Nam, Hye Jin; Jung, Duk-Young; Ahn, Hee Choon; Choi, Kihang; Furukawa, Hiroyasu; Kim, Jaheon; Chemical Communications; vol. 46; nb. 18; (2010); p. 3086 - 3088 View in Reaxys With C2H6OS*C25H29N2P*Cl2Ru, potassium tert-butylate, hydrogen in isopropyl alcohol, tert-butyl alcohol, Time= 12h, T= 70 °C , Inert atmosphere, enantioselective reaction Phillips, Scott D.; Fuentes, Jose A.; Clarke, Matthew L.; Chemistry - A European Journal; vol. 16; nb. 27; (2010); p. 8002 - 8005 View in Reaxys

20/96

2016-06-28 15:56:50

100 With [OsCl(PhNH2)(.eta.6-p-cymene)(tert-butyl isocyanide)](tetraphenylborate), hydrogen in toluene, Time= 22h, T= %Chromat. 80 °C , p= 38002.6Torr , Autoclave Albertin, Gabriele; Antoniutti, Stefano; Castro, Jesus; Paganelli, Stefano; Journal of Organometallic Chemistry; vol. 695; nb. 18; (2010); p. 2142 - 2152 View in Reaxys 100 With C30H44ClN2O4P2Rh, hydrogen, triethylamine in tetrahydrofuran, Time= 5h, T= 80 °C , p= 3040.2Torr , Auto%Chromat. clave Mohanty, Sasmita; Balakrishna, Maravanji S.; Journal of Chemical Sciences; vol. 122; nb. 2; (2010); p. 137 - 142 View in Reaxys With methanol, water, T= 99.84 °C , p= 15001.5Torr Xiang, Yizhi; Li, Xiaonian; Lu, Chunshan; Ma, Lei; Zhang, Qunfeng; Applied Catalysis A: General; vol. 375; nb. 2; (2010); p. 289 - 294 View in Reaxys With chlorobis(ethylene)rhodium(I) dimer, hydrogen, tris(4-tridecafluoro-n-hexylphenyl)phosphine in toluene, Time= 1h, T= 63 °C , p= 760.051Torr Audic, Nicolas; Dyer, Philip W.; Hope, Eric G.; Stuart, Alison M.; Suhard, Samuel; Advanced Synthesis and Catalysis; vol. 352; nb. 13; (2010); p. 2241 - 2250 View in Reaxys With [Pt(1,4-bis(diphenylphosphanyl)butane)(H2O)2][OTf]2, hydrogen, sodium dodecyl-sulfate in water, Time= 22h, T= 70 °C , p= 30003Torr , Autoclave, Gas phase Gottardo, Marina; Scarso, Alessandro; Paganelli, Stefano; Strukul, Giorgio; Advanced Synthesis and Catalysis; vol. 352; nb. 13; (2010); p. 2251 - 2262 View in Reaxys 100 With RhCl[2,6-bis{1-(4-trifluoromethylphenyl)iminoethyl}pyridine], potassium tert-butylate, hydrogen in isopropyl al%Chromat. cohol, Time= 0.0333333h, T= 60 °C , p= 760.051Torr Buil, Maria L.; Esteruelas, Miguel A.; Niembro, Sandra; Olivan, Montserrat; Orzechowski, Lars; Pelayo, Cristina; Vallribera, Adelina; Organometallics; vol. 29; nb. 19; (2010); p. 4375 - 4383 View in Reaxys With C213H233ClO31PRh, hydrogen in 1,4-dioxane, Time= 1h, p= 75007.5Torr , Autoclave Natarajan, Baskar; Jayaraman, Narayanaswamy; Journal of Organometallic Chemistry; vol. 696; nb. 3; (2011); p. 722 - 730 View in Reaxys With C14H9N2O2Rh, hydrogen in N,N-dimethyl-formamide Sagar, Priyanka; Rani, Varsha; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 40; nb. 10; (2010); p. 754 - 761 View in Reaxys With 1,2,3-trimethoxybenzene, [Rh{κ4-NNBN-B-(azaindolyl)3}(nortricyclyl)], hydrogen in benzene-d6, Time= 18h, T= 85 °C , p= 1875.19Torr Tsoureas, Nikolaos; Kuo, Yu-Ying; Haddow, Mairi F.; Owen, Gareth R.; Chemical Communications; vol. 47; nb. 1; (2011); p. 484 - 486 View in Reaxys With hydrogen, tin(IV) oxide in ethanol, Time= 5h, T= 70 °C , p= 760.051Torr Adnan, Rohana; Razana, Nur Ariesma; Rahman, Ismail Abdul; Farrukh, Muhammad Akhyar; Journal of the Chinese Chemical Society; vol. 57; nb. 2; (2010); p. 222 - 229 View in Reaxys

21/96

2016-06-28 15:56:50

99 %Chromat.

With hydrogen, ethylmagnesium chloride in tetrahydrofuran, Time= 24h, T= 100 °C , p= 15001.5Torr Stein, Mario; Wieland, Joerg; Steurer, Peter; Toelle, Folke; Muelhaupt, Rolf; Breit, Bernhard; Advanced Synthesis and Catalysis; vol. 353; nb. 4; (2011); p. 523 - 527 View in Reaxys

99 %Chromat.

With Fe3O4Rh, hydrazine hydrate in ethanol, Time= 14h, T= 80 °C , Inert atmosphere Jang, Youngjin; Kim, Seyoung; Jun, Samuel Woojoo; Kim, Byung Hyo; Hwang, Sunhwan; Song, In Kyu; Kim, B. Moon; Hyeon, Taeghwan; Chemical Communications; vol. 47; nb. 12; (2011); p. 3601 - 3603 View in Reaxys With gold on titanium oxide, hydrogen in toluene, Time= 8h, T= 60 °C , p= 760.051Torr Noujima, Akifumi; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Angewandte Chemie - International Edition; vol. 50; nb. 13; (2011); p. 2986 - 2989 View in Reaxys With hydrogen in n-heptane, T= 26.84 °C , p= 22502.3Torr , Autoclave, Kinetics Pelzer, Katrin; Haevecker, Michael; Boualleg, Malika; Candy, Jean-Pierre; Basset, Jean-Marie; Angewandte Chemie - International Edition; vol. 50; nb. 22; (2011); p. 5170 - 5173 View in Reaxys

6 %Spectr. With C39H57MoN2PSi2, phenylsilane, Time= 23h, T= 50 °C , Inert atmosphere Khalimon, Andrey Y.; Simionescu, Razvan; Nikonov, Georgii I.; Journal of the American Chemical Society; vol. 133; nb. 18; (2011); p. 7033 - 7053 View in Reaxys With hydrogen in water, Time= 9h, T= 90 °C Hu, Yu; Yu, Yinyin; Hou, Zhenshan; Yang, Hanming; Feng, Bo; Li, Huan; Qiao, Yunxiang; Wang, Xiangrui; Hua, Li; Pan, Zhenyan; Zhao, Xiuge; Chemistry - An Asian Journal; vol. 5; nb. 5; (2010); p. 1178 - 1184 View in Reaxys With triethylsilane, [ReBr(η2-C2H4)(NO)(η3-Sixantphos)], hydrogen in toluene, T= 80 °C , p= 7500.75Torr , Autoclave, Kinetics, Reagent/catalyst, Solvent, Temperature Dudle, Balz; Rajesh, Kunjanpillai; Blacque, Olivier; Berke, Heinz; Journal of the American Chemical Society; vol. 133; nb. 21; (2011); p. 8168 - 8178 View in Reaxys 14.9 g

With palladium/alumina, hydrogen, Time= 1.5h, T= 20 °C , neat (no solvent) Oyamada, Hidekazu; Naito, Takeshi; Kobayashi, Shu; Beilstein Journal of Organic Chemistry; vol. 7; (2011); p. 735 - 739; Art.No: 83 View in Reaxys With hydrogen in methanol, T= 20 °C , p= 760.051Torr , Darkness Nakamula, Ikuse; Yamanoi, Yoshinori; Imaoka, Takane; Yamamoto, Kimihisa; Nishihara, Hiroshi; Angewandte Chemie - International Edition; vol. 50; nb. 26; (2011); p. 5830 - 5833 View in Reaxys With BF4 (1-)*C17H22ClN2Ru(1+), isopropyl alcohol, potassium hydoxide in water, Time= 0.333333h, T= 90 °C , Inert atmosphere Horn, Sabine; Albrecht, Martin; Chemical Communications; vol. 47; nb. 31; (2011); p. 8802 - 8804 View in Reaxys With hydrogen in methanol, T= 30 °C Bryan, Marian C.; Hein, Christopher D.; Doherty, Elizabeth M.; Wernick, David; Eschelbach, John W.; Petersen, James V.; Beilstein Journal of Organic Chemistry; vol. 7; (2011); p. 1141 - 1149; Art.No: 132 View in Reaxys

22/96

2016-06-28 15:56:50

98 %Chromat.

With hydrogen in N,N-dimethyl-formamide, Time= 3.7h, p= 760.051Torr Islam, Manirul; Mondal, Paramita; Roy, Anupam Singha; Tuhina, Kazi; Transition Metal Chemistry; vol. 35; nb. 4; (2010); p. 427 - 435 View in Reaxys With 5 palladium on Al2O3, hydrogen in ethyl acetate, T= 70 °C Kirilin, Alexey; Mki-Arvela, Pivi; Rupp, Matthias; Toukoniitty, Esa; Kumar, Narendra; Kordas, Krizstian; Kustov, Leonid M.; Salmi, Tapio; Murzin, Dmitry Yu.; Research on Chemical Intermediates; vol. 36; nb. 1; (2010); p. 193 - 210 View in Reaxys Kirilin, Alexey; Maeki-Arvela, Paeivi; Rupp, Matthias; Toukoniitty, Esa; Kumar, Narendra; Kordas, Krizstian; Kustov, Leonid M.; Salmi, Tapio; Murzin, Dmitry Yu.; Research on Chemical Intermediates; vol. 36; nb. 2; (2010); p. 193 - 210 View in Reaxys With hydrogen in water, T= 25 °C , p= 7500.75Torr Zhu, Wenwen; Yang, Hanming; Yu, Yinyin; Hua, Li; Li, Huan; Feng, Bo; Hou, Zhenshan; Physical Chemistry Chemical Physics; vol. 13; nb. 30; (2011); p. 13492 - 13500 View in Reaxys With Rh/TiO2, hydrogen in [(2)H6]acetone, T= 20 °C Koptyug, Igor V.; Zhivonitko, Vladimir V.; Kovtunov, Kirill V.; ChemPhysChem; vol. 11; nb. 14; (2010); p. 3086 3088 View in Reaxys With phosphorus, hydrogen, bis(dibenzylideneacetone)-palladium(0) in N,N-dimethyl-formamide, T= 30 °C , p= 760.051Torr , Inert atmosphere Belykh; Skripov; Belonogova; Umanets; Stepanova; Schmidt; Kinetics and Catalysis; vol. 52; nb. 5; (2011); p. 702 - 710 View in Reaxys

25 %Chromat.

With C15H21I2IrN4O8S2 (2-)*2K(1+), glycerol, potassium hydoxide in dimethyl sulfoxide, Time= 14h, T= 120 °C , Aerobic conditions Azua, Arturo; Mata, Jose A.; Peris, Eduardo; Organometallics; vol. 30; nb. 20; (2011); p. 5532 - 5536 View in Reaxys With hydrogen, Time= 1.5h, T= 50 °C , p= 3000.3Torr , Ionic liquid Luska, Kylie L.; Moores, Audrey; Advanced Synthesis and Catalysis; vol. 353; nb. 17; (2011); p. 3167 - 3177 View in Reaxys With hydrogen in methanol, Time= 0.5h, T= 25 °C , p= 15001.5Torr , Inert atmosphere Wang, Yanfei; Biradar, Ankush V.; Duncan, Cole T.; Asefa, Tewodros; Journal of Materials Chemistry; vol. 20; nb. 36; (2010); p. 7834 - 7841 View in Reaxys With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II), water, isopropyl alcohol, p-benozquinone, copper dichloride in tert-butyl alcohol Dong, Guangbin; Teo, Peili; Wickens, Zachary K.; Grubbs, Robert H.; Science; vol. 333; nb. 6049; (2011); p. 1609 - 1612 View in Reaxys 2.3. Catalytic, recycling and kinetic experiments Unless specified otherwise, all hydrogenation reactions were carried out at 353 K in small glass vials placed inside a 200-mL autoclave with vigorous magnetic stirring (P900 RPM). Conversions and selectivities were measured by 1H NMR and gas chromatographic techniques. All hydrogenated products were initially identified by using authentic commercial samples of the expected products. The recycling experiments with 1 and 2 were carried out at 353 K under 50 and 40 bar H2 pressure, respectively, with a substrate-to-Ru molar ratio of 283 and 625 in 5 mL of metha-

23/96

2016-06-28 15:56:50

nol and water, respectively. Recycling experiments with 2 covering five successive batches were also carried out with styrene as the substrate, with a styrene-to-Ru molar ratio of 625 in 5 mL of methanol. Catalyst 1 was filtered off, washed several times with methanol, and used for the second batch. For the reaction with 2, the product was separated from the aqueous solution by ethyl acetate extraction(2 x 10 mL). The aqueous solution of 2 was then reused. A few recycling experiments were also carried out, where 2 was precipitated from the water solution by the addition of acetone and reused. The results obtained by both these methods of catalyst recovery were comparable. With hydrogen in methanol, water, Time= 4h, T= 79.84 °C , p= 30003Torr Indra, Arindam; Maity, Niladri; Maity, Prasenjit; Bhaduri, Sumit; Lahiri, Goutam Kumar; Journal of Catalysis; vol. 284; nb. 2; (2011); p. 176 - 183 View in Reaxys With hydrogen in ethyl acetate, Time= 0.166667h, T= 29.84 °C , p= 7500.75Torr Mao, Hui; Liao, Xuepin; Shi, Bi; Catalysis Communications; vol. 16; nb. 1; (2011); p. 210 - 214 View in Reaxys With hydrogen in ethanol, T= 80 °C , p= 15001.5Torr , Autoclave Liu, Zheng; Li, Zhilin; Wang, Feng; Liu, Jingjun; Ji, Jing; Park, Ki Chul; Endo, Morinobu; Materials Research Bulletin; vol. 47; nb. 2; (2012); p. 338 - 343 View in Reaxys With hydrogen in ethanol, Time= 1.5h, T= 20 °C Harraz; El-Hout; Killa; Ibrahim; Journal of Catalysis; vol. 286; (2012); p. 184 - 192 View in Reaxys With hydrogen in methanol, Time= 0.166667h, T= 20 °C , p= 7500.75Torr Biradar, Ankush V.; Biradar, Archana A.; Asefa, Tewodros; Langmuir; vol. 27; nb. 23; (2011); p. 14408 - 14418 View in Reaxys 97 %Chromat.

With water, ammonium chloride in methanol, nickel anode, Electrochemical reaction Vilar, Marcio; Navarro, Marcelo; Electrochimica Acta; vol. 59; (2012); p. 270 - 278 View in Reaxys With hydrogen, rhodium in n-heptane, toluene, Time= 1h, T= 60 °C , p= 7500.75Torr , Autoclave, Ionic liquid Zeng, Yan; Wang, Yanhua; Jiang, Jingyang; Jin, Zilin; Catalysis Communications; vol. 19; (2012); p. 70 - 73 View in Reaxys

80 %Chromat.

With [Cp*Ru(CO)2]2, hydrogen in benzene, Time= 6h, T= 170 °C , p= 3040.2Torr , Autoclave Stanowski, Sylvain; Nicholas, Kenneth M.; Srivastava, Radhey S.; Organometallics; vol. 31; nb. 2; (2012); p. 515 - 518 View in Reaxys With C14H6O8S2 (2-)*2H2O*Mg(2+), hydrogen in toluene, Time= 4h, T= 99.84 °C Platero-Prats, Ana E.; Iglesias, Marta; Snejko, Natalia; Monge, Angeles; Gutierrez-Puebla; Crystal Growth and Design; vol. 11; nb. 5; (2011); p. 1750 - 1758 View in Reaxys

100 With iron-iron oxide core-shell nanoparticles, hydrogen in ethanol, Time= 24h, T= 80 °C , p= 30003Torr , Autoclave %Chromat. Hudson, Reuben; Riviere, Antoine; Cirtiu, Ciprian M.; Luska, Kylie L.; Moores, Audrey; Chemical Communications; vol. 48; nb. 27; (2012); p. 3360 - 3362 View in Reaxys 100 %Spectr.

With C48H58ClN4O2PRu, hydrogen, Time= 6h, T= 45 °C , p= 3040.2Torr Lund, Clinton L.; Sgro, Michael J.; Cariou, Renan; Stephan, Douglas W.; Organometallics; vol. 31; nb. 3; (2012); p. 802 - 805 View in Reaxys

24/96

2016-06-28 15:56:50

With hydrogen in hexane, Time= 2.5h, p= 760.051Torr Lee, Kyu Hyung; Lee, Byeongno; Lee, Kyu Reon; Yi, Mi Hye; Hur, Nam Hwi; Chemical Communications; vol. 48; nb. 37; (2012); p. 4414 - 4416 View in Reaxys With hydrogen in water, Time= 1h, T= 50 °C , p= 750.075Torr Guerrero; Roucoux; Denicourt-Nowicki; Bricout; Monflier; Collire; Fajerwerg; Philippot; Catalysis Today; vol. 183; nb. 1; (2012); p. 34 - 41 View in Reaxys 52 %Spectr.

With hydrogen, Time= 2h, T= 100 °C , Ionic liquid, Ambient pressure Banerjee, Abhinandan; Theron, Robin; Scott, Robert W. J.; ChemSusChem; vol. 5; nb. 1; (2012); p. 109 - 116 View in Reaxys With hydrogen in methanol, Time= 0.3h, T= 25 °C , p= 15001.5Torr Wang, Yanfei; Biradar, Ankush V.; Asefa, Tewodros; ChemSusChem; vol. 5; nb. 1; (2012); p. 132 - 139 View in Reaxys With hydrogen in pentan-1-ol, water, Time= 1h, T= 60 °C , p= 7500.75Torr , Autoclave Chen, Zhijun; Wang, Yanhua; Jiang, Jingyang; Jin, Zilin; Chinese Journal of Catalysis; vol. 32; nb. 6-8; (2011); p. 1133 - 1137 View in Reaxys With oxygen, guanidine nitrate, hydrazine hydrate in ethanol, Time= 14h, T= 20 °C , p= 760.051Torr Lamani, Manjunath; Guralamata, Ravikumara Siddappa; Prabhu, Kandikere Ramaiah; Chemical Communications; vol. 48; nb. 52; (2012); p. 6583 - 6585 View in Reaxys With hydrogen in tetrahydrofuran, Time= 2h, T= 25 °C Wu, Yuen; Cai, Shuangfei; Wang, Dingsheng; He, Wei; Li, Yadong; Journal of the American Chemical Society; vol. 134; nb. 21; (2012); p. 8975 - 8981 View in Reaxys With hydrogen in methanol, Time= 1h, T= 20 °C , p= 750.075Torr Pandarus, Valerica; Gingras, Genevieve; Beland, Francois; Ciriminna, Rosaria; Pagliaro, Mario; Organic Process Research and Development; vol. 16; nb. 6; (2012); p. 1230 - 1234 View in Reaxys

57 %Chromat.

1.9 :Using the conditions shown in Scheme 5,2-phenylethanol (2a) was obtained in 77percent yield with exceptionally high anti-Markovnikov selectivity (38:1). Under the standard conditions, the reaction proceeded with an excellent product selectivity and byproducts (3a to 6a) were all formed in less than 2percent yield. The absence of the Pd catalyst shut down the production of oxygenated products completely, although the over-reduction product (ethylbenzene) was still formed in 26percent yield. Without Shvo's catalyst, no alcohol products were observed and aldehyde 5a was the major product. CuCl2 was originally intended as a co-oxidant and later appeared to play a critical role in slowing down the over-reduction, as the absence of CuCl2 led to significantly increased yields of ethylbenzene. 1,4Benzoquinone (BQ) is widely used as a hydrogen acceptor and two-electron oxidant in PdII-catalyzed reactions, and was found to be the best co-oxidant for this transformation, and omission of this component resulted in no alcohol formation. The role of i-PrOH as the reductant was highlighted by formation of aldehyde 5a (57percent yield) almost exclusively in its absence. t-BuOH proved to be responsible for enhanced reactivity and selectivity where without tBuOH, lower yields and regioselectivity of the primary alcohol was obtained. As expected, removal of water from the reaction mixture (using 4 Molecular sieves) is detrimental since no oxygenated product was observed under anhydrous conditions. With isopropyl alcohol, p-benozquinone, copper dichloride, dichloro bis(acetonitrile) palladium(II), 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) in tert-butyl alcohol, T= 85 °C , Product distribution / selectivity Patent; Dong, Guangbin; Grubbs, Robert H.; Teo, Peili; Wickens, Zach K.; US2012/172634; (2012); (A1) English

25/96

2016-06-28 15:56:50

View in Reaxys With hydrogen, Time= 12h, T= 35 °C , p= 750.075Torr Pan, Yingyi; Ma, Deyun; Liu, Huimin; Wu, Hao; He, Dehua; Li, Yingwei; Journal of Materials Chemistry; vol. 22; nb. 21; (2012); p. 10834 - 10839 View in Reaxys 78 %Spectr.

With hydrogen in water, Time= 24h, T= 20 °C , p= 62059.4Torr Zhang, Shiyong; Zhao, Yan; Chemical Communications; vol. 48; nb. 80; (2012); p. 9998 - 10000 View in Reaxys

100 With tetrakis[3,5-bis(trifluoromethyl)phenyl]boric acid bis(diethyl ether) complex, C32H63CoNP2Si, hydrogen in tetra%Chromat. hydrofuran, Time= 24h, T= 25 °C , p= 760.051Torr , Reagent/catalyst, Solvent, Time Zhang, Guoqi; Scott, Brian L.; Hanson, Susan K.; Angewandte Chemie - International Edition; vol. 51; nb. 48; (2012); p. 12102 - 12106; Angew. Chem.; (2012); p. 12077 View in Reaxys Catalytic hydrogenation of unsaturated organic compounds General procedure: a certain amount of BT-CF-Au/Pd catalyst (containing 2.5 μmol metal Pd), cyclohexene (10.0 mmol) and methanol (10.0 mL) were introduced into a 50.0 mL stainless steel autoclave equipped with a stirring bar. Then, the catalytic hydrogenation was conducted under 1.0 MPa of H2 at 298 K, and the obtained products were analyzed by gas chromatography With hydrogen in methanol, T= 24.84 °C , p= 7500.75Torr , Autoclave Ma, Jun; Huang, Xin; Liao, Xuepin; Shi, Bi; Journal of Molecular Catalysis A: Chemical; vol. 366; (2013); p. 8 - 16 View in Reaxys With Rh0.67Ni0.33, hydrogen in ethyl acetate, Time= 0.25h, T= 25 °C , p= 760.051Torr , Autoclave, Time Duan, Haohong; Wang, Dingsheng; Kou, Yuan; Li, Yadong; Chemical Communications; vol. 49; nb. 3; (2013); p. 303 - 305 View in Reaxys With acetylacetonatodicarbonylrhodium(l), carbon monoxide, C60H64O6P2, hydrogen in toluene, Time= 1h, T= 140 °C , p= 7500.75Torr Boymans, Evert; Janssen, Michele; Mueller, Christian; Lutz, Martin; Vogt, Dieter; Dalton Transactions; vol. 42; nb. 1; (2013); p. 137 - 142 View in Reaxys With hydrogen in tetrahydrofuran, T= 25 °C , p= 2250.23Torr Lara, Patricia; Ayvali, Tugce; Casanove, Marie-Jose; Lecante, Pierre; Mayoral, Alvaro; Fazzini, Pier-Francesco; Philippot, Karine; Chaudret, Bruno; Dalton Transactions; vol. 42; nb. 2; (2013); p. 372 - 382 View in Reaxys With hydrogen, Time= 0.5h, T= 80 °C , p= 3800.26 - 7600.51Torr , Autoclave, Temperature, Time, Reagent/catalyst Karakhanov; Maksimov; Zolotukhina; Kardashev; Filippova; Petroleum Chemistry; vol. 52; nb. 5; (2012); p. 289 - 298; Neftekhimiya; vol. 52; nb. 5; (2012); p. 323 - 332,10 View in Reaxys With hydrogen in isopropyl alcohol, T= 60 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst Niembro, Sandra; Donnici, Silvia; Shafir, Alexandr; Vallribera, Adelina; Buil, Maria L.; Esteruelas, Miguel A.; Larramona, Carmen; New Journal of Chemistry; vol. 37; nb. 2; (2013); p. 278 - 282 View in Reaxys 100 With [NiH(bis[2-(dicyclohexylphosphanyl)ethyl]amine)]B(C6H5)4, hydrogen in tetrahydrofuran-d8, Time= 24h, T= 80 %Chromat. °C , p= 3040.2Torr , Sealed tube Vasudevan, Kalyan V.; Scott, Brian L.; Hanson, Susan K.; European Journal of Inorganic Chemistry; nb. 30; (2012); p. 4898 - 4906

26/96

2016-06-28 15:56:50

View in Reaxys With sodium formate in water, Time= 4h, T= 79.84 °C , p= 30003Torr , Concentration, Reagent/catalyst, Solvent, Time, chemoselective reaction Indra, Arindam; Maity, Prasenjit; Bhaduri, Sumit; Lahiri, Goutam Kumar; ChemCatChem; vol. 5; nb. 1; (2013); p. 322 - 330 View in Reaxys 89 %Chromat.

With Rh4Co, cetyltrimethylammonim bromide, hydrazine hydrate in toluene, Time= 3h, T= 60 °C , Schlenk technique, Inert atmosphere, Catalytic behavior, Reagent/catalyst Lin, Jin; Chen, Jing; Su, Weiping; Advanced Synthesis and Catalysis; vol. 355; nb. 1; (2013); p. 41 - 46 View in Reaxys With hydrogen in ethyl acetate, Time= 5h, T= 45 °C , p= 760.051Torr , Inert atmosphere, Schlenk technique, Time Zhu, Wenwen; Yu, Yinyin; Yang, Hanmin; Hua, Li; Qiao, Yunxiang; Zhao, Xiuge; Hou, Zhenshan; Chemistry - A European Journal; vol. 19; nb. 6; (2013); p. 2059 - 2066 View in Reaxys With RuCl2(PPh3)[(EtSC2H4)2NH], potassium tert-butylate, hydrogen in tetrahydrofuran, Time= 20h, T= 40 °C , p= 37503.8Torr , Glovebox, Inert atmosphere Spasyuk, Denis; Smith, Samantha; Gusev, Dmitry G.; Angewandte Chemie - International Edition; vol. 52; nb. 9; (2013); p. 2538 - 2542; Angew. Chem.; vol. 125; nb. 9; (2013); p. 2598 - 2602,5 View in Reaxys

100 With hydrogen in methanol, Time= 0.5h, T= 20 °C , p= 760.051Torr %Chromat. 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 palladium 10 on activated carbon in tetrahydrofuran, T= 20 °C Zhang, Guoqi; Hanson, Susan K.; Organic Letters; vol. 15; nb. 3; (2013); p. 650 - 653 View in Reaxys Catalytic tests For the hydrogenation of unsaturated compounds, Pt/xTS, Pt/ SBA-15, or Pt/TiO2 catalyst (0.1 g) was pretreated under hydrogen flow (40 mL min 1) at 673 K for 2 h before use. The catalyst was then mixed with solvent (20 mL) and substrate (21 mmol). The mixture was subsequently transferred to a 100-mL autoclave. The hydrogenation reaction began with stirring (1200 rpm) at a designated temperature after hydrogen (4.0 MPa) was introduced into the autoclave. The reaction was stopped after a proper time, and the products were analyzed by GC-FID (GC-2014, Shimadzu Co.) equipped with a capillary column (DM-WAX, 30 m 0.25 mm 0.25 lm). With hydrogen in ethanol, water, Time= 1h, T= 59.84 °C , p= 30003Torr , Autoclave, Catalytic behavior Li, Xiaohong; Zheng, Wenli; Pan, Huiyan; Yu, Yin; Chen, Li; Wu, Peng; Journal of Catalysis; vol. 300; (2013); p. 9 - 19 View in Reaxys With Dimethylphenylsilane, [ReI2(NO)(PiPr3)2(H2O)](THF)2, tris(pentafluorophenyl)borate, hydrogen in neat (no solvent), Time= 0.333333h, T= 23 °C , p= 7500.75Torr , Catalytic behavior, Reagent/catalyst, Temperature, Concentration Jiang, Yanfeng; Schirmer, Birgitta; Blacque, Olivier; Fox, Thomas; Grimme, Stefan; Berke, Heinz; Journal of the American Chemical Society; vol. 135; nb. 10; (2013); p. 4088 - 4102 View in Reaxys With iron(III) trifluoromethanesulfonate, sodium triethylborohydride in tetrahydrofuran, 1-methyl-pyrrolidin-2-one, Time= 16h, T= -20 - 20 °C , Inert atmosphere, Reagent/catalyst Carter, Tom S.; Guiet, Lea; Frank, Dominik J.; West, James; Thomas, Stephen P.; Advanced Synthesis and Catalysis; vol. 355; nb. 5; (2013); p. 880 - 884

27/96

2016-06-28 15:56:50

View in Reaxys With formic acid, 5 palladium on charcoal, ammonium formate in methanol, water, T= 25 °C , Kinetics Sawadjoon, Supaporn; Lundstedt, Anna; Samec, Joseph S.M.; ACS Catalysis; vol. 3; nb. 4; (2013); p. 635 - 642 View in Reaxys 87 %Chromat.

