1-Phenylpropan-1-ol (1-Phenyl-1-propanol) [C9H12O] by Asch

Query Query

Results

Date

280 reactions in Reaxys

2018-07-03 17h:11m:28s (UTC)

1. Query

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='93-54-9') AND (IDE.INCHI='DYUQAZSOFZSPHD-UHFFFAOYSA-N') NOT (RX.RXRN=1906759))

1/120

2018-07-03 17:12:41

Mg Br

Rx-ID: 600049 View in Reaxys 1/280 Yield 100 %

Conditions & References With methylaluminum bis(2,6-di-tert-butylphenoxide) in diethyl ether, toluene, Time= 2h, T= -78 °C Maruoka, Keiji; Itoh, Takayuki; Sakurai, Minoru; Nonoshita, Katsumasa; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 110; (1988); p. 3588 - 3597 View in Reaxys

87 %

in diethyl ether, T= 0 - 20 °C Ahern, Theresa; Mueller-Bunz, Helge; Guiry, Patrick J.; Journal of Organic Chemistry; vol. 71; nb. 20; (2006); p. 7596 7602 View in Reaxys

73 %

Stage 1: in tetrahydrofuran, Time= 24h, T= 30 °C , Inert atmosphere Stage 2: With water in tetrahydrofuran, Inert atmosphere Orita, Akihiro; Yasui, Yutaka; Otera, Junzo; Organic Process Research and Development; vol. 4; nb. 5; (2000); p. 337 - 341 View in Reaxys

68 %

With dibenzo-18-crown-6 in diethyl ether, benzene, various aldehydes and alkyl(aryl)calcium(magnesium) halides, Product distribution Bogatskii, A. V.; Chumachenko, T. K.; Luk'yanenko, N. G.; Lyamtseva, L. N.; Starovoit, I. A.; Doklady Chemistry; vol. 251; (1980); p. 105 - 107; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 251; nb. 1; (1980); p. 113 - 115 View in Reaxys

29 %

Stage 1: With zinc diacetate in tert-butyl methyl ether, Time= 1h, T= 0 - 20 °C Stage 2: in tert-butyl methyl ether, Time= 4h, T= 20 °C Jagtap; Joshi; Tetrahedron Letters; vol. 52; nb. 48; (2011); p. 6501 - 6503 View in Reaxys With hydrogenchloride, di-phenyl-methyl-phosphine, zirconocene dichloride, Yield given. Multistep reaction Suzuki, Noriyuki; Rousset, Christophe J.; Aoyagi, Koichiro; Kotora, Martin; Takahashi, Tamotsu; et al.; Journal of Organometallic Chemistry; vol. 473; nb. 1-2; (1994); p. 117 - 128 View in Reaxys Grignard; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys Angle; Arnaiz; Tetrahedron Letters; vol. 32; nb. 21; (1991); p. 2327 - 2330 View in Reaxys Shostakovskii, V. M.; Zlatkina, V. L.; Vasil'vitskii, A. E.; Nefedov, G. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; (1982); p. 1877 - 1883; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 9; (1982); p. 2126 - 2133 View in Reaxys Jin, Myung-Jong; Ahn, Sum-Jin; Lee, Kyoung-Soo; Tetrahedron Letters; vol. 37; nb. 48; (1996); p. 8767 - 8770 View in Reaxys Braga, Antonio L.; Paixao, Marcio W.; Luedtke, Diogo S.; Silveira, Claudio C.; Rodrigues, Oscar E. D.; Organic Letters; vol. 5; nb. 15; (2003); p. 2635 - 2638 View in Reaxys in tetrahydrofuran, diethyl ether, Time= 2h, Heating Yueh, Wang; Bauld, Nathan L.; Journal of Physical Organic Chemistry; vol. 9; nb. 8; (1996); p. 529 - 538 View in Reaxys in tetrahydrofuran, T= 0 °C Li, Chengliang; Jin, Tao; Zhang, Xinglu; Li, Chunju; Jia, Xueshun; Li, Jian; Organic Letters; vol. 18; nb. 8; (2016); p. 1916 - 1919

2/120

2018-07-03 17:12:41

View in Reaxys Inert atmosphere Dilek, Ömer; Tezeren, Mustafa A.; Tilki, Tahir; Ertürk, Erkan; Tetrahedron; vol. 74; nb. 2; (2018); p. 268 - 286 View in Reaxys H (v2)

Rx-ID: 600052 View in Reaxys 2/280 Yield 99 %

Conditions & References With (1R,2S)-2-aminomethyl-2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptane in hexane, Time= 48h Dimitrov, Vladimir; Dobrikov, Georgi; Genov, Miroslav; Tetrahedron Asymmetry; vol. 12; nb. 9; (2001); p. 1323 - 1329 View in Reaxys

99 %

With polystyrene bond triphenylphosphonium chloride in toluene, T= 0 - 23 °C , Inert atmosphere, chemoselective reaction Werner, Thomas; Riahi, Abdol Majid; Schramm, Heiko; Synthesis; nb. 21; (2011); p. 3482 - 3490; Art.No: N59811SS View in Reaxys

99 %

With 15-crown-5, sodium iodide in toluene, Time= 24h, T= 0 - 23 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst, Solvent Werner, Thomas; Bauer, Matthias; Riahi, Abdol Majid; Schramm, Heiko; European Journal of Organic Chemistry; vol. 2014; nb. 22; (2014); p. 4876 - 4883 View in Reaxys

99 %

Stage 1: With C30H33NO2P2 in hexane, Time= 0.5h, T= -78 °C , Inert atmosphere Stage 2:Time= 1.5h, T= 20 °C , Reagent/catalyst Del Aguila-Sanchez, Miguel A.; Santos-Bastos, Neidemar M.; Ramalho-Freitas, Maria C.; Garcia Lopez, Jesus; Costa De Souza, Marcos; Camargos-Resende, Jackson A. L.; Casimiro, Maria; Alves-Romeiro, Gilberto; Iglesias, Maria Jose; Lopez Ortiz, Fernando; Dalton Transactions; vol. 43; nb. 37; (2014); p. 14079 - 14091 View in Reaxys

97 %

Stage 1: With vanadiumtetrachloride in tetrahydrofuran, hexane, Time= 1h, T= -78 °C , complexation Stage 2: in tetrahydrofuran, hexane, Time= 5h, T= 0 °C , Alkylation Kataoka, Yasutaka; Makihira, Isamu; Utsunomiya, Masaru; Tani, Kazuhide; Journal of Organic Chemistry; vol. 62; nb. 24; (1997); p. 8540 - 8543 View in Reaxys

95 %

With titanium(IV) isopropylate, 3-phenyl-N-((R)-1-phenylethyl)-2-(tosylamino)propanamide in hexane, toluene, Time= 24h, T= 0 °C , Inert atmosphere Gou, Shaohua; Ye, Zhongbin; Chang, Jing; Gou, Guangjun; Feng, Mingming; Applied Organometallic Chemistry; vol. 25; nb. 6; (2011); p. 448 - 453 View in Reaxys

92 %

With (+)-η5-(pentamethylcyclopentadienyl)-η5-(2-((2-hydroxy-2,2-diphenylethyl)oxymethyl)pyrrolyl)iron in toluene, Time= 24h, Ambient temperature Dosa, Peter I.; Ruble, J. Craig; Fu, Gregory C.; Journal of Organic Chemistry; vol. 62; nb. 3; (1997); p. 444 - 445 View in Reaxys

90 %

With ephedrine in hexane, Time= 36h, enantioselectivity; var. O-alkylated ephedrine; other p-substituted benzaldehydes, Product distribution Naeslund, Jan; Welch, Christopher J.; Tetrahedron: Asymmetry; vol. 2; nb. 11; (1991); p. 1123 - 1126 View in Reaxys

90 %

in toluene, Time= 10h, Ambient temperature, enantioselective addition; catalyst: 1,2-isopropylidene-5-deoxy-5-morpholino-η-Dxylofuranose

3/120

2018-07-03 17:12:41

Cho, Byung Tae; Kim, Namdu; Tetrahedron Letters; vol. 35; nb. 24; (1994); p. 4115 - 4118 View in Reaxys 90 %

With 5-Deoxy-1,2-O-isopropylidene-5-morpholino-η-D-xylofuranose in toluene, Time= 10h, Ambient temperature Cho, Byung Tae; Kim, Namdu; Tetrahedron Letters; vol. 35; nb. 24; (1994); p. 4115 - 4118 View in Reaxys

90 %

Stage 1: With N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)furan-2-carboxamide in hexane, toluene, T= -77 °C Stage 2: With hydrogenchloride, water in hexane, toluene Ananthi, Nallamuthu; Balakrishnan, Umesh; Vinu, Ajayan; Ariga, Katsuhiko; Velmathi, Sivan; Tetrahedron Asymmetry; vol. 20; nb. 15; (2009); p. 1731 - 1735 View in Reaxys

89 %

With titanium(IV) isopropylate, ephedrine-derived triol 13 in toluene, Time= 48h, T= 0 °C , Condensation Armstrong, Susan K.; Clunas, Scott; Synthesis; nb. 2; (2000); p. 281 - 288 View in Reaxys

88 %

Stage 1: With (R)-Me-(2,6,6-Me3-3-MeNHCH2-bicyclo[3.1.1]hept-2-yl)amine in hexane, T= 20 °C Stage 2: in hexane, toluene, T= 20 °C Szakonyi, Zsolt; Balazs, Arpad; Martinek, Tamas A.; Fueloep, Ferenc; Tetrahedron Asymmetry; vol. 17; nb. 2; (2006); p. 199 - 204 View in Reaxys

87 %

With chiral bicyclo[3.1.1]heptane-2,3-diol-based reagent in hexane, T= 20 °C Szakonyi, Zsolt; Hetenyi, Anasztazia; Fueloep, Ferenc; Tetrahedron; vol. 64; nb. 6; (2008); p. 1034 - 1039 View in Reaxys

87 %

Stage 1: With titanium(IV) isopropylate, 3,3'-bis(4-phenyl-1H-1,2,3-triazol-1-yl)-BINOL in toluene, Time= 0.5h, T= 20 - 25 °C , Inert atmosphere Stage 2: in hexane, toluene, Time= 15h, T= 20 - 25 °C , Inert atmosphere Beckendorf, Stephan; Mancheno, Olga Garcia; Synthesis (Germany); vol. 44; nb. 14; (2012); p. 2162 - 2172; Art.No: SS-2012-C0311-ST View in Reaxys

83 %

4.16. General procedure for the reaction of aldehydes withdiethylzinc in the presence of chiral catalyst General procedure: To the respective catalyst (0.1 mmol), 1 M Et2Zn in n-hexane solution (3 mL, 3 mmol) was added under an argon atmosphere at room temperature. The reaction was stirred for 25 min at room temperature, and benzaldehyde (1 mmol) was then added to the solution, with subsequent stirring at room temperature for a further 20 h. The reaction was quenched with saturated NH4Cl solution(15 mL) and the mixture was extracted with EtOAc (2 x 20 mL). The combined organic phase was washed with H2O (10 mL), dried (Na2SO4) and evaporated under vacuum. The crude secondary alcohols obtained were purified by flash column chromatography (n-hexane/EtOAc = 4/1). The ee and absolute configuration of the resulting material were determined by chiral GC, using a chiral stationary phase (Chirasil-Dex CB column) at 90 °C.33,34 Stage 1: With (1R,2S,3S,8R)-2-azidomethyl-9,9-dimethyl-3-oxa-5-azatricyclo[6.1.1.02,6]decan-4-one in hexane, Time= 0.416667h, T= 20 °C , Inert atmosphere Stage 2: in hexane, Time= 20h, T= 20 °C , Inert atmosphere, Reagent/catalyst Gonda, Tímea; Balázs, Attila; Tóth, Gábor; Fülöp, Ferenc; Szakonyi, Zsolt; Tetrahedron; vol. 73; nb. 18; (2017); p. 2638 2648 View in Reaxys

77 %

With amine-(tris-phenolate) titanium triflate in hexane, dichloromethane, Time= 6h, T= 0 °C , Inert atmosphere Bull, Steven D.; Davidson, Matthew G.; Johnson, Andrew L.; Mahon, Mary F.; Robinson, Diane E. J. E.; Chemistry - An Asian Journal; vol. 5; nb. 3; (2010); p. 612 - 620 View in Reaxys

76 %

With C36H24O8P2, titanium(IV)isopropoxide in hexane, toluene, Time= 16h, T= 20 °C , Inert atmosphere Bouhachicha; Ngo Ndimba; Roisnel; Lalli; Argouarch; New Journal of Chemistry; vol. 41; nb. 12; (2017); p. 4767 - 4770

4/120

2018-07-03 17:12:41

View in Reaxys 72 %

With (1S,2S,5R)-1-(2'-aminoethyl)-2-iso-propyl-5-methylcyclohexan-1-ol in hexane, Time= 72h Panev, Stefan; Linden, Anthony; Dimitrov, Vladimir; Tetrahedron Asymmetry; vol. 12; nb. 9; (2001); p. 1313 - 1321 View in Reaxys

68 %

With (2R,2'R)-2,2'-{benzene-1,4-diylbis[methylylidenenitrilo]}dibutan-1-ol in hexane, toluene, Time= 40h, T= 30 °C Salehi; Dabiri; Kozehgary; Journal of the Iranian Chemical Society; vol. 7; nb. 1; (2010); p. 100 - 106 View in Reaxys

67 %

With 2-methyl-1,3-dithian in toluene, Time= 24h, T= 20 - 25 °C , Addition Wilken, Joerg; Winter, Martin; Stahl, Ingfried; Martens, Juergen; Tetrahedron Asymmetry; vol. 11; nb. 5; (2000); p. 1067 1071 View in Reaxys

67 %

4.6 General procedure for the catalytic asymmetric addition of Et2Zn to aldehydes General procedure: Ligand 1c (0.188mmol) was dissolved in toluene (2mL) and Et2Zn (2M in toluene, 2.26mmol) was added in one portion after which the reaction was stirred for 45min. at ambient temperature. The mixture was then cooled to −20°C and the aldehyde (1.88mmol) was added as dissolved in toluene (2mL) into the reaction. The resulting mixture was stirred for 24h at −20°C. The reaction was quenched with saturated ammonium chloride (10mL) and extracted with ethyl acetate (3×10mL). The combined organic extracts were dried over Na2SO4 and concentrated. Purification of the crude product was carried out by micro distillation under reduced pressure. The product was subjected to HPLC by using Chiralcel OD-H column and GC by using Supelco η-Dex capillary column to determine the ee values. With (S)-3-amino-2-(hydroxy(phenyl)methyl)quinazolin-4(3H)-one in toluene, T= 0 °C , Inert atmosphere, Schlenk technique Karabuga, Semistan; Karakaya, Idris; Ulukanli, Sabri; Tetrahedron Asymmetry; vol. 25; nb. 10-11; (2014); p. 851 - 855 View in Reaxys

66 %

With titanium(IV) isopropylate, 1,1'-Dihydroxy-4,4'-diphenyl-5,5'-bipyrazolyl in toluene, Time= 7.5h, T= 0 °C Rist; Begtrup; Journal of the Chemical Society. Perkin Transactions 1; nb. 13; (2001); p. 1566 - 1568 View in Reaxys

66 %

Stage 1: With Se-(1S,2S)-2-(dimethylamino)-1-phenylpropyl 2,2-dimethylpropaneselenoate in toluene, Time= 0.5h, T= 20 °C , Inert atmosphere Stage 2: in toluene, Time= 24h, T= -20 °C , Inert atmosphere, optical yield given as percent ee, enantioselective reaction Soares, Letiére C.; Alberto, Eduardo E.; Schwab, Ricardo S.; Taube, Paulo S.; Nascimento, Vanessa; Rodrigues, Oscar E. D.; Braga, Antonio L.; Organic and Biomolecular Chemistry; vol. 10; nb. 32; (2012); p. 6595 - 6599 View in Reaxys

58 %

With cerium(III) isopropanolate in toluene, Time= 34h, T= 25 °C Fischer, Stefan; Groth, Ulrich; Jeske, Mario; Schuetz, Thorben; Synlett; nb. 11; (2002); p. 1922 - 1924 View in Reaxys

53 %

With titanium(IV) isopropylate, (1S,8S,9R)-5-(2-hydroxy-phenyl)-8,10,10-trimethyl-6-aza-tricyclo[7.1.1.0(2,7)]undeca-2(7),3,5trien-8-ol in toluene Wu, Pei-Shan; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 59; nb. 6; (2012); p. 768 - 781 View in Reaxys

50 %

With titanium(IV) isopropylate, (Sax)-O-(2'-hydroxy-[1,1'-binaphthalen]-2-yl)-O-hydrogen-2-methylphenylphosphonothioate in dichloromethane, Time= 1h, T= 0 °C , Inert atmosphere, Reagent/catalyst, Solvent, enantioselective reaction Kuwabara, Kazuma; Maekawa, Yuuki; Minoura, Mao; Murai, Toshiaki; Organic Letters; vol. 20; nb. 5; (2018); p. 1375 1379 View in Reaxys

44 %

With (R)-(4-methoxyquinolin-2-yl)(phenyl)methanol in hexane, toluene, T= 0 - 20 °C , Inert atmosphere, enantioselective reaction

5/120

2018-07-03 17:12:41

Eidamshaus, Christian; Reissig, Hans-Ulrich; Tetrahedron Asymmetry; vol. 22; nb. 16-17; (2011); p. 1644 - 1652 View in Reaxys 42 %

Stage 1: With (1R,2R)-1,2-bis(2η-bromophenyl)-ethane-1,2-diol in hexane, toluene, Time= 0.333333h, T= 20 °C , Inert atmosphere Stage 2: in hexane, toluene, Time= 24h, T= 0 °C , Inert atmosphere Gök, Yaar; Külolu, Soner; Gök, Halil Zeki; Kekec, Levent; Applied Organometallic Chemistry; vol. 28; nb. 11; (2014); p. 835 - 838 View in Reaxys

42 %

With (1R,2R)-1,2-bis(2η-bromophenyl)-ethane-1,2-diol in hexane, toluene, Time= 24h, T= 20 °C Gök, Yaşar; Küloglu, Soner; Gök, Halil Zeki; Kekecş, Levent; Journal of Pharmacy and Pharmacology; vol. 28; nb. 11; (2014); p. 835 - 838 View in Reaxys

35 %

With magnesia, (S)-1-benzyl-3-((S)-1-hydroxy-3-phenylpropan-2-yl)-5-isobutyl-4,5-dihydro-1H-imidazol-3-ium chloride, potassium tert-butylate in tetrahydrofuran, hexane, Time= 15h, T= -10 °C , Inert atmosphere, Reagent/catalyst Faraji, Laleh; Jadidi, Khosrow; Notash, Behrouz; Tetrahedron Letters; vol. 55; nb. 2; (2014); p. 346 - 350 View in Reaxys

20 %

4.5 Asymmetric ethylation of arylaldehyde with diethylzinc General procedure: Diethylzinc (1.1ml, 1M solution in hexane) was added to a stirred solution of ligand (0.033mmol) in toluene (1.0ml) under Ar at room temperature. After stirring the resulting reaction mixture at this temperature for 15min, benzaldehyde (0.05ml, 0.55mmol) was added. Stirring was continued for 24h at room temperature. At the end of this period, the reaction mixture was diluted with ethyl acetate (10ml), quenched with a saturated aqueous solution of NH4Cl (10ml), and the two layers were separated. The aqueous layer was extracted with ethyl acetate (2×10ml). The combined organic layers were dried over Na2SO4, concentrated and purified by flash column chromatography on silica gel using hexane–ethyl acetate. 1-Phenyl-1-propanol was obtained in 81percent yield (61mg, 0.446 mmol). Chiral HPLC was used to determine the ee. Other asymmetric reaction using various aldehydes and ligands were examined with the same procedure. With (R)-N-(1-phenylethyl)-2-chromonecarboxamide in hexane, toluene, Time= 24h, T= 20 °C , Inert atmosphere, enantioselective reaction Ueda, Yuki; Yagishita, Fumitoshi; Ishikawa, Hiroki; Kaji, Yuki; Baba, Nozomi; Kasashima, Yoshio; Mino, Takashi; Sakamoto, Masami; Tetrahedron; vol. 71; nb. 36; (2015); p. 6254 - 6258; Art.No: 26920 View in Reaxys

19 %

With 2,6-bis(4S-(CH2OH)-5R-(p-SMeC6H4)-2-oxazolin-2-yl)pyridine in hexane, toluene, Time= 96h, T= 0 °C , Product distribution, Further Variations: Reagents, reaction times Schinnerl, Marina; Seitz, Michael; Kaiser, Anja; Reiser, Oliver; Organic Letters; vol. 3; nb. 26; (2001); p. 4259 - 4262 View in Reaxys

11 %

Stage 1: With (1R,2R)-1,2-bis(3η-bromophenyl)-ethane-1,2-diol in hexane, dichloromethane, Time= 0.333333h, T= 20 °C , Inert atmosphere Stage 2: in hexane, dichloromethane, Time= 24h, T= 20 °C , Inert atmosphere, Reagent/catalyst, Solvent Gök, Yaşar; Kiliçarslan, Seda; Gök, Halil Zeki; Karayiğit, İlker Ümit; Chirality; (2016); p. 593 - 598 View in Reaxys

9.3 %

With racemic copolymer (copoly(1/2)) in tetrahydrofuran, Time= 24h, T= 0 °C , Schlenk technique, Inert atmosphere, Reagent/ catalyst Liu, Lijia; Long, Qing; Aoki, Toshiki; Zhang, Geng; Kaneko, Takashi; Teraguchi, Masahiro; Zhang, Chunhong; Wang, Yudan; Chirality; vol. 27; nb. 8; (2015); p. 454 - 458 View in Reaxys man zerlegt das Reaktionsprodukt mit Wasser Wagner; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 16; (1884); p. 322; Chemische Berichte; 17 Ref. <1884>, 317 View in Reaxys

6/120

2018-07-03 17:12:41

With titanium(IV) isopropylate in toluene, Time= 12h, Ambient temperature, Yield given Yoshioka, Masato; Kawakita, Takashi; Ohno, Masaji; Tetrahedron Letters; vol. 30; nb. 13; (1989); p. 1657 - 1660 View in Reaxys 70 % Chromat.