With iron, hydrogen in 1,3,5-trimethyl-benzene, Time= 20h, T= 20 °C , p= 7500.75Torr , Autoclave Kelsen, Vinciane; Wendt, Bianca; Werkmeister, Svenja; Junge, Kathrin; Beller, Matthias; Chaudret, Bruno; Chemical Communications; vol. 49; nb. 33; (2013); p. 3416 - 3418 View in Reaxys With C31H28PZr(1+)*C24BF20 (1-), hydrogen, Time= 0.5h, T= 20 °C , p= 1125.11Torr , Catalytic behavior, Reagent/catalyst Xu, Xin; Kehr, Gerald; Daniliuc, Constantin G.; Erker, Gerhard; Journal of the American Chemical Society; vol. 135; nb. 17; (2013); p. 6465 - 6476 View in Reaxys With (tris(phosphine)borane)Fe(N2), hydrogen in benzene-d6, T= 20 °C , p= 760.051Torr , Inert atmosphere, Catalytic behavior Fong, Henry; Moret, Marc-Etienne; Lee, Yunho; Peters, Jonas C.; Organometallics; vol. 32; nb. 10; (2013); p. 3053 - 3062 View in Reaxys With ammonium hydroxide, hydrazine hydrate in ethanol, Time= 3h, T= 60 °C , Catalytic behavior, Reagent/catalyst, Time Dhakshinamoorthy, Amarajothi; Navalon, Sergio; Sempere, David; Alvaro, Mercedes; Garcia, Hermenegildo; Chemical Communications; vol. 49; nb. 23; (2013); p. 2359 - 2361 View in Reaxys

100 With [(bis[(2-dicyclohexylphosphino)ethyl]amine)cobalt(II)(CH2SiMe3)]tetraphenylborate, hydrogen in tetrahydrofur%Chromat. an, Time= 24h, T= 25 °C , p= 760.051Torr , Inert atmosphere, Sealed tube, Reagent/catalyst Zhang, Guoqi; Vasudevan, Kalyan V.; Scott, Brian L.; Hanson, Susan K.; Journal of the American Chemical Society; vol. 135; nb. 23; (2013); p. 8668 - 8681 View in Reaxys 65 %Spectr.

With hydrogen, Piers' borane in benzene-d6, Time= 72h, T= 140 °C , p= 4500.45Torr Wang, Yuwen; Chen, Weiqiang; Lu, Zhenpin; Li, Zhen Hua; Wang, Huadong; Angewandte Chemie - International Edition; vol. 52; nb. 29; (2013); p. 7496 - 7499; Angew. Chem.; vol. 125; nb. 29; (2013); p. 7644 - 7647,4 View in Reaxys With hydrogen in methanol, Time= 1h, T= 25 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst Takahashi, Masaki; Imaoka, Takane; Hongo, Yushi; Yamamoto, Kimihisa; Angewandte Chemie - International Edition; vol. 52; nb. 29; (2013); p. 7419 - 7421; Angew. Chem.; vol. 125; nb. 29; (2013); p. 7567 - 7569,3 View in Reaxys With hydrogenchloride, hydrogen in water, ethyl acetate, Time= 0.833333h, T= 20 °C , p= 760.051Torr , pH= 3 - 4, Reagent/catalyst, Time, Solvent Yang, Hengquan; Zhou, Ting; Zhang, Wenjuan; Angewandte Chemie - International Edition; vol. 52; nb. 29; (2013); p. 7455 - 7459; Angew. Chem.; vol. 125; nb. 29; (2013); p. 7603 - 7607,5 View in Reaxys With 5 Pd/C, hydrogen in ethanol, Time= 2h, T= 25 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst Li, Huan; Chen, Guangxu; Yang, Huayan; Wang, Xingli; Liang, Jinghong; Liu, Pengxin; Chen, Mei; Zheng, Nanfeng; Angewandte Chemie - International Edition; vol. 52; nb. 32; (2013); p. 8368 - 8372; Angew. Chem.; vol. 125; nb. 32; (2013); p. 8526 - 8530,5 View in Reaxys

28/96

2016-06-28 15:56:50

Aerobic reduction of styrene with supramolecular flavin catalyst General procedure: A solution of styrene (0.063mmol), 1 (0.0025mmol), receptors 2–5 (0.0125mmol), NH2NH2·H2O (0.25mmol), and decane (internal standard) was stirred in CH3CN (0.4mL) at 30°C in a sealed tube containing 3.14mL of air. The yields of ethylbenzene were determined by GLC analysis using an internal standard. The reaction profiles are shown in Fig.6. With 2,6-bis(3-{4-[3,4,5-tris(3,4,5-tridodecyloxybenzyloxy)benzyloxy]phenyl}propanoylamino)pyridine, lumiflavin, oxygen, hydrazine hydrate in acetonitrile, T= 30 °C , Sealed tube, Reagent/catalyst Imada, Yasushi; Kugimiya, Yudai; Iwata, Shotaro; Komiya, Naruyoshi; Naota, Takeshi; Tetrahedron; vol. 69; nb. 40; (2013); p. 8572 - 8578 View in Reaxys 100 Catalytic activity measurements %Chromat. General procedure: The reaction was performed in a 10 mL stainless-steel reactor equipped with a magnetic stirrer. In a typical hydrogenation experiment, catalyst and 0.2 g of styrene together with 5 mL of methanol were mixed and air was replaced by H2. The reactor was filled with H2 until the pressure was 10 bar. The reaction was started by stirring at room temperature. After the reaction, the filtrate was analysed by gas chromatography (QP5050, Shimadzu) equipped with a Rxi-5ms capillary column (30 m × 0.25 mm × 0.5 m) and a flame ionization detector (FID). With hydrogen in methanol, Time= 0.0833333h, T= 20 °C , p= 7500.75Torr , Catalytic behavior, Reagent/catalyst, Time, Solvent Zhang, Yanmei; Quek, Xian-Yang; Wu, Leilei; Guan, Yejun; Hensen, Emiel J.; Journal of Molecular Catalysis A: Chemical; vol. 379; (2013); p. 53 - 58 View in Reaxys With (C6F5)3B(IDipp)Ir(1,5-cyclooctadiene), hydrogen in neat (no solvent), Time= 2h, p= 6000.6Torr Kolychev, Eugene L.; Kronig, Sabrina; Brandhorst, Kai; Freytag, Matthias; Jones, Peter G.; Tamm, Matthias; Journal of the American Chemical Society; vol. 135; nb. 33; (2013); p. 12448 - 12459 View in Reaxys 99.9 The typical procedure for hydrogenation of unsaturated carbon-carbon bonds using the H2-MNB-basedstrat%Chromat. egy General procedure: The hydrogenation was carried out in a 100 mL vial equipped with an MNB-generator withoutadditional stirring. Alkene or alkyne 1 (20 mmol) was dissolved in MeOH (80 mL), and then warmed to 30 °C.Using the MNB-generator (MA3-FS), H2-MNBs were introduced into the reactor in the presence of palladium onalumina spheres (0.5percentPd, 2–4 mm, 0.1 mmol, 0.5 molpercent) at an H2-flow rate of 5 mL/min. The samples of thereaction mixture were taken out periodically to monitor the reaction progress using the GC analysis. After thecompletion of the hydrogenation reaction, MeOH was evaporated in vacuo to afford the desired alkane 1 withexcellent purity. With hydrogen in methanol, Time= 2h, T= 30 °C , Time, Temperature, Concentration Mase, Nobuyuki; Isomura, Shogo; Toda, Mitsuo; Watanabe, Naoharu; Synlett; vol. 24; nb. 17; (2013); p. 2225 2228 View in Reaxys With C24H44BCoN4P2, hydrogen in benzene-d6, Time= 0.05h, T= 20 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst Lin, Tzu-Pin; Peters, Jonas C.; Journal of the American Chemical Society; vol. 135; nb. 41; (2013); p. 15310 15313 View in Reaxys Hydrogenation Reaction General procedure: All catalytic hydrogenation reactions were carried out in a Teflon-lined stainless steel autoclave (150 mL). Typically, the hydrogenation reactions of propenyl and styrene were performed at 30 °C and 1 MPaH2 using methanol (20 mL) as solvent. The hydrogenation reaction of linoleic acid was performed at 80 °C and 2 MPa H2 using the deoxygenated decane (50 mL) as solvent. The concentration of the reactants and products were analyzed by gas chromatograph (Shimadzu, CG-2010). The activity of the catalyst was evaluated according to the initial hydrogenation rate (mol/Pd mol h) value determined by the initial slope of the curve of product yield vs. time.

29/96

2016-06-28 15:56:50

With palladium/alumina, hydrogen in methanol, T= 30 °C , p= 7500.75Torr , Autoclave, Catalytic behavior, Kinetics, Reagent/catalyst Liu, Jing; Huang, Fuming; Liao, Xuepin; Shi, Bi; Bulletin of the Korean Chemical Society; vol. 34; nb. 9; (2013); p. 2650 - 2656 View in Reaxys With [Sr(diphenylmethane-4,4’-dicarboxylate)(H2O)], hydrogen in toluene, Time= 0.5h, T= 59.84 °C , p= 3800.26Torr , Catalytic behavior, Kinetics, Reagent/catalyst, Time, Temperature, chemoselective reaction Platero-Prats, Ana E.; Snejko, Natalia; Iglesias, Marta; Monge, Angeles; Gutierrez-Puebla, Enrique; Chemistry - A European Journal; vol. 19; nb. 46; (2013); p. 15572 - 15582 View in Reaxys 100 With [Rh(η3-C3H5)3], hydrogen in tetrahydrofuran, methanol, n-heptane, Time= 1h, T= 20 °C , p= 30003Torr , Auto%Chromat. clave, Glovebox, Reagent/catalyst, Temperature, Concentration, Time Castelbou, Jessica Llop; Gual, Aitor; Mercade, Elisabet; Claver, Carmen; Godard, Cyril; Catalysis Science and Technology; vol. 3; nb. 10; (2013); p. 2828 - 2833 View in Reaxys With methanol in benzene, Time= 1.5h, T= 409.84 °C , p= 70Torr , Inert atmosphere, Flow reactor, Reagent/catalyst Hattori, Hideshi; Alabi, Wahab O.; Jermy, B. Rabindran; Aitani, Abdullah M.; Al-Khattaf, Sulaiman S.; Catalysis Letters; vol. 143; nb. 10; (2013); p. 1025 - 1029 View in Reaxys 99 %Chromat.

With C21H34FeO2Si4, hydrogen in toluene, Time= 6h, T= 20 °C , p= 760.051Torr , Schlenk technique Sunada, Yusuke; Tsutsumi, Hironori; Shigeta, Keisuke; Yoshida, Ryota; Hashimoto, Toru; Nagashima, Hideo; Dalton Transactions; vol. 42; nb. 48; (2013); p. 16687 - 16692 View in Reaxys With hydrogen, T= 25 °C , p= 760.051Torr Wang, Chenyu; Lin, Cuikun; Zhang, Lihua; Quan, Zewei; Sun, Kai; Zhao, Bo; Wang, Feng; Porter, Nathan; Wang, Yuxuan; Fang, Jiye; Chemistry - A European Journal; vol. 20; nb. 6; (2014); p. 1753 - 1759 View in Reaxys With methanol in toluene, Time= 2h, T= 20 °C , Inert atmosphere, Sealed tube, Irradiation Zhao, Yubao; Pan, Feng; Li, Hui; Xu, Guo Qin; Chen, Wei; ChemCatChem; vol. 6; nb. 2; (2014); p. 454 - 458 View in Reaxys With hydrogen in methanol, Time= 0.166667h, T= 30 °C , p= 7500.75Torr , Autoclave, Kinetics, Reagent/catalyst Liu, Jing; Liao, Xuepin; Shi, Bi; Research on Chemical Intermediates; vol. 40; nb. 1; (2014); p. 249 - 258 View in Reaxys With H2 in [(2)H6]acetone Abdulhussain, Safaa; Breitzke, Hergen; Ratajczyk, Tomasz; Gruenberg, Anna; Srour, Mohamad; Arnaut, Danjela; Weidler, Heiko; Kunz, Ulrike; Kleebe, Hans Joachim; Bommerich, Ute; Bernarding, Johannes; Gutmann, Torsten; Buntkowsky, Gerd; Chemistry - A European Journal; vol. 20; nb. 4; (2014); p. 1159 - 1166 View in Reaxys

100 %Spectr.

With hydrogen in water, Time= 6.5h, T= 20 °C , p= 10343.2Torr , Autoclave Weiss, Ester; Dutta, Bishnu; Schnell, Yafit; Abu-Reziq, Raed; Journal of Materials Chemistry A; vol. 2; nb. 11; (2014); p. 3971 - 3977 View in Reaxys With hydrogen in isopropyl alcohol, Time= 0.416667h, p= 760.051Torr , Schlenk technique, Sonication Linhardt, Roland; Kainz, Quirin M.; Grass, Robert N.; Stark, Wendelin J.; Reiser, Oliver; RSC Advances; vol. 4; nb. 17; (2014); p. 8541 - 8549 View in Reaxys

30/96

2016-06-28 15:56:50

99 %Chromat.

With hydrogen in ethanol, Time= 0.5h, T= 20 °C , p= 760.051Torr Kim, Eunsuk; Jeong, Han Saem; Kim, B. Moon; Catalysis Communications; vol. 45; (2014); p. 25 - 29 View in Reaxys With (η6-C6H6)OsCl{(2,6-Me2-C6H3NCMe)2CH}, hydrogen in tetrahydrofuran, Time= 0.5h, T= 80 °C , p= 30003Torr , Inert atmosphere, Autoclave, Catalytic behavior, Reagent/catalyst Schreiber, Dominique F.; O'Connor, Crystal; Grave, Christian; Mueller-Bunz, Helge; Scopelliti, Rosario; Dyson, Paul J.; Phillips, Andrew D.; Organometallics; vol. 32; nb. 24; (2013); p. 7345 - 7356 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 hydrogen in methanol, Time= 1h, T= 25 °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 palladium, hydrogen in ethanol, T= 30 °C , p= 760.051Torr Dai, Yan; Liu, Shengjie; Zheng, Nanfeng; Journal of the American Chemical Society; vol. 136; nb. 15; (2014); p. 5583 - 5586 View in Reaxys With Wilkinson's catalyst, hydrogen in toluene, T= 120 °C , p= 1500.15Torr Haywood, Tom; Miller, Philip W.; ChemCatChem; vol. 6; nb. 5; (2014); p. 1199 - 1203 View in Reaxys Catalytic Activity Test General procedure: The stainless steel autoclave with inserted glass tube was used as pressurized vessel to study the catalytic activity. The hydrogen pressure maintained between 20–60 bar for different conditions, temperature is fixed at 313 K for all reactions, solvent effect (pentane and toluene) studied at fixed reaction time of 5 hours. Conversion of the respective substrate was analyzed by gas chromatography, using SPB non-polar capillary column. With Ru3(CO)9-(diphenylarsino)methane-tris(flurophenyl)phosphine, hydrogen in toluene, Time= 5h, T= 39.84 °C , p= 30003Torr , Autoclave, Reagent/catalyst Shawakataly, Omar Bin; Jothiramalingam; Khan; Synthesis and Reactivity in Inorganic, Metal-Organic and NanoMetal Chemistry; vol. 44; nb. 7; (2014); p. 935 - 941 View in Reaxys

99 %Chromat.

Procedure for hydrogenation General procedure: A round-bottom flask wascharged with alkene or alkyne (1 mmol) and EtOH (1 mL)[except for cinchonine (3 mL) because of its lowersolubility]. To this mixture was added hydrazinemonohydrate (4 mmol), then the reaction was placed underan atmosphere of oxygen (balloon). The resulting mixturewas stirred at 35 °C for the appropriate time. Afterconsumption of the starting material, the solvent wasremoved under vacuum and the residue was extracted withEtOAc. The organic phase was dried over MgSO4 (forisolated products). Volatile products were not isolated andthey were analyzed directly by using GC-MS. With oxygen, hydrazine hydrate in ethanol, Time= 24h, T= 35 °C , Solvent, Reagent/catalyst Menges, Nurettin; Balci, Metin; Synlett; vol. 25; nb. 5; (2014); p. 671 - 676; Art.No: ST-2013-D1049-L

31/96

2016-06-28 15:56:50

View in Reaxys With hydrogen in ethanol, Time= 0.5h, T= 40 °C , p= 1500.15Torr , Autoclave Rasero-Almansa, Antonia M.; Corma, Avelino; Iglesias, Marta; Sanchez, Felix; Green Chemistry; vol. 16; nb. 7; (2014); p. 3522 - 3527 View in Reaxys With hydrogen in ethyl acetate, Time= 1h, T= 100 °C , p= 15001.5Torr Mao, Hui; Peng, Shengjie; Yu, Hong; Chen, Jing; Zhao, Shilin; Huo, Fengwei; Journal of Materials Chemistry A; vol. 2; nb. 16; (2014); p. 5847 - 5851 View in Reaxys 1 : Procedure for Monitoring Styrene/n-Heptane Transfer Hydrogenation Over Time: Hydrogen transfer catalyst 2 (17.7 mg, 0.030 mmol) was dissolved in 2 mL of a standard solution of styrene (250 mM) and adamantane (25.3 mM) in n-heptane in a 4 mL screw top vial containing a Teflon-coated stir bar. The vial was sealed with a Teflon-lined screw cap. The mixture was heated to 100° C. for 30 seconds in an aluminum block heater inside an argon-filled glovebox to dissolve the precatalysts and ensure a homogeneous solution, and then immediately cooled to −35° C. in the freezer. An aliquot (0.1 mL, representing to) was removed and placed into a GC autosampler vial; this aliquot was then diluted with dichloromethane to a total volume of 1 mL before analysis by GC. [0133] The reaction mixture was heated to 100° C. in the aluminum block heater, and at specified times (1, 2, 3, 4, 5, 6, 7, 8, 10, 12, and 18 hours) the vial was removed and cooled to −35° C. in the freezer before taking an aliquot for analysis by GC. The concentrations of styrene and ethylbenzene were then plotted versus time to give time course profiles of the transfer hydrogenation reaction. These data were overlaid on the styrene/ethylbenzene concentrations from the tandem reaction (see FIG. 49). With [(1,3-bis((di-tert-butylphosphino)methyl)benzene(-1H))IrH2] in n-heptane, Time= 18h, T= 100 °C , Inert atmosphere, Schlenk technique, Time Patent; California Institute of Technology; Leitch, David; Labinger, Jay A.; Bercaw, John E.; Lam, Yan Choi; US2014/200376; (2014); (A1) English View in Reaxys > 99 With formic acid in water, Time= 0.25h, T= 298 °C , Green chemistry, Catalytic behavior, Kinetics, Solvent, Reagent/ %Chromat. catalyst Gong, Ling-Hong; Cai, Yi-Yu; Li, Xin-Hao; Zhang, Ya-Nan; Su, Juan; Chen, Jie-Sheng; Green Chemistry; vol. 16; nb. 8; (2014); p. 3746 - 3751 View in Reaxys 99 %Chromat.

With N,N′-Bis(2-pyridylmethylidene)-1,2-trans-(R,R + S,S)-cyclohexanediamine, hydrogen, isopropylmagnesium chloride, iron(II) chloride in tetrahydrofuran, Time= 3h, T= -20 - 20 °C , p= 750.075Torr Frank, Dominik J.; Guiet, Lea; Kaeslin, Alexander; Murphy, Elliot; Thomas, Stephen P.; RSC Advances; vol. 3; nb. 48; (2013); p. 25698 - 25701 View in Reaxys

100 With hydrogen, caesium carbonate in toluene, Time= 0.25h, T= 100 °C , p= 760.051Torr , Inert atmosphere, Schlenk %Chromat. technique, Catalytic behavior, Reagent/catalyst Sabater, Sara; Mata, Jose A.; Peris, Eduardo; ACS Catalysis; vol. 4; nb. 6; (2014); p. 2038 - 2047 View in Reaxys With carbon dioxide, hydrogen in toluene, T= 0 °C , p= 11251.1Torr , Autoclave, Catalytic behavior, Reagent/catalyst Yoshida, Hiroshi; Zama, Toshiaki; Fujita, Shin-Ichiro; Panpranot, Joongjai; Arai, Masahiko; RSC Advances; vol. 4; nb. 47; (2014); p. 24922 - 24928 View in Reaxys 95 %Chromat.

With hydrogen in dodecane, 1,3,5-trimethyl-benzene, Time= 24h, T= 20 °C , p= 2250.23Torr , Reagent/catalyst Kelsen, Vinciane; Meffre, Anca; Fazzini, Pier-Francesco; Lecante, Pierre; Chaudret, Bruno; ChemCatChem; vol. 6; nb. 6; (2014); p. 1714 - 1720 View in Reaxys

32/96

2016-06-28 15:56:50

With hydrogen in water, Time= 0.583333h, T= 40 °C , p= 2625.26Torr , Autoclave, Solvent Fu, Luman; Li, Shuru; Han, Zhongyuan; Liu, Huifang; Yang, Hengquan; Chemical Communications; vol. 50; nb. 70; (2014); p. 10045 - 10048 View in Reaxys With Rh-SBA-15 in methanol, Time= 0.166h, T= 20 °C , Catalytic behavior, Time, Concentration Bhorali, Nayanmoni; Ganguli, Jatindra Nath; Catalysis Letters; vol. 143; nb. 3; (2013); p. 276 - 281 View in Reaxys With hydrogen in water, Time= 2h, T= 20 °C , p= 7500.75Torr , Catalytic behavior, Reagent/catalyst, Pressure Noel, Sebastien; Leger, Bastien; Ponchel, Anne; Philippot, Karine; Denicourt-Nowicki, Audrey; Roucoux, Alain; Monflier, Eric; Catalysis Today; vol. 235; (2014); p. 20 - 32 View in Reaxys 2.4. Activity measurement General procedure: The catalytic performance of several carbon materials prepared was tested in liquid-phase reduction of nitrobenzene, styrene, and 3-nitrostyrene by hydrazine. The Teflon-coated reactor was loaded with carbon catalyst, substrate, and hydrazine hydrate, purged by 0.2 MPa N2, and heated to a reaction temperature of 100 °C on a heating place. The reaction mixture was stirred by a magnetic stirrer at 100 °C for a certain period of time. The multiphase reaction mixture was so mixed at a stirring rate of >400 rpm that the influence of agitation was negligible. Then, the reactor was cooled by ice water and the liquid phase was separated by filtration. The liquid mixture was analyzed by gas chromatography (GL Science 390B) using decane as an internal standard. The conversion was determined from the amounts of substrate before and after reaction and the selectivity from the amount of a product divided by the total amount of all products detected. With hydrazine, Time= 2h, T= 100 °C , Inert atmosphere, Reagent/catalyst, chemoselective reaction Fujita, Shin-Ichiro; Watanabe, Hiroyuki; Katagiri, Ayaka; Yoshida, Hiroshi; Arai, Masahiko; Journal of Molecular Catalysis A: Chemical; vol. 393; (2014); p. 257 - 262 View in Reaxys With Rh, hydrogen in cyclohexane, T= 20 °C , p= 760.051Torr , Flow reactor, Green chemistry, Industrial scale, Catalytic behavior Yap, Swee Kun; Yuan, Yuan; Zheng, Lu; Wong, Wai Kuan; Zhang, Jiaguang; Yan, Ning; Khan, Saif A.; Green Chemistry; vol. 16; nb. 11; (2014); p. 4654 - 4658 View in Reaxys 98 %Chromat.

2.3. Catalytic activity test General procedure: Typically, 1.0 mmol nitrobenzene, styrene or benzaldehyde, 10 mg catalyst and 2 mL EtOH were added into a glass tube (50 mL), respectively. Then, it was exchanged with H2 and the reaction was carried out in the presence of H2 at atmospheric pressure (H2 balloon) at the given temperature. After reaction, 154 mg biphenyl and 10 mL EtOH were added for quantitative analysis by GC-FID (Agilent 7890A). With hydrogen in ethanol, Time= 0.333333h, T= 25 °C , p= 760.051Torr , Reagent/catalyst Wang, Yanan; Deng, Youquan; Shi, Feng; Journal of Molecular Catalysis A: Chemical; vol. 395; (2014); p. 195 201 View in Reaxys 4.3. Catalytic experiments General procedure for hydrogenation of styrene in supercritical carbon dioxide: the reactionwas carried out in a 125mL stainless steel reactor equipped with a magnetic stirrer.The reactor was purged with argon prior to the introduction of Ru-catalyst and styrene(amount of catalyst = 0.02 mmol, substrate/catalyst ratio = 500) via a cannula transfer. Whenmethanol was used as co-solvent, catalysts were prior dissolved in 1mL of degassedmethanol. After introduction of H2 (10 bar), CO2 was admitted, leading to a total reactionpressure of 120 bar. The reaction temperature was controlled by an internal thermocouple.After a reaction time of 16 h, the reactor was cooled down to 0 °C, the pressure was gentlyreleased, and the liquid phase was transferred to a Schlenk tube. Trap-to-trap distillationunder vacuum at ambient temperature allowed separation of volatile compounds that werequantitatively analyzed by GC (Thermo Scientific FOCUS GC, TR-Wax 30m capillarycolumn, FID detector).

33/96

2016-06-28 15:56:50

With tri-ruthenium(0)dodecacarbonyl, hydrogen in methanol, Time= 16h, T= 0 °C , p= 7500.75Torr , Autoclave, Inert atmosphere, Reagent/catalyst, Solvent Johnpeter, Justin P.; Plasseraud, Laurent; Schmitt, Frederic; Juillerat-Jeanneret, Lucienne; Therrien, Bruno; Journal of Coordination Chemistry; vol. 66; nb. 10; (2013); p. 1753 - 1762 View in Reaxys General procedure: For the hydrogenation of styrene with hydrogen, a benzene solution containing 5molpercent styrene was fed at the rate of 0.12ml/min into a hydrogen carrier flowing at 40ml/min (STP). For the hydrogenation of styrene with methanol (transfer hydrogenation), a mixture containing styrene (4.3molpercent), methanol (17molpercent) and benzene (78.7molpercent) was fed at the rate of 0.12ml/min into an N2 carrier flowing at 40ml/min (STP). The amount of catalyst and the reaction temperature were the same as those for the side-chain alkylation, 400mg and 683K, respectively. With methanol in benzene, T= 409.84 °C , Inert atmosphere, Reagent/catalyst Alabi, Wahab O.; Tope, Balkrishna B.; Jermy, Rabindran B.; Aitani, Abdullah M.; Hattori, Hideshi; Al-Khattaf, Sulaiman S.; Catalysis Today; vol. 226; (2014); p. 117 - 123 View in Reaxys 83 %Spectr.

With [IMesCH2N2(NMe)C2Ph]RuHCl(p-cymene), hydrogen in dichloromethane-d2, Time= 24h, T= 50 °C , p= 3040.2Torr , Inert atmosphere, Schlenk technique, Time, Reagent/catalyst, Solvent, Temperature Bagh, Bidraha; Stephan, Douglas W.; Dalton Transactions; vol. 43; nb. 41; (2014); p. 15638 - 15645 View in Reaxys With hydrogen in toluene, T= 79.84 °C , p= 15001.5Torr , Catalytic behavior, Reagent/catalyst, chemoselective reaction Carrara; Badano; Betti; Lederhos; Rintoul; Coloma-Pascual; Vera; Quiroga; Catalysis Communications; vol. 61; (2015); p. 72 - 77 View in Reaxys With hydrogen in toluene, Time= 1h, T= 27 °C , p= 760.051Torr , Catalytic behavior, Kinetics, Time, Reagent/catalyst Acham, Vaibhav R.; Biradar, Ankush V.; Dongare, Mohan K.; Kemnitz, Erhard; Umbarkar, Shubhangi B.; ChemCatChem; vol. 6; nb. 11; (2014); p. 3182 - 3191 View in Reaxys With hydrogen in methanol, Time= 3h, T= 25 °C , p= 760.051Torr Maji, Tanmoy; Banerjee, Sanjib; Biswas, Mrinmoy; Mandal, Tarun K.; RSC Advances; vol. 4; nb. 93; (2014); p. 51745 - 51753 View in Reaxys With hydrogen in hexane, T= 20 °C , p= 750.075Torr , Catalytic behavior, Solvent PA©lisson, Carl-Hugo; Denicourt-Nowicki, Audrey; Meriadec, Cristelle; Greneche, Jean-Marc; Roucoux, Alain; ChemCatChem; vol. 7; nb. 2; (2015); p. 309 - 315 View in Reaxys With C64H106B2Co2N4P4, hydrogen in benzene-d6, T= 20 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst Lin, Tzu-Pin; Peters, Jonas C.; Journal of the American Chemical Society; vol. 136; nb. 39; (2014); p. 13672 13683 View in Reaxys 3 : 2.4. Catalytic test General procedure: A catalyst and a substrate (4 mg of the catalyst per 1 ml of sub-strate) were placed in a thermostated steel autoclave equippedwith an insert test tube and a magnetic stirrer. If necessary, the solvent was added before sealing the autoclave tightly, filling it with5–10 atm hydrogen, and connecting it to a thermostat. The reaction was performed with vigorous stirring at 80 °C for 15 min or1 h; afterwards, the autoclave was cooled to below room temperature. The products were analysed using gas-liquid chromatography(GLC) on a ChromPack CP9001 gas chromatograph with a flameionisation detector. The column was 30 m × 0.2 mm with an SE-30 grafted phase.