With titanium(IV) isopropylate in toluene, Time= 6h, T= -25 °C Seebach, Dieter; Plattner, Dietmar A.; Beck, Albert K.; Wang, Yan Ming; Hunziker, Daniel; Petter, Walter; Helvetica Chimica Acta; vol. 75; nb. 7; (1992); p. 2171 - 2209 View in Reaxys With (+/-)-3-exo-(dimethylamino)isoborneol, dimethyl zinc(II) in toluene, T= 40 °C , Rate constant Kitamura, Masato; Hiromasa, Oka; Noyori, Ryoji; Tetrahedron; vol. 55; nb. 12; (1999); p. 3605 - 3614 View in Reaxys With titanium(IV) isopropylate in hexane, toluene, T= 20 °C , Alkylation, addition Paquette, Leo A.; Zhou, Renjie; Journal of Organic Chemistry; vol. 64; nb. 21; (1999); p. 7929 - 7934 View in Reaxys

80 % Chromat.

With titanium(IV) isopropylate, (S)-4,4',6,6'-tetraperfluorooctyl-1,1'-binaphthyl-2,2'-diol in hexane, Time= 1h, T= 45 °C , Alkylation Tian; Kin Shing Chan; Tetrahedron Letters; vol. 41; nb. 45; (2000); p. 8813 - 8816 View in Reaxys With ((R)-(-)-thiolan-2-yl)diphenylmethanol in hexane, Time= 20h, T= 0 °C , Product distribution, Further Variations: Catalysts Shiina, Isamu; Konishi, Katsuhiko; Kuramoto, Yu-suke; Chemistry Letters; nb. 2; (2002); p. 164 - 165 View in Reaxys With (S)-diphenyl(1-methylpyrrolidin-2-yl)methanol in toluene, Time= 20h, T= 20 °C Kell, Roger J; Hodge, Philip; Nisar, Mohammad; Watson, David; Bioorganic and medicinal chemistry letters; vol. 12; nb. 14; (2002); p. 1803 - 1807 View in Reaxys With titanium(IV) isopropylate, (1S,2R,4S,1'S,2'R,4'S)-C28H44N2O6S2 (o-substituted benzene) in toluene, Time= 3h, T= 25 °C Yus, Miguel; Ramon, Diego J.; Prieto, Oscar; Tetrahedron Asymmetry; vol. 14; nb. 9; (2003); p. 1103 - 1114 View in Reaxys With [(R)-FHPC](1R,2R)-CHDA in hexane, toluene, Time= 15h, T= 25 °C Danilova, Tatyana I.; Rozenberg, Valeria I.; Starikova, Zoya A.; Braese, Stefan; Tetrahedron Asymmetry; vol. 15; nb. 2; (2004); p. 223 - 229 View in Reaxys in tetrahydrofuran, toluene, T= 50 °C , Product distribution, Further Variations: Reaction partners Roberts, William P.; Ghosh, Indranath; Jacobi, Peter A.; Canadian Journal of Chemistry; vol. 82; nb. 2; (2004); p. 279 - 284 View in Reaxys

88 % Spectr.

With (1'R,1''R,2'R,2''R)-N,N'-bis-[2-(morpholin-4-yl)cyclohexyl]pyridine-2,6-dicarboxamide, nickel diacetate in hexane, toluene, Time= 16h, T= 20 °C Gonzalez-Sabin, Javier; Gotor, Vicente; Rebolledo, Francisca; Tetrahedron Asymmetry; vol. 17; nb. 3; (2006); p. 449 - 454 View in Reaxys Stage 1: With (S)-[1,1']-binaphthalenyl-2,2'-diol, titanium(IV) isopropylate in toluene, Time= 1h, T= 20 °C Stage 2: With phenylacetylene in toluene, T= 20 °C Xu, Zhaoqing; Lin, Li; Xu, Jiangke; Yan, Wenjin; Wang, Rui; Advanced Synthesis and Catalysis; vol. 348; nb. 4-5; (2006); p. 506 - 514 View in Reaxys With titanium(IV) isopropylate in dichloromethane, Time= 5h, T= 0 °C

7/120

2018-07-03 17:12:41

Harada, Toshiro; Kanda, Kousou; Organic Letters; vol. 8; nb. 17; (2006); p. 3817 - 3819 View in Reaxys Stage 1: With Al-MTS, T= 0 °C , Addition Stage 2: With hydrogenchloride, Hydrolysis, Further stages. Abramson; Lasperas; Galarneau; Desplantier-Giscard; Brunel; Chemical Communications; nb. 18; (2000); p. 1773 - 1774 View in Reaxys With (SpS)-[2.2]paracyclophane N,O-ligand in hexane, toluene, Time= 12h, T= 0 °C , Product distribution, Further Variations: Catalysts Dahmen, Stefan; Braese, Stefan; Chemical Communications; nb. 1; (2002); p. 26 - 27 View in Reaxys With (-)-3-exo-(N-morpholino)isoborneol in toluene, T= 25 °C , Alkylation, Kinetics Rosner, Thorsten; Sears, Patrick J.; Nugent, William A.; Blackmond, Donna G.; Organic Letters; vol. 2; nb. 16; (2000); p. 2511 - 2513 View in Reaxys With polymer-supported chiral aziridine-based reagent in toluene, T= 0 - 20 °C Page, Philip C. Bulman; Allin, Steven M.; Dilly, Suzanne J.; Buckley, Benjamin R.; Synthetic Communications; vol. 37; nb. 12; (2007); p. 2019 - 2030 View in Reaxys Stage 1: With (+)-methyl [(2S,3R)-4-methyl-2,3-bis(p-tolylsulfonylamino)]pentanoate in hexane, dichloromethane, Time= 0.166667h, T= 20 °C Stage 2: With titanium(IV) isopropylate in hexane, dichloromethane, Time= 0.5h, T= 20 °C Stage 3:Further stages Viso, Alma; Fernandez de la Pradilla, Roberto; Urena, Mercedes; Tetrahedron; vol. 65; nb. 18; (2009); p. 3757 - 3766 View in Reaxys 48 %Chromat.

Stage 1: With (1S,5S,7R)-(3-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]oct-7-yl)methanol in hexane, toluene, Time= 0.5h Stage 2: in hexane, toluene, Time= 18h, T= 20 °C Stage 3: With hydrogenchloride, water in hexane, toluene Scarpi, Dina; Occhiato, Ernesto G.; Guarna, Antonio; Tetrahedron Asymmetry; vol. 20; nb. 3; (2009); p. 340 - 350 View in Reaxys

12 %Chromat.

Stage 1: With N,N'-[(2η-hydroxy)pinan-3-ylidene]ethane-1,2-diamine in hexane, toluene, Time= 0.0833333h Stage 2: in hexane, toluene, Time= 24h, T= -10 °C Stage 3: With ammonium chloride in hexane, water, toluene Salehi, Peyman; Dabiri, Minoo; Kozehgary, Gholamreza; Baghbanzadeh, Mostafa; Tetrahedron Asymmetry; vol. 20; nb. 22; (2009); p. 2609 - 2611 View in Reaxys With titanium(IV) isopropylate, C52H34O10 (4-)*2Cu(2+) in toluene, Inert atmosphere Ma, Liqing; Falkowski, Joseph M.; Abney, Carter; Lin, Wenbin; Nature Chemistry; vol. 2; nb. 10; (2010); p. 838 - 846 View in Reaxys 4.6.5. Asymmetric addition of diethylzinc to benzaldehyde in the presence of ligands 11-14 To a solution of 11-14 (2.5 mol percent) in anhydrous benzene (5 mL) was added diethylzinc (3 mmol, 1.0 M solution in hexane) under argon and the reaction was stirred for 10 min at room temperature. The solution was cooled at 0 °C, and benzaldehyde (1 mmol) was added slowly. After being stirred for 2 h at 0 °C, and 12 h at room temperature, the reaction was quenched with 1 M aqueous HCl (20 mL). The mixture was extracted with Et2O, and the combined organic layer dried over Na2SO4. After removal of the solvent under reduced pressure, the residue was purified by column chromatography (hexane/ethyl acetate, 10:1) to afford 1-phenyl-1-propanol (15) as a colorless liquid in 43-74percent yield. The ee values of 15 range from 3 to 7percent. Stage 1: With 4-oxa-1,7-dithia[7](6,6')-2,2'-bis(cyclopenta[c]pyridine)cyclophane sulfoxide in hexane, benzene, Time= 0.166667h, T= 20 °C , Inert atmosphere Stage 2: in hexane, benzene, Time= 14h, T= 0 - 20 °C , Inert atmosphere

8/120

2018-07-03 17:12:41

Stage 3: With hydrogenchloride in hexane, water, benzene, T= 20 °C Lawecka, Justyna; Karczmarzyk, Zbigniew; Wolinska, Ewa; Olender, Ewa; Branowska, Danuta; Rykowski, Andrzej; Tetrahedron; vol. 67; nb. 17; (2011); p. 3098 - 3104 View in Reaxys With [(Cu4I4)3Zn8(μ4-O)(INA)12(H2O)4]·2(CH3COO)·x(solvate) in hexane, Time= 8h, T= 0 °C , Sealed tube, Schlenk technique, Inert atmosphere, Catalytic behavior, Reagent/catalyst, Temperature, Time Tan, Yan-Xi; He, Yan-Ping; Zhang, Jian; Chemistry of Materials; vol. 24; nb. 24; (2012); p. 4711 - 4716 View in Reaxys General procedure for testing of asymmetric induction of the prepared diols. General procedure: The Diol (0,15eq) was mixed with an equimolar quantity of titanium isopropoxide in toluene solution. The mixture was stirred for 20h at room temperature and then concentrated to dryness. The residue was re-evaporated with toluene to remove traces of 2-propanol. The prepared solid was dissolved in toluene, titanium isopropoxide (1eq) was added, and the solution was cooled to -40ºC. Then benzaldehyde (1eq) was added followed by a dropwise addition of diethylzink (1.2eq). The yellowish solution was stirred for 24h at -40ºC. The conversion and enantiomeric excess was monitored by GC. With titanium(IV) isopropylate, η-conidendreic acid dimethyl ester dimethyl ether in toluene, Time= 24h, T= -40 °C Brusentsev, Yury; Sandberg, Thomas; Hotokka, Matti; Sjoeholm, Rainer; Eklund, Patrik; Tetrahedron Letters; vol. 54; nb. 9; (2013); p. 1112 - 1115 View in Reaxys With [In(5-aminoisophthalate)2]·(tetraphenylphosphonium)·4H2O in hexane, Time= 24h, T= 25 °C , Inert atmosphere, Schlenk technique, Time Chen, Yan-Fei; Ma, Yun-Cui; Chen, Shu-Mei; Crystal Growth and Design; vol. 13; nb. 10; (2013); p. 4154 - 4157 View in Reaxys Activated catalyst 1 (24 mg) dried under vacuum at 200 °C for 2 h was placed ina 25 ml Schlenk flask and then vacuumized for 10 min. The n-hexane(2 ml) solvent was added via syringe under nitrogen. After themixture stirred for 30 min, benzaldehyde (0.25 ml) and diethylzinc(in n-hexane, 0.75 ml) were added. The new mixture was stirredunder nitrogen at 25 °C. In a certain time interval, a small amount ofsolution was taken out and quenched with saturated NH4Cl solutionand ethyl acetate. The composition of the reaction mixture was determinedby gas chromatograph (GC) analysis (Fig. S3). We can observeracemic phenylpropanol (R- and S-) with the same yield in the products.After 24 h, the reaction led to a 48.6percent conversion of benzaldehydeand it is basically stopped (Fig. 2b). With [CdMg(1,2,4,5-benzenetetracarboxylate)(DMF)(H2O)3] in hexane, T= 25 °C , Schlenk technique, Inert atmosphere Chen, Yan-Fei; Ma, Yun-Cui; Zhang, Hua-Bin; Chen, Shu-Mei; Inorganic Chemistry Communications; vol. 43; (2014); p. 27 - 30 View in Reaxys 4.6. Addition of diethylzinc on aryldehydes General procedure: 4.6.1. General procedure. In an oven-dried 5 mL flask under argon atmosphere, the ligand (0.1 equiv, 0.1 mmol) was dissolved in 2.5 mL of anhydrous toluene and diethylzinc (1.5 M in toluene, 2 mmol) was added dropwise. The solution was cooled to 0 °C for 15 min and the aldehyde (1 equiv, 1 mmol) was added as a single portion. The mixture was then warmed to room temperature and stirred for 48 h before 1 N HCl was added. The resulting alcohol was extracted with three portions of EtOAc. The organic layers were then combined, washed with brine, dried with Na2SO4, and concentrated in vacuo, giving an oil from which conversion and enantiomeric excess were determined by GC. In one case involving benzaldehyde and ligand 23a (Table 3, entry 1), the crude product was purified by flash chromatography (5:95 EtOAc/hexanes), giving 81percent isolated yield of 32. Commercially available (S)-1-phenyl-1-propanol was used for enantiomer identification on the GC chromatograms. Products 33 and 35, as control experiments, were also prepared from Grignard addition reactions and analyzed by GC. Stage 1: With (2R,5S)-2,5-dibenzyl-1,4-dimethylpiperazine in toluene, Time= 0.25h, T= 0 °C , Inert atmosphere Stage 2: in toluene, Time= 48h, T= 0 - 20 °C , Inert atmosphere, Reagent/catalyst Bérubé, Christopher; Cardinal, Sébastien; Boudreault, Pierre-Luc; Barbeau, Xavier; Delcey, Nicolas; Giguère, Martin; Gleeton, Dave; Voyer, Normand; Tetrahedron; vol. 71; nb. 42; (2015); p. 8077 - 8084 View in Reaxys Schlenk technique

9/120

2018-07-03 17:12:41

Escorihuela, Jorge; Burguete, M. Isabel; Ujaque, Gregori; Lledós, Agustí; Luis, Santiago V.; Organic and Biomolecular Chemistry; vol. 14; nb. 47; (2016); p. 11125 - 11136 View in Reaxys With Cu(2+)*2C6H2O4S(2-)*2C3H7NO*Ca(2+) in hexane, T= 25 °C , Schlenk technique, Inert atmosphere Liu, Qi-Feng; Liu, Wei; Cao, Yi-Po; Dong, Yan-Li; Liu, Hui-Min; Inorganic and Nano-Metal Chemistry; vol. 47; nb. 1; (2017); p. 153 - 157 View in Reaxys O

Rx-ID: 724547 View in Reaxys 3/280 Yield 100 %

Conditions & References With potassium hydride, ditriptylethylborane in tetrahydrofuran, Time= 0.0833333h Smith, Keith; Pelter, Andrew; Norbury, Andrew; Tetrahedron Letters; vol. 32; nb. 43; (1991); p. 6243 - 6246 View in Reaxys

100 %

With zirconium dioxide hydrate, isopropyl alcohol, Time= 0.5h, T= 130 °C , Meerwein-Ponndorf-Verley Reduction Battilocchio, Claudio; Hawkins, Joel M.; Ley, Steven V.; Organic Letters; vol. 15; nb. 9; (2013); p. 2278 - 2281 View in Reaxys

100 %

With hydrogen in methanol, Time= 24h, T= 40 °C , chemoselective reaction Ichikawa, Tomohiro; Netsu, Moeko; Mizuno, Masahiro; Mizusaki, Tomoteru; Takagi, Yukio; Sawama, Yoshinari; Monguchi, Yasunari; Sajiki, Hironao; Advanced Synthesis and Catalysis; vol. 359; nb. 13; (2017); p. 2269 - 2279 View in Reaxys

99 %

Stage 1: With Trimethyl borate, dimethylsulfide borane complex, (-)-3-amino-6,6-dimethyl-2-hydroxy-bicyclo[3.1.1]heptane in tetrahydrofuran, T= 20 °C Stage 2: With methanol in tetrahydrofuran Krzeminski, Marek P.; Wojtczak, Andrzej; Tetrahedron Letters; vol. 46; nb. 48; (2005); p. 8299 - 8302 View in Reaxys

99.0 %

With sodium tetrahydroborate in ethanol, Time= 5h Wiles, Charlotte; Watts, Paul; Haswell, Stephen J.; Tetrahedron Letters; vol. 47; nb. 30; (2006); p. 5261 - 5264 View in Reaxys

99 %

With C53H46ClN3P2Ru, potassium isopropoxide, isopropyl alcohol, Time= 0.0166667h, T= 82 °C , p= 750.075Torr Du, Wangming; Wang, Liandi; Wu, Ping; Yu, Zhengkun; Chemistry - A European Journal; vol. 18; nb. 37; (2012); p. 11550 - 11554 View in Reaxys

99 %

With C38H52ClIrN2O2, potassium hydroxide in isopropyl alcohol, Time= 2h, T= 85 °C , Inert atmosphere Guelcemal, Derya; Goekce, Aytac Guerhan; Guelcemal, Sueleyman; Cetinkaya, Bekir; RSC Advances; vol. 4; nb. 50; (2014); p. 26222 - 26230 View in Reaxys

99 %

Stage 1: With C107H90Cl2N10P4Ru2 (2+)*2Cl(1-) in isopropyl alcohol, Time= 0.166667h, T= 82 °C , Inert atmosphere Stage 2: With potassium isopropoxide in isopropyl alcohol, Time= 2h, Inert atmosphere, Catalytic behavior Chai, Huining; Liu, Tingting; Zheng, Daoyuan; Yu, Zhengkun; Organometallics; vol. 36; nb. 21; (2017); p. 4268 - 4277 View in Reaxys

98 %

With hydrogen, Ni-Gr2 in methanol, Time= 15h, T= 90 °C , p= 22800Torr Savoia, Diego; Tagliavini, Emilio; Trombini, Claudio; Umani-Ronchi, Achille; Journal of Organic Chemistry; vol. 46; (1981); p. 5344 - 5348

10/120

2018-07-03 17:12:41

View in Reaxys 98 %

With bis<4-(R)-phenyl-oxazolin-2-yl-ethyl>amine*<RuCl2(C6H6)>2, sodium isopropylate in isopropyl alcohol, toluene, Time= 22h, T= 23 °C Jiang, Yutong; Jiang, Qiongzhong; Zhu, Guoxin; Zhang, Xumu; Tetrahedron Letters; vol. 38; nb. 37; (1997); p. 6565 - 6568 View in Reaxys

98 %

2.2. Typical catalytic hydrogenation General procedure: In a glove box, an autoclave was charged with the desired ketone (0.5 mmol), toluene (2 mL), Mn complex 1 (14 mg, 5 molpercent) followed by t-BuOK (5.6 mg, 10 molpercent), in this order. The autoclave is then closed and charged with H2 (50 bar). With [(N,Nη-bis(diisopropylphosphino)-2,6-diaminopyridine)Mn(CO)3][Br], potassium tert-butylate, hydrogen in toluene, Time= 38h, T= 130 °C , p= 37503.8Torr , Glovebox, Autoclave, Time Bruneau-Voisine, Antoine; Wang, Ding; Roisnel, Thierry; Darcel, Christophe; Sortais, Jean-Baptiste; Catalysis Communications; vol. 92; (2017); p. 1 - 4 View in Reaxys

97 %

Stage 1: With triphenylphosphine-copper(I) hydride hexamer Stage 2: Lipshutz, Bruce H.; Chrisman, Will; Noson, Kevin; Journal of Organometallic Chemistry; vol. 624; nb. 1-2; (2001); p. 367 371 View in Reaxys

97 %

With formic acid, triethylamine, Pd(0)EnCat in ethyl acetate, Time= 22h, T= 24 °C Yu, Jin-Quan; Wu, Hai-Chen; Ramarao, Chandrashekar; Spencer, Jonathan B; Ley, Steven V; Chemical communications (Cambridge, England); nb. 6; (2003); p. 678 - 679 View in Reaxys

97 %

With isopropyl alcohol, Time= 24h, T= 85 °C , Inert atmosphere Shimura, Katsuya; Shimizu, Ken-Ichi; Green Chemistry; vol. 14; nb. 11; (2012); p. 2983 - 2985 View in Reaxys

97 %

With RuH(η2-H2BH2){9,9-dimethyl-4,5-bis(diisopropylphosphino)-xanthene} in isopropyl alcohol, T= 80 °C , Inert atmosphere, Schlenk technique Alos, Joaquin; Bolano, Tamara; Esteruelas, Miguel A.; Olivan, Montserrat; Onate, Enrique; Valencia, Marta; Inorganic Chemistry; vol. 53; nb. 2; (2014); p. 1195 - 1209 View in Reaxys

96 %

With polymethylhydrosiloxane, copper(II) acetate (1,3-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene) in toluene, Time= 0.3h Yun, Jaesook; Kim, Daesung; Yun, Hoseop; Chemical Communications; nb. 41; (2005); p. 5181 - 5183 View in Reaxys

96 %

Stage 1: With Triethoxysilane, diethylzinc, N,N-dimethyl-N'-(4-tert-butylphenyl)formamidine in tetrahydrofuran, hexane, T= 20 - 60 °C , Inert atmosphere Stage 2: With sodium hydroxide in tetrahydrofuran, hexane, water, Time= 1h, T= 0 °C Enthaler, Stephan; Schroeder, Kristin; Inoue, Shigeyoshi; Eckhardt, Bjoern; Junge, Kathrin; Beller, Matthias; Driess, Matthias; European Journal of Organic Chemistry; nb. 25; (2010); p. 4893 - 4901 View in Reaxys

96 %

2.4. General procedure for hydrogenation under hydrogen pressure General procedure: The stainless steel autoclave was charged with the previously prepared aqueous suspension of Col-Ni-CMC Nps (8 mL, from 40 mg of NiCl2·6H2O and 10 mL, from 50 mg of NiCl2·6H2O) for ketone hydrogenation. The appropriate nitro-aromatic ([substrate]/[metal] = 100) in 2 mL of MeOH, was added into the autoclave and dihydrogen was admitted to the system at constant pressure (10 to 40 bars). The mixture was stirred until the reaction was finished. Samples for gas chromatographic analysis were removed from time to time. The residue was extracted with diethyl ether (3 × 25 mL). The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure Pure products were obtained by column chromatography over silica gel using hexane/ethyl acetate as eluent.