34/96

2016-06-28 15:56:50

With hydrogen, Time= 0.25h, T= 80 °C , p= 3800.26Torr , Autoclave, Catalytic behavior, Reagent/catalyst Karakhanov, Edward A.; Maksimov, Anton L.; Zakharian, Elena M.; Kardasheva, Yulia S.; Savilov, Sergey V.; Truhmanova, Nadezhda I.; Ivanov, Andrey O.; Vinokurov, Vladimir A.; Journal of Molecular Catalysis A: Chemical; vol. 397; (2015); p. 1 - 18 View in Reaxys 92 %Chromat.

With hydrazine hydrate in chloroform, Time= 24h, T= 25 °C , p= 760.051Torr , Kinetics, Catalytic behavior, Reagent/ catalyst Imada, Yasushi; Osaki, Motonari; Noguchi, Mikiko; Maeda, Takatoshi; Fujiki, Misa; Kawamorita, Soichiro; Komiya, Naruyoshi; Naota, Takeshi; ChemCatChem; vol. 7; nb. 1; (2015); p. 99 - 106 View in Reaxys

98 %Chromat.

With iridium, hydrogen in ethanol, Time= 5h, T= 25 °C Mekhaev; Pervova; Kazakov; Bratskaya; Pestov; Russian Journal of Organic Chemistry; vol. 51; nb. 2; (2015); p. 279 - 280; Zh. Org. Khim.; vol. 51; nb. 2; (2015); p. 289 - 290,2 View in Reaxys With 5 palladium on charcoal in n-heptane, Time= 4h, T= 40 °C Bi, Qing-Yuan; Lin, Jian-Dong; Liu, Yong-Mei; Du, Xian-Long; Wang, Jian-Qiang; He, He-Yong; Cao, Yong; Angewandte Chemie - International Edition; vol. 53; nb. 49; (2014); p. 13583 - 13587; Angew. Chem.; vol. 126; nb. 49; (2014); p. 13801 - 13805,5 View in Reaxys

39 %Chromat.

With cis-[1-(2,6-diisopropylphenyl)-3-(3-sodium sulfonatopropyl)imidazol-2-ylidene](dimethyl sulfoxide)dimethylplatinum(II), hydrogen in water, Time= 2.25h, T= 20 °C , p= 750.075Torr , Inert atmosphere, Catalytic behavior Baquero, Edwin A.; Tricard, Simon; Flores, Juan Carlos; De Jesffls, Ernesto; Chaudret, Bruno; Angewandte Chemie - International Edition; vol. 53; nb. 48; (2014); p. 13220 - 13224; Angew. Chem.; vol. 126; nb. 48; (2014); p. 13436 - 13440,5 View in Reaxys With hydrogen in N,N-dimethyl-formamide, T= 25 °C , p= 760.051Torr , Kinetics Berenblyum; Al-Wadhaf; Katsman; Petroleum Chemistry; vol. 55; nb. 2; (2015); p. 118 - 126; Neftekhimiya; vol. 55; nb. 2; (2015); p. 125 - 133,9 View in Reaxys With hydrogen, Time= 4h, T= 45 °C , p= 7500.75Torr , Ionic liquid, chemoselective reaction Wu, Zhifeng; Jiang, Heyan; RSC Advances; vol. 5; nb. 44; (2015); p. 34622 - 34629 View in Reaxys With [Ca2Na2(chelidamic acid(-3H))2(H2O)6], hydrogen in toluene, Time= 4h, T= 59.84 °C , p= 760.051Torr , Catalytic behavior Saha, Debraj; Maity, Tanmoy; Koner, Subratanath; European Journal of Inorganic Chemistry; vol. 2015; nb. 6; (2015); p. 1053 - 1064 View in Reaxys With C54H57F3N4O6RuS, hydrogen in dichloromethane, Time= 0.5h, T= 25 °C , p= 15001.5Torr , Inert atmosphere, Sealed tube, Reagent/catalyst Pranckevicius, Conor; Fan, Louie; Stephan, Douglas W.; Journal of the American Chemical Society; vol. 137; nb. 16; (2015); p. 5582 - 5589 View in Reaxys With Pd(OAc)2 dopped triglycidyl 1-ethyl-3-methylimidazoliumacetate polyether in methanol, Time= 2h, T= 20 °C Arnold, Ulrich; Altesleben, Christiane; Behrens, Silke; Essig, Sarah; Lautenschütz, Ludger; Schild, Dieter; Sauer, Jörg; Catalysis Today; vol. 246; (2015); p. 116 - 124 View in Reaxys

35/96

2016-06-28 15:56:50

With hydrogen, 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, Time= 1h, T= 59.84 °C , p= 15001.5Torr , Autoclave, Catalytic behavior, Reagent/catalyst Zhang, Bin; Yuan, Yuan; Philippot, Karine; Yan, Ning; Catalysis Science and Technology; vol. 5; nb. 3; (2015); p. 1683 - 1692 View in Reaxys With (iPrDI)Co(η3-C3H5), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tert-butyl methyl ether, Time= 48h, T= 23 °C Palmer, W. Neil; Diao, Tianning; Pappas, Iraklis; Chirik, Paul J.; ACS Catalysis; vol. 5; nb. 2; (2015); p. 622 - 626 View in Reaxys With platinum, hydrogen in methanol, Time= 1h, T= 50 °C Xie, Ruigang; Pan, Yue; Gu, Hongwei; RSC Advances; vol. 5; nb. 21; (2015); p. 16497 - 16500 View in Reaxys With hydrogen, Time= 1h, T= 25 °C , p= 2250.23Torr , Reagent/catalyst Martnez-Prieto; Urbaneja; Palma; Cmpora; Philippot; Chaudret; Chemical Communications; vol. 51; nb. 22; (2015); p. 4647 - 4650 View in Reaxys With hydrogen in water, Time= 1h, T= 20 °C , p= 760.051Torr , Irradiation, Reagent/catalyst Zhao, Xueyu; Long, Ran; Liu, Dong; Luo, Binbin; Xiong, Yujie; Journal of Materials Chemistry A; vol. 3; nb. 18; (2015); p. 9390 - 9394 View in Reaxys 99.54 Catalyst evaluation %Chromat. General procedure: The hydrogenation reactions were carried out in a 100 mL stainless steel high-pressure batchtype reactor. 20 mmol of the substrates and a certain amount of catalyst samples (1–3 wtpercentRh/NZ-CP) were charged into the reactor and the reactor was sealed with 1.0 MPa N2and H2 to remove the air and then, the reactor was then heated up to the desired temperature. After completion of the reaction, the reactor was cooled down to room temperatureand then depressurized. The catalyst was easily isolated from the reaction mixture using centrifuge technique. The composition of reaction mixture was analyzed by GC using an Agilent gas chro-matograph fitted with a FactorFour HP5-MS capillary column. The turnover frequency (TOF) was calculated as the number of molesof reactant consumed per mol of catalyst exposed on surface per hour. With hydrogen in neat (no solvent), Time= 0.25h, T= 20 °C , p= 7600.51Torr , Autoclave, Green chemistry, Catalytic behavior Baghbanian, Seyed Meysam; Farhang, Maryam; Vahdat, Seyed Mohammad; Tajbakhsh, Mahmood; Journal of Molecular Catalysis A: Chemical; vol. 407; (2015); p. 128 - 136; Art.No: 9543 View in Reaxys With hydrogen in ethanol, Time= 1.5h, T= 25 °C , Catalytic behavior Yang, Shuliang; Cao, Changyan; Sun, Yongbin; Huang, Peipei; Wei, Fangfang; Song, Weiguo; Angewandte Chemie - International Edition; vol. 54; nb. 9; (2015); p. 2661 - 2664; Angew. Chem.; vol. 127; nb. 9; (2015); p. 2699 - 2702,3 View in Reaxys With hydrogen, T= 30 °C , p= 7500.75Torr , Autoclave Jiang, He-Yan; Zheng, Xu-Xu; Catalysis Science and Technology; vol. 5; nb. 7; (2015); p. 3728 - 3734 View in Reaxys 99 %Chromat.

With hydrogen in ethanol, T= 25 °C , p= 3724.25Torr , Flow reactor, Solvent, Pressure, chemoselective reaction Osako, Takao; Torii, Kaoru; Tazawa, Aya; Uozumi, Yasuhiro; RSC Advances; vol. 5; nb. 57; (2015); p. 45760 45766 View in Reaxys

> 99 With hydrogen, Time= 0.916667h, T= 50 °C , p= 15001.5Torr , Catalytic behavior, Reagent/catalyst, Temperature %Chromat.

36/96

2016-06-28 15:56:50

Xue, Zhimin; Sun, Xiaofu; Li, Zhonghao; Mu, Tiancheng; Chemical Communications; vol. 51; nb. 54; (2015); p. 10811 - 10814 View in Reaxys With iridium(III) chloride trihydrate in ethylene glycol, Time= 0.0833333h, T= 250 °C , Inert atmosphere, Microwave irradiation Tashiro, Shohei; Yamada, Mihoko; Shionoya, Mitsuhiko; Angewandte Chemie - International Edition; vol. 54; nb. 18; (2015); p. 5351 - 5354; Angew. Chem.; vol. 127; nb. 18; (2015); p. 5441 - 5444,4 View in Reaxys With palladium, hydrogen in ethanol, T= 30 °C , p= 750.075Torr , Catalytic behavior Zhao, Xiaojing; Zhao, Yun; Fu, Gang; Zheng, Nanfeng; Chemical Communications; vol. 51; nb. 60; (2015); p. 12016 - 12019 View in Reaxys With hydrogen in ethanol, T= 0 - 25 °C , p= 760.051Torr , High pressure, Reagent/catalyst Li, Liuyi; Zhao, Huaixia; Wang, Ruihu; ACS Catalysis; vol. 5; nb. 2; (2015); p. 948 - 955 View in Reaxys Ca. 100 %Spectr.

With Ru{κ4(Si,H,O,P)-tBu2xantSiP(H)}(H)Cl(PPh3), hydrogen in benzene-d6, Time= 48h, T= 60 °C , p= 760.051Torr , Sealed tube, Catalytic behavior Komuro, Takashi; Arai, Takafumi; Kikuchi, Kei; Tobita, Hiromi; Organometallics; vol. 34; nb. 7; (2015); p. 1211 1217 View in Reaxys With hydrogen in ethanol, Time= 1h, T= 30 °C , p= 7500.75Torr , Autoclave, Inert atmosphere, Catalytic behavior Liu, Ping; Li, Gen; Chang, Wan-Ting; Wu, Meng-Yao; Li, Yong-Xin; Wang, Jun; RSC Advances; vol. 5; nb. 89; (2015); p. 72785 - 72792 View in Reaxys 1 :The 50 mg 1percent Pd-20percent MoO3/5iO2 (impregnated) was activated for the period up to 0.5 h under the constant flow of hydrogen of 2 ml/min in the toluene (10 mL) with constant stirring at room temperature 27° C. To this solution 0.0.5 g styrene was added. The reaction was continued for 3 h. The samples were collected after specified time interval and analyzed by GC. The reaction was monitored by GC analysis. The products were confirmed by GC and GCMS analysis. In this reaction only product obtained was ethyl benzene with 100percent conversion and >99.5percent selectivity. With hydrogen in toluene, Time= 3h, T= 27 °C , Reagent/catalyst, Solvent Patent; Council of Scientific and Industrial Research; Umbarkar, Shubhangi Bhalchandra; Dongare, Mohan Keraba; Acham, Vaibhav Ravindrakumar; US2015/239821; (2015); (A1) English View in Reaxys Catalytic hydrogenation We first choose styrene as a model substrate to explore the catalytic performance of Rh NPs 1 under mild conditions. Fig. 5 showed the effect of reaction time on the product yield. The hydrogenation of styrene produced only ethylbenzene in this system. It was found that the yield increased linearly with time with no inductionperiod. A CS2poisoning test was also carried out on the Rh NPs 1to determine whether a homogeneous mechanism was involved during the hydrogenation of styrene [28]. In such an experiment,the conversion was 52.8percent after the initial 10 min; CS2was thenadded under argon atmosphere and the reaction was completelyterminated as evidenced by no change in the conversion after anadditional reaction time of 50 min. This result supported a heterogeneous mechanism for the hydrogenation of styrene employing Rh NPs and removed the possibility of active homogeneous speciesin the system. In addition, it was found that the amount of leach-ing from catalyst Rh NPs 1 was negligible by ICP-AES analysis inconsecutive catalytic cycles. The catalyst could be reused by simple liquid–liquid extraction after reaction. The procedure was repeated10 times and the results indicated that Rh NPs 1 could be recycledwithout any loss of catalytic activity (Fig. 6). The average diameterof the spent Rh NPs 1 after 10 recycles of styrene hydrogenationwas 8.76 nm (Fig. 2, image 6 and S6s). When Rh NPs 5 was used asa catalyst for the catalytic cycles, it showed poor activity. Further-more, Rh NPs 5 suffered 49.8percent deactivation throughout only threecontinuous hydrogenation recycling steps and was almost inactive after four recycling steps.

37/96

2016-06-28 15:56:50

With hydrogen, T= 25 °C , p= 7500.75Torr , Reagent/catalyst Jiang, He-Yan; Zheng, Xu-Xu; Applied Catalysis A: General; vol. 499; (2015); p. 118 - 123 View in Reaxys Homogeneous experiments experiments A typical procedure for the catalytic hydrogenation of alkenes was as follows. A Parr High pressure reactor with an in built cooling, heating and stirring systems was charged with styrene (0.56 mL,5.00 mmol), catalyst (5 mg, 0.01 mmol) and methanol (50 mL) andsealed. It was then evacuated, flushed with H2 three times and the pressure adjusted to 10 bar. The mixture was stirred at 500 rpm under constant hydrogen pressure for the duration of the reaction period. After the reaction time, the autoclave was vented and samples drawn for GC analyses. The samples were filtered using 0.45 m micro filters and the solutions analyzed by Varian CP-3800 GC (ZB-5HT column 30 m × 0.25 mm × 0.10 m). Commercial ethylbenzene was used as an authentic standard to determine the percentage conversion of styrene to ethylbenzene. Percentage conversions were determined by comparing the peak areas of ethylbenzene (product) and styrene substrate. With [η6-(2-phenoxyethanol)RuCl(2-(2-pyridyl)benzoimidazole)]Cl, hydrogen in methanol, Time= 1h, T= 25 °C , p= 7500.75Torr , Autoclave, Catalytic behavior, Reagent/catalyst, Temperature, Pressure Ogweno, Aloice O.; Ojwach, Stephen O.; Akerman, Matthew P.; Applied Catalysis A: General; vol. 486; (2014); p. 250 - 258 View in Reaxys With borane-ammonia complex, C17H45N5Si3Zr, Time= 6h, T= 65 °C , Inert atmosphere Erickson, Karla A.; Stelmach, John P. W.; Mucha, Neil T.; Waterman, Rory; Organometallics; vol. 34; nb. 19; (2015); p. 4693 - 4699 View in Reaxys General procedure: The reactions were performed using a conventional continuous-flow micro-reactor operated at atmospheric pressure [10]. Typically, a weighed crystalline cluster sample (30 mg) of CuxMo6S8–δ(x = 2.94, δ≈ 0.3) (1) stored in air was packed in a borosilicate glass tube (3 mm i.d.), andplaced in the center of an electric furnace. The catalyst sample was initially heated from room temperature to a fixed tempera-ture between 250 and 500C over 15 min in a hydrogen stream(2.4 L/h), and then held at this temperature for 45 min. Withoutchanging the temperature, the reaction was initiated by feedingreactant (0.5 mmol/h) into the hydrogen stream using a syringepump. The reaction was monitored every 30 min by sampling thereaction gas (1 mL) via a six-way valve kept at 150C, followedby analysis using an on-line gas–liquid chromatograph (GLC). Thereactor effluent was frozen in an ice-water trap for determination ofmaterial balance and subsequent analysis of the products. Catalyticreactions using the other catalysts were performed in the sameway [4]. With Cu2.94Mo6S7.7, hydrogen, Time= 3h, T= 300 °C , p= 760.051Torr , Flow reactor, Catalytic behavior Kamiguchi, Satoshi; Arai, Kanako; Okumura, Kazu; Iida, Hajime; Nagashima, Sayoko; Chihara, Teiji; Applied Catalysis A: General; vol. 505; (2015); p. 417 - 421 View in Reaxys With hydrogen in toluene, T= 40 °C , p= 2250.23Torr , Schlenk technique, Glovebox, Catalytic behavior, Reagent/ catalyst Romanenko, Iuliia; Gajan, David; Sayah, Reine; Crozet, Delphine; Jeanneau, Erwan; Lucas, Christine; Leroux, Lnaic; Veyre, Laurent; Lesage, Anne; Emsley, Lyndon; Lacte, Emmanuel; Thieuleux, Chlo; Angewandte Chemie - International Edition; vol. 54; nb. 44; (2015); p. 12937 - 12941; Angew. Chem.; vol. 127; nb. 44; (2015); p. 13129 - 13133,4 View in Reaxys 99 %Chromat.

A general procedure for the recycling of Fe3O4 catalyst in olefin reductions To an oven-dried, two-necked 25 mL round-bottom flask equipped with a magnetic stir bar and a reflux condenser, Fe3O4 (92 mg, 0.40 mmol) and ethanol (6.0 mL) were added, and the mixture was sonicated in an ultrasonic bath for 1 minute under N2 atmosphere. Styrene (1.0 mmol) and hydrazine monohydrate (380 μL, 8 equiv) were added. Then the reaction mixture was stirred at 80 °C under argon atmosphere until the reaction was completed. After magnetic separation of the catalyst (see Fig. 2), the remaining solution was decanted, then directly analyzed with gas chromatography. The remaining catalyst was washed with ethanol (5 mL × 2), dried under vacuum, and reused for the next cycle of the reaction.

38/96

2016-06-28 15:56:50

With iron oxide, hydrazine hydrate in ethanol, Time= 16h, T= 80 °C , Inert atmosphere, Catalytic behavior, Temperature, Solvent Kim, Eunsuk; Kim, Seyoung; Moon Kim; Bulletin of the Korean Chemical Society; vol. 32; (2011); p. 3183 - 3186 View in Reaxys With tungsten oxide, hydrogen in cyclohexane, Catalytic behavior, Reagent/catalyst Song, Jiajia; Huang, Zhen-Feng; Pan, Lun; Zou, Ji-Jun; Zhang, Xiangwen; Wang, Li; ACS Catalysis; vol. 5; nb. 11; (2015); p. 6594 - 6599 View in Reaxys With borane-ammonia complex in water, Time= 0.333333h, T= 24.84 °C Zhao, Tian-Jian; Zhang, Ya-Nan; Wang, Kai-Xue; Su, Juan; Wei, Xiao; Li, Xin-Hao; RSC Advances; vol. 5; nb. 124; (2015); p. 102736 - 102740 View in Reaxys 3.2.3. Transfer Hydrogenations in Ionic Liquids with Metal Nanoparticles General procedure: Exemplary procedure (Table 2; entry 1): In a typical transfer hydrogenation experiment, a vial was charged with the ruthenium nanocatalyst mixture of previously synthesized ruthenium nanoparticles (3 mg Ru) in ionic liquid (1.28 g; RuBMMIM][NTf2]) [37] and 9 mmol cyclohexene. Subsequently, 1.7 mmol EDAB was added and the vial was sealed. The reaction mixture was stirred overnight at 70 °C and then cooled to room temperature. A defined amount of CDCl3 as solvent and hexamethyldisilane (HMDS; Si2Me6) as internal standard was added to the mixture and homogenized. A sample was taken and the product yield was determined by NMR spectroscopy (Tables 2 and 3). The Pd-catalyzed reactions used 600 mg [(CN)BMIM][NTf2] and 0.5 mg Pd nanoparticles prepared as previously published [39]. With ethane 1,2-diaminoborane, T= 70 °C , Sealed tube, Catalytic behavior, Reagent/catalyst, chemoselective reaction Sahler, Sebastian; Scott, Martin; Gedig, Christian; Prechtl, Martin H.G.; Molecules; vol. 20; nb. 9; (2015); p. 17058 - 17069 View in Reaxys With hydrogen, palladium in ethanol, Time= 0.5h, T= 20 °C , Reagent/catalyst Zhang, Ying; Wang, Mingsong; Zhu, Enbo; Zheng, Yuebing; Huang, Yu; Huang, Xiaoqing; Nano Letters; vol. 15; nb. 11; (2015); p. 7519 - 7525 View in Reaxys With hydrogen in methanol, Time= 0.666667h, T= 20 °C , p= 750.075Torr , Inert atmosphere, Schlenk technique Moreno-Marrodan, Carmen; Liguori, Francesca; Mercad, Elisabet; Godard, Cyril; Claver, Carmen; Barbaro, Pierluigi; Catalysis Science and Technology; vol. 5; nb. 7; (2015); p. 3762 - 3772 View in Reaxys With hydrogen in ethanol, T= 25 °C , p= 2250.23Torr , Schlenk technique, Inert atmosphere, Catalytic behavior, Reagent/catalyst Guarnizo; Angurell; Rossell; Llorca; Muller; Seco; RSC Advances; vol. 5; nb. 111; (2015); p. 91340 - 91348 View in Reaxys 100 With hydrogen in tetrahydrofuran, Time= 6h, T= 22 °C , p= 760.051Torr , Inert atmosphere, Schlenk technique, Cat%Chromat. alytic behavior Lu, Feng; Didier, Astruc; European Journal of Inorganic Chemistry; vol. 2015; nb. 34; (2015); p. 5595 - 5600 View in Reaxys 100 With hydrogen in n-heptane, Time= 16h, T= 80 °C , p= 30003Torr , Autoclave, Glovebox %Chromat. Castelbou, Jessica Llop; Blondeau, Pascal; Claver, Carmen; Godard, Cyril; RSC Advances; vol. 5; nb. 117; (2015); p. 97036 - 97043 View in Reaxys

39/96

2016-06-28 15:56:50

98 %Chromat.

With silver nanoparticles/cellulose nanocrystals, hydrogen in water, Time= 24h, T= 100 °C , p= 30003Torr , Autoclave Kaushik, Madhu; Li, Alain You; Hudson, Reuben; Masnadi, Mitra; Li, Chao-Jun; Moores, Audrey; Green Chemistry; vol. 18; nb. 1; (2016); p. 129 - 133 View in Reaxys With C22H40IrO3P2Pol, hydrogen in pentane Solid phase= silica, T= 20 °C , p= 750.075Torr , Schlenk technique, Inert atmosphere, Catalytic behavior, Kinetics, Mechanism, Reagent/catalyst Rimoldi; Fodor; Van Bokhoven; Mezzetti; Catalysis Science and Technology; vol. 5; nb. 9; (2015); p. 4575 - 4586 View in Reaxys

95 %Chromat.

With maghemite-palladium nanocomposite, hydrogen in ethanol, Time= 0.0125h, T= 50 °C Rathi, Anuj K.; Gawande, Manoj B.; Ranc, Vaclav; Pechousek, Jiri; Petr, Martin; Cepe, Klara; Varma, Rajender S.; Zboril, Radek; Catalysis Science and Technology; vol. 6; nb. 1; (2016); p. 152 - 160 View in Reaxys With hydrogen, Time= 0.5h, T= 30 °C , p= 7500.75Torr , Autoclave, Inert atmosphere, Catalytic behavior Zou, Rui; Wen, Shipeng; Zhang, Liqun; Liu, Li; Yue, Dongmei; RSC Advances; vol. 5; nb. 121; (2015); p. 99884 - 99891 View in Reaxys With C30H54B2P2Rh2, hydrogen in toluene, Time= 24h, T= 20 °C , p= 760.051Torr , Schlenk technique, Reagent/ catalyst Perez, Viridiana; Audet, Pierre; Bi, Wenhua; Fontaine, Frdric-Georges; Dalton Transactions; vol. 45; nb. 5; (2016); p. 2130 - 2137 View in Reaxys 2.3.1. Hydrogenation reaction General procedure: Hydrogenation reaction for the catalytic activity of synthesizedcatalysts were performed in 100 ml Parr autoclave with suitablehydrogen pressure and temperatures. To check the catalytic activ-ities of catalysts like RhCl(PPh3)3and Cata.1a/1b/1c/1d,a knownamount of olefins (10 mmol), catalysts [neat RhCl(PPh3)3complex:5 mg or Cata.1a/1b/1c/1d: 15 mg] and 55 ml toluene were takenin an auto clave and stirred continuously with hydrogen pressure(150 Psi) at room temperature (28–32C). Moreover, the catalyticactivites of neat RuHCl(CO)(PPh3)3complex and Cata.2a/2b/2c/2dwere investigated by using a procedure as: a known amountof olefins (10 mmol), catalyst [neat RuHCl(CO)(PPh3)3complex:12 mg or Cata.2a/2b/2c/2d: 25 mg] and 55 ml toluene were takenin an auto clave and stirred continuously with hydrogen pressure(250 Psi) at 90C. The progress of the reaction in all synthesizedcatalysts were monitored by the withdrawing samples at differ-ent time intervals and analyzed by Gas Chromatography (HP 6890)equipped with a flame ionized detector and a capillary column(HP-5, 5 m cross-linked methyl silicone gum, 0.2 mm × 50 m). With hydrogen in toluene, Time= 0.45h, T= 90 °C , p= 12929Torr , Autoclave, Reagent/catalyst Lazar, Anish; George, Shoy C.; Jithesh; Vinod; Singh; Applied Catalysis A: General; vol. 513; (2016); p. 138 146 View in Reaxys With hydrogen in decane, ethanol, T= 25 °C , p= 760.051Torr Li, Xiaoyu; Tang, Aidong; RSC Advances; vol. 6; nb. 19; (2016); p. 15585 - 15591 View in Reaxys With borane-ammonia complex, carbonyl(pentamethylcyclopentadienyl)cobalt diiodide, Catalytic behavior Pagano, Justin K.; Stelmach, John P. W.; Waterman, Rory; Dalton Transactions; vol. 44; nb. 27; (2015); p. 12074 - 12077 View in Reaxys With hydrogen in ethanol, T= 150 °C , p= 7500.75Torr Tian, Song; Li, Xiang; Wang, Anjie; Prins, Roel; Chen, Yongying; Hu, Yongkang; Angewandte Chemie - International Edition; vol. 55; nb. 12; (2016); p. 4030 - 4034; Angew. Chem.; vol. 128; (2016); p. 4098 - 4102,5

40/96

2016-06-28 15:56:50

View in Reaxys With hydrogen in methanol, Time= 0.25h, T= 30 °C , p= 3750.38Torr , Autoclave, Catalytic behavior, Temperature Lazar, Anish; Vinod, Chathakudath P.; Singh, Anand Pal; New Journal of Chemistry; vol. 40; nb. 3; (2016); p. 2423 - 2432 View in Reaxys 97 %Chromat.