11/120

2018-07-03 17:12:41

With hydrogen in water, Time= 24h, T= 20 °C , p= 30003Torr , Autoclave Harrad, Mohamed Anouar; Boualy, Brahim; El Firdoussi, Larbi; Mehdi, Ahmad; Santi, Claudio; Giovagnoli, Stefano; Nocchetti, Morena; Ait Ali, Mustapha; Catalysis Communications; vol. 32; (2013); p. 92 - 100 View in Reaxys 96 %

With C37H30Cl2N3OPRu, sodium isopropylate, isopropyl alcohol, Time= 0.166667h, Reflux Sahin, Irfan; Emir, Sedat; Ispir, Esin; Karakaya, Idris; Gumus, Selcuk; Ulusoy, Mahmut; Karabuga, Semistan; Catalysis Communications; vol. 85; (2016); p. 30 - 33 View in Reaxys

95 %

With sodium tetrahydroborate in ethanol, Time= 0.5h, Ambient temperature Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro; Journal of Organic Chemistry; vol. 60; nb. 8; (1995); p. 2430 2435 View in Reaxys

95 %

With diphenylsilane, hydrogen, [(o-dppbe)Rh(COD)]OTf in tetrahydrofuran, Time= 1h, T= 20 °C , p= 15001.2Torr Comte, Virginie; Balan, Cedric; Le Gendre, Pierre; Moise, Claude; Chemical Communications; nb. 7; (2007); p. 713 - 715 View in Reaxys

95 %

With polymeric xylylene-ionene borohydride in isopropyl alcohol, Time= 1.2h, Heating Lakouraj, Moslem M.; Tajbakhsh, Mahmood; Mahalli, Majid S.; Monatshefte fur Chemie; vol. 139; nb. 2; (2008); p. 117 123 View in Reaxys

95 %

Stage 1: With triethyl borane, sodium methylate in tetrahydrofuran, diethyl ether, Time= 4h, T= 20 °C , Inert atmosphere Stage 2: With sodium hydroxide in tetrahydrofuran, methanol, diethyl ether, Time= 2h, T= 20 °C Peng, Dongjie; Zhang, Mintao; Huang, Zheng; Chemistry - A European Journal; vol. 21; nb. 42; (2015); p. 14737 - 14741 View in Reaxys

95%

With [Re(NH{CH2CH2P(iPr2)}2)(CO)3]Br, potassium tert-butylate, hydrogen in toluene, Time= 24h, T= 70 °C , p= 22502.3Torr , Inert atmosphere, Glovebox, Autoclave Wei, Duo; Roisnel, Thierry; Darcel, Christophe; Clot, Eric; Sortais, Jean-Baptiste; ChemCatChem; vol. 9; nb. 1; (2017); p. 80 - 83 View in Reaxys

93 %

With trimethoxysilane, dilithium pinacolate in diethyl ether, hexane, Time= 15h, Ambient temperature Hosomi, Akira; Hayashida, Hisashi; Kohra, Shinya; Tominaga, Yoshinori; Journal of the Chemical Society, Chemical Communications; nb. 18; (1986); p. 1411 - 1412 View in Reaxys

93 %

With C37H28Cl2N5PRu, isopropyl alcohol, sodium hydroxide, Time= 0.00277778h, T= 82 °C , p= 750.075Torr , Inert atmosphere, Catalytic behavior Li, Ke; Niu, Jun-Long; Yang, Ming-Ze; Li, Zhen; Wu, Li-Yuan; Hao, Xin-Qi; Song, Mao-Ping; Organometallics; vol. 34; nb. 7; (2015); p. 1170 - 1176 View in Reaxys

92 %

With ammonium formate, Raney Ni W-2 in methanol, Time= 3h, Ambient temperature Chen; Zhang; Yuan; Synthetic Communications; vol. 21; nb. 1; (1991); p. 107 - 109 View in Reaxys

92 %

Stage 1: With iron(II) acetate, tricyclohexylphosphine in tetrahydrofuran, T= 65 °C , Inert atmosphere Stage 2: in tetrahydrofuran, T= 65 °C , Inert atmosphere Stage 3: With water, sodium hydroxide in tetrahydrofuran, methanol, T= 0 - 20 °C , Inert atmosphere Addis, Daniele; Shaikh, Nadim; Zhou, Shaolin; Das, Shoubhik; Junge, Kathrin; Beller, Matthius; Chemistry - An Asian Journal; vol. 5; nb. 7; (2010); p. 1687 - 1691

12/120

2018-07-03 17:12:41

View in Reaxys 92 %

With hydrogen, T= 80 °C , p= 150015Torr Upadhyay, Praveenkumar; Srivastava, Vivek; Letters in Organic Chemistry; vol. 12; nb. 8; (2015); p. 528 - 533 View in Reaxys

92 %

With silatrane, potassium tert-butylate in tetrahydrofuran, N,N-dimethyl-formamide, Time= 0.5h, T= 20 °C Varjosaari, Sami E.; Skrypai, Vladislav; Suating, Paolo; Hurley, Joseph J. M.; Gilbert, Thomas M.; Adler, Marc J.; European Journal of Organic Chemistry; vol. 2017; nb. 2; (2017); p. 229 - 232 View in Reaxys

92 %

With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O), isopropyl alcohol in water, Time= 6h, T= 82 °C , Inert atmosphere, Schlenk technique, chemoselective reaction Wang, Rongzhou; Tang, Yawen; Xu, Meng; Meng, Chong; Li, Feng; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 2274 - 2281 View in Reaxys

92 %

With Mn(CO)3Br(k2P,N-Ph2PN(H)Py), hydrogen, potassium hexamethylsilazane in toluene, Time= 20h, T= 50 °C , p= 37503.8Torr , Glovebox, Autoclave, Inert atmosphere Wei, Duo; Bruneau-Voisine, Antoine; Chauvin, Téo; Dorcet, Vincent; Roisnel, Thierry; Valyaev, Dmitry A.; Lugan, Noël; Sortais, Jean-Baptiste; Advanced Synthesis and Catalysis; vol. 360; nb. 4; (2018); p. 676 - 681 View in Reaxys

91 %

With isopropyl alcohol, lithium tert-butoxide, Time= 0.5h, T= 180 °C Sedelmeier, Joerg; Ley, Steven V.; Baxendale, Ian R.; Green Chemistry; vol. 11; nb. 5; (2009); p. 683 - 685 View in Reaxys

91 %

Stage 1: With C39H46ClCuN2, phenylsilane, potassium tert-butylate in tetrahydrofuran, Time= 0.333333h, T= 20 °C , Schlenk technique, Inert atmosphere, Glovebox Stage 2: With water, sodium hydroxide in tetrahydrofuran, methanol, Time= 1h, Schlenk technique, Glovebox, Reagent/catalyst, chemoselective reaction Roy, Sudipta Raha; Sau, Samaresh Chandra; Mandal, Swadhin K.; Journal of Organic Chemistry; vol. 79; nb. 19; (2014); p. 9150 - 9160 View in Reaxys

91 %

2.1. Representative procedure for transfer hydrogenation reaction ofacetophenone General procedure: To a solution of acetophenone (58 μL, 0.5 mmol) in 2-propanol (0.5 mL) was added a stock solution of manganese pentacarbonyl bromide (0.5 mL, 0.005 mol·L−1; 2.7 mg, 0.010 mmol, in 2 mL 2-propanol)followed, in this order, by a stock solution of ethylenediamine (0.5 mL,0.005 mol·L−1; 1.0 μL, 0.0125 mmol, in 2.5 mL 2-propanol) and tBuOK (0.5 mL, 0.010 mol·L−1; 2.4 mg, 0.020 mmol, in 2 mL 2-propanol). The reaction mixture was stirred for 3 h at 80 °C in an oil bath. The solution was then filtered through a small pad of silica (2 cm in a Pasteur pip-ette). The silica was washed with ethyl acetate. The filtrate was evaporated and the conversion was determined by 1H NMR. The crude residue was then puried by column chromatography (SiO 2 , mixture of petroleum ether/ethyl acetate or dietyl ether as eluent. Enantiomeric excesses were determined by GC analyses performedon GC-2014 (Shimadzu) 2010 apparatus equipped with Supelco beta-DEX 120 column (30 m × 0.25 mm). The determination of the absoluteconguration was done by comparison with (S)-alcohol obtained bykinetic resolution of racemic alcohols with Novozym 435 (CandidaAntarctica Lipase B) and by comparison of the retention times with the literature [32–34]. With bromopentacarbonylmanganese(I), potassium tert-butylate, ethylenediamine in isopropyl alcohol, Time= 3h, T= 80 °C Wang, Ding; Bruneau-Voisine, Antoine; Sortais, Jean-Baptiste; Catalysis Communications; vol. 105; (2018); p. 31 - 36 View in Reaxys

90 %

Stage 1: With 2,6-xylenol, Triethoxysilane, diethylzinc in tetrahydrofuran, hexane, Time= 0.5h, T= 60 °C , Inert atmosphere Stage 2: With sodium hydroxide in tetrahydrofuran, methanol, hexane, water, Time= 1h, T= 0 °C Enthaler, Stephan; Eckhardt, Bjoern; Inoue, Shigeyoshi; Irran, Elisabeth; Driess, Matthias; Chemistry - An Asian Journal; vol. 5; nb. 9; (2010); p. 2027 - 2035 View in Reaxys

13/120

2018-07-03 17:12:41

90 %

General procedure for reduction of ketones by NHC-BH3 9a-r General procedure: To a solution of ketone (0.25 mmol) in DCM (1 mL) was added NHC-BH3 4 (24-27 mg, 0.2-0.25 mmol) and anhydrous FeCl3 (0.125-0.25 mmol) at room temperature, the mixture was stirred for 30 min-1 h. The residue was dried in vacuo and purified by flash column chromatography (silica gel) to give the corresponding alcohols 9a-r. With iron(III) chloride, C6H13BN2 in dichloromethane, T= 20 °C Wang, Ming-Hui; Chen, Ling-Yan; Tetrahedron Letters; vol. 58; nb. 8; (2017); p. 732 - 735 View in Reaxys