With [{CyPN(H)P}Co(CH2SiMe3)]-BArF 4, isopropyl alcohol in tetrahydrofuran, Time= 24h, T= 100 °C , Schlenk technique, Inert atmosphere, Catalytic behavior, Reagent/catalyst, Solvent, Temperature Zhang, Guoqi; Yin, Zhiwei; Tan, Jiawen; RSC Advances; vol. 6; nb. 27; (2016); p. 22419 - 22423 View in Reaxys With C39H64N2PtSn, hydrogen in (2)H8-toluene, Time= 24h, T= 20 °C , p= 760.051Torr , Schlenk technique Koppaka, Anjaneyulu; Captain, Burjor; Inorganic Chemistry; vol. 55; nb. 6; (2016); p. 2679 - 2681 View in Reaxys With hydrogen in toluene, Time= 16h, T= 40 °C , p= 750.075Torr , Autoclave, Inert atmosphere, Catalytic behavior, Solvent, Reagent/catalyst, Temperature, Pressure, chemoselective reaction Rühling, Andreas; Schaepe, Kira; Rakers, Lena; Vonhören, Benjamin; Tegeder, Patricia; Ravoo, Bart Jan; Glorius, Frank; Angewandte Chemie - International Edition; vol. 55; nb. 19; (2016); p. 5856 - 5860; Angew. Chem.; vol. 128; nb. 19; (2016); p. 5950 - 5955,6 View in Reaxys 2.4 General procedure for the catalytic hydrogenation General procedure: The hydrogenation experiments were carried out in a glass-lined, 100-mL stainless steel autoclave containing a magnetic stirring bar. In a typical run, the autoclave was charged successively under nitrogen with bis-rhodium complex 9 (0.006 g, 0.005 mmol, 1 molpercent of Rh) dissolved in the solvent (5 mL of THF) and substrate (1.0 mmol). Once closed, the autoclave was flushed twice with hydrogen, then pressurised. At the end of the catalytic run, the autoclave was depressurized and the resulting solution was passed through a Millipore filter and analyzed by GC (Varian 3900 gas chromatograph equipped with a WCOT fused-silica column: 25 m × 0.25 mm). With P,P′-{5,17-bis(diphenylphosphino)-25,26,27,28-tetrahydroxycalix[4] arene}-bis[chlorido(1,5-cyclooctadiene)]rhodium(I) in tetrahydrofuran, Time= 5h, T= 20 °C , p= 3750.38Torr , Autoclave, Inert atmosphere, Catalytic behavior Monnereau, Laure; Semeril, David; Matt, Dominique; Toupet, Loic; Polyhedron; vol. 51; nb. 1; (2013); p. 70 - 74 View in Reaxys ydrogenationofstyrene General procedure: All hydrogenation reactions were carried out at room temperature under hydrogen (1atm.) in water. For this purpose ,0.002mmol of the Pd nanoparticles (0.1mol percent,2ml from a 1mM aqueous solution) and 50mg decaneas internal standard for GC were placed in a two-neck flask(10ml) .After completion there action volume with water toatotal volume of 8ml,the flask was connected to a vacuum line/hydrogen setupand theair inside the flask was removed via vacuum-hydrogen flow (4 times). There action mixture was put under ahydrogen atmosphere (1 atm.) with stirring for15 min and then styrene (2 mmol, 208mg) was added via aseptum (timepoint =0). Samples (0.3–0.4ml) were removed after 5, 15, 30, 60, 120, 180,240, 300,360and 960 minand extracted with Et2O (2ml). After separation of thephases the organic phase was analyzed by GC With hydrogen in water, T= 19.84 °C , p= 30402Torr , Catalytic behavior, Reagent/catalyst, Time Bulut, Safak; Fei, Zhaofu; Siankevich, Sviatlana; Zhang, Jiaguang; Yan, Ning; Dyson, Paul J.; Catalysis Today; vol. 247; (2015); p. 96 - 103 View in Reaxys With hydrogen in toluene, T= 80 °C Yao, Yancai; He, Dong Sheng; Lin, Yue; Feng, Xiaoqian; Wang, Xin; Yin, Peiqun; Hong, Xun; Zhou, Gang; Wu, Yuen; Li, Yadong; Angewandte Chemie - International Edition; vol. 55; nb. 18; (2016); p. 5501 - 5505; Angew. Chem.; vol. 128; nb. 18; (2016); p. 5591 - 5595,5 View in Reaxys With hydrogen in pentan-1-ol, water, Time= 1h, T= 60 °C , p= 7500.75Torr , Autoclave

41/96

2016-06-28 15:56:50

Chen, Zhijun; Wang, Yanhua; Jiang, Jingyang; Jin, Zilin; Chinese Journal of Catalysis; vol. 32; nb. 6-8; (2011); p. 1133 - 1137 View in Reaxys With (PNPiPr)Fe(H)(CO), hydrogen in benzene-d6, Time= 24h, T= 23 °C , p= 760.051Torr , Inert atmosphere, Schlenk technique, Glovebox, Reagent/catalyst, Temperature Xu, Ruibo; Chakraborty, Sumit; Bellows, Sarina M.; Yuan, Hongmei; Cundari, Thomas R.; Jones, William D.; ACS Catalysis; vol. 6; nb. 3; (2016); p. 2127 - 2135 View in Reaxys With hydrogen, Time= 1h, Catalytic behavior, Reagent/catalyst Liu, Pengxin; Zhao, Yun; Qin, Ruixuan; Mo, Shiguang; Chen, Guangxu; Gu, Lin; Chevrier, Daniel M.; Zhang, Peng; Guo, Qing; Zang, Dandan; Wu, Binghui; Fu, Gang; Zheng, Nanfeng; Science; vol. 352; nb. 6287; (2016); p. 797 - 801 View in Reaxys With hydrogen, Time= 6h, T= 25 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst, Time Zhong, Hong; Liu, Caiping; Wang, Yangxin; Wang, Ruihu; Hong, Maochun; Chemical Science; vol. 7; nb. 3; (2016); p. 2188 - 2194 View in Reaxys > 99 With hydrogen in methanol, Time= 0.166667h, T= 20 °C , p= 760.051Torr , Reagent/catalyst, Time %Chromat. etinkaya, Yasin; Metin, Önder; Balci, Metin; RSC Advances; vol. 6; nb. 34; (2016); p. 28538 - 28542 View in Reaxys

Rx-ID: 39025 View in Reaxys 3/154 Yield

Conditions & References With lithium aluminium tetrahydride, hydrogen, benzene, T= 120 °C , p= 44130.5Torr , Behandeln des Reaktionsgemisches mit Sauerstoff und anschliessend mit wss. Aceton Patent; Standard Oil Co. of Indiana; US2873290; (1955) View in Reaxys With lithium triethylborohydride, other reagents; rel. rates, Product distribution Brown, Herbert C.; Kim, Suk-Choong; Journal of Organic Chemistry; vol. 49; nb. 6; (1984); p. 1064 - 1071 View in Reaxys With sodium tetrahydroborate, oxygen, palladium diacetate in ethylene glycol dimethyl ether, isopropyl alcohol, Time= 18h, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts Okamoto, Tadashi; Oka, Shinzaburo; Journal of Organic Chemistry; vol. 49; nb. 9; (1984); p. 1589 - 1594 View in Reaxys With sodium tetrahydroborate, oxygen, cobalt 1,8(11),15(18),22(25)-tetraethoxyphthalocyaninate in tetrahydrofuran, ethanol, Kinetics, Further Variations: Catalysts Lyubimtsev; Nifant'ev; Russian Chemical Bulletin; vol. 53; nb. 2; (2004); p. 346 - 350 View in Reaxys O

Rx-ID: 718129 View in Reaxys 4/154

42/96

2016-06-28 15:56:50

Yield

Conditions & References T= 150 °C Goldfinger; Naidus; Mark; Journal of the American Chemical Society; vol. 65; (1943); p. 995 View in Reaxys

SiH

Rx-ID: 1545040 View in Reaxys 5/154 Yield

Conditions & References

76 %, 2 %, With platinum (II) chloride, Time= 4h, T= 24.9 °C , Product distribution 11 %, 11 % Skoda-Foeldes, Rita; Kollar, Laszlo; Heil, Balint; Journal of Organometallic Chemistry; vol. 366; (1989); p. 275 280 View in Reaxys 2 %, 11 %, With platinum (II) chloride, Time= 4h, T= 24.9 °C 11 %, 76 % Skoda-Foeldes, Rita; Kollar, Laszlo; Heil, Balint; Journal of Organometallic Chemistry; vol. 366; (1989); p. 275 280 View in Reaxys 76 %, 2 %, With platinum (II) chloride, Time= 4h, T= 24.9 °C 11 %, 11 % Skoda-Foeldes, Rita; Kollar, Laszlo; Heil, Balint; Journal of Organometallic Chemistry; vol. 366; (1989); p. 275 280 View in Reaxys 76 %, 11 %, 11 %, 2 %

With platinum (II) chloride, Time= 4h, T= 24.9 °C

40 %, 27 %, 23 %, 10 %

With RhCl(PPh3)3 in toluene, Time= 2h, T= 65 °C

Skoda-Foeldes, Rita; Kollar, Laszlo; Heil, Balint; Journal of Organometallic Chemistry; vol. 366; (1989); p. 275 280 View in Reaxys

Skoda-Foeldes, Rita; Kollar, Laszlo; Heil, Balint; Journal of Organometallic Chemistry; vol. 408; nb. 3; (1991); p. 297 - 304 View in Reaxys With platinum (II) chloride, Time= 4h, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts Skoda-Foeldes, Rita; Kollar, Laszlo; Heil, Balint; Journal of Organometallic Chemistry; vol. 408; nb. 3; (1991); p. 297 - 304 View in Reaxys With RhCl(PPh3)3 in toluene, Time= 2h, T= 65 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Skoda-Foeldes, Rita; Kollar, Laszlo; Heil, Balint; Journal of Organometallic Chemistry; vol. 408; nb. 3; (1991); p. 297 - 304 View in Reaxys With RuC3*3H2O, (m-Br-C6H4)PPh2, Time= 5h, T= 90 °C , Inert atmosphere Xue, Mei; Li, Jiayun; Peng, Jiajian; Bai, Ying; Zhang, Guodong; Xiao, Wenjun; Lai, Guoqiao; Applied Organometallic Chemistry; vol. 28; nb. 2; (2014); p. 120 - 126 View in Reaxys

43/96

2016-06-28 15:56:50

SiH

Rx-ID: 1545041 View in Reaxys 6/154 Yield

Conditions & References With trans-PtCl2(PhCH=CH2)2 in benzene-d6, var. ratio of catalyst precursor to reagent, rate measurements, deuterium kinetic isotope effect, Mechanism Caseri, W.; Pregosin, P. S.; Journal of Organometallic Chemistry; vol. 356; (1988); p. 259 - 270 View in Reaxys With bis(4-fluorophenylimino)acenaphthalene platinum in toluene, Time= 2h, T= 30 °C , Product distribution, Further Variations: Reagents Sprengers, Jeroen W.; De Greef, Michiel; Duin, Marcel A.; Elsevier, Cornelis J.; European Journal of Inorganic Chemistry; nb. 20; (2003); p. 3811 - 3819 View in Reaxys With [(2,6-diethyl-4,8-dimethyl-s-indacenide){Rh(COD)}] in toluene, T= 80 °C , Product distribution, Further Variations: Catalysts Esponda, Edgardo; Adams, Christopher; Burgos, Francisco; Chavez, Ivonne; Manriquez, Juan M.; Delpech, Fabien; Castel, Annie; Gornitzka, Heinz; Riviere-Baudet, Monique; Riviere, Pierre; Journal of Organometallic Chemistry; vol. 691; nb. 13; (2006); p. 3011 - 3017 View in Reaxys

SiH

Rx-ID: 1545042 View in Reaxys 7/154 Yield 96 % Chromat., 93 % Chromat.

Conditions & References With tri-ruthenium(0)dodecacarbonyl in benzene, Time= 5h, T= 80 °C Seki, Yoshio; Takeshita, Kenji; Kawamoto, Kazuaki; Murai, Shinji; Sonoda, Noboru; Journal of Organic Chemistry; vol. 51; nb. 20; (1986); p. 3890 - 3895 View in Reaxys

SiH

Rx-ID: 1545248 View in Reaxys 8/154 Yield

Conditions & References With Wilkinson's catalyst in benzene, Time= 6h, T= 40 °C , other temperatures; other Rh complexes; also presence of air or argon, Product distribution, Mechanism Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 7; (1980); p. 2085 - 2099 View in Reaxys

21.5 % Turnov., 60.1 %

With Wilkinson's catalyst in benzene, Time= 6h, T= 70 °C , other solvents, inaerobic conditions or the presence of air oxygen, Product distribution

44/96

2016-06-28 15:56:50

Turnov., 18.4 % Turnov.

Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 8; (1980); p. 2240 - 2246 View in Reaxys With Wilkinson's catalyst in benzene, Time= 6h, T= 40 °C , Yield given. Yields of byproduct given Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 7; (1980); p. 2085 - 2099 View in Reaxys With Wilkinson's catalyst in benzene, Time= 6h, T= 60 °C , Yield given. Yields of byproduct given Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 7; (1980); p. 2085 - 2099 View in Reaxys

60.1 % Turnov., 18.4 % Turnov., 21.5 % Turnov.

With Wilkinson's catalyst in benzene, Time= 6h, T= 70 °C Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 8; (1980); p. 2240 - 2246 View in Reaxys

With Wilkinson's catalyst in benzene, Time= 6h, T= 100 °C , Yield given. Yields of byproduct given Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 7; (1980); p. 2085 - 2099 View in Reaxys

SiH

Rx-ID: 1545249 View in Reaxys 9/154 Yield 43.7 % Turnov., 56.3 % Turnov.

Conditions & References With Wilkinson's catalyst in N,N,N',N',N'',N''-hexamethylphosphoric triamide, Time= 6h, T= 70 °C Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 8; (1980); p. 2240 - 2246 View in Reaxys

SiH

Rx-ID: 1545281 View in Reaxys 10/154 Yield

Conditions & References With Wilkinson's catalyst in benzene, Time= 6h, T= 100 °C , other temperature (60 deg C); other complex, Product distribution, Mechanism Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 7; (1980); p. 2085 - 2099 View in Reaxys

100 % Turnov.

With Wilkinson's catalyst, Time= 6h, T= 100 °C Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 7; (1980); p. 2085 - 2099 View in Reaxys

45/96

2016-06-28 15:56:50

H2 Si E

SiH

Rx-ID: 1545713 View in Reaxys 11/154 Yield 77 % Chromat., 16 % Chromat., 7 % Chromat.

Conditions & References With dibutylzirconocene in toluene, Time= 1.2h, T= 25 °C , other olefins, Product distribution Kesti, Michael R.; Abdulrahman, Maie; Waymouth, Robert M.; Journal of Organometallic Chemistry; vol. 417; nb. 1/2; (1991); p. C12 - C15 View in Reaxys

Mg Cl

Rx-ID: 1545822 View in Reaxys 12/154 Yield 9 %, 86 %

Conditions & References With zirconocene dichloride in diethyl ether, benzene, Ambient temperature Negishi, Ei-ichi; Miller, Joseph A.; Yoshida, Tadao; Tetrahedron Letters; vol. 25; nb. 32; (1984); p. 3407 - 3410 View in Reaxys

Rx-ID: 1546461 View in Reaxys 13/154 Yield 31 %, 42 %, 3 %

Conditions & References With hydrogen, PtCl(SnCl3)lt;(S,S)-BDPPgt; in toluene, Time= 55h, T= 40 °C , p= 60004.8Torr Kollar, Laszlo; Bakos, Jozsef; Toth, Imre; Heil, Balint; Journal of Organometallic Chemistry; vol. 350; (1988); p. 277 - 284 View in Reaxys

Rx-ID: 1546483 View in Reaxys 14/154 Yield 0.3 %, 1.5 %, 2.8 %

Conditions & References With hydrogen, (.eta.3-C3H5)Co[P(OMe)3]3, Time= 20.5h, Ambient temperature Bleeke, J. R.; Muetterties, E. L.; Journal of the American Chemical Society; vol. 103; nb. 3; (1981); p. 556 - 564 View in Reaxys

2.8 %, 1.5 %, 0.3 %

With hydrogen, (.eta.3-C3H5)Co[P(OMe)3]3, Time= 20.5h, Ambient temperature Bleeke, J. R.; Muetterties, E. L.; Journal of the American Chemical Society; vol. 103; nb. 3; (1981); p. 556 - 564 View in Reaxys

0.3 %, 2.8 %, 1.5 %

46/96

2016-06-28 15:56:50

Rx-ID: 1546493 View in Reaxys 15/154 Yield 82 %, 10 %

Conditions & References With methanol, Time= 2h, UV-irradiation Shimakoshi, Hisashi; Hisaeda, Yoshio; ChemPlusChem; vol. 79; nb. 9; (2014); p. 1250 - 1253 View in Reaxys

50 %, 4 %

With Ti(III)-citrate, Tris buffer, tetra(n-butyl)ammonium hydroxide, B12 in ethanol, pH= 8 Shey, Justin; McGinley, Chris M.; McCauley, Kevin M.; Dearth, Anthony S.; Young, Brian T.; Van der Donk, Wilfred A.; Journal of Organic Chemistry; vol. 67; nb. 3; (2002); p. 837 - 846 View in Reaxys With hydrogen in acetone, Time= 0.5h, T= -78 °C , p= 2Torr Beeri,A.; Berman,E.; Vishkautsan,R.; Journal of the American Chemical Society; vol. 108; (1986); p. 6413 View in Reaxys

Rx-ID: 1546494 View in Reaxys 16/154 Yield

Conditions & References

12 %, 8 %, With sodium tetrahydroborate, (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride, oxygen in ethanol, ben39 % zene, Time= 2h, Ambient temperature, other styrene, other (porphinato)manganese(III) catalyst, var. time, also absence of oxygen, Product distribution, Mechanism Takeuchi, Masayuki; Kano, Koji; Bulletin of the Chemical Society of Japan; vol. 67; nb. 6; (1994); p. 1726 - 1733 View in Reaxys 12 %, 8 %, With sodium tetrahydroborate, (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride, oxygen in ethanol, ben39 % zene, Time= 2h, Ambient temperature Takeuchi, Masayuki; Kano, Koji; Bulletin of the Chemical Society of Japan; vol. 67; nb. 6; (1994); p. 1726 - 1733 View in Reaxys With sodium tetrahydroborate, oxygen, 5,10,15,20-tetraphenyl-21H,23H-porphine Co(II) in ethylene glycol dimethyl ether, isopropyl alcohol, Time= 25h, Ambient temperature, other substrates, other catalysts, other reagent (NaBD4), other reaction conditions, Mechanism, Product distribution Okamoto, Tadashi; Oka, Shinzaburo; Journal of Organic Chemistry; vol. 49; nb. 9; (1984); p. 1589 - 1594 View in Reaxys With sodium tetrahydroborate, oxygen, Co(cyclam)(py)Cl2 in ethylene glycol dimethyl ether, isopropyl alcohol, Time= 168h, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts Okamoto, Tadashi; Oka, Shinzaburo; Journal of Organic Chemistry; vol. 49; nb. 9; (1984); p. 1589 - 1594 View in Reaxys

H H racemate

Rx-ID: 1546495 View in Reaxys 17/154 Yield

Conditions & References

65 %, 7 %, With sodium tetrahydroborate, 5,10,15,20-tetrakisphenylporphyrinatoiron(III) chloride in ethanol, Time= 1h, Ambient 7% temperature, other (para-substituted phenyl) complexes, var. solvents and reaction times, Product distribution, Mechanism

47/96

2016-06-28 15:56:50

Kano, Koji; Takeuchi, Masayuki; Hashimoto, Shizunobu; Yoshida, Zen-ichi; Journal of the Chemical Society, Chemical Communications; nb. 24; (1991); p. 1728 - 1729 View in Reaxys

Rx-ID: 1546500 View in Reaxys 18/154 Yield 6 %, 94 %

Conditions & References With Aliquatreg; 336, Rhodium trichloride in water, 1,2-DICHLOROETHANE, Time= 5h, T= 30 °C Blum, Jochanan; Amer, Ibrahim; Zoran, Amikam; Sasson, Yoel; Tetrahedron Letters; vol. 24; nb. 38; (1983); p. 4139 - 4142 View in Reaxys

93 %, 0.8 %

0.8 %, 93 %

With hydrogen, HRh(CO)lt;P(NC6H4)3gt;3, Time= 1.66667h, T= 79.9 °C , p= 3750.3Torr Trzeciak, Anna M.; Glowiak, Tadeusz; Ziolkowski, Jozef J.; Journal of Organometallic Chemistry; vol. 552; nb. 1-2; (1998); p. 159 - 164 View in Reaxys With hydrogen, [Rd(cod)(sulphos)]-Pd, silica gel in pentane, Time= 2h, T= 40 °C , p= 22501.8Torr , Product distribution, Further Variations: Catalysts Bianchini, Claudio; Dal Santo, Vladimiro; Meli, Andrea; Moneti, Simonetta; Moreno, Marta; Oberhauser, Werner; Psaro, Rinaldo; Sordelli, Laura; Vizza, Francesco; Angewandte Chemie - International Edition; vol. 42; nb. 23; (2003); p. 2636 - 2639 View in Reaxys With (2,2'-bpy), hydrogen, rhodium, T= 20 °C , p= 30402Torr , Ionic liquid, Inert atmosphere, Reactivity, Pressure, Reagent/catalyst, Solvent, Temperature Leger, Bastien; Denicourt-Nowicki, Audrey; Roucoux, Alain; Olivier-Bourbigou, Helene; Advanced Synthesis and Catalysis; vol. 350; nb. 1; (2008); p. 153 - 159 View in Reaxys

71 %Chro- With hydrogen, HEA16Cl, randomly methylated β-cyclodextrin in water, Time= 7h, T= 20 °C , p= 750.075Torr mat., 29 %Chromat. Hubert, Claudie; Denicourt-Nowicki, Audrey; Roucoux, Alain; Landy, David; Leger, Bastien; Crowyn, Gregory; Monflier, Eric; Chemical Communications; nb. 10; (2009); p. 1228 - 1230 View in Reaxys 5 :Example 5Influence of the Quantity of 2-2' Bipyridine LigandApplication to the Hydrogenation of Styrene at 80° C., 4 MPaThe suspension of metal nanoparticles of rhodium in the ionic liquid [BMI][PF6] is produced as described in Example 1, except that the quantity of 2-2' bipyridine ligand that is introduced during the synthesis is made to vary. The catalytic tests are carried out as described in Example 4. The results are combined in Table 1. Example 4General Procedure for Hydrogenation Under Pressure of Molecular Hydrogen2 ml of a suspension of metal nanoparticles of rhodium in the ionic liquid [BMI][PF6] that is prepared according to Example 1 and 100 equivalents/metal of substrate to be hydrogenated are introduced into a stainless steel autoclave that is equipped with a magnetic rod. The autoclave is then purged 4 times with hydrogen, the temperature is set at 80° C., and then the hydrogen pressure is set at 4 MPa. The reaction starts up with the beginning of the stirring. The progression of the reaction is tracked by GPC [gas phase chromatography]. At the end of the reaction, the catalytic system is dispersed into 10 ml of acetonitrile CH3CN, centrifuged for 10 minutes (15,300 rpm-1; 20° C.). The sample is then analyzed by GPC. With hydrogen, (2,2'-bpy), rhodium, 1-n-butyl-3-methylimidazolium hexafluorophosphate, Time= 15h, T= 80 °C , p= 30003Torr , Autoclave, Product distribution / selectivity Patent; IFP; US2010/228064; (2010); (A1) English

48/96

2016-06-28 15:56:50

View in Reaxys 75 %Chro- With hydrogen in ethanol, Time= 6h, T= 50 °C , p= 30003Torr , chemoselective reaction mat., 25 %Chromat. Jahjah, Mohamad; Kihn, Yolande; Teuma, Emmanuelle; Gomez, Montserrat; Journal of Molecular Catalysis A: Chemical; vol. 332; nb. 1-2; (2010); p. 106 - 112 View in Reaxys 65 %Chro- With hydrogen in ethanol, Time= 6h, T= 50 °C , p= 30003Torr , chemoselective reaction mat., 35 %Chromat. Jahjah, Mohamad; Kihn, Yolande; Teuma, Emmanuelle; Gomez, Montserrat; Journal of Molecular Catalysis A: Chemical; vol. 332; nb. 1-2; (2010); p. 106 - 112 View in Reaxys With hydrogen, Time= 15h, T= 80 °C , p= 30402Torr , Ionic liquid, Autoclave Leger, Bastien; Denicourt-Nowicki, Audrey; Olivier-Bourbigou, Helene; Roucoux, Alain; Tetrahedron Letters; vol. 50; nb. 47; (2009); p. 6531 - 6533 View in Reaxys 55.7 With hydrogen in water, Time= 2h, T= 60 °C , p= 15201Torr , Autoclave %Chromat., 44.2 Yan, Ning; Yuan, Yuan; Dyson, Paul J.; Chemical Communications; vol. 47; nb. 9; (2011); p. 2529 - 2531 %Chromat. View in Reaxys With hydrogen in hexane, Time= 3h, T= 25 °C , p= 750.075Torr Boutros, Maya; Shirley, Guillaume; Onfroy, Thomas; Launay, Franck; Applied Catalysis A: General; vol. 394; nb. 1-2; (2011); p. 158 - 165 View in Reaxys With 5 Rh/C, hydrogen in hexane, Time= 3h, T= 25 °C , p= 750.075Torr Boutros, Maya; Shirley, Guillaume; Onfroy, Thomas; Launay, Franck; Applied Catalysis A: General; vol. 394; nb. 1-2; (2011); p. 158 - 165 View in Reaxys With hydrogen, Time= 2h, T= 20 °C , p= 7500.75Torr , Autoclave, Neat (no solvent) Pelisson, Carl-Hugo; Vono, Lucas L.R.; Hubert, Claudie; Denicourt-Nowicki, Audrey; Rossi, Liane M.; Roucoux, Alain; Catalysis Today; vol. 183; nb. 1; (2012); p. 124 - 129 View in Reaxys With hydrogen, Time= 4h, T= 20 °C , p= 7500.75Torr , Autoclave, Neat (no solvent) Pelisson, Carl-Hugo; Vono, Lucas L.R.; Hubert, Claudie; Denicourt-Nowicki, Audrey; Rossi, Liane M.; Roucoux, Alain; Catalysis Today; vol. 183; nb. 1; (2012); p. 124 - 129 View in Reaxys With Ru, hydrogen, T= 30 °C , p= 900.09Torr , Reagent/catalyst Salas, Gorka; Campbell, Paul S.; Santini, Catherine C.; Philippot, Karine; Costa Gomes, Margarida F.; Padua, Agilio A.H.; Dalton Transactions; vol. 41; nb. 45; (2012); p. 13919 - 13926 View in Reaxys With Rh0.67Ni0.33, hydrogen in ethyl acetate, Time= 1h, T= 25 °C , p= 30402Torr , Autoclave Duan, Haohong; Wang, Dingsheng; Kou, Yuan; Li, Yadong; Chemical Communications; vol. 49; nb. 3; (2013); p. 303 - 305 View in Reaxys 79 %Chro- With [Rh(η3-C3H5)3], hydrogen in tetrahydrofuran, methanol, n-heptane, Time= 16h, T= 20 °C , p= 30003Torr , Automat., 21 clave, Glovebox, Reagent/catalyst, Temperature, Concentration, Time %Chromat. Castelbou, Jessica Llop; Gual, Aitor; Mercade, Elisabet; Claver, Carmen; Godard, Cyril; Catalysis Science and Technology; vol. 3; nb. 10; (2013); p. 2828 - 2833 View in Reaxys

49/96

2016-06-28 15:56:50

With hydrogen in water, Time= 2h, T= 20 °C , p= 7500.75Torr , Autoclave, Catalytic behavior Guerrero, Miguel; Coppel, Yannick; Chau, Nguyet Tran Thanh; Roucoux, Alain; Denicourt-Nowicki, Audrey; Monflier, Eric; Bricout, Herve; Lecante, Pierre; Philippot, Karine; ChemCatChem; vol. 5; nb. 12; (2013); p. 3802 - 3811 View in Reaxys With Chromium (III) chloride, lithium aluminium tetrahydride in tetrahydrofuran, Time= 6h, Overall yield = 58 percent; Overall yield = 7 g Popov; Mokhov; Nebykov; Russian Journal of General Chemistry; vol. 84; nb. 3; (2014); p. 444 - 448; Zh. Obshch. Khim.; vol. 84; nb. 3; (2014); p. 385 - 390,6 View in Reaxys With hydrogen, Time= 24h, T= 25 °C , p= 2250.23Torr Martnez-Prieto; Urbaneja; Palma; Cmpora; Philippot; Chaudret; Chemical Communications; vol. 51; nb. 22; (2015); p. 4647 - 4650 View in Reaxys With hydrogen, Time= 5h, T= 25 °C , p= 2250.23Torr , Reagent/catalyst Martnez-Prieto; Urbaneja; Palma; Cmpora; Philippot; Chaudret; Chemical Communications; vol. 51; nb. 22; (2015); p. 4647 - 4650 View in Reaxys 73 %Chro- With hydrogen in n-heptane, Time= 16h, T= 80 °C , p= 30003Torr , Autoclave, Glovebox mat., 26 %Chromat. Castelbou, Jessica Llop; Blondeau, Pascal; Claver, Carmen; Godard, Cyril; RSC Advances; vol. 5; nb. 117; (2015); p. 97036 - 97043 View in Reaxys 87 %Chro- With hydrogen in n-heptane, Time= 16h, T= 80 °C , p= 30003Torr , Autoclave, Glovebox mat., 13 %Chromat. Castelbou, Jessica Llop; Blondeau, Pascal; Claver, Carmen; Godard, Cyril; RSC Advances; vol. 5; nb. 117; (2015); p. 97036 - 97043 View in Reaxys Catalytic Testing Procedure General procedure: Catalytic hydrogenation tests were conducted in asteel autoclave in a hydrogen atmosphere under a highpressure and vigorous stirring of the reaction mixture.The precursor and 2 mL of the substrate were placedinto the glass cartridge of the autoclave. After that, theautoclave was filled with hydrogen to a pressure of50 atm and held at a temperature of 350° for 1–10 h;the hydrogen/substrate molar ratio was 60 mol/mol.Model feedstocks and light cycle oil produced on acatalytic cracking unit (LCO) were used in the experiments (Table 1). With 1-butyl-1-methylpiperidinium nickel thiotungstate, hydrogen in cetane, Time= 10h, T= 350 °C , p= 37503.8Torr , Autoclave Sizova; Serdyukov; Maksimov; Petroleum Chemistry; vol. 55; nb. 6; (2015); p. 470 - 480; Neftekhimiya; vol. 55; nb. 4; (2015); p. 319 - 330,12 View in Reaxys

Rx-ID: 1546502 View in Reaxys 19/154 Yield

Conditions & References With sodium tetrahydroborate, 18-crown-6 ether, titanium(III) chloride in tetrahydrofuran, Time= 3h, T= 30 °C , various catalyst, temp., and time, Product distribution Lee, Hyung Soo; Isagawa, Kakuzo; Toyoda, Hiromu; Otsuji, Yoshio; Chemistry Letters; (1984); p. 673 - 676 View in Reaxys With sodium hydroxide, lithium borohydride, Cp2Ti(BH4), dihydrogen peroxide, multistep reaction: regio- and or stereoselectivities for hydroboration

50/96

2016-06-28 15:56:50

Burgess, Kevin; Van Der Donk, Wilfred A.; Journal of the American Chemical Society; vol. 116; nb. 15; (1994); p. 6561 - 6569 View in Reaxys With sodium hydroxide, lithium borohydride, dihydrogen peroxide, Cp2Ti(BH4), 1) THF, 65 deg C, 9 h; var. reag. in 1) step: Cp2TiBH4, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Burgess, Kevin; Van Der Donk, Wilfred A.; Tetrahedron Letters; vol. 34; nb. 43; (1993); p. 6817 - 6820 View in Reaxys With sodium tetrahydroborate, 18-crown-6 ether, dihydrogen peroxide, sodium methylate, bis(cyclopentadienyl)titanium dichloride, 1.) THF, 30 deg C, 3 h, 2.) THF, methanol, 40 deg C, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Lee, Hyung Soo; Isagawa, Kakuzo; Toyoda, Hiromu; Otsuji, Yoshio; Chemistry Letters; (1984); p. 673 - 676 View in Reaxys With sodium hydroxide, lithium borohydride, dihydrogen peroxide, Cp2Ti(BH4), 1) THF, 65 deg C, 9 h (or 19 h), var. reag. in step: Cp2TiBH4 or BH3, or BH3 with LiBH4, add of 18-crown-6, var. temp., Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Burgess, Kevin; Van Der Donk, Wilfred A.; Tetrahedron Letters; vol. 34; nb. 43; (1993); p. 6817 - 6820 View in Reaxys With sodium tetrahydroborate, 18-crown-6 ether, dihydrogen peroxide, sodium methylate, titanium(III) chloride, 1.) THF, 30 deg C, 3 h, 2.) THF, methanol, 40 deg C, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Lee, Hyung Soo; Isagawa, Kakuzo; Toyoda, Hiromu; Otsuji, Yoshio; Chemistry Letters; (1984); p. 673 - 676 View in Reaxys With sodium hydroxide, lithium borohydride, dihydrogen peroxide, Cp2Ti(BH4), 1) THF, 65 deg C, 9 h; var. reag. in 1) step: Cp2TiBH4 or BH3, or BH3 with LiBH4, NaBH4 and 18-crown-6, var. temp. and time, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Burgess, Kevin; Van Der Donk, Wilfred A.; Tetrahedron Letters; vol. 34; nb. 43; (1993); p. 6817 - 6820 View in Reaxys With benzo[1,3,2]dioxaborole, Pt(COD)Cl2, tri-cyclo-hexyl-phosphine in tetrahydrofuran, Time= 3h, T= 25 °C Lillo, Vanesa; Mata, Jose A.; Segarra, Anna M.; Peris, Eduardo; Fernandez, Elena; Chemical Communications; nb. 21; (2007); p. 2184 - 2186 View in Reaxys With benzo[1,3,2]dioxaborole, [Pt(PPh3)4] in tetrahydrofuran, Time= 3h, T= 25 °C Lillo, Vanesa; Mata, Jose A.; Segarra, Anna M.; Peris, Eduardo; Fernandez, Elena; Chemical Communications; nb. 21; (2007); p. 2184 - 2186 View in Reaxys 5.9 %Chromat., 32 %Chromat., 48 %Chromat.

1.4 :Using the conditions shown in Scheme 5,2-phenylethanol (2a) was obtained in 77percent yield with exceptionally high anti-Markovnikov selectivity (38:1). Under the standard conditions, the reaction proceeded with an excellent product selectivity and byproducts (3a to 6a) were all formed in less than 2percent yield. The absence of the Pd catalyst shut down the production of oxygenated products completely, although the over-reduction product (ethylbenzene) was still formed in 26percent yield. Without Shvo's catalyst, no alcohol products were observed and aldehyde 5a was the major product. CuCl2 was originally intended as a co-oxidant and later appeared to play a critical role in slowing down the over-reduction, as the absence of CuCl2 led to significantly increased yields of ethylbenzene. 1,4Benzoquinone (BQ) is widely used as a hydrogen acceptor and two-electron oxidant in PdII-catalyzed reactions, and was found to be the best co-oxidant for this transformation, and omission of this component resulted in no alcohol formation. The role of i-PrOH as the reductant was highlighted by formation of aldehyde 5a (57percent yield) almost exclusively in its absence. t-BuOH proved to be responsible for enhanced reactivity and selectivity where without tBuOH, lower yields and regioselectivity of the primary alcohol was obtained. As expected, removal of water from the reaction mixture (using 4 Molecular sieves) is detrimental since no oxygenated product was observed under anhydrous conditions.

51/96

2016-06-28 15:56:50

With isopropyl alcohol, p-benozquinone, dichloro bis(acetonitrile) palladium(II), {[2,3,4,5-Ph4(η5C4CO)]2H}Ru2(CO)4(μ-H) in tert-butyl alcohol, T= 85 °C , Product distribution / selectivity Patent; Dong, Guangbin; Grubbs, Robert H.; Teo, Peili; Wickens, Zach K.; US2012/172634; (2012); (A1) English View in Reaxys

Rx-ID: 1546503 View in Reaxys 20/154 Yield 86 %, 9 %

Conditions & References With zirconocene dichloride, 1,1-dimethylethylmagnesium chloride in diethyl ether, benzene, Ambient temperature Negishi, Ei-ichi; Miller, Joseph A.; Yoshida, Tadao; Tetrahedron Letters; vol. 25; nb. 32; (1984); p. 3407 - 3410 View in Reaxys

Rx-ID: 1546504 View in Reaxys 21/154 Yield

Conditions & References With carbon monoxide, hydrogen, dicobalt octacarbonyl in pyridine, Time= 12h, T= 140 °C , p= 75005.9Torr , var. styrenes; var. metal carbonyls; other solvents and temp., Product distribution Fontaine, M.; Hubert, A. J.; Noels, A. F.; Demonceau, A.; Teyssie, P.; Journal of Organometallic Chemistry; vol. 417; nb. 1/2; (1991); p. C28 - C31 View in Reaxys

Rx-ID: 1546516 View in Reaxys 22/154 Yield

Conditions & References With Schwartz's reagent, water-d2, 1.) dioxane, r.t.; 2.a) 45 deg C, 15 h, Multistep reaction Annby, Ulf; Gronowitz, Salo; Hallberg, Anders; Journal of Organometallic Chemistry; vol. 368; (1989); p. 295 302 View in Reaxys With lithium aluminium tetrahydride, aluminum tri-bromide, water-d2, 1.) benzene, 30 - 40 deg C, 10 min, Yield given. Multistep reaction Gorobets, E. V.; Shitikova, O. V.; Lomakina, S. I.; Tolstikov, G. A.; Kuchin, A. V.; Russian Chemical Bulletin; vol. 42; nb. 9; (1993); p. 1573 - 1578; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 9; (1993); p. 1637 1642 View in Reaxys 2H

Rx-ID: 1546540 View in Reaxys 23/154 Yield 90 % Chromat.

Conditions & References With bis(cyclopentadienyl)titanium dichloride, NaAlH4, water-d2 in tetrahydrofuran, Time= 2h, Ambient temperature, other complex aluminum hydrides, Product distribution Ashby, Eugene C.; Noding, Stephen A.; Journal of Organic Chemistry; vol. 45; nb. 6; (1980); p. 1035 - 1041 View in Reaxys

52/96

2016-06-28 15:56:50

With bis(cyclopentadienyl)titanium dichloride, NaAlH4, water-d2, 1) THF, room temp., 2 h; 2) D2O, Yield given. Multistep reaction Ashby, Eugene C.; Noding, Stephen A.; Journal of Organic Chemistry; vol. 45; nb. 6; (1980); p. 1035 - 1041 View in Reaxys Stage 1: With (C5H3N)(MeC=N(C6H4-2,6-iPr2))2, ethylmagnesium bromide, iron(II) chloride in tetrahydrofuran, diethyl ether, Time= 0.0166667h, T= 20 °C , Inert atmosphere Stage 2: With methanol-d4 in tetrahydrofuran, diethyl ether, Time= 0.5h, Inert atmosphere Greenhalgh, Mark D.; Thomas, Stephen P.; Journal of the American Chemical Society; vol. 134; nb. 29; (2012); p. 11900 - 11903 View in Reaxys 2

Rx-ID: 1546541 View in Reaxys 24/154 Yield

Conditions & References With deuterium tetracarbonylcobalt(-I), carbon monoxide in dichloromethane, T= 0 °C , Rate constant Roth, Jerome A.; Wiseman, Paul; Ruszala, Lois; Journal of Organometallic Chemistry; vol. 240; nb. 3; (1982); p. 271 - 276 View in Reaxys With C28H18Co(1-)*K(1+)*2C4H10O2, deuterium, T= 20 °C , p= 1500.15Torr Gaertner, Dominik; Welther, Alice; Rad, Babak Rezaei; Wolf, Robert; Von Wangelin, Axel Jacobi; Angewandte Chemie - International Edition; vol. 53; nb. 14; (2014); p. 3722 - 3726; Angew. Chem.; vol. 126; nb. 14; (2014); p. 3796 - 3800,5 View in Reaxys

Rx-ID: 1546609 View in Reaxys 25/154 Yield

Conditions & References With oxygen, TEAB, (TPP)Fe(II) in ethylene glycol dimethyl ether, isopropyl alcohol, Time= 25h, Ambient temperature, further transition metal catalysts; effect of catalyst on the product yield/distribution, Product distribution Okamoto, Tadashi; Sasaki, Yoshihiro; Sasaki, Ken; Oka, Shinzaburo; Bulletin of the Chemical Society of Japan; vol. 60; nb. 12; (1987); p. 4449 - 4450 View in Reaxys

Rx-ID: 1546610 View in Reaxys 26/154 Yield

Conditions & References

48 % Chromat., 2 % Chromat., 24 % Chromat.

With oxygen, cobalt(II) 2,4-pentanedionate in isopropyl alcohol, Time= 1h, T= 75 °C

48 % Chromat., 24 % Chromat., 2 % Chromat.

With oxygen, cobalt(II) 2,4-pentanedionate in isopropyl alcohol, Time= 1h, T= 75 °C , Product distribution

Mukaiyama, Teruaki; Isayama, Shigeru; Inoki, Satoshi; Kato, Koji; Yamada, Tohru; Takai, Toshihiro; Chemistry Letters; (1989); p. 449 - 452 View in Reaxys

Kato; Yamada; Takai; Inoki; Isayama; Bulletin of the Chemical Society of Japan; vol. 63; nb. 1; (1990); p. 179 186 View in Reaxys

53/96

2016-06-28 15:56:50

2 % Chromat., 24 % Chromat., 48 % Chromat.

With oxygen, cobalt(II) 2,4-pentanedionate in isopropyl alcohol, Time= 1h, T= 75 °C Mukaiyama, Teruaki; Isayama, Shigeru; Inoki, Satoshi; Kato, Koji; Yamada, Tohru; Takai, Toshihiro; Chemistry Letters; (1989); p. 449 - 452 View in Reaxys

Rx-ID: 1546614 View in Reaxys 27/154 Yield

Conditions & References With hydrogen, K doped ZnO, Time= 2h, T= 299.9 °C , p= 1500.1Torr , other temp., differently modified ZnO2; initial rate of hydrogenation, Product distribution Kijenski, Jacek; Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques; vol. 29; nb. 5-6; (1981); p. 225 - 230 View in Reaxys 2H

2H 2H

Rx-ID: 2086026 View in Reaxys 28/154 Yield

Conditions & References With hydrogen, tetrahydridotris(triphenylphosphine)ruthenium(IV), p= 2280Torr , Ambient temperature, Mechanism Kirss, Rein U.; Eisenschmid, Thomas C.; Eisenberg, Richard; Journal of the American Chemical Society; vol. 110; nb. 25; (1988); p. 8564 - 8566 View in Reaxys Stage 1: With iron(III) trifluoromethanesulfonate, NaBEt3H in 1-methyl-pyrrolidin-2-one, THF-d8 (tetrahydrofurand8), Time= 18h, T= -24 - 20 °C , Inert atmosphere, Schlenk technique Stage 2: With hydrogenchloride, ammonium chloride in water, Inert atmosphere, Schlenk technique Carter, Tom S.; Guiet, Lea; Frank, Dominik J.; West, James; Thomas, Stephen P.; Advanced Synthesis and Catalysis; vol. 355; nb. 5; (2013); p. 880 - 884 View in Reaxys

SiH

Rx-ID: 3936341 View in Reaxys 29/154 Yield 37 %, 31 %, 32 %

Conditions & References With platinum (II) chloride, Time= 96h, T= 24.9 °C , Product distribution Skoda-Foeldes, Rita; Kollar, Laszlo; Heil, Balint; Journal of Organometallic Chemistry; vol. 366; (1989); p. 275 280 View in Reaxys

37 %, 31 %, 32 %

With platinum (II) chloride, Time= 96h, T= 24.9 °C Skoda-Foeldes, Rita; Kollar, Laszlo; Heil, Balint; Journal of Organometallic Chemistry; vol. 366; (1989); p. 275 280 View in Reaxys

54/96

2016-06-28 15:56:50

37 %, 32 %, 31 %

With platinum (II) chloride, Time= 96h, T= 24.9 °C Skoda-Foeldes, Rita; Kollar, Laszlo; Heil, Balint; Journal of Organometallic Chemistry; vol. 366; (1989); p. 275 280 View in Reaxys

31 %, 32 %, 37 %

With platinum (II) chloride, Time= 96h, T= 24.9 °C Skoda-Foeldes, Rita; Kollar, Laszlo; Heil, Balint; Journal of Organometallic Chemistry; vol. 366; (1989); p. 275 280 View in Reaxys

Rx-ID: 4334942 View in Reaxys 30/154 Yield 51 %, 43 %, 10 %

Conditions & References With C28H32PZr(1+)*C19H3BF15 (1-), hydrogen, Time= 2h, T= 20 °C , Glovebox, Schlenk technique Normand, Adrien T.; Daniliuc, Constantin G.; Wibbeling, Birgit; Kehr, Gerald; Le Gendre, Pierre; Erker, Gerhard; Journal of the American Chemical Society; vol. 137; nb. 33; (2015); p. 10796 - 10808 View in Reaxys With 18-crown-6 ether in tetrahydrofuran, Time= 0.25h, T= 20 °C , also reaction with α-methylstyrene, Mechanism, Product distribution Jedlinski, Zbigniew; Czech, Aleksander; Janeczek, Henryk; Kowalczuk, Marek; Journal of the American Chemical Society; vol. 117; nb. 33; (1995); p. 8678 - 8679 View in Reaxys

Rx-ID: 4556317 View in Reaxys 31/154 Yield

Conditions & References With deuterium, palladium(0) bis(p-tolylimino)acenaphthene dimethylfumaric acid Harthun, Andreas; Giernoth, Ralf; Elsevier, Cornelis J.; Bargon, Joachim; Chemical Communications; nb. 21; (1996); p. 2483 - 2484 View in Reaxys

SiH

Rx-ID: 4605428 View in Reaxys 32/154 Yield

Conditions & References With lt;(phen)Pd(η3)-CH(CH3)C6H5gt;+lt;B(3,5-(CF3)2C6H3)4gt;-, Time= 24h, T= 85 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts LaPointe, Anne M.; Rix, Francis C.; Brookhart, Maurice; Journal of the American Chemical Society; vol. 119; nb. 5; (1997); p. 906 - 917 View in Reaxys With Rh(η4-1,5-cycloC8H12){κ2-(3-iPr2P-2-Me2N-indenide)} in toluene, Time= 2.5h, T= 80 °C , Product distribution, Further Variations: Catalysts, Solvents, Temperatures Stradiotto, Mark; Cipot, Judy; McDonald, Robert; Journal of the American Chemical Society; vol. 125; nb. 19; (2003); p. 5618 - 5619

55/96

2016-06-28 15:56:50

View in Reaxys 2.1 General procedure for the dehydrogenative silylation of styrene General procedure: A two-necked flask equipped with a magnetic stirring bar was charged with the catalytic amount of complex (0.015mmol). The reactor was evacuated and filled with dinitrogen. Styrene (0.52mL, 4.5mmol) and toluene (5mL) were added, and the mixture was stirred for 5min. Then Et3SiH (0.24mL, 1.5mmol) was added. The reaction flask was immersed in an 80°C thermo-stabilized bath. The progress of the reaction was monitored by GC (disappearance of Et3SiH). The products were identified by 1H NMR, by GC–MS, and by comparison with the literature data [28]. With anti-[Cp*Fe-(2,6-diethyl-4,8-dimethyl-s-indaceneiide)-Rh(COD)] in toluene, Time= 1h, T= 80 °C , Inert atmosphere, Reagent/catalyst, Time Adams; Riviere; Riviere-Baudet; Morales-Verdejo; Dahrouch; Morales; Castel; Delpech; Manriquez; Chavez; Journal of Organometallic Chemistry; vol. 749; (2014); p. 266 - 274 View in Reaxys

SiH

Rx-ID: 4605434 View in Reaxys 33/154 Yield

H N

E N

Rx-ID: 4757046 View in Reaxys 34/154 Yield

Conditions & References

57 % Chromat., 55 % Chromat.

With bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate, triphenylphosphine in tetrahydrofuran, Time= 20h, Heating, Title compound not separated from byproducts

49 % Chromat., 45 % Chromat.

With triphenylphosphine, lt;(1,2,5,6-η)-1,5-cyclooctadiengt;bis(piperidine)rhodium(I) tetrafluoroborate in tetrahydrofuran, Time= 20h, Heating

72 % Chromat.

With 2-(7-diphenylphosphino-heptyl)-pyridine, bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate in tetrahydrofuran, Time= 20h, T= 100 °C

Beller, Matthias; Eichberger, Martin; Trauthwein, Harald; Angewandte Chemie (International Edition in English); vol. 36; nb. 20; (1997); p. 2225 - 2227 View in Reaxys

Beller, Matthias; Trauthwein, Harald; Eichberger, Martin; Breindl, Claudia; Mueller, Thomas E.; Zapf, Alexander; Journal of Organometallic Chemistry; vol. 566; nb. 1-2; (1998); p. 277 - 285 View in Reaxys

Tillack, Annegret; Trauthwein, Harald; Hartung, Christian G.; Eichberger, Martin; Pitter, Stephan; Jansen, Achim; Beller, Matthias; Monatshefte fur Chemie; vol. 131; nb. 12; (2000); p. 1327 - 1334 View in Reaxys With [Rh{Ph2P(CH2)3OEt}2]PF6 in tetrahydrofuran, Time= 2h, T= 80 °C , Inert atmosphere

56/96

2016-06-28 15:56:50

Jimenez, M. Victoria; Perez-Torrente, Jesus J.; Bartolome, M. Isabel; Lahoz, Fernando J.; Oro, Luis A.; Chemical Communications; vol. 46; nb. 29; (2010); p. 5322 - 5324 View in Reaxys With [Rh{κ2-P,O-Ph2P(CH2)3OEt}2][PF6] in tetrahydrofuran, Time= 1h, T= 80 °C , Inert atmosphere, Schlenk technique, Molecular sieve, Reagent/catalyst, Concentration, regioselective reaction Jimenez, M. Victoria; Bartolome, M. Isabel; Perez-Torrente, Jesus J.; Gomez, Daniel; Modrego, F. Javier; Oro, Luis A.; ChemCatChem; vol. 5; nb. 1; (2013); p. 263 - 276 View in Reaxys

H N E N

Rx-ID: 4758829 View in Reaxys 35/154 Yield 80 % Chromat., 45 % Chromat.

Conditions & References With bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate, triphenylphosphine in tetrahydrofuran, Time= 20h, Heating, Title compound not separated from byproducts Beller, Matthias; Eichberger, Martin; Trauthwein, Harald; Angewandte Chemie (International Edition in English); vol. 36; nb. 20; (1997); p. 2225 - 2227 View in Reaxys

N H

Rx-ID: 4780639 View in Reaxys 36/154 Yield

Conditions & References

44 % Chromat., 48 % Chromat.

With bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate, triphenylphosphine in tetrahydrofuran, Time= 20h, Heating, Title compound not separated from byproducts

52 % Chromat.

With 2-(7-diphenylphosphino-heptyl)-pyridine, bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate in tetrahydrofuran, Time= 20h, T= 100 °C

Beller, Matthias; Eichberger, Martin; Trauthwein, Harald; Angewandte Chemie (International Edition in English); vol. 36; nb. 20; (1997); p. 2225 - 2227 View in Reaxys

N H

Rx-ID: 4783816 View in Reaxys 37/154 Yield 54 % Chromat., 40 % Chromat.

57/96

2016-06-28 15:56:50

28 % Chromat., 31 % Chromat.

With triphenylphosphine, lt;(1,2,5,6-η)-1,5-cyclooctadiengt;bis(diethylamine)rhodium(I) tetrafluoroborate in tetrahydrofuran, Time= 20h, Heating

40 % Chromat.

With triphenylphosphine, bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate in tetrahydrofuran, Time= 20h, Heating

Rx-ID: 4789841 View in Reaxys 38/154 Yield 9 % Chromat., 9 % Chromat.

H H

H H racemate

Rx-ID: 4979240 View in Reaxys 39/154 Yield

Conditions & References With water, aluminium, multistep reaction; also for α-methylstyrene, other group 13 metals Joly, Helen A.; Kepes, Maria; Roy, Natalie; Prpic, Jason; Canadian Journal of Chemistry; vol. 76; nb. 4; (1998); p. 400 - 406 View in Reaxys

O B O

E O

B O

Rx-ID: 5135236 View in Reaxys 40/154 Yield

Conditions & References

94 %, 3 %, With [RhCl(η2:η2-cycloocta-1,5-diene)]2 in toluene, pinacolborane and vinylarene were added to a mixt. of Rh-com3 %, 92 % plex in toluene under Ar, the mixt. was stirred at room temp. for 4 h; diluted with toluene, washed with water, dried over MgSO4, evapd., distilled with Kugelrohr or chromy. on silica gel Murata, Miki; Kawakita, Koji; Asana, Taichi; Watanabe, Shinji; Masuda, Yuzuru; Bulletin of the Chemical Society of Japan; vol. 75; nb. 4; (2002); p. 825 - 829 ; (from Gmelin) View in Reaxys

58/96

2016-06-28 15:56:50

With [RhCl(η2:η2-cycloocta-1,5-diene)]2 in toluene, Time= 4h, Ambient temperature, Yield given, Yields of byproduct given Murata, Miki; Watanabe, Shinji; Masuda, Yuzuru; Tetrahedron Letters; vol. 40; nb. 13; (1999); p. 2585 - 2588 View in Reaxys

H N

E O

Rx-ID: 5254677 View in Reaxys 41/154 Yield 74 % Chromat., 14 % Chromat., 84 % Chromat.

Conditions & References With triphenylphosphine, bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate in tetrahydrofuran, Time= 20h, Heating, Substitution, Amination; Hydroamination, Product distribution, Further Variations: Catalysts, Reagents, Solvents, Temperatures Beller; Trauthwein; Eichberger; Breindl; Herwig; Mueller; Thiel; Chemistry - A European Journal; vol. 5; nb. 4; (1999); p. 1306 - 1319 View in Reaxys

27 % Chromat., 6 % Chromat.

With (Z,Z)-1,5-cyclooctadiene, triphenylphosphine, bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate in tetrahydrofuran, Time= 20h, Heating, Product distribution, Further Variations: Reaction partners, Reagents, ratio

76 % Chromat.

With 2-(7-diphenylphosphino-heptyl)-pyridine, bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate in tetrahydrofuran, Time= 20h, T= 100 °C

copper chromite Rx-ID: 6674670 View in Reaxys 42/154 Yield

Conditions & References T= 125 °C , p= 91938.4Torr , Hydrogenation Zartman; Adkins; Journal of the American Chemical Society; vol. 54; (1932); p. 1668,1669 View in Reaxys

hexaammine-calcium(0) Rx-ID: 6674671 View in Reaxys 43/154

Yield

Conditions & References Boer; Duinker; Recueil des Travaux Chimiques des Pays-Bas; vol. 77; (1958); p. 346,359 View in Reaxys

hydrogen Rx-ID: 6674672 View in Reaxys 44/154 Yield

Conditions & References Leiten durch ein rotgluehendes Rohr

59/96

2016-06-28 15:56:50

Berthelot; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 67; (1868); p. 847; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1868); p. 359 View in Reaxys

nickel Rx-ID: 6674673 View in Reaxys 45/154 Yield

Conditions & References T= 20 °C , p= 1838.8Torr , Hydrogenation Zartman; Adkins; Journal of the American Chemical Society; vol. 54; (1932); p. 1668,1669 View in Reaxys

palladium coal Rx-ID: 6674674 View in Reaxys 46/154 Yield

Conditions & References Hydrogenation Waterman; de Kok; Recueil des Travaux Chimiques des Pays-Bas; vol. 53; (1934); p. 1131,1138 View in Reaxys

Raney nickel Rx-ID: 6674675 View in Reaxys 47/154 Yield

Conditions & References T= 25 - 46 °C , p= 200 - 1500Torr , Hydrogenation, Kinetics Freund; Hulburt; Journal of Physical Chemistry; vol. 61; (1957); p. 909 View in Reaxys

lithium

secondary amines Rx-ID: 6674676 View in Reaxys 48/154

Yield

Conditions & References Ziegler et al.; Justus Liebigs Annalen der Chemie; vol. 511; (1934); p. 79,81, 83, 86 View in Reaxys H

sodium ammonium

Rx-ID: 6674677 View in Reaxys 49/154 Yield

Conditions & References Lebeau; Picon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 157; (1913); p. 223 View in Reaxys

sodium Rx-ID: 6674678 View in Reaxys 50/154

Yield

Conditions & References Klages; Keil; Chemische Berichte; vol. 36; (1903); p. 1635 View in Reaxys

60/96

2016-06-28 15:56:50

sodium

secondary amines Rx-ID: 6674679 View in Reaxys 51/154

Yield

Conditions & References Ziegler et al.; Justus Liebigs Annalen der Chemie; vol. 511; (1934); p. 79,81, 83, 86 View in Reaxys

sulfur

Rx-ID: 6674682 View in Reaxys 52/154 Yield

Conditions & References T= 210 - 225 °C Baumann; Fromm; Chemische Berichte; vol. 28; (1895); p. 898 View in Reaxys

sodium

Rx-ID: 6674686 View in Reaxys 53/154 Yield

Conditions & References Midgley; Henne; Leicester; Journal of the American Chemical Society; vol. 58; (1936); p. 1961 View in Reaxys O

platinum black Rx-ID: 6674688 View in Reaxys 54/154 Yield

Conditions & References Hydrogenation Willstaetter; King; Chemische Berichte; vol. 46; (1913); p. 535 View in Reaxys

paraformaldehyde O

Rx-ID: 6675065 View in Reaxys 55/154 Yield

Conditions & References With RhH2(O2COH)(P(i-Pr)3)2 in tetrahydrofuran, Time= 20h, T= 120 °C , Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts Okano, Tamon; Kobayashi, Teruyuki; Konishi, Hisatoshi; Kiji, Jitsuo; Tetrahedron Letters; vol. 23; nb. 47; (1982); p. 4967 - 4968 View in Reaxys

61/96

2016-06-28 15:56:50

xylene, toluene Rx-ID: 7089272 View in Reaxys 56/154 Yield

Conditions & References With hydrogen, beim Leiten durch ein rotgluehendes Rohr Berthelot; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 67; (1868); p. 847; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1868); p. 359 View in Reaxys

paraformaldehyde O

Rx-ID: 7161282 View in Reaxys 57/154 Yield

paraformaldehyde O

Rx-ID: 7161283 View in Reaxys 58/154 Yield

paraformaldehyde

Rx-ID: 7250414 View in Reaxys 59/154 Yield

62/96

2016-06-28 15:56:50

Rx-ID: 8519790 View in Reaxys 60/154 Yield

Conditions & References Stage 1: With zirconocene dichloride, Time= 12h, T= 22 - 23 °C , Metallation, cycloalumination Stage 2: With hydrogenchloride, Hydrolysis, Further byproducts given Ibragimov; Khafizova; Satenov; Khalilov; Yakovleva; Rusakov; Dzhemilev; Russian Chemical Bulletin; vol. 48; nb. 8; (1999); p. 1574 - 1580 View in Reaxys

2H 2H

Rx-ID: 8534820 View in Reaxys 61/154 Yield

Conditions & References Stage 1: With zirconocene dichloride, Time= 12h, T= 22 - 23 °C , Metallation, cycloalumination Stage 2: With diclazuril in water-d2, Hydrolysis, Further byproducts given Ibragimov; Khafizova; Satenov; Khalilov; Yakovleva; Rusakov; Dzhemilev; Russian Chemical Bulletin; vol. 48; nb. 8; (1999); p. 1574 - 1580 View in Reaxys O

O SiH O

Rx-ID: 8544425 View in Reaxys 62/154 Yield

Conditions & References With [{Ni(η-CH2=CHSiMe2)2O}2{μ-(η-CH2=CHSiMe2)2O}], Time= 0.5h, T= 120 °C , dehydrogenative coupling Maciejewski; Marciniec; Kownacki; Journal of Organometallic Chemistry; vol. 597; nb. 1-2; (2000); p. 175 - 181 View in Reaxys

SiH

Rx-ID: 8544446 View in Reaxys 63/154 Yield

Conditions & References With [{Ni(η-CH2=CHSiMe2)2O}2{μ-(η-CH2=CHSiMe2)2O}], Time= 1h, T= 120 °C , dehydrogenative coupling

63/96

2016-06-28 15:56:50

Maciejewski; Marciniec; Kownacki; Journal of Organometallic Chemistry; vol. 597; nb. 1-2; (2000); p. 175 - 181 View in Reaxys

H N

F F

NH 2

Rx-ID: 8666296 View in Reaxys 64/154 Yield

Conditions & References

48 %, 11 % With triphenylphosphine, bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate in toluene, Time= 48h, T= 140 °C , Chromat. Cyclization, Anti-Markovnikov hydroamination Beller, Matthias; Thiel, Oliver R.; Trauthwein, Harald; Hartung, Christian G.; Chemistry - A European Journal; vol. 6; nb. 14; (2000); p. 2513 - 2522 View in Reaxys

H N

NH 2

Rx-ID: 8688994 View in Reaxys 65/154 Yield 19 %, 7 % Chromat.