89 %

With potassium tert-butylate, ytterbium(III) triflate, RhCl(PPh3)3 in isopropyl alcohol, Time= 2h, T= 35 °C , Product distribution, Further Variations: Reagents, Catalysts, catalyst additive ratio Matsunaga, Hirofumi; Yoshioka, Naoko; Kunieda, Takehisa; Tetrahedron Letters; vol. 42; nb. 50; (2001); p. 8857 - 8859 View in Reaxys

89 %

With isopropyl alcohol, sodium hydroxide, Time= 0.25h, T= 120 - 130 °C , Microwave irradiation Yoshida, Kenta; Gonzalez-Arellano, Camino; Luque, Rafael; Gai, Pratibha L.; Applied Catalysis A: General; vol. 379; nb. 1-2; (2010); p. 38 - 44 View in Reaxys

89 %

With water, 1,8-diazabicyclo[5.4.0]undec-7-ene, bis(pinacol)diborane, Time= 10h, T= 60 °C , Sealed tube, chemoselective reaction Xuan, Qingqing; Zhao, Cong; Song, Qiuling; Organic and Biomolecular Chemistry; vol. 15; nb. 24; (2017); p. 5140 - 5144 View in Reaxys

89 %

With [Cu(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)](PF6), [Co(OTf) (Py2 Tstacn)](OTf), water, triethylamine in acetonitrile, Time= 5h, T= 30 °C , Irradiation, Inert atmosphere Call, Arnau; Casadevall, Carla; Acuña-Parés, Ferran; Casitas, Alicia; Lloret-Fillol, Julio; Chemical Science; vol. 8; nb. 7; (2017); p. 4739 - 4749 View in Reaxys

88 %

With lithium aluminium tetrahydride in tetrahydrofuran, benzene, magnetic field B0 1.2 Zadel, Guido; Eisenbraun, Catja; Wolff, Gerd-Joachim; Breitmaier, Eberhard; Angewandte Chemie; vol. 106; nb. 4; (1994); p. 460 - 463 View in Reaxys

88 %

With Butane-1,4-diol, potassium tert-butylate, carbonyl(dihydrido)tris(triphenylphosphine)ruthenium(II) in tetrahydrofuran, Time= 48h, Heating Maytum, Hannah C.; Tavassoli, Bahareh; Williams, Jonathan M.J.; Organic Letters; vol. 9; nb. 21; (2007); p. 4387 - 4389 View in Reaxys

88 %

With [RuH2(CO)(PPh3)3], Butane-1,4-diol, potassium tert-butylate, bis(2-diphenylphosphinophenyl)ether in toluene, Time= 48h, Inert atmosphere, Reflux Maytum, Hannah C.; Francos, Javier; Whatrup, David J.; Williams, Jonathan M. J.; Chemistry - An Asian Journal; vol. 5; nb. 3; (2010); p. 538 - 542 View in Reaxys

87 %

Stage 1: With 2,5,6,7-tetrahydro-2-phenyl-3H-pyrrolo[2,1-c]-1,2,4-triazol-3-ylidenium chloride, diphenylsilane, sodium hydride in N,N-dimethyl-formamide, mineral oil, Time= 5h, T= 20 °C Stage 2: With tetrabutyl ammonium fluoride in tetrahydrofuran, N,N-dimethyl-formamide, Time= 0.5h Zhao, Qiwu; Curran, Dennis P.; Malacria, Max; Fensterbank, Louis; Goddard, Jean-Philippe; Lacote, Emmanuel; Synlett; nb. 3; (2012); p. 433 - 437 View in Reaxys

87 %

Stage 1: With cyclopentadienyl iron(II) dicarbonyl dimer, diethoxymethylane, Time= 24h, T= 100 °C Stage 2: With water, sodium hydroxide in methanol

14/120

2018-07-03 17:12:41

Jung, Thais Cordeiro; Argouarch, Gilles; Van De Weghe, Pierre; Catalysis Communications; vol. 78; (2016); p. 52 - 54 View in Reaxys 85 %

Representative procedure for metal-catalysed transfer hydrogenation General procedure: To an oven dried, argon purged, ampoule containing [Ru(p-cymene)Cl2]2 (15.3 mg, 0.05 mmol, 2.5 molpercent), substrate (1 mmol) and dry thf (to make a total of 3 mL), a solution of dimethylamine borane in thf was added. The ampoule was sealed and heated at 70 °C for 24 hours then cooled to room temperature; Method A - The reaction mixture was diluted with CH2Cl2 (30 mL) and passed through a short pad of silica followed by diethyl ether (100 mL). The solvents were concentrated in vacuo to afford the crude product. With [RhCl2(p-cymene)]2, dimethylamine borane in tetrahydrofuran, Time= 24h, T= 70 °C , Inert atmosphere, Sealed ampoule Nixon, Tracy D.; Whittlesey, Michael K.; Williams, Jonathan M.J.; Tetrahedron Letters; vol. 52; nb. 49; (2011); p. 6652 6654 View in Reaxys

84 %

With formic acid, triethylamine in ethyl acetate, Time= 24h, T= 25 °C , Inert atmosphere Erathodiyil, Nandanan; Ooi, Samuel; Seayad, Abdul M.; Han, Yu; Lee, Su Seong; Ying, Jackie Y.; Chemistry - A European Journal; vol. 14; nb. 10; (2008); p. 3118 - 3125 View in Reaxys

84 %

4 :General Procedure for Transfer Hydrogenation of KetonesAn oven-dried reaction vial was charged with ketone (1 mmol), formic acid/triethylamine mixture (1:1) or ammonium formate (5 mmol), catalyst (10 mol percent of 5percent Pd/Urea-MCF) and ethylacetate or water (5 ml) under argon. The resulting reaction mixture was stirred at room temperature for 24 h, and the progress of the reaction was monitored by GC. After completion of the reaction, the mixture was filtered through a sintered glass funnel, washed with ethylacetate (5.x.5 ml), and dried under vacuum. The catalyst was recycled 10 times. With formic acid, triethylamine, Pd/urea-MCF catalyst with Pd nanoclusters of 2-3 nm in ethyl acetate, Time= 24h, T= 25 °C , Inert atmosphere, Product distribution / selectivity Patent; Agency for Science ,Technology and Research; US2010/113832; (2010); (A1) English View in Reaxys

84 %

With formic acid, triethylamine in ethyl acetate, Time= 24h, T= 25 °C , Inert atmosphere Lee, Su Seong; Riduan, Siti Nurhanna; Erathodiyil, Nandanan; Lim, Jaehong; Cheong, Jian Liang; Cha, Junhoe; Han, Yu; Ying, Jackie Y.; Chemistry - A European Journal; vol. 18; nb. 24; (2012); p. 7394 - 7403 View in Reaxys

84 %

With C9H8BrMnN2O3, potassium tert-butylate in isopropyl alcohol, Time= 16h, T= 30 °C , Inert atmosphere, Schlenk technique, Glovebox Bruneau-Voisine, Antoine; Wang, Ding; Dorcet, Vincent; Roisnel, Thierry; Darcel, Christophe; Sortais, Jean-Baptiste; Organic Letters; vol. 19; nb. 13; (2017); p. 3656 - 3659 View in Reaxys

83 %

Stage 1: With diphenylsilane, bis-N-heterocyclic carbene rhodium(III) in toluene, Time= 48h, T= 20 °C Stage 2: With hydrogenchloride, methanol in toluene, T= 20 °C , Further stages. Chen, Tao; Liu, Xu-Guang; Shi, Min; Tetrahedron; vol. 63; nb. 23; (2007); p. 4874 - 4880 View in Reaxys

83 %

Stage 1: With n-butyllithium, iron(II) acetate, 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride in tetrahydrofuran, hexane, T= 65 °C , Inert atmosphere Stage 2: With sodium hydroxide in tetrahydrofuran, methanol, hexane, water, Time= 3h, T= 20 °C , Inert atmosphere Buitrago, Elina; Zani, Lorenzo; Adolfsson, Hans; Applied Organometallic Chemistry; vol. 25; nb. 10; (2011); p. 748 - 752 View in Reaxys

81 %

With C33H34ClIrNS(1+)*F6P(1-) in isopropyl alcohol, Time= 6h, T= 80 °C , Reagent/catalyst Dubey, Pooja; Gupta, Sonu; Singh, Ajai K.; Dalton Transactions; vol. 47; nb. 11; (2018); p. 3764 - 3774 View in Reaxys

15/120

2018-07-03 17:12:41

80 %

With ammonium formate, 10 wt. % palladium on activated carbon in methanol, Heating, other aromatic aldehydes and ketones; var. solvents and temp., Product distribution, Mechanism Ram; Spicer; Synthetic Communications; vol. 22; nb. 18; (1992); p. 2673 - 2681 View in Reaxys

80 %

With potassium hydroxide, 18-crown-6 ether, isopropyl alcohol, chloro(1,5-cyclooctadiene)rhodium(I) dimer, (2,6-bis[(4S)-(-)isopropyl-2-oxazolin-2-yl]pyridine), Time= 10h, T= 85 °C Iovel'; Rubina; Popelis; Gaukhman; Lukevits; Chemistry of Heterocyclic Compounds; vol. 32; nb. 3; (1996); p. 294 - 307 View in Reaxys

80 %

4.2. Typical experimental procedure: transfer hydrogenation ofcarbonyl 1 using EtOH as solvent and hydrogen source in thepresence of NaOH General procedure: NaOHA dried Schlenk tube (100 mL) equipped with a magneticstirring bar was charged under a nitrogen atmosphere with 1(130 L, 1 mmol), NaOH (80 mg, 2 mmol), and EtOH (2 mL), thenthe Schlenk tube was sealed. The mixture was heated at 80Cfor 15–24 h. After cooling to room temperature, the solution wasquenched with water (10 ml), the obtained mixture was thenextracted with ethyl acetate (3 × 5 mL). The combined organicphase was washed with brine (2 × 5 mL) and dried over Na2SO4and filtered. The filtrate was removed under reduced pressureto obtain the crude product that was further purified by silicagel chromatography (pentane/ethyl acetate as eluent) yieldingpure 2. With ethanol, sodium hydroxide, Time= 24h, T= 80 °C , Schlenk technique, Inert atmosphere, Green chemistry Wang, Dong; Deraedt, Christophe; Ruiz, Jaime; Astruc, Didier; Journal of Molecular Catalysis A: Chemical; vol. 400; (2015); p. 14 - 21 View in Reaxys

80 %

With C46H60Fe2N4SSi, hydrogen in toluene, Time= 20h, T= 50 °C , p= 37503.8Torr , Autoclave, Catalytic behavior Luecke, Marcel-Philip; Porwal, Digvijay; Kostenko, Arseni; Zhou, Yu-Peng; Yao, Shenglai; Keck, Matthias; Limberg, Christian; Oestreich, Martin; Driess, Matthias; Dalton Transactions; vol. 46; nb. 47; (2017); p. 16412 - 16418 View in Reaxys