Conditions & References With triphenylphosphine, bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate in toluene, Time= 48h, T= 140 °C , Cyclization, Anti-Markovnikov hydroamination Beller, Matthias; Thiel, Oliver R.; Trauthwein, Harald; Hartung, Christian G.; Chemistry - A European Journal; vol. 6; nb. 14; (2000); p. 2513 - 2522 View in Reaxys

NH 2

H N

Rx-ID: 8689126 View in Reaxys 66/154 Yield 31 %, 10 % Chromat.

64/96

2016-06-28 15:56:50

H N N

H 2N

Rx-ID: 8691565 View in Reaxys 67/154 Yield 31 %, 10 % Chromat.

H N O

NH 2

O O

Rx-ID: 8692452 View in Reaxys 68/154 Yield 39 %, 7 % Chromat.

Conditions & References With triphenylphosphine, bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate in toluene, Time= 48h, T= 140 °C , Cyclization, Ani-Markovnikov hydroamination Beller, Matthias; Thiel, Oliver R.; Trauthwein, Harald; Hartung, Christian G.; Chemistry - A European Journal; vol. 6; nb. 14; (2000); p. 2513 - 2522 View in Reaxys

H N N

H 2N

Rx-ID: 8700130 View in Reaxys 69/154 Yield 40 %, 6 % Chromat.

H N

NH 2 F F

Rx-ID: 8705592 View in Reaxys 70/154

65/96

2016-06-28 15:56:50

Yield 26 %, 12 % Chromat.

Rx-ID: 9445908 View in Reaxys 71/154 Yield

Conditions & References Stage 1: With titanocene dichloride, diethylaluminium chloride, magnesium in tetrahydrofuran, Time= 8h, T= 21 - 22 °C Stage 2: With diclazuril in tetrahydrofuran, water-d2 Dzhemilev; Ibragimov; Yakovleva; Khafizova; Borisova; Yakupova; Russian Chemical Bulletin; vol. 52; nb. 7; (2003); p. 1573 - 1583 View in Reaxys 2H

Rx-ID: 9764073 View in Reaxys 72/154 Yield

Conditions & References With triethylsilane, water-d2, di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium in 1,4-dioxane, Time= 8h, T= 75 °C Mizuta, Tomoya; Sakaguchi, Satoshi; Ishii, Yasutaka; Journal of Organic Chemistry; vol. 70; nb. 6; (2005); p. 2195 - 2199 View in Reaxys

Rx-ID: 9934174 View in Reaxys 73/154 Yield 88 % Chromat., 6 % Chromat., 6 % Chromat. 65 %Chromat., 18 %Spectr., 17 %Chromat.

Conditions & References With hydrogen, Rh on carbon in dichloromethane, Time= 0.5h, T= 100 °C , p= 15001.2Torr , Product distribution, Further Variations: Catalysts Craythorne, Steven J.; Crozier, Alan R.; Lorenzini, Fabio; Marr, Andrew C.; Marr, Patricia C.; Journal of Organometallic Chemistry; vol. 690; nb. 15; (2005); p. 3518 - 3521 View in Reaxys With [Rh(η3-C3H5)3], hydrogen, triphenylphosphine in n-heptane, Time= 16h, T= 80 °C , p= 30003Torr , Autoclave, Glovebox, Reagent/catalyst, Time Castelbou, Jessica Llop; Gual, Aitor; Mercade, Elisabet; Claver, Carmen; Godard, Cyril; Catalysis Science and Technology; vol. 3; nb. 10; (2013); p. 2828 - 2833 View in Reaxys

66/96

2016-06-28 15:56:50

H2 Si Si

Rx-ID: 10103328 View in Reaxys 74/154 Yield

Conditions & References With [Rh(i-Pr3P)2]OTf in deuterated toluene, T= -30 °C Goikhman, Roman; Milstein, David; Chemistry - A European Journal; vol. 11; nb. 10; (2005); p. 2983 - 2988 View in Reaxys

Al 2H

Rx-ID: 10272727 View in Reaxys 75/154 Yield

Conditions & References Stage 1: With diethylaluminium chloride, triphenylphosphine in hexane, Time= 8h, T= 20 °C Stage 2: With diclazuril, water-d2 in hexane Ibragimov; Khafizova; Gil'fanova; Yakupova; Borisova; Dzhemilev; Russian Chemical Bulletin; vol. 52; nb. 11; (2003); p. 2434 - 2439 View in Reaxys 2H

Rx-ID: 10272811 View in Reaxys 76/154 Yield

Conditions & References Stage 1: With diethylaluminium chloride, magnesium, triphenylphosphine, CoCl2 in tetrahydrofuran, Time= 8h, T= 20 °C Stage 2: With diclazuril, water-d2 in tetrahydrofuran Ibragimov; Khafizova; Gil'fanova; Yakupova; Borisova; Dzhemilev; Russian Chemical Bulletin; vol. 52; nb. 11; (2003); p. 2434 - 2439 View in Reaxys O N

H 2N

Rx-ID: 23402385 View in Reaxys 77/154 Yield 89 %, 99 %

Conditions & References 69 :Following a procedure similar to Example 45, reduction reaction was carried out using 5 percent rhodium/carbon powder, and ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as a metal compound as a catalyst of the present invention, and styrene (K' ) as a substrate. The results are shown in the following table. Aniline and the reduced substrate (ethylbenzene (L')) were identified as a result of comparison with various spectrum of commercially available products. With hydrogen, 5 rhodium-on-charcoal, tris(acetylacetonato)cobalt in tetrahydrofuran, Time= 16h, T= 20 °C Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1541582; (2005); (A1) English View in Reaxys

80 %, 98 %

68 :Following a procedure similar to Example 45, reduction reaction was carried out using 5 percent rhodium/carbon powder, and ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as a metal compound as a catalyst of the present invention, and styrene (K' ) as a substrate. The results are shown in the following table. Aniline and the reduced substrate (ethylbenzene (L')) were identified as a result of comparison with various spectrum of commercially available products.

67/96

2016-06-28 15:56:50

With hydrogen, 5 rhodium-on-charcoal, ferrous acetate in tetrahydrofuran, Time= 16h, T= 20 °C Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1541582; (2005); (A1) English View in Reaxys 31 - 73 %, 93 - 98 %

18; 19 :Following a procedure similar to Example 45, reduction reaction was carried out using 5 percent rhodium/ carbon powder, and ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as a metal compound as a catalyst of the present invention, and styrene (K' ) as a substrate. The results are shown in the following table. Aniline and the reduced substrate (ethylbenzene (L')) were identified as a result of comparison with various spectrum of commercially available products. With hydrogen, 5 rhodium-on-charcoal in tetrahydrofuran, Time= 16h, T= 20 °C , Product distribution / selectivity Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1541582; (2005); (A1) English View in Reaxys With hydrogen, Time= 24h, T= 110 °C , p= 4560.31Torr , Autoclave, chemoselective reaction Mitsudome, Takato; Mikami, Yusuke; Matoba, Motoshi; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Angewandte Chemie - International Edition; vol. 51; nb. 1; (2012); p. 136 - 139 View in Reaxys Br Br

Rx-ID: 23659072 View in Reaxys 78/154 Yield

Conditions & References 16 With sodium bromite, acetic acid, hydrazine in water, Time= 4h, T= 60 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; JP2005/350427; (2005); (A) Japanese View in Reaxys

Rx-ID: 26121848 View in Reaxys 79/154 Yield

Conditions & References in ammonia Birch, A. J.; Quarterly Reviews, Chemical Society; vol. 4; (1950); p. 69 - 93 ; (from Gmelin) View in Reaxys in ammonia, NH3 (liquid) vol. Na: SVol.3; 1.5.5, page 947 - 953 ; (from Gmelin) View in Reaxys

(v3) (v3)

(v3)

O (v3)

O O

(v6)

(v3)

(v6) (v6)

Ru (v3)

(v3)

(v3) (v3)

(v3)

(v7) (v7)

(v3)

15O

(v3)

O O Ru (v7) O Ru Ru (v7) O O (v3) O O(v7) (v3) (v3) O O

(v7)

(v3)

(v3)O(v3) (v3)

(v3)

(v2)

(v3)

(v5) (v5) (v5) (v5) (v5)

(v5)

(v5) (v5)(v6) (v5) H (v5) H (v5)(v5)(v5)

H Ru

(v3)

Ru Ru

(v9)

O O

(v3)

(v5)

OO (v3) (v3) O (v3)

13O

(v2)

(v3)

(v3) (v3) (v10) O

(v7)

O O

(v3)

H 2Ru 3

(v3)

O O Ru (v8) O Ru O

(v3) (v3)

Ru 6

(v9)

(v3)

O (v8)

O Ru (v8) Ru OO

RuO (v7) O O (v3) O (v3)

(v3) (v3) (v3)

(v3)

Rx-ID: 27011007 View in Reaxys 80/154

68/96

2016-06-28 15:56:50

Yield 6 %, 1 %, 1 %, 1 %, <1 %

Conditions & References in n-heptane, (N2); addn. of styrene in heptane to the Ru cluster in refluxing heptaneover 1 h, further reflux (2 h); solvent removal (vac.), TLC (SiO2; hexane/CH2Cl2) Johnson, Brian F. G.; Matters, Justin M.; Escarpa Gaede, Petra; Ingham, Scott L.; Choi, Nicholas; et al.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1997); p. 3251 - 3258 ; (from Gmelin) View in Reaxys

5 %, 5 %, 2 %, 2 %, <1 %

in octane, (N2); addn. of styrene in octane to the Ru cluster in refluxing octane over 20 min, further reflux (2 h); solvent removal (vac.), TLC (SiO2; hexane/CH2Cl2) Johnson, Brian F. G.; Matters, Justin M.; Escarpa Gaede, Petra; Ingham, Scott L.; Choi, Nicholas; et al.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1997); p. 3251 - 3258 ; (from Gmelin) View in Reaxys

5 %, 3 %, 1 %, 2 %, 1%

in cyclohexane, (N2); addn. of styrene in cyclohexane to the Ru cluster in refluxing cyclohexane over 20 min, further reflux (22 h); solvent removal (vac.), TLC (SiO2; hexane/CH2Cl2) Johnson, Brian F. G.; Matters, Justin M.; Escarpa Gaede, Petra; Ingham, Scott L.; Choi, Nicholas; et al.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1997); p. 3251 - 3258 ; (from Gmelin) View in Reaxys

(v3)

Rx-ID: 27102825 View in Reaxys 81/154 Yield

Conditions & References in further solvent(s), evapn. of Cr into soln. contg. polystyrene in diethylene glycol dibutylether at -50°C over 2 h; to soln. THF added, filtered, to filtrate methanol added, soln. cooled to -80°C to give brown-green ppt., this sepd., washed with methanol Francis, Colin G.; Timms, Peter L.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 8; (1980); p. 1401 - 1407 ; (from Gmelin) View in Reaxys

racemate

Rx-ID: 28479830 View in Reaxys 82/154 Yield

Conditions & References With {CaH(dipp-nacnac)(thf)}2, hydrogen in benzene, Time= 15h, T= 20 °C , p= 75007.5Torr , Inert atmosphere, Autoclave Spielmann, Jan; Buch, Frank; Harder, Sjoerd; Angewandte Chemie - International Edition; vol. 47; nb. 49; (2008); p. 9434 - 9438 View in Reaxys

69/96

2016-06-28 15:56:50

SiH Si

Rx-ID: 28958554 View in Reaxys 83/154 Yield

Conditions & References With C8H16Cl2O4Pt2 in benzene-d6, T= 27 °C , Inert atmosphere Schwieger, Sebastian; Herzog, Renate; Wagner, Christoph; Steinborn, Dirk; Journal of Organometallic Chemistry; vol. 694; nb. 22; (2009); p. 3548 - 3558 View in Reaxys

Z E

Rx-ID: 29075321 View in Reaxys 84/154 Yield

Conditions & References With palladium on activated charcoal, hydrogen in N,N-dimethyl-formamide, T= 119.84 °C , p= 750.075Torr , Continuous flow reactor, Heck reaction Fan, Xiaolei; Manchon, Maria Gonzalez; Wilson, Karen; Tennison, Steve; Kozynchenko, Alexander; Lapkin, Alexei A.; Plucinski, Pawel K.; Journal of Catalysis; vol. 267; nb. 2; (2009); p. 114 - 120 View in Reaxys

Rx-ID: 29075322 View in Reaxys 85/154 Yield

Conditions & References With palladium on activated charcoal, hydrogen in N,N-dimethyl-formamide, T= 119.84 °C , p= 3000.3Torr , Continuous flow reactor, Heck reaction Fan, Xiaolei; Manchon, Maria Gonzalez; Wilson, Karen; Tennison, Steve; Kozynchenko, Alexander; Lapkin, Alexei A.; Plucinski, Pawel K.; Journal of Catalysis; vol. 267; nb. 2; (2009); p. 114 - 120 View in Reaxys With palladium on activated charcoal, hydrogen in ethanol, T= 119.84 °C , p= 3000.3Torr , Inert atmosphere, Continuous flow reactor, Heck reaction Fan, Xiaolei; Manchon, Maria Gonzalez; Wilson, Karen; Tennison, Steve; Kozynchenko, Alexander; Lapkin, Alexei A.; Plucinski, Pawel K.; Journal of Catalysis; vol. 267; nb. 2; (2009); p. 114 - 120 View in Reaxys

Rx-ID: 29075323 View in Reaxys 86/154 Yield

Conditions & References With palladium on activated charcoal, hydrogen in N,N-dimethyl-formamide, T= 119.84 °C , p= 6000.6Torr , Continuous flow reactor, Heck reaction Fan, Xiaolei; Manchon, Maria Gonzalez; Wilson, Karen; Tennison, Steve; Kozynchenko, Alexander; Lapkin, Alexei A.; Plucinski, Pawel K.; Journal of Catalysis; vol. 267; nb. 2; (2009); p. 114 - 120

70/96

2016-06-28 15:56:50

View in Reaxys H HO

Rx-ID: 29281423 View in Reaxys 87/154 Yield > 99 %, 7 %

Conditions & References With 3 Au/meso-CeO2, potassium formiate in water, T= 25 °C , chemoselective reaction He, Lin; Ni, Ji; Wang, Lu-Cun; Yu, Feng-Jiao; Cao, Yong; He, He-Yong; Fan, Kang-Nian; Chemistry - A European Journal; vol. 15; nb. 44; (2009); p. 11833 - 11836 View in Reaxys With gold supported on mesoporous ceria, hydrogen in isopropyl alcohol, Time= 1h, T= 100 °C , p= 7500.75Torr Wang, Miao-Miao; He, Lin; Liu, Yong-Mei; Cao, Yong; He, He-Yong; Fan, Kang-Nian; Green Chemistry; vol. 13; nb. 3; (2011); p. 602 - 607 View in Reaxys

99 %Chro- With [H(OEt2)2]+[[3,5-(CF3)2C6H3]4B]-, C32H63CoNP2Si, hydrogen in tetrahydrofuran, Time= 24h, T= 25 °C , p= mat., 16 760.051Torr %Chromat. Zhang, Guoqi; Scott, Brian L.; Hanson, Susan K.; Angewandte Chemie - International Edition; vol. 51; nb. 48; (2012); p. 12102 - 12106; Angew. Chem.; (2012); p. 12077 View in Reaxys

O SiH

O Si

O Si O

Rx-ID: 29286104 View in Reaxys 88/154 Yield

Conditions & References With tri[1-methyl-2-diphenylposphino-3-ethylimidazolium hexafluorophosphate] rhodium chloride, Time= 5h, T= 70 °C , Ionic liquid, regioselective reaction Li, Jiayun; Peng, Jiajian; Bai, Ying; Zhang, Guodong; Lai, Guoqiao; Li, Xiaonian; Journal of Organometallic Chemistry; vol. 695; nb. 3; (2010); p. 431 - 436 View in Reaxys

72.8 %Chromat., 15.3 %Chromat., 11.9 %Chromat.

With tris (triphenylphosphine)rhodium(I) chloride, silica gel, Time= 2h, T= 90 °C , regioselective reaction Li, Jiayun; Peng, Jiajian; Bai, Ying; Hu, Yingqian; Qiu, Huayu; Lai, Guoqiao; Li, Xiaonian; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 185; nb. 2; (2010); p. 484 - 490 View in Reaxys

Catalytic hydrosilylation of alkene with triethoxysilane Typical hydrosilylation reaction procedures were as follows: Agiven amount of catalyst and ionic liquid were added to a 10 mLround bottomed flask equipped with a magnetic stirrer and thealkene and silane were then added. This mixture was heated to theappropriate temperature and the hydrosilylation reaction wasallowed to proceed with constant stirring for 5 h. At the end of thereaction, the product phase was separated from the catalyst bydecantation and the conversion of alkene and the selectivity weredetermined by GC. The catalyst was recharged with fresh alkeneand silane for the next catalytic run. With Wilkinson's catalyst, 1-n-butyl-3-methylimidazolium hexafluorophosphate, Time= 2h, T= 70 °C Li, Jiayun; Peng, Jiajian; Bai, Ying; Lai, Guoqiao; Li, Xiaonian; Journal of Organometallic Chemistry; vol. 696; nb. 10; (2011); p. 2116 - 2121 View in Reaxys With Wilkinson's catalyst, 1-n-butyl-3-methylimidazolium tetrafluoroborate, Time= 2h, T= 70 °C , p= 60006Torr , Autoclave

71/96

2016-06-28 15:56:50

Li, Jiayun; Peng, Jiajian; Zhang, Guodong; Bai, Ying; Lai, Guoqiao; Li, Xiaonian; New Journal of Chemistry; vol. 34; nb. 7; (2010); p. 1330 - 1334 View in Reaxys With chlorohydridotris(triphenylphosphine)ruthenium, tetrakis(diethylamino)phosphonium hexafluorophosphate, Time= 2h, T= 95 °C Wang, Diliang; Li, Jiayun; Peng, Jiajian; Bai, Ying; Lai, Guoqiao; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 186; nb. 11; (2011); p. 2258 - 2266 View in Reaxys 2 : Catalytic hydrosilylation of alkene with triethoxysilane General procedure: Typical hydrosilylation reaction procedures were as follows: A given amount of catalyst and ionic liquid was added to a 10 mL round bottomed flask equipped with a magnetic stirrer and then the alkene and silane were added. After heating the mixture at the appropriate temperature, the hydrosilylation reaction was preceded with constant stirring for 5 h. At the end of the reaction, the product phase was separated from the catalyst by decantation and the conversion of alkene and the selectivity were determined by GC. The catalyst was recharged with fresh alkene and silane for the next catalytic run With Wilkinson's catalyst, 1-(2-carboxyethyl)-3-methylimidazolium trifluoromethanesulfonate, Time= 5h, T= 90 °C , Reagent/catalyst Ma, Chao; Li, Jiayun; Peng, Jiajian; Bai, Ying; Zhang, Guodong; Xiao, Wenjun; Lai, Guoqiao; Journal of Organometallic Chemistry; vol. 727; (2013); p. 28 - 36 View in Reaxys General methods General procedure: All catalysis reaction operations were performed in a 10 mL flat-bottomed tube without protection from air. The alkene (4.0 mmol) and the requisite amount of catalyst were placed in a dried tube and the reaction mixture was stirred for 5 min. Thereafter, the silane (4.4 mmol) was added and the resulting mixture was heated and stirred for the requisite time and then cooled to room temperature. The product phase was separated by decantation and the conversion of the alkene and the selectivity were determined by GC–MS analysis on an Agilent 26890N/ 59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). 1H NMR (400 MHz) and 13C NMR (100.6 MHz) spectra were recorded on a Bruker Advance spectrometer using TMS as an internal standard. Methanol-d4 and DMSO-d6 were used as solvents. Stage 1: With Wilkinson's catalyst, Time= 0.0833333h Stage 2:, Time= 5h, T= 90 °C Xu, Yisong; Bai, Ying; Peng, Jiajian; Li, Jiayun; Xiao, Wenjun; Lai, Guoqiao; Journal of Organometallic Chemistry; vol. 765; (2014); p. 59 - 63 View in Reaxys Catalytic Test Typical hydrosilylation reaction procedures were as follows: styrene (20 mmol) andPt-catalysts (0.005 mmol; Speier’s catalystwith or without carboxylic acids)were combinedand stirred at reaction temperature for 10 min in a 20-mL round flask equipped with amechanical stirrer. Then, triethoxysilane (22 mmol) was added to the reaction mixture. Theproducts were detected by a GC with FID detector. Stage 1: With H2PtCl6*6H2O, acetic acid, Time= 0.166667h, T= 60 °C Stage 2:, Time= 0.116667h, Reagent/catalyst, Temperature Ding, Shunmin; Deng, Shengjun; Zhang, Ning; Yang, Longhua; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 189; nb. 6; (2014); p. 803 - 811 View in Reaxys 2H

Rx-ID: 29835321 View in Reaxys 89/154 Yield

Conditions & References With methanol, water-d2, T= 99.84 °C , p= 15001.5Torr

72/96

2016-06-28 15:56:50

Xiang, Yizhi; Li, Xiaonian; Lu, Chunshan; Ma, Lei; Zhang, Qunfeng; Applied Catalysis A: General; vol. 375; nb. 2; (2010); p. 289 - 294 View in Reaxys

O B

H O

Rx-ID: 29855780 View in Reaxys 90/154 Yield

Conditions & References

39 With (η4-1,5-cyclooctadiene)(1,3-dimesityl-4-oxo-4H-5-methyl-6-(trifluoromethanesulfonato)pyrimidin-2-ylidene)rho%Spectr., dium(I) trifluoromethanesulfonate in dichloromethane, Time= 1.5h, T= 0 °C , Inert atmosphere 6 %Spectr. Cesar, Vincent; Lugan, Noel; Lavigne, Guy; Chemistry - A European Journal; vol. 16; nb. 37; (2010); p. 11432 11442 View in Reaxys

O B

Rx-ID: 29855781 View in Reaxys 91/154 Yield 44 %Spectr., 37 %Spectr., 10 %Spectr. 13 %Spectr., 22 %Spectr., 13 %Spectr.

Conditions & References With C31H37N2O2Rh in dichloromethane, Time= 1.5h, T= 0 °C , Inert atmosphere Cesar, Vincent; Lugan, Noel; Lavigne, Guy; Chemistry - A European Journal; vol. 16; nb. 37; (2010); p. 11432 11442 View in Reaxys With (η4-1,5-cyclooctadiene)(1,3-dimesityl-4-oxo-4H-5-methyl-6-methoxypyrimidin-2-ylidene)rhodium(I) trifluoromethanesulfonate in dichloromethane, Time= 1.5h, T= 0 °C , Inert atmosphere Cesar, Vincent; Lugan, Noel; Lavigne, Guy; Chemistry - A European Journal; vol. 16; nb. 37; (2010); p. 11432 11442 View in Reaxys

2H 2H

Rx-ID: 29884370 View in Reaxys 92/154 Yield

Conditions & References With [(.eta.6-benzene)(PCy3)(CO)RuD]BF4 in dichloromethane, Time= 0.5h, T= 20 °C Lee, Do W.; Yi, Chae S.; Organometallics; vol. 29; nb. 15; (2010); p. 3413 - 3417 View in Reaxys

Rx-ID: 29980912 View in Reaxys 93/154

73/96

2016-06-28 15:56:50

Yield

Conditions & References With rac-EBTHIZrCl2, hydrogen, Time= 9h, T= 50 °C , p= 760.051Torr Galdi, Nunzia; Izzo, Lorella; Oliva, Leone; Organometallics; vol. 29; nb. 20; (2010); p. 4434 - 4439 View in Reaxys

SiH

O Si

Rx-ID: 30051558 View in Reaxys 94/154 Yield

Conditions & References With Rhodium trichloride, 1-(5-diphenylphosphinopentyl)-3-octylimidazolium hexafluorophosphate, Time= 5h, T= 90 °C , Inert atmosphere, Ionic liquid, chemoselective reaction Li, Jiayun; Peng, Jiajian; Wang, Diliang; Bai, Ying; Jiang, Jianxiong; Lai, Guoqiao; Journal of Organometallic Chemistry; vol. 696; nb. 1; (2011); p. 263 - 268 View in Reaxys With 1-butylpyridinium hexafluorophosphate, chlorohydridotris(triphenylphosphine)ruthenium, Time= 2h, T= 95 °C Wang, Diliang; Li, Jiayun; Peng, Jiajian; Bai, Ying; Lai, Guoqiao; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 186; nb. 11; (2011); p. 2258 - 2266 View in Reaxys Stage 1: With [Pt]/phthalic anhydride modified polyethylene glycol, Time= 0.0833333h Stage 2:Time= 3h, T= 90 °C , regioselective reaction Bai, Ying; Peng, Jiajian; Li, Jiayun; Lai, Guoqiao; Applied Organometallic Chemistry; vol. 25; nb. 5; (2011); p. 400 - 405 View in Reaxys 1 : Catalytic hydrosilylation of alkene with triethoxysilane General procedure: Typical hydrosilylation reaction procedures were as follows: A given amount of catalyst and ionic liquid was added to a 10 mL round bottomed flask equipped with a magnetic stirrer and then the alkene and silane were added. After heating the mixture at the appropriate temperature, the hydrosilylation reaction was preceded with constant stirring for 5 h. At the end of the reaction, the product phase was separated from the catalyst by decantation and the conversion of alkene and the selectivity were determined by GC. The catalyst was recharged with fresh alkene and silane for the next catalytic run With Wilkinson's catalyst, 1-(2-carboxyethyl)-3-methylimidazolium inner salt, Time= 5h, T= 90 °C Ma, Chao; Li, Jiayun; Peng, Jiajian; Bai, Ying; Zhang, Guodong; Xiao, Wenjun; Lai, Guoqiao; Journal of Organometallic Chemistry; vol. 727; (2013); p. 28 - 36 View in Reaxys 2.2 The catalytic hydrosilylation reaction General procedure: All catalytic reaction was performed in a 10 mL flat-bottomed tube without protection from air. The alkenes (4.0 mmol) and a requisite amount of catalyst and ionic liquid were placed in a dried tube and the reaction mixture stirred for 5 min. Thereafter, the silane (4.4 mmol) was added, the resulting reaction mixture heated with stirring for a requisite time and then allowed to cool to room temperature. The product phase was separated by decantation and the conversion of the alkenes and selectivity determined by GC-MS analysis using an Agilent 26890N/ 59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). With Wilkinson's catalyst, Heating, Catalytic behavior, Reagent/catalyst Bai, Ying; Zhang, Fengxiang; Li, Jiayun; Xu, Yisong; Peng, Jiajian; Xiao, Wenjun; Journal of Organometallic Chemistry; vol. 794; (2015); p. 65 - 69; Art.No: 19129 View in Reaxys

74/96

2016-06-28 15:56:50

O B

Rx-ID: 32217708 View in Reaxys 95/154 Yield 32 %, 53 %, 15 %

Conditions & References With [Mo(H)(Cl)(P(CH3)3)3(N(C6H3(CH3CHCH3)2))] in benzene-d6, react. of HBCat with 0.4 M soln. of PhCHCH2 (1:1 molar ratio) in C6D6 attemp. of 22°C for 20 h in presence of 5 molpercent of Mo complex as ca talyst; detd. by NMR Khalimon, Andrey Y.; Farha, Philip; Kuzmina, Lyudmila G.; Nikonov, Georgii I.; Chemical Communications; vol. 48; nb. 3; (2012); p. 455 - 457 ; (from Gmelin) View in Reaxys With tetramethylsilane, (2,6-diisopropylphenyl-N=)Mo(H)(Cl)(PMe3)3 in benzene-d6, Time= 20h, T= 22 °C , Inert atmosphere Khalimon, Andrey Y.; Farha, Philip; Kuzmina, Lyudmila G.; Nikonov, Georgii I.; Chemical Communications; vol. 48; nb. 3; (2012); p. 455 - 457 View in Reaxys

32 %Spectr., 53 %Spectr., 15 %Spectr.

With (2,6-diisopropylphenyl-N=)Mo(H)(Cl)(PMe3)3 in benzene-d6, Time= 20h, T= 22 °C , Inert atmosphere, Catalytic behavior, Reagent/catalyst, Time Khalimon, Andrey Y.; Farha, Philip M.; Nikonov, Georgii I.; Dalton Transactions; vol. 44; nb. 43; (2015); p. 18945 - 18956 View in Reaxys

O SiH O

O O

O Si O

Rx-ID: 32673739 View in Reaxys 96/154 Yield

Conditions & References With chlorohydridotris(triphenylphosphine)ruthenium, (diethylamino)tri(piperidin-1-yl)phosphonium hexafluorophosphate, Time= 2h, T= 95 °C Wang, Diliang; Li, Jiayun; Peng, Jiajian; Bai, Ying; Lai, Guoqiao; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 186; nb. 11; (2011); p. 2258 - 2266 View in Reaxys With RuC3*3H2O, (m-Br-C6H4)PPh2, Time= 5h, T= 90 °C , Inert atmosphere, Reagent/catalyst Xue, Mei; Li, Jiayun; Peng, Jiajian; Bai, Ying; Zhang, Guodong; Xiao, Wenjun; Lai, Guoqiao; Applied Organometallic Chemistry; vol. 28; nb. 2; (2014); p. 120 - 126 View in Reaxys General methods General procedure: All catalysis reaction operations were performed in a 10 mL flat-bottomed tube without protection from air. The alkene (4.0 mmol) and the requisite amount of catalyst were placed in a dried tube and the reaction mixture was stirred for 5 min. Thereafter, the silane (4.4 mmol) was added and the resulting mixture was heated and stirred for the requisite time and then cooled to room temperature. The product phase was separated by decantation and the conversion of the alkene and the selectivity were determined by GC–MS analysis on an Agilent 26890N/ 59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). 1H NMR (400 MHz) and 13C NMR (100.6 MHz) spectra were recorded on a Bruker Advance spectrometer using TMS as an internal standard. Methanol-d4 and DMSO-d6 were used as solvents.

75/96

2016-06-28 15:56:50

Stage 1: With Wilkinson's catalyst, Time= 0.0833333h Stage 2:, Time= 5h, T= 90 °C , Reagent/catalyst Xu, Yisong; Bai, Ying; Peng, Jiajian; Li, Jiayun; Xiao, Wenjun; Lai, Guoqiao; Journal of Organometallic Chemistry; vol. 765; (2014); p. 59 - 63 View in Reaxys General methods General procedure: All catalysis reaction operations were performed in a 10 mL flat-bottomed tube without protection from air. The alkene (4.0 mmol) and the requisite amount of catalyst were placed in a dried tube and the reaction mixture was stirred for 5 min. Thereafter, the silane (4.4 mmol) was added and the resulting mixture was heated and stirred for the requisite time and then cooled to room temperature. The product phase was separated by decantation and the conversion of the alkene and the selectivity were determined by GC–MS analysis on an Agilent 26890N/ 59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). 1H NMR (400 MHz) and 13C NMR (100.6 MHz) spectra were recorded on a Bruker Advance spectrometer using TMS as an internal standard. Methanol-d4 and DMSO-d6 were used as solvents. Stage 1: With Wilkinson's catalyst, Time= 0.0833333h Stage 2:, Time= 5h, T= 90 °C Xu, Yisong; Bai, Ying; Peng, Jiajian; Li, Jiayun; Xiao, Wenjun; Lai, Guoqiao; Journal of Organometallic Chemistry; vol. 765; (2014); p. 59 - 63 View in Reaxys General methods General procedure: All catalysis reaction operations were performed in a 10 mL flat-bottomed tube without protection from air. The alkene (4.0 mmol) and the requisite amount of catalyst were placed in a dried tube and the reaction mixture was stirred for 5 min. Thereafter, the silane (4.4 mmol) was added and the resulting mixture was heated and stirred for the requisite time and then cooled to room temperature. The product phase was separated by decantation and the conversion of the alkene and the selectivity were determined by GC–MS analysis on an Agilent 26890N/ 59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). 1H NMR (400 MHz) and 13C NMR (100.6 MHz) spectra were recorded on a Bruker Advance spectrometer using TMS as an internal standard. Methanol-d4 and DMSO-d6 were used as solvents. Stage 1: With Wilkinson's catalyst, Time= 0.0833333h Stage 2:, Time= 5h, T= 90 °C Xu, Yisong; Bai, Ying; Peng, Jiajian; Li, Jiayun; Xiao, Wenjun; Lai, Guoqiao; Journal of Organometallic Chemistry; vol. 765; (2014); p. 59 - 63 View in Reaxys General methods General procedure: All catalysis reaction operations were performed in a 10 mL flat-bottomed tube without protection from air. The alkene (4.0 mmol) and the requisite amount of catalyst were placed in a dried tube and the reaction mixture was stirred for 5 min. Thereafter, the silane (4.4 mmol) was added and the resulting mixture was heated and stirred for the requisite time and then cooled to room temperature. The product phase was separated by decantation and the conversion of the alkene and the selectivity were determined by GC–MS analysis on an Agilent 26890N/ 59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). 1H NMR (400 MHz) and 13C NMR (100.6 MHz) spectra were recorded on a Bruker Advance spectrometer using TMS as an internal standard. Methanol-d4 and DMSO-d6 were used as solvents. Stage 1: With Rhodium trichloride, Time= 0.0833333h Stage 2:, Time= 5h, T= 90 °C Xu, Yisong; Bai, Ying; Peng, Jiajian; Li, Jiayun; Xiao, Wenjun; Lai, Guoqiao; Journal of Organometallic Chemistry; vol. 765; (2014); p. 59 - 63 View in Reaxys General methods General procedure: All catalysis reaction operations were performed in a 10 mL flat-bottomed tube without protection from air. The alkene (4.0 mmol) and the requisite amount of catalyst were placed in a dried tube and the reaction mixture was stirred for 5 min. Thereafter, the silane (4.4 mmol) was added and the resulting mixture was heated and stirred for the requisite time and then cooled to room temperature. The product phase was separated by decantation and the conversion of the alkene and the selectivity were determined by GC–MS analysis on an Agilent 26890N/

76/96

2016-06-28 15:56:50

59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). 1H NMR (400 MHz) and 13C NMR (100.6 MHz) spectra were recorded on a Bruker Advance spectrometer using TMS as an internal standard. Methanol-d4 and DMSO-d6 were used as solvents. Stage 1: With Rhodium trichloride, Time= 0.0833333h Stage 2:, Time= 5h, T= 90 °C , Reagent/catalyst Xu, Yisong; Bai, Ying; Peng, Jiajian; Li, Jiayun; Xiao, Wenjun; Lai, Guoqiao; Journal of Organometallic Chemistry; vol. 765; (2014); p. 59 - 63 View in Reaxys General methods General procedure: All catalysis reaction operations were performed in a 10 mL flat-bottomed tube without protection from air. The alkene (4.0 mmol) and the requisite amount of catalyst were placed in a dried tube and the reaction mixture was stirred for 5 min. Thereafter, the silane (4.4 mmol) was added and the resulting mixture was heated and stirred for the requisite time and then cooled to room temperature. The product phase was separated by decantation and the conversion of the alkene and the selectivity were determined by GC–MS analysis on an Agilent 26890N/ 59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). 1H NMR (400 MHz) and 13C NMR (100.6 MHz) spectra were recorded on a Bruker Advance spectrometer using TMS as an internal standard. Methanol-d4 and DMSO-d6 were used as solvents. Stage 1: With Rhodium trichloride, Time= 0.0833333h Stage 2:, Time= 5h, T= 90 °C , Reagent/catalyst Xu, Yisong; Bai, Ying; Peng, Jiajian; Li, Jiayun; Xiao, Wenjun; Lai, Guoqiao; Journal of Organometallic Chemistry; vol. 765; (2014); p. 59 - 63 View in Reaxys General methods General procedure: All catalysis reaction operations were performed in a 10 mL flat-bottomed tube without protection from air. The alkene (4.0 mmol) and the requisite amount of catalyst were placed in a dried tube and the reaction mixture was stirred for 5 min. Thereafter, the silane (4.4 mmol) was added and the resulting mixture was heated and stirred for the requisite time and then cooled to room temperature. The product phase was separated by decantation and the conversion of the alkene and the selectivity were determined by GC–MS analysis on an Agilent 26890N/ 59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). 1H NMR (400 MHz) and 13C NMR (100.6 MHz) spectra were recorded on a Bruker Advance spectrometer using TMS as an internal standard. Methanol-d4 and DMSO-d6 were used as solvents. Stage 1: With Rhodium trichloride, Time= 0.0833333h Stage 2:, Time= 5h, T= 90 °C Xu, Yisong; Bai, Ying; Peng, Jiajian; Li, Jiayun; Xiao, Wenjun; Lai, Guoqiao; Journal of Organometallic Chemistry; vol. 765; (2014); p. 59 - 63 View in Reaxys 2.2 The catalytic hydrosilylation reaction General procedure: All catalytic reaction was performed in a 10 mL flat-bottomed tube without protection from air. The alkenes (4.0 mmol) and a requisite amount of catalyst and ionic liquid were placed in a dried tube and the reaction mixture stirred for 5 min. Thereafter, the silane (4.4 mmol) was added, the resulting reaction mixture heated with stirring for a requisite time and then allowed to cool to room temperature. The product phase was separated by decantation and the conversion of the alkenes and selectivity determined by GC-MS analysis using an Agilent 26890N/ 59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). With Wilkinson's catalyst, Heating, Catalytic behavior, Reagent/catalyst Bai, Ying; Zhang, Fengxiang; Li, Jiayun; Xu, Yisong; Peng, Jiajian; Xiao, Wenjun; Journal of Organometallic Chemistry; vol. 794; (2015); p. 65 - 69; Art.No: 19129 View in Reaxys 2.2 The catalytic hydrosilylation reaction General procedure: All catalytic reaction was performed in a 10 mL flat-bottomed tube without protection from air. The alkenes (4.0 mmol) and a requisite amount of catalyst and ionic liquid were placed in a dried tube and the reaction mixture stirred for 5 min. Thereafter, the silane (4.4 mmol) was added, the resulting reaction mixture heated with stirring for a requisite time and then allowed to cool to room temperature. The product phase was separated by de-

77/96

2016-06-28 15:56:50

cantation and the conversion of the alkenes and selectivity determined by GC-MS analysis using an Agilent 26890N/ 59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). With Wilkinson's catalyst, Heating, Catalytic behavior, Reagent/catalyst Bai, Ying; Zhang, Fengxiang; Li, Jiayun; Xu, Yisong; Peng, Jiajian; Xiao, Wenjun; Journal of Organometallic Chemistry; vol. 794; (2015); p. 65 - 69; Art.No: 19129 View in Reaxys 2.2 The catalytic hydrosilylation reaction General procedure: All catalytic reaction was performed in a 10 mL flat-bottomed tube without protection from air. The alkenes (4.0 mmol) and a requisite amount of catalyst and ionic liquid were placed in a dried tube and the reaction mixture stirred for 5 min. Thereafter, the silane (4.4 mmol) was added, the resulting reaction mixture heated with stirring for a requisite time and then allowed to cool to room temperature. The product phase was separated by decantation and the conversion of the alkenes and selectivity determined by GC-MS analysis using an Agilent 26890N/ 59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). With Wilkinson's catalyst, Heating, Catalytic behavior Bai, Ying; Zhang, Fengxiang; Li, Jiayun; Xu, Yisong; Peng, Jiajian; Xiao, Wenjun; Journal of Organometallic Chemistry; vol. 794; (2015); p. 65 - 69; Art.No: 19129 View in Reaxys

O O

Rx-ID: 34532813 View in Reaxys 97/154 Yield 3 %Chromat., 21 %Chromat., 11 %Chromat., 8 %Chromat., 60 %Chromat.

Conditions & References With [Ni(1,2-bis(di-isopropylphosphino)ethane)(μ-H)]2 in tetrahydrofuran, Time= 36h, T= 120 °C , Schlenk technique, Inert atmosphere, Catalytic behavior Gonzalez-Sebastian, Lucero; Flores-Alamo, Marcos; Garcia, Juventino J.; Organometallics; vol. 31; nb. 23; (2012); p. 8200 - 8207 View in Reaxys

O HO

Rx-ID: 34532815 View in Reaxys 98/154 Yield 10 %Chromat., 13 %Chromat., 73 %Chromat.

Rx-ID: 34534686 View in Reaxys 99/154 Yield 75%, 23%

Conditions & References With 1-(N,N-dimethylamino)pyrene, triethylamine in acetonitrile, T= 20 °C , Irradiation

78/96

2016-06-28 15:56:50

Penner, Alexander; Baetzner, Effi; Wagenknecht, Hans-Achim; Synlett; vol. 23; nb. 19; (2012); p. 2803 - 2807 View in Reaxys

Rx-ID: 34542517 View in Reaxys 100/154 Yield

Conditions & References With [rhodium(I)(carbonyl)2(acetylacetonate)], carbon monoxide, C60H64O6P2, hydrogen in toluene, Time= 1h, T= 140 °C , p= 7500.75Torr , Temperature, Reagent/catalyst, Pressure, regioselective reaction Boymans, Evert; Janssen, Michele; Mueller, Christian; Lutz, Martin; Vogt, Dieter; Dalton Transactions; vol. 42; nb. 1; (2013); p. 137 - 142 View in Reaxys

H N

E N

Rx-ID: 34834270 View in Reaxys 101/154 Yield

Conditions & References With [Rh{κ2-P,O-Ph2P(CH2)3OEt}2][PF6] in tetrahydrofuran, Time= 0.5h, T= 80 °C , Inert atmosphere, Schlenk technique, Molecular sieve, Reagent/catalyst, Concentration, regioselective reaction Jimenez, M. Victoria; Bartolome, M. Isabel; Perez-Torrente, Jesus J.; Gomez, Daniel; Modrego, F. Javier; Oro, Luis A.; ChemCatChem; vol. 5; nb. 1; (2013); p. 263 - 276 View in Reaxys

H N

Rx-ID: 34834274 View in Reaxys 102/154 Yield

Conditions & References With [Rh{κ2-P,O-Ph2P(CH2)3OEt}2][PF6] in tetrahydrofuran, Time= 1h, T= 80 °C , Inert atmosphere, Schlenk technique, Molecular sieve, regioselective reaction Jimenez, M. Victoria; Bartolome, M. Isabel; Perez-Torrente, Jesus J.; Gomez, Daniel; Modrego, F. Javier; Oro, Luis A.; ChemCatChem; vol. 5; nb. 1; (2013); p. 263 - 276 View in Reaxys

H N

Rx-ID: 34834275 View in Reaxys 103/154 Yield

Conditions & References With [Rh{κ2-P,O-Ph2P(CH2)3OEt}2][PF6] in tetrahydrofuran, Time= 2h, T= 80 °C , Inert atmosphere, Schlenk technique, Molecular sieve, regioselective reaction

79/96

2016-06-28 15:56:50

Jimenez, M. Victoria; Bartolome, M. Isabel; Perez-Torrente, Jesus J.; Gomez, Daniel; Modrego, F. Javier; Oro, Luis A.; ChemCatChem; vol. 5; nb. 1; (2013); p. 263 - 276 View in Reaxys

N H

Rx-ID: 34834276 View in Reaxys 104/154 Yield

Conditions & References With [Rh{κ2-P,O-Ph2P(CH2)3OEt}2][PF6] in tetrahydrofuran, Time= 8h, T= 80 °C , Inert atmosphere, Schlenk technique, Molecular sieve, Time, regioselective reaction Jimenez, M. Victoria; Bartolome, M. Isabel; Perez-Torrente, Jesus J.; Gomez, Daniel; Modrego, F. Javier; Oro, Luis A.; ChemCatChem; vol. 5; nb. 1; (2013); p. 263 - 276 View in Reaxys

N H

Rx-ID: 34834277 View in Reaxys 105/154 Yield

Conditions & References With [Rh{κ2-P,O-Ph2P(CH2)3OEt}2][PF6] in tetrahydrofuran, Time= 6h, T= 80 °C , Inert atmosphere, Schlenk technique, Molecular sieve, regioselective reaction Jimenez, M. Victoria; Bartolome, M. Isabel; Perez-Torrente, Jesus J.; Gomez, Daniel; Modrego, F. Javier; Oro, Luis A.; ChemCatChem; vol. 5; nb. 1; (2013); p. 263 - 276 View in Reaxys

B O

Rx-ID: 35138621 View in Reaxys 106/154 Yield

Conditions & References

51%, 45%, Stage 1: With 6-di-tert-butylphosphinomethyl-2,2'-bipyridine in toluene, Time= 0.0166667h, Inert atmosphere, Glo20% vebox, Schlenk technique Stage 2: With NaBEt3H in toluene, Time= 0.5h, T= 25 °C , Inert atmosphere, Glovebox, Schlenk technique Zhang, Lei; Peng, Dongjie; Leng, Xuebing; Huang, Zheng; Angewandte Chemie - International Edition; vol. 52; nb. 13; (2013); p. 3676 - 3680; Angew. Chem.; vol. 52; nb. 13; (2013); p. 3676 - 3680,5 View in Reaxys

HO HO H HO

OH H OH

Rx-ID: 35212547 View in Reaxys 107/154 Yield 54 %Spectr.,

80/96

2016-06-28 15:56:50

34 %Spectr.

Verendel, J. Johan; Nordlund, Michael; Andersson, Pher G.; ChemSusChem; vol. 6; nb. 3; (2013); p. 426 - 429 View in Reaxys

OH H

Rx-ID: 35212548 View in Reaxys 108/154 Yield 48 %Spectr., 46 %Spectr.

Conditions & References Stage 1: With di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium, (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, Time= 44h, T= 210 °C , Inert atmosphere Stage 2: With RuH(CO)(PPh3)3 in benzene, Inert atmosphere Verendel, J. Johan; Nordlund, Michael; Andersson, Pher G.; ChemSusChem; vol. 6; nb. 3; (2013); p. 426 - 429 View in Reaxys

OH H

Rx-ID: 35212554 View in Reaxys 109/154 Yield 66 %Spectr., 28 %Spectr.

Rx-ID: 35260927 View in Reaxys 110/154 Yield 8%

Conditions & References Typical procedure for the hydroformylation General procedure: [{Rh(cod)}2(μ-Cl)2] (5 μmol), phosphorus ligand (20 μmol), and solvent (6.3 mL) were added to a pressure reactor (25 mL). After addition of formaldehyde (37 percent in H2O, 6 mmol) and substrate (5 mmol) the reaction mixture was purged with nitrogen for several times and heated with stirring (1000 rpm) to the indicated reaction temperature. Once the desired temperature was achieved, H2 was introduced and the reaction mixture was stirred for the indicated reaction time. After cooling to room temperature the gas was released and the reaction mixture was again purged with nitrogen. Dodecane was added as an internal standard and brine in order to separate the phases. The organic phase was finally analyzed by GC.#10; With [RhCl(η2:η2-cycloocta-1,5-diene)]2, 1,3-bis-(diphenylphosphino)propane, hydrogen in water, toluene, Time= 20h, T= 120 °C , p= 7500.75Torr , regioselective reaction Uhlemann, Marcus; Doerfelt, Stephan; Boerner, Armin; Tetrahedron Letters; vol. 54; nb. 18; (2013); p. 2209 2211 View in Reaxys

81/96

2016-06-28 15:56:50

Rx-ID: 35463953 View in Reaxys 111/154 Yield 91 %, 9 %

Conditions & References With bis(cyclopentadienyl)zirconium dimethyl, [Ph3C][B(C6F5)4], hydrogen, Time= 0.5h, T= 20 °C , p= 1125.11Torr Xu, Xin; Kehr, Gerald; Daniliuc, Constantin G.; Erker, Gerhard; Journal of the American Chemical Society; vol. 135; nb. 17; (2013); p. 6465 - 6476 View in Reaxys 2H 2H 2H

Rx-ID: 35601303 View in Reaxys 112/154 Yield

Conditions & References With [(tris[2-(diisopropylphosphino)phenyl]borane)Fe(N2)], deuterium, p= 760.051Torr , Inert atmosphere Fong, Henry; Moret, Marc-Etienne; Lee, Yunho; Peters, Jonas C.; Organometallics; vol. 32; nb. 10; (2013); p. 3053 - 3062 View in Reaxys

Rx-ID: 35611904 View in Reaxys 113/154 Yield

Conditions & References With Cu nanoparticles dispersed on La2O2CO3 in 1,3,5-trimethyl-benzene, Time= 10h, T= 149.84 °C , Inert atmosphere, Time, Overall yield = 97 percent 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 View in Reaxys

O B O

B O

Rx-ID: 35679623 View in Reaxys 114/154 Yield 73 %, 11 %, 6 %, 7 %

Conditions & References With [(2,6-(2,4,6-Me3-C6H2-NdCMe)2C5H3N)Fe(N2)]2(μ2-N2) in neat (no solvent), T= 25 °C , Inert atmosphere Obligacion, Jennifer V.; Chirik, Paul J.; Organic Letters; vol. 15; nb. 11; (2013); p. 2680 - 2683 View in Reaxys

Rx-ID: 35949457 View in Reaxys 115/154 Yield 100 %

Conditions & References With C52H46ClN3P2Ru in dichloromethane-d2, Time= 16h, T= 50 °C , p= 3040.2Torr , Reagent/catalyst, Time

82/96

2016-06-28 15:56:50

Bagh, Bidraha; McKinty, Adam M.; Lough, Alan J.; Stephan, Douglas W.; Dalton Transactions; vol. 44; nb. 6; (2015); p. 2712 - 2723 View in Reaxys 100 %Spectr.

With [Ir(6-Neo)(COD)Cl] in ethanol, Time= 1h, p= 3750.38Torr , Solvent Dunsford, Jay J.; Tromp, Dorette S.; Cavell, Kingsley J.; Elsevier, Cornelis J.; Kariuki, Benson M.; Dalton Transactions; vol. 42; nb. 20; (2013); p. 7318 - 7329 View in Reaxys , Time= 24h, T= 80 °C , p= 30003Torr , Reagent/catalyst Nandan, Devaki; Sreenivasulu, Peta; Viswanadham, Nagabhatla; Chiang, Ken; Newnham, Jarrod; Dalton Transactions; vol. 43; nb. 31; (2014); p. 12077 - 12084 View in Reaxys

SiH

Rx-ID: 36725952 View in Reaxys 116/154 Yield

SiH

Rx-ID: 36725953 View in Reaxys 117/154 Yield 10 %, 90 %

Conditions & References With C11H14FeO4Si2 in toluene, Time= 24h, T= 20 °C , Inert atmosphere, Schlenk technique Marciniec, Bogdan; Kownacka, Agnieszka; Kownacki, Ireneusz; Hoffmann, Marcin; Taylor, Richard; Journal of Organometallic Chemistry; vol. 791; (2015); p. 58 - 65 View in Reaxys

56 %, 27 %

With C11H14FeO4Si2 in toluene, Time= 48h, T= 10 °C , Inert atmosphere, Schlenk technique Marciniec, Bogdan; Kownacka, Agnieszka; Kownacki, Ireneusz; Hoffmann, Marcin; Taylor, Richard; Journal of Organometallic Chemistry; vol. 791; (2015); p. 58 - 65 View in Reaxys 2.1 General procedure for the dehydrogenative silylation of styrene General procedure: A two-necked flask equipped with a magnetic stirring bar was charged with the catalytic amount of complex (0.015mmol). The reactor was evacuated and filled with dinitrogen. Styrene (0.52mL, 4.5mmol) and toluene (5mL) were added, and the mixture was stirred for 5min. Then Et3SiH (0.24mL, 1.5mmol) was added. The reaction flask was immersed in an 80°C thermo-stabilized bath. The progress of the reaction was monitored by GC

83/96

2016-06-28 15:56:50

(disappearance of Et3SiH). The products were identified by 1H NMR, by GC–MS, and by comparison with the literature data [28]. With anti-[Cp*Fe-(2,6-diethyl-4,8-dimethyl-s-indaceneiide)-Rh(COD)] in toluene, Time= 2.33333h, T= 80 °C , Inert atmosphere, Time Adams; Riviere; Riviere-Baudet; Morales-Verdejo; Dahrouch; Morales; Castel; Delpech; Manriquez; Chavez; Journal of Organometallic Chemistry; vol. 749; (2014); p. 266 - 274 View in Reaxys 4.2 General procedure for the catalytic hydrosilylations according to Tables1–4 General procedure: A solution of the appropriate substrate (0.5mmol), the silane (0.6mmol) and the proper catalytic amount of the rhenium complex in the given solvent (0.8ml) was stirred for an appropriate period of time at proper temperature under nitrogen atmosphere. Upon completion, the reaction mixture was filtered over Celite. The resulting solution was analyzed by NMR spectroscopy and GC–MS. The yields are listed in Tables1–4. With [Re(CH3CN)3Br2(NO)] in toluene, Time= 2h, T= 110 - 115 °C , Inert atmosphere Dong, Hailin; Jiang, Yanfeng; Berke, Heinz; Journal of Organometallic Chemistry; vol. 750; (2014); p. 17 - 22 View in Reaxys

SiH

O O

Si O

Rx-ID: 36725954 View in Reaxys 118/154 Yield

Conditions & References 2.1 General procedure for the dehydrogenative silylation of styrene General procedure: A two-necked flask equipped with a magnetic stirring bar was charged with the catalytic amount of complex (0.015mmol). The reactor was evacuated and filled with dinitrogen. Styrene (0.52mL, 4.5mmol) and toluene (5mL) were added, and the mixture was stirred for 5min. Then Et3SiH (0.24mL, 1.5mmol) was added. The reaction flask was immersed in an 80°C thermo-stabilized bath. The progress of the reaction was monitored by GC (disappearance of Et3SiH). The products were identified by 1H NMR, by GC–MS, and by comparison with the literature data [28]. With anti-[Cp*Fe-(2,6-diethyl-4,8-dimethyl-s-indaceneiide)-Rh(COD)] in toluene, Time= 2.33333h, T= 80 °C , Inert atmosphere, Time, Reagent/catalyst Adams; Riviere; Riviere-Baudet; Morales-Verdejo; Dahrouch; Morales; Castel; Delpech; Manriquez; Chavez; Journal of Organometallic Chemistry; vol. 749; (2014); p. 266 - 274 View in Reaxys General methods General procedure: All catalysis reaction operations were performed in a 10 mL flat-bottomed tube without protection from air. The alkene (4.0 mmol) and the requisite amount of catalyst were placed in a dried tube and the reaction mixture was stirred for 5 min. Thereafter, the silane (4.4 mmol) was added and the resulting mixture was heated and stirred for the requisite time and then cooled to room temperature. The product phase was separated by decantation and the conversion of the alkene and the selectivity were determined by GC–MS analysis on an Agilent 26890N/ 59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). 1H NMR (400 MHz) and 13C NMR (100.6 MHz) spectra were recorded on a Bruker Advance spectrometer using TMS as an internal standard. Methanol-d4 and DMSO-d6 were used as solvents. Stage 1: With Wilkinson's catalyst, Time= 0.0833333h Stage 2:, Time= 5h, T= 90 °C Xu, Yisong; Bai, Ying; Peng, Jiajian; Li, Jiayun; Xiao, Wenjun; Lai, Guoqiao; Journal of Organometallic Chemistry; vol. 765; (2014); p. 59 - 63 View in Reaxys

11 %Spectr.,

With (η4-1,3,5,7-cyclooctatetraene)2Fe(CNAd), adamantan-1-isonitrile in neat (no solvent), Time= 3h, T= 80 °C

84/96

2016-06-28 15:56:50

8 %Spectr., 18 %Spectr.