79 %

With Triethoxysilane, C43H48FeP4 in tetrahydrofuran, Time= 16h, T= 50 °C Zhao, Hua; Sun, Hongjian; Li, Xiaoyan; Organometallics; vol. 33; nb. 13; (2014); p. 3535 - 3539 View in Reaxys

77 %

2.2. General procedure for catalytic hydrosilylation of aldehydes General procedure: To a 25 mL Schlenk tube containing a solution of 1 in 2 mL of THF was added an aldehyde (1.0 mmol) and (EtO)3 SiH (0.20 g, 1.2 mmol). The reaction mixture was stirred at 50–55 °C until there was no aldehyde left (monitored by TLC and GC–MS). The reaction was then quenched byMeOH (2mL) and a 10percent aqueous solution of NaOH (5 mL) with vigorous stirring at 60 °C for about 24 h.The organic product was extracted with diethyl ether (10 mL × 3), dried over anhydrous MgSO4, and concentrated under vacuum. The alcohol product was further purified using flash column chromatography (elute with 5–10percent ethyl acetate in petroleum ether). The 1H NMR and 13C NMR spectra of the alcohol products are providedin Supporting information. Stage 1: With Triethoxysilane, [cis-Fe(H)(SPh)(PMe3)4] in tetrahydrofuran, Time= 24h, T= 60 °C Stage 2: With methanol, sodium hydroxide in tetrahydrofuran, water, Time= 24h, T= 60 °C Xue, Benjing; Sun, Hongjian; Niu, Qingfen; Li, Xiaoyan; Fuhr, Olaf; Fenske, Dieter; Catalysis Communications; vol. 94; (2017); p. 23 - 28 View in Reaxys

73 %

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

73 %

With potassium hydroxide, ephedrine, [(η6-C6H6)Ru(μ-Cl)Cl]2 in isopropyl alcohol, T= 20 °C Ursini, Cleber V.; Dias, Gilson H.M.; Rodrigues, J. Augusto R.; Journal of Organometallic Chemistry; vol. 690; nb. 13; (2005); p. 3176 - 3186 View in Reaxys

16/120

2018-07-03 17:12:41

72 %

With methanol, T= 20 °C , Neat (no solvent) Shalbaf; Asian Journal of Chemistry; vol. 22; nb. 9; (2010); p. 6761 - 6764 View in Reaxys

70 %

With isopropyl alcohol, zirconium(VI) oxide, Time= 10h, Heating, Rate constant Shibagaki, Makoto; Takahashi, Kyoko; Matasushita, Hajime; Bulletin of the Chemical Society of Japan; vol. 61; (1988); p. 3283 - 3288 View in Reaxys

70 %

With isopropyl alcohol, zirconium(VI) oxide, Time= 10h, Heating Shibagaki, Makoto; Takahashi, Kyoko; Matasushita, Hajime; Bulletin of the Chemical Society of Japan; vol. 61; (1988); p. 3283 - 3288 View in Reaxys

68 %

With isopropyl alcohol, Time= 48h, T= 80 °C , chemoselective reaction Vijayakrishna, Kari; Charan, K. T. Prabhu; Manojkumar, Kasina; Venkatesh, Sadhana; Pothanagandhi, Nellepalli; Sivaramakrishna, Akella; Mayuri, Pinapeddavari; Kumar, Annamalai Senthil; Sreedhar; ChemCatChem; vol. 8; nb. 6; (2016); p. 1139 - 1145 View in Reaxys

66 %

With isopropylmagnesium bromide, bis(neomenthylcyclopentadienyl)titanium dichloride in diethyl ether, Time= 4h, T= 20 - 30 °C Zhang, Yongmin; Hu, Zuyao; Tetrahedron Letters; vol. 29; nb. 33; (1988); p. 4113 - 4114 View in Reaxys

64 %

With potassium hydroxide, Cr(L-Ala)2 in water, N,N-dimethyl-formamide, Time= 18h, Ambient temperature, pH=9.9 Patonay; Hajdu; Jeko; Levai; Micskei; Zucchi; Tetrahedron Letters; vol. 40; nb. 7; (1999); p. 1373 - 1374 View in Reaxys

63 %

With (2R,3R,11R,12R)-tetraphenyl-18-crown-6*(NH3BF3), boron trifluoride diethyl etherate in toluene, Time= 1.25h, T= -78 °C Allwood, Billy L.; Shahriari-Zavareh, Hooshang; Stoddart, J. Fraser; Williams, David J.; Journal of the Chemical Society, Chemical Communications; nb. 22; (1984); p. 1461 - 1464 View in Reaxys

57 %

With formic acid, C18H24ClIrN3 in water, Time= 4h, T= 80 °C , Schlenk technique, Inert atmosphere, chemoselective reaction Liu, Ji-Tian; Yang, Shiyi; Tang, Weiping; Yang, Zhanhui; Xu, Jiaxi; Green Chemistry; vol. 20; nb. 9; (2018); p. 2118 - 2124 View in Reaxys

47 %

With N-formyl-(S)-proline benzamide, trichlorosilane in dichloromethane, Time= 24h, T= 0 - 20 °C , Reduction Iwasaki, Fumiaki; Onomura, Osamu; Mishima, Katsuhiko; Maki, Toshihide; Matsumura, Yoshihiro; Tetrahedron Letters; vol. 40; nb. 42; (1999); p. 7507 - 7511 View in Reaxys

39.5 %

With titanium(IV) isopropylate, 2,2'-azobis(isobutyronitrile), tetranaphthyl-TADDOL, diphenylstibane in hexane, Time= 16h, Heating Breunig; Probst; Journal of Organometallic Chemistry; vol. 571; nb. 2; (1998); p. 297 - 303 View in Reaxys

37 %

With 1,1'-(1,2-ethanediyl)bisbenzene, lithium diisopropyl amide in tetrahydrofuran, toluene, Time= 1h, T= -78 °C Davis, Franklin A.; Sheppard, Aurelia C.; Chen, Bang-Chi; Haque, M. Serajul; Journal of the American Chemical Society; vol. 112; nb. 18; (1990); p. 6679 - 6690 View in Reaxys

35 %

With lithium aluminium tetrahydride, 2,5-di-C-benzyl-1,3:4,6-di-O-benzylidene-D-mannitol in diethyl ether, Time= 2h, Heating, variation of diolatohydridoaluminate(III) complexes; optical yield; main isomer, Product distribution

17/120

2018-07-03 17:12:41

Baggett, Neil; Simmonds, Richard J.; Stribblehill, Peter; Carbohydrate Research; vol. 162; (1987); p. 153 - 158 View in Reaxys 26.1%

34 : EXAMPLE 34 EXAMPLE 34 12.2 mg (2*10-5 moles) of [Ir(PPEI)COD]+ ClO4 - (+) were suspended in 50 ml of isopropanol and oxidized with air for 4 hours. The resulting solution was degasified for 20 minutes at reflux in a nitrogen stream and then treated with 1.88 ml of a deaerated isopropanol solution of KOH (4 mg of KOH). The solution, after a preliminary 30-minute reduction in a nitrogen stream, was treated with 2.56 ml of deaerated propiophenone. After 150 minutes a conversion to phenylpropanol (+) of 96.6percent with an e.e. of 26.1percent was obtained. Ratios: [substratum]/[cat.]=1000; [KOH]/[cat.]=3.56. With potassium hydroxide in nitrogen, isopropyl alcohol Patent; Montedison S.p.A.; US4290961; (1981); (A) English View in Reaxys

26.1%

36 : EXAMPLE 36 EXAMPLE 36 6.1 mg (1*10-5 moles) of [Ir(PPEI)COD]+ ClO4 - (+) were suspended in 50 ml of isopropanol and oxidized with air for 4 hours. The yellow solution obtained was then degasified at reflux in a nitrogen stream for 20 minutes and then treated with 4.0 ml of an isopropanol solution of KOH (4 mg of KOH). The solution, after a preliminary reduction for 30 minutes at reflux in a nitrogen flow, was treated with 2.56 ml of deaerated propiophenone. After 180 minutes, a conversion to phenylpropanol (+) of 89.3percent with an e.e. of 26.1percent was obtained. Ratios: [substratum]/[cat.]=2000; [KOH]/[cat.]=3.56. With potassium hydroxide in nitrogen, isopropyl alcohol Patent; Montedison S.p.A.; US4290961; (1981); (A) English View in Reaxys

26.1%

35 : EXAMPLE 35 EXAMPLE 35 12.2 mg (2*10-5 moles) of [Ir(PPEI)COD]+ ClO4 - (+) were suspended in 50 ml of isopropanol and oxidized with air for 4 hours. The resulting solution was degasified for 20 minutes at reflux in N2 and then treated with 4.5 ml of a deaerated isopropanol solution of KOH (8 mg of KOH). The solution, after a preliminary 30-minute reduction in a nitrogen stream, was treated with 2.56 ml of deaerated propiophenone. After a 120-minute reaction, a conversion to phenylpropanol (+) of 93.3percent with an e.e. of 26.1percent was obtained. Ratios: [substratum]/[cat.]=1000; [KOH]/[cat.]=7.2. With potassium hydroxide in N2, nitrogen, isopropyl alcohol Patent; Montedison S.p.A.; US4290961; (1981); (A) English View in Reaxys

25.07%

32 : EXAMPLE 32 EXAMPLE 32 24.4 mg (4*10-5 moles) of [Ir(PPEI)COD]+ ClO4 - (-) suspended in 100 ml of isopropanol were oxidized with air for 4 hours. The resulting yellow solution was degasified for 20 minutes at reflux in a nitrogen stream and treated with 1.94 ml of an isopropanol solution of KOH (4 mg of KOH). After a 30-minute reduction in a nitrogen stream, 5.3 ml of deaerated propiophenone were added. After a 240-minute reaction, a conversion to phenylpropanol (-) of 98.5percent with an e.e. of 25.07percent was obtained. The polarimetric determination was effected on the hydrogenation product distilled at reduced pressure. Ratios: [substratum]/[cat.]=1000; [KOH]/[cat.]=1.8. With potassium hydroxide in nitrogen, isopropyl alcohol Patent; Montedison S.p.A.; US4290961; (1981); (A) English View in Reaxys

23 %

With sodium hydroxide, aluminium in methanol, Time= 4h Bhar, Sanjay; Guha, Sharmistha; Tetrahedron Letters; vol. 45; nb. 19; (2004); p. 3775 - 3777

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

18/120

2018-07-03 17:12:41

View in Reaxys 21 %

With Triethoxysilane, C27H42FeP4S in tetrahydrofuran, Time= 24h, T= 50 °C , Schlenk technique, Green chemistry, Catalytic behavior Xue, Benjing; Sun, Hongjian; Li, Xiaoyan; RSC Advances; vol. 5; nb. 64; (2015); p. 52000 - 52006 View in Reaxys

20 %

With hydrogen in water, Time= 10h, T= 75 °C , p= 22502.3Torr , Autoclave, Sealed tube, Ionic liquid, chemoselective reaction Jiang, He-Yan; Xu, Jie; Sun, Bin; Applied Organometallic Chemistry; vol. 32; nb. 4; (2018); Art.No: E4260 View in Reaxys