Sunada, Yusuke; Noda, Daisuke; Soejima, Hiroe; Tsutsumi, Hironori; Nagashima, Hideo; Organometallics; vol. 34; nb. 12; (2015); p. 2896 - 2906 View in Reaxys 2.2 The catalytic hydrosilylation reaction General procedure: All catalytic reaction was performed in a 10 mL flat-bottomed tube without protection from air. The alkenes (4.0 mmol) and a requisite amount of catalyst and ionic liquid were placed in a dried tube and the reaction mixture stirred for 5 min. Thereafter, the silane (4.4 mmol) was added, the resulting reaction mixture heated with stirring for a requisite time and then allowed to cool to room temperature. The product phase was separated by decantation and the conversion of the alkenes and selectivity determined by GC-MS analysis using an Agilent 26890N/ 59731 apparatus equipped with a DB-5 column (30 m × 2.5 mm × 0.25 μm). With Wilkinson's catalyst, Heating, Catalytic behavior Bai, Ying; Zhang, Fengxiang; Li, Jiayun; Xu, Yisong; Peng, Jiajian; Xiao, Wenjun; Journal of Organometallic Chemistry; vol. 794; (2015); p. 65 - 69; Art.No: 19129 View in Reaxys

Rx-ID: 36890469 View in Reaxys 119/154 Yield

Conditions & References With tributylphosphine, hydrogen, lithium tri-t-butoxyaluminum hydride, cobalt(II) 2,4-pentanedionate in n-heptane, T= 30 °C , p= 1520.1Torr , Sealed tube, Catalytic behavior, Reagent/catalyst, Temperature Titova; Belykh; Ratovskii; Rokhin; Soroka; Schmidt; Kinetics and Catalysis; vol. 54; nb. 4; (2013); p. 431 - 442; Kinet. Katal.; vol. 54; nb. 4; (2013); p. 453 - 465,13 View in Reaxys

Rx-ID: 37072967 View in Reaxys 120/154 Yield

Conditions & References With hydrogen in ethanol, water, Time= 4h, T= 50 °C , p= 1500.15Torr , Reagent/catalyst, chemoselective reaction Shaabani, Ahmad; Mahyari, Mojtaba; Catalysis Letters; vol. 143; nb. 12; (2013); p. 1277 - 1284 View in Reaxys

O B

E O

B O

Rx-ID: 37353733 View in Reaxys 121/154 Yield 55 %Spectr., 11 %Spectr., 12 %Spectr., 19 %Spectr.

Conditions & References With [(1,3-bis(2,4,6-trimethylphenyl) imidazol-2-ylidene)Fe(CO)4], 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane in neat (no solvent), Time= 24h, T= 20 °C , Inert atmosphere, UV-irradiation, Schlenk technique Zheng, Jianxia; Sortais, Jean-Baptiste; Darcel, Christophe; ChemCatChem; vol. 6; nb. 3; (2014); p. 763 - 766 View in Reaxys

85/96

2016-06-28 15:56:50

Rx-ID: 37611491 View in Reaxys 122/154 Yield 95 %, 18 %

Conditions & References With C28H18Co(1-)*K(1+)*2C4H10O2, hydrogen, Time= 3h, T= 20 °C , p= 1500.15Torr Gaertner, Dominik; Welther, Alice; Rad, Babak Rezaei; Wolf, Robert; Von Wangelin, Axel Jacobi; Angewandte Chemie - International Edition; vol. 53; nb. 14; (2014); p. 3722 - 3726; Angew. Chem.; vol. 126; nb. 14; (2014); p. 3796 - 3800,5 View in Reaxys O

Rx-ID: 37869832 View in Reaxys 123/154 Yield

Conditions & References , Time= 0.416667h, UV-irradiation Imamura, Kazuya; Okubo, Yuki; Ito, Tomohiko; Tanaka, Atsuhiro; Hashimoto, Keiji; Kominami, Hiroshi; RSC Advances; vol. 4; nb. 38; (2014); p. 19883 - 19886 View in Reaxys

Rx-ID: 38245270 View in Reaxys 124/154 Yield

Conditions & References 1 : Procedure for Monitoring Styrene/n-Heptane Coupling Reactions Over Time: Dimerization catalyst 1 (6.6 mg, 0.016 mmol) and 2 (17.7 mg, 0.030 mmol) were dissolved in 2 mL of a standard solution of styrene (250 mM) and adamantane (25.3 mM) in n-heptane in a 4 mL screw top vial containing a Tefloncoated stir bar. The vial was sealed with a Teflon-lined screw cap. The mixture was heated to 100° C. for 30 seconds in an aluminum block heater inside an argon-filled glovebox to dissolve the precatalysts and ensure a homogeneous solution, and then immediately cooled to −35° C. in the freezer. An aliquot (0.1 mL, representing to) was removed and placed into a GC autosampler vial; this aliquot was then diluted with dichloromethane to a total volume of 1 mL before analysis by GC. [0130] The reaction mixture was heated to 100° C. in the aluminum block heater, and at specified times (1, 2, 3, 4, 5, 6, 7, 8, 10, 12, and 18 hours) the vial was removed and cooled to −35° C. in the freezer before taking an aliquot for analysis by GC. The concentrations of all major species were then plotted versus time to give time course profiles of the tandem reaction (see FIG. 48). The effects of the cooperativity in Styrene/n-Heptane Coupling by dimerization catalyst 1 and hydrogen transfer catalyst 2 is presented in Table 4. With IrH2{C6H3-2,6-(CH2PBu(t)2)2}, Cp*TaCl2(C2H4), Time= 72h, T= 100 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Time, Temperature, Concentration Patent; California Institute of Technology; Leitch, David; Labinger, Jay A.; Bercaw, John E.; Lam, Yan Choi; US2014/200376; (2014); (A1) English View in Reaxys

Rx-ID: 38675046 View in Reaxys 125/154 Yield

Conditions & References With C47H37ClIrN2O3PS2, potassium tert-butylate in toluene, Time= 12h, T= 110 °C , Inert atmosphere, Catalytic behavior, Reagent/catalyst, Solvent, Temperature

86/96

2016-06-28 15:56:50

Zhao, Keyan; Wang, Dawei; Wang, Huijun; Zhu, Zhenzhong; Ding, Yuqiang; Inorganic Chemistry Communications; vol. 47; (2014); p. 131 - 133 View in Reaxys

SiH

Si O

Rx-ID: 40264866 View in Reaxys 126/154 Yield 75 %Spectr., 11 %Spectr., 14 %Spectr. 83 %Spectr., 7 %Spectr., 10 %Spectr.

Conditions & References With cyclohexyl isonitrile, (η4-1,3,5,7-cyclooctatetraene)2Fe(CNAd) in neat (no solvent), Time= 3h, T= 80 °C , Reagent/catalyst Sunada, Yusuke; Noda, Daisuke; Soejima, Hiroe; Tsutsumi, Hironori; Nagashima, Hideo; Organometallics; vol. 34; nb. 12; (2015); p. 2896 - 2906 View in Reaxys With iron(II) pivalate, 1-adamantanecarbonitrile in neat (no solvent), Time= 3h, T= 80 °C , Reagent/catalyst Noda, Daisuke; Tahara, Atsushi; Sunada, Yusuke; Nagashima, Hideo; Journal of the American Chemical Society; vol. 138; nb. 8; (2016); p. 2480 - 2483 View in Reaxys

SiH

Rx-ID: 40264867 View in Reaxys 127/154 Yield 49 %, 51 %Spectr.

Conditions & References With (η4-1,3,5,7-cyclooctatetraene)2Fe(CNAd), mesitylene isonitrile in neat (no solvent), Time= 3h, T= 80 °C Sunada, Yusuke; Noda, Daisuke; Soejima, Hiroe; Tsutsumi, Hironori; Nagashima, Hideo; Organometallics; vol. 34; nb. 12; (2015); p. 2896 - 2906 View in Reaxys

Si SiH

Rx-ID: 40264868 View in Reaxys 128/154 Yield

Conditions & References

90 With (η4-1,3,5,7-cyclooctatetraene)2Fe(CNAd), adamantan-1-isonitrile in neat (no solvent), Time= 3h, T= 80 °C , Re%Spectr., agent/catalyst 6 %Spectr. Sunada, Yusuke; Noda, Daisuke; Soejima, Hiroe; Tsutsumi, Hironori; Nagashima, Hideo; Organometallics; vol. 34; nb. 12; (2015); p. 2896 - 2906 View in Reaxys

SiH O

O Si

Rx-ID: 40264869 View in Reaxys 129/154 Yield 51 %Spectr.,

Conditions & References With (η4-1,3,5,7-cyclooctatetraene)2Fe(CNAd), adamantan-1-isonitrile in neat (no solvent), Time= 3h, T= 80 °C

87/96

2016-06-28 15:56:50

45 %Spectr.

Sunada, Yusuke; Noda, Daisuke; Soejima, Hiroe; Tsutsumi, Hironori; Nagashima, Hideo; Organometallics; vol. 34; nb. 12; (2015); p. 2896 - 2906 View in Reaxys With C11H14FeO4Si2 in toluene, T= 80 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst Marciniec, Bogdan; Kownacka, Agnieszka; Kownacki, Ireneusz; Hoffmann, Marcin; Taylor, Richard; Journal of Organometallic Chemistry; vol. 791; (2015); p. 58 - 65 View in Reaxys

SiH

Rx-ID: 40264870 View in Reaxys 130/154 Yield 35 %Spectr., 31 %Spectr.

Conditions & References With (η4-1,3,5,7-cyclooctatetraene)2Fe(CNAd), adamantan-1-isonitrile in neat (no solvent), Time= 3h, T= 80 °C Sunada, Yusuke; Noda, Daisuke; Soejima, Hiroe; Tsutsumi, Hironori; Nagashima, Hideo; Organometallics; vol. 34; nb. 12; (2015); p. 2896 - 2906 View in Reaxys With C11H14FeO4Si2 in toluene, T= 80 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst Marciniec, Bogdan; Kownacka, Agnieszka; Kownacki, Ireneusz; Hoffmann, Marcin; Taylor, Richard; Journal of Organometallic Chemistry; vol. 791; (2015); p. 58 - 65 View in Reaxys

H2 Si SiH

SiH

Rx-ID: 40264871 View in Reaxys 131/154 Yield 59 %Spectr., 22 %Spectr., 19 %Spectr.

H2 Si H 3Si

Rx-ID: 40264872 View in Reaxys 132/154 Yield

Conditions & References

10 With (η4-1,3,5,7-cyclooctatetraene)2Fe(CNAd), adamantan-1-isonitrile in neat (no solvent), Time= 3h, T= 80 °C %Spectr., 6 %Spectr. Sunada, Yusuke; Noda, Daisuke; Soejima, Hiroe; Tsutsumi, Hironori; Nagashima, Hideo; Organometallics; vol. 34; nb. 12; (2015); p. 2896 - 2906 View in Reaxys

88/96

2016-06-28 15:56:50

Si SiH

Rx-ID: 40730545 View in Reaxys 133/154 Yield 100 %

Conditions & References a) [HSiMe2Ph]: [styrene] = 1 : 2; (50 – 70oC) In the kinetic reactor,0.28 mL of dimethylphenylsilane (1.8•10-3 mol), 0.42 mL (3.6•10-3mol) of styrene, 1 mL of toluene and 0.17 mL decane were placed under argonatmosphere. Then, the reactor was placed in an oil bath and warmed for about 30min. After reaching the required reaction temperature, 0.006 g (1.8•10-5mol) of iron complex 1 wasintroduced. Changes in the concentrations of reagents and products weremonitored by GC analysis using the internal standard method. The reactions wereconducted at three different temperatures: 50, 60 and 70 oC. Thesamples for GC analysis were frozen in dry ice. With C11H14FeO4Si2 in toluene, Time= 24h, T= 50 °C , Inert atmosphere, Schlenk technique, Kinetics, Reagent/catalyst, Temperature Marciniec, Bogdan; Kownacka, Agnieszka; Kownacki, Ireneusz; Hoffmann, Marcin; Taylor, Richard; Journal of Organometallic Chemistry; vol. 791; (2015); p. 58 - 65 View in Reaxys

Rx-ID: 41109973 View in Reaxys 134/154 Yield

Conditions & References With allyl nickel bromide dimer, (1R,3S)-3-(naphthalen-1-yloxy)-1-phenyl-2-[(R)-1-phenylethyl]-2,3-dihydro-1H-naphtho[1,2-e][1,3,2]oxazaphosphinine, Na[B(3,5-(CF3)2C6H3)4] in dichloromethane, Time= 0.333333h, T= -50 °C , p= 900.09Torr , Reagent/catalyst, enantioselective reaction Schmitz, Christian; Leitner, Walter; Franci, Giancarlo; European Journal of Organic Chemistry; vol. 2015; nb. 28; (2015); p. 6205 - 6230 View in Reaxys With allyl nickel bromide dimer, (1R,3S)-N-methyl-1-phenyl-N,2-bis[(R)-1-phenylethyl]-1H-naphtho[1,2-e][1,3,2]oxaza-phosphinine-3(2H)-amine, Na[B(3,5-(CF3)2C6H3)4] in dichloromethane, Time= 0.333333h, T= -50 °C , p= 900.09Torr , Reagent/catalyst, enantioselective reaction Schmitz, Christian; Leitner, Walter; Franci, Giancarlo; European Journal of Organic Chemistry; vol. 2015; nb. 28; (2015); p. 6205 - 6230 View in Reaxys

SiH

Rx-ID: 42233648 View in Reaxys 135/154 Yield

Conditions & References

11 With iron(II) pivalate, 1-adamantanecarbonitrile in neat (no solvent), Time= 3h, T= 80 °C , Reagent/catalyst %Spectr., 9 %Spectr. Noda, Daisuke; Tahara, Atsushi; Sunada, Yusuke; Nagashima, Hideo; Journal of the American Chemical Society; vol. 138; nb. 8; (2016); p. 2480 - 2483 View in Reaxys

89/96

2016-06-28 15:56:50

Rx-ID: 42480876 View in Reaxys 136/154 Yield 60 %

Conditions & References Stage 1: With palladium diacetate, tricyclopentylphosphine in toluene, Time= 0.166667h, T= 20 °C , Glovebox, Inert atmosphere Stage 2: With Triethoxysilane, (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride, lithium tert-butoxide in toluene, Time= 6h, T= 100 °C , Glovebox, Inert atmosphere, Reagent/catalyst, regioselective reaction Semba, Kazuhiko; Ariyama, Kenta; Zheng, Hong; Kameyama, Ryohei; Sakaki, Shigeyoshi; Nakao, Yoshiaki; Angewandte Chemie - International Edition; vol. 55; nb. 21; (2016); p. 6275 - 6279; Angew. Chem.; vol. 128; nb. 21; (2016); p. 6383 - 6387,5 View in Reaxys

Rx-ID: 42480877 View in Reaxys 137/154 Yield 60 %, 49 %Chromat., 31 %Chromat.

Conditions & References Stage 1: With palladium diacetate, tricyclopentylphosphine in toluene, Time= 0.166667h, T= 20 °C , Glovebox, Inert atmosphere Stage 2: With Triethoxysilane, (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride, cesium fluoride in toluene, Time= 6h, T= 100 °C , Glovebox, Inert atmosphere Semba, Kazuhiko; Ariyama, Kenta; Zheng, Hong; Kameyama, Ryohei; Sakaki, Shigeyoshi; Nakao, Yoshiaki; Angewandte Chemie - International Edition; vol. 55; nb. 21; (2016); p. 6275 - 6279; Angew. Chem.; vol. 128; nb. 21; (2016); p. 6383 - 6387,5 View in Reaxys

Rx-ID: 42480878 View in Reaxys 138/154 Yield

Conditions & References Stage 1: With palladium diacetate, tricyclopentylphosphine in toluene, Time= 0.166667h, T= 20 °C , Glovebox, Inert atmosphere Stage 2: With Triethoxysilane, (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride, caesium carbonate in toluene, Time= 6h, T= 100 °C , Glovebox, Inert atmosphere, Reagent/catalyst Semba, Kazuhiko; Ariyama, Kenta; Zheng, Hong; Kameyama, Ryohei; Sakaki, Shigeyoshi; Nakao, Yoshiaki; Angewandte Chemie - International Edition; vol. 55; nb. 21; (2016); p. 6275 - 6279; Angew. Chem.; vol. 128; nb. 21; (2016); p. 6383 - 6387,5 View in Reaxys

SiH

Rx-ID: 1545263 View in Reaxys 139/154

90/96

2016-06-28 15:56:50

Yield

Conditions & References With Wilkinson's catalyst in benzene, Time= 6h, T= 70 °C , other temperature (60 deg C); also presence of air or argon, Product distribution, Mechanism Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 7; (1980); p. 2085 - 2099 View in Reaxys With Wilkinson's catalyst in benzene, Time= 6h, T= 70 °C , Yield given. Yields of byproduct given Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 7; (1980); p. 2085 - 2099 View in Reaxys With Wilkinson's catalyst in benzene, Time= 6h, T= 70 °C , Yield given. Yields of byproduct given Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 7; (1980); p. 2085 - 2099 View in Reaxys

SiH

Rx-ID: 1545264 View in Reaxys 140/154 Yield

SiH

E Si

Rx-ID: 1545282 View in Reaxys 141/154 Yield

Conditions & References With lt;Rhlt;P(C6H5)3gt;3gt; in benzene, Time= 6h, T= 70 °C , other temperature (60 deg C); also presence of air or argon, Product distribution, Mechanism Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 7; (1980); p. 2085 - 2099 View in Reaxys With Wilkinson's catalyst in benzene, Time= 6h, T= 70 °C , Yield given. Yields of byproduct given Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 7; (1980); p. 2085 - 2099 View in Reaxys

91/96

2016-06-28 15:56:50

With Wilkinson's catalyst in benzene, Time= 6h, T= 70 °C , Yield given. Yields of byproduct given Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 7; (1980); p. 2085 - 2099 View in Reaxys

SiH

Rx-ID: 1545283 View in Reaxys 142/154 Yield

Conditions & References With Wilkinson's catalyst in tetrahydrofuran, Time= 6h, T= 70 °C , other solvents, Product distribution Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 8; (1980); p. 2240 - 2246 View in Reaxys With Wilkinson's catalyst in N,N,N',N',N'',N''-hexamethylphosphoric triamide, Time= 6h, T= 70 °C , Yield given. Yields of byproduct given Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 8; (1980); p. 2240 - 2246 View in Reaxys With Wilkinson's catalyst in various solvent(s), Time= 6h, T= 70 °C , Yield given. Yields of byproduct given Kuncova, Gabriela; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 8; (1980); p. 2240 - 2246 View in Reaxys

racemate

1,3-diphenylbutane, (E)-1,3-diphenyl-1-butene

racemate

Rx-ID: 7065041 View in Reaxys 143/154 Yield

Conditions & References in benzene, Time= 3h, T= 120 °C , thermolysis; formation of possible mechanism of thermolysis and radical reactions, Product distribution Engel, Paul S.; Duan, Shaoming; Arhancet, Graciela B.; Journal of Organic Chemistry; vol. 62; nb. 11; (1997); p. 3537 - 3541 View in Reaxys

92/96

2016-06-28 15:56:50

(v3)

O H

(v3)

(v5)

(v3)

O (v5)

O Co O

(v3)

Co TB-5 Co TB-5 (v5) O O

(v3)

O O

(v3)

(v5)

(v3)

(v5)

(v3) (v3)

(v3)

O O

(v3)

Rx-ID: 26634157 View in Reaxys 144/154 Yield

Conditions & References With carbon monoxide in n-heptane, Kinetics, Heptane soln. in the presence of CO, 15°C; not sepd., detected by IR spectra and gas chromy.; Ungvary, Ferenc; Marko, Laszlo; Organometallics; vol. 1; (1982); p. 1120 - 1125 ; (from Gmelin) View in Reaxys

(v4)

F F

B– FF

(v4)

N (v4)

Rh + OC-6 (v6)

B– FF

(v4) (v4)

(v4)

Rh + SP-4

(v4)

Rx-ID: 26913033 View in Reaxys 145/154 Yield

Conditions & References in CD3NO2, addn. of styrene to a soln. of the rhodium complex, warming for 1 h to 40°C; cooling to room temp., (1)H-NMR Nuernberg, Oliver; Werner, Helmut; Journal of Organometallic Chemistry; vol. 460; nb. 2; (1993); p. 163 - 176 ; (from Gmelin) View in Reaxys

(v3) (v3)

95.1

O O O

O Ti

(v3)

(v4)

4.9

O O

(v3)

O Ti

(v4)

Rx-ID: 27376423 View in Reaxys 146/154 Yield 13.5 %

Conditions & References With 2,2'-azo-bisisobutyronitrile in n-heptane, degassing and sealing in glass tube, 70°C, 5 h; product filtration off, washing (heptane), vacuum drying (40°C) Klabunovskii; Karpeiskaya; Dzhandimalieva; Golubeva; Pomogailo; Russian Chemical Bulletin; vol. 48; nb. 9; (1999); p. 1717 - 1721 ; (from Gmelin) View in Reaxys

93/96

2016-06-28 15:56:50

(v3) (v3)

-1 (v3)

(v3) (v3)

(v3)

(v3)(v3)

O O

(v2) Os (v6) H – (v7) + O Os O (v4) P C –(v3) O

+Os (v7)

O N

(v3) O(v3) O (v3)

(v3)

O (v3) O Os (v7)Os +(v4)O (v6) +Os P O (v3) H– -1 (v7) O (v2) (v4) –C O (v3) (v3) O

(v4) (v3)

(v3)

Rx-ID: 27420336 View in Reaxys 147/154 Yield 72-78 %

Conditions & References With azobisisobutyronitrile in neat (no solvent), under dry Ar atm.; HOs3(OCNMe2)(CO)9(PPh2CH2CHCH2), styrene and azobisisobutyronitrile placed in glass ampoule; mixt. was degassed; ampoule was sealed in vac.; heated at 70°C for 3 h; dissolved in benzene; pptd. (EtOH); dried at 30°C (vac.) Pomogailo, Svetlana I.; Shilov, Gennady V.; Ershova, Victoria A.; Virovets, Alexander V.; Pogrebnyak, Vladimir M.; Podberezskaya, Nina V.; Golovin, Anatoly V.; Dzhardimalieva, Gulzhian I.; Pomogailo, Anatolii D.; Journal of Organometallic Chemistry; vol. 690; nb. 19; (2005); p. 4258 - 4264 ; (from Gmelin) View in Reaxys With azobisisobutyronitrile in toluene, under dry Ar atm.; HOs3(OCNMe2)(CO)9(PPh2CH2CHCH2), styrene, toluene andazobisisobutyronitrile placed in glass ampoule; mixt. was degassed; amp oule was sealed in vac.; heated at 70°C for 3 h; dissolved in benzene; pptd. (EtOH); dried at 30°C (vac.) Pomogailo, Svetlana I.; Shilov, Gennady V.; Ershova, Victoria A.; Virovets, Alexander V.; Pogrebnyak, Vladimir M.; Podberezskaya, Nina V.; Golovin, Anatoly V.; Dzhardimalieva, Gulzhian I.; Pomogailo, Anatolii D.; Journal of Organometallic Chemistry; vol. 690; nb. 19; (2005); p. 4258 - 4264 ; (from Gmelin) View in Reaxys

(v5)(v4) – (v5) C (v4) N (v2) (v3) (v5) – 3+(v9) – H – N – Y3+ (v5) N H Y (v9) (v3) Si (v2)(v5)(v5) N C– (v4) (v4) (v5)

(v5)

(v4) (v5) (v5)

(v5) (v5)(v4) (v5) C–

CH –2

(v5) Si

(v3)– C – Y3+ N

C–

N–

(v10)

(v4)

racemate

Y3+

Rx-ID: 27708930 View in Reaxys 148/154 Yield 52 %, 0 %

Conditions & References in hexane, under Ar; soln. of the Y complex in hexane treated with styrene; mixt. heated to 60 °C for 3 h; react. mixt. cooled to room temp.; vol. of solvent reduced in vacuo; crystals obtained by cooling overnight at -30 °C; elem. anal. Voth, Peter; Spaniol, Thomas P.; Okuda, Jun; Organometallics; vol. 22; nb. 19; (2003); p. 3921 - 3926 ; (from Gmelin) View in Reaxys

Rx-ID: 35212552 View in Reaxys 149/154 Yield 11 %Spectr.

Conditions & References Stage 1: With di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium, (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, Time= 44h, T= 185 °C , Inert atmosphere Stage 2: With RuH(CO)(PPh3)3 in 1,3,5-trimethyl-benzene, benzene, Inert atmosphere Verendel, J. Johan; Nordlund, Michael; Andersson, Pher G.; ChemSusChem; vol. 6; nb. 3; (2013); p. 426 - 429 View in Reaxys

94/96

2016-06-28 15:56:50

N N (v1) – (v2)H 2+ (v4) P H Fe N(v4) –OC-6 P B(v6) N (v4)

(v4)

Fe P (v5) (v4)

(v4)

Rx-ID: 35601286 View in Reaxys 150/154 Yield

Conditions & References in benzene-d6, p= 760.051Torr , Inert atmosphere Fong, Henry; Moret, Marc-Etienne; Lee, Yunho; Peters, Jonas C.; Organometallics; vol. 32; nb. 10; (2013); p. 3053 - 3062 View in Reaxys H N

Me3 SiO(Me2 SiO)13.5 (MeSiO)5.5 SiMe3

Ru3 CO12

Rx-ID: 25041710 View in Reaxys 151/154 Yield

Conditions & References 15 : EXAMPLE 15 EXAMPLE 15 To a 45 cc high pressure bomb was added 3.75 g (0.0025 mol) Me3 SiO(Me2 SiO)13.5 (MeSiO)5.5 SiMe3, 5.26 g (0.05 mol) styrene, 2.0 g xylene and 1000 ppm (8.1 mg) Ru3 CO12 as a catalsyt. Phenothiazine (75.6 mg) was also added to help prevent polymerization of the styrene. The bomb was then heated in a fluidized sand bath at 125° C. for 10 hours after which time the reaction was cooled to room temperature. The solvent and excess styrene as well as ethylbenzene formed during the course of the reaction was removed under vacuum. Analysis by 1 H-NMR showed the product to be STR10 in anhydrous xylene Patent; Union Carbide Corporation; US4668812; (1987); (A1) English View in Reaxys

(v3)

(v5) (v5) (v5) (v5) (v5)

(v3)

(v5)

(v3)

(v9)

(v3)

(v5)(v5) (v5) (v5) (v5) (v9)

(v3)

(v5)

Cr O

(v3)

Rx-ID: 26318884 View in Reaxys 152/154 Yield

Conditions & References by homogenic polymerisation vol. Cr: Org.Verb.; 5, page 403 - 404 View in Reaxys Pittman, C. U.; et al.; Southeast-Southwest Regional Meeting Am. Chem. Soc., New Orleans 1970 after Chem. Eng. News 48 {1970} 36/7 ; (from Gmelin) View in Reaxys

HO OH

Rx-ID: 35212546 View in Reaxys 153/154

95/96

2016-06-28 15:56:50

Yield 60 %Spectr., 32 %Spectr.

O OH

Rx-ID: 35212553 View in Reaxys 154/154 Yield 64 %Spectr., 23 %Spectr.

Conditions & References Stage 1: With di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium, (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, Time= 44h, T= 210 °C , Inert atmosphere Stage 2: With RuH(CO)(PPh3)3 in benzene, Inert atmosphere, Temperature, Solvent Verendel, J. Johan; Nordlund, Michael; Andersson, Pher G.; ChemSusChem; vol. 6; nb. 3; (2013); p. 426 - 429 View in Reaxys

96/96

2016-06-28 15:56:50