With rac-octan-2-ol, magnesium oxide, Time= 4h, T= 179.85 °C , Reduction, hydrogen transfer Glinski; Polish Journal of Chemistry; vol. 74; nb. 8; (2000); p. 1207 - 1209 View in Reaxys With Compound (3) in tetrahydrofuran, diethyl ether, Time= 0.583333h, T= 20 °C , Product distribution Babler, James H.; Invergo, Benedict J.; Tetrahedron Letters; vol. 22; (1981); p. 621 - 622 View in Reaxys With potassium dihydrogenphosphate, sodium formate in various solvent(s), Time= 45h, Ambient temperature, Product distribution Babler, James H.; Sarussi, Steven J.; Journal of Organic Chemistry; vol. 46; nb. 16; (1981); p. 3367 - 3369 View in Reaxys With sodium tetrahydroborate, ethyl 2-hydroxypropionate in benzene, Ambient temperature, studies on optical yields at various ratios of reagents and in further solvent, Product distribution Bianchi, Giorgio; Achilli, Fiorella; Gamba, Anna; Vercesi, Dina; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 417 - 422 View in Reaxys With sodium tetrahydroborate, L-(-)-2-acetoxypropionic acid in benzene, Ambient temperature, studies on optical yields at various ratios of reagents and in further solvent, Product distribution Bianchi, Giorgio; Achilli, Fiorella; Gamba, Anna; Vercesi, Dina; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 417 - 422 View in Reaxys With triethylsilane, perchloric acid in acetonitrile, T= 24.9 °C , Rate constant Fukuzumi, Shunichi; Fujita, Morifumi; Chemistry Letters; (1991); p. 2059 - 2062 View in Reaxys With perchloric acid in acetonitrile, T= 57.9 °C , kinetic isotope effects also investigated with AcrH2-CD3 and AcrD2, Rate constant Fukuzumi, Shunichi; Chiba, Makoto; Tanaka, Toshio; Chemistry Letters; (1989); p. 31 - 34 View in Reaxys

70 % Chromat.

With Butane-1,4-diol, [(C6H5)3P]3Ru(CO)(Cl)H, Time= 20h, T= 140 °C , catalytic reduction; further ruthenium(II) catalysts Marcec, Radovan; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 39; nb. 12; (1984); p. 1823 - 1824 View in Reaxys With (endo-camphanyl)magnesium chloride in diethyl ether, Time= 1h, T= 20 °C , asymmetric addition/reduction with Grignard reagents, Product distribution Falorni, Massimo; Lardicci, Luciano; Uccello-Barretta, Gloria; Giacomelli, Giampaolo; Gazzetta Chimica Italiana; vol. 118; nb. 7; (1988); p. 495 - 500 View in Reaxys

19/120

2018-07-03 17:12:41

With potassium hydroxide, hydrogen, 10 wt. % palladium on activated carbon in 2,2,4-trimethylpentane, T= 50 °C , Product distribution Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro; Gazzetta Chimica Italiana; vol. 126; nb. 6; (1996); p. 317 - 328 View in Reaxys With 1,2-bis(3,5-di-t-butylsalicyl)benzene, trimethylaluminum, diisobutylaluminium hydride in diethyl ether, dichloromethane, Time= 1h, T= -78 °C , relative reactivity (vs acetophenone) Ohba, Yoshihiro; Ito, Kazuaki; Maeda, Hiroyuki; Ebara, Hiroaki; Takaki, Shin; Nagasawa, Tomomi; Bulletin of the Chemical Society of Japan; vol. 71; nb. 10; (1998); p. 2393 - 2402 View in Reaxys With ethanol, nickel, T= 125 °C , p= 125036Torr , Hydrogenation Adkins; Cramer; Journal of the American Chemical Society; vol. 52; (1930); p. 4349,4354 View in Reaxys With lithium aluminium tetrahydride, diethyl ether Zeiss; Tsutsui; Journal of the American Chemical Society; vol. 75; (1953); p. 897,899 View in Reaxys With methanol, palladium, N,N-diethylnicotinamide, Hydrogenation Kindler et al.; Justus Liebigs Annalen der Chemie; vol. 605; (1957); p. 200,210 View in Reaxys With sodium amalgam, ethanol Errera; Gazzetta Chimica Italiana; vol. 16; (1886); p. 322 View in Reaxys Barry; Chemische Berichte; vol. 6; (1873); p. 1008 View in Reaxys With ethanol, sodium Klages; Chemische Berichte; vol. 35; (1902); p. 2263; Chemische Berichte; vol. 38; (1905); p. 913 View in Reaxys With sodium hydroxide, ethanol, nickel, T= 125 °C , p= 125036Torr , Hydrogenation Delepine; Horeau; Bulletin de la Societe Chimique de France; vol. <5> 4; (1937); p. 31,41 View in Reaxys With ethanol, copper oxide-chromium oxide, T= 95 - 150 °C , p= 147102 - 220652Torr , Hydrogenation Cox; Adkins; Journal of the American Chemical Society; vol. 61; (1939); p. 3364,3369 View in Reaxys With cyclohexane, copper-aluminium oxide catalyst, T= 115 °C , p= 73550.8Torr , Hydrogenation Ipatieff; Haensel; Journal of the American Chemical Society; vol. 64; (1942); p. 520 View in Reaxys With ethanol, nickel, T= 95 - 150 °C , p= 147102 - 220652Torr , Hydrogenation Cox; Adkins; Journal of the American Chemical Society; vol. 61; (1939); p. 3364,3369 View in Reaxys With sodium tetrahydroborate Balsells, R. Erra; Frasca, A. R.; Tetrahedron; vol. 38; nb. 16; (1982); p. 2525 - 2538 View in Reaxys Kano, Taichi; Sasaki, Kouji; Maruoka, Keiji; Organic Letters; vol. 7; nb. 7; (2005); p. 1347 - 1349 View in Reaxys With sodium tetrahydroborate

20/120

2018-07-03 17:12:41

Kelkar, S. V.; Joshi, G. S.; Kulkarni, G. H.; Mitra, R. B.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 26; (1987); p. 68 - 70 View in Reaxys Morris, David J.; Hayes, Aidan M.; Wills, Martin; Journal of Organic Chemistry; vol. 71; nb. 18; (2006); p. 7035 - 7044 View in Reaxys 100 % Chromat.

With zirconium(VI) oxide in isopropyl alcohol, Time= 10h, Heating Matsushita, Hajime; Ishiguro, Shigeo; Ichinose, Hiroshi; Izumi, Akira; Mizusaki, Shigenobu; Chemistry Letters; (1985); p. 731 - 734 View in Reaxys With perchloric acid in acetonitrile, T= 331 °C Fukuzumi, Shunichi; Chiba, Makoto; Tanaka, Toshio; Chemistry Letters; (1989); p. 31 - 34 View in Reaxys With lithium aluminium tetrahydride Pritzkow, Wilhelm; Thomas, Gerda; Willecke, Lothar; Journal fuer Praktische Chemie (Leipzig); vol. 327; nb. 5; (1985); p. 847 - 851 View in Reaxys With triethylsilane, perchloric acid in acetonitrile, T= 24.9 °C Fukuzumi, Shunichi; Fujita, Morifumi; Chemistry Letters; (1991); p. 2059 - 2062 View in Reaxys With sodium tetrahydroborate in methanol, Ambient temperature Fernholz, Erhard; Schloeder, Diane; Liu, Kevin K.-C.; Bradshaw, Curt W.; Huang, Hongmei; et al.; Journal of Organic Chemistry; vol. 57; nb. 17; (1992); p. 4756 - 4761 View in Reaxys

10 % Turnov.

With sodium methylate, isopropyl alcohol, Rhpy3Cl3 in ethanol, Time= 3h, T= 83 °C Kvintovics, P.; Heil, B.; Journal of Organometallic Chemistry; vol. 361; (1989); p. 117 - 122 View in Reaxys With borane in tetrahydrofuran Wakita, Yoshiaki; Yasunaga, Tomoyuki; Kojima, Masaharu; Journal of Organometallic Chemistry; vol. 288; (1985); p. 261 268 View in Reaxys

81 % Spectr.

With aluminum isopropoxide, trifluoroacetic acid in benzene, Time= 0.25h, Ambient temperature Akamanchi; Varalakshmy; Tetrahedron Letters; vol. 36; nb. 20; (1995); p. 3571 - 3572 View in Reaxys

20 % Spectr.

With aluminum isopropoxide, isopropyl alcohol, trifluoroacetic acid in benzene, Time= 24h, Ambient temperature Akamanchi, Krishnacharya G.; Noorani, Varalakshmy R.; Tetrahedron Letters; vol. 36; nb. 28; (1995); p. 5085 - 5088 View in Reaxys

12 % Turnov.

With sodium hydroxide, isopropyl alcohol, <RuCl2(PPh3)<1-(diphenylphosphino)-2-ethoxy-1-(2-pyridyl)ethane>>, Time= 1h, T= 82 °C Yang, Hong; Alvarez, Marie; Lugan, Noel; Mathieu, Rene; Journal of the Chemical Society, Chemical Communications; nb. 17; (1995); p. 1721 - 1722 View in Reaxys

57 % Chromat.

With isopropyl alcohol, potassium hydroxide, hydridochlorotris(triphenylphosphine)ruthenium(II), Time= 1h, T= 85 °C Mizushima, Eiichiro; Yamaguchi, Motowo; Yamagishi, Takamichi; Chemistry Letters; nb. 3; (1997); p. 237 - 238 View in Reaxys

21/120

2018-07-03 17:12:41

With potassium phosphate buffer, pig testicular 20η-hydroxysteroid dehydrogenase, NADPH, T= 37 °C , pH= 6.5, Reduction, Enzyme kinetics Nakajin, Shizuo; Tamura, Fumihiro; Takase, Noriko; Toyoshima, Satoshi; Biological and Pharmaceutical Bulletin; vol. 20; nb. 11; (1997); p. 1215 - 1218 View in Reaxys With 2-butanol, Sn-beta (2 wt percent SnO2) zeolite, Time= 20h, T= 100 °C , Meerwein-Ponndorf-Verley reduction Corma, Avelino; Domine, Marcelo E.; Valencia, Susana; Journal of Catalysis; vol. 215; nb. 2; (2003); p. 294 - 304 View in Reaxys With sodium tetrahydroborate in ethanol Hu, Aiguo; Ngo, Helen L.; Lin, Wenbin; Organic Letters; vol. 6; nb. 17; (2004); p. 2937 - 2940 View in Reaxys Stage 1: With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, isopropyl alcohol, [2-(diphenylphosphinoyl)-ethyl]-(R)-sec-butyl-amine, Time= 0.5h, T= 83 °C Stage 2: With potassium hydroxide, Time= 2h, T= 29 °C Rahman, Mohammed S.; Oliana, Marco; Hii, King Kuok; Tetrahedron Asymmetry; vol. 15; nb. 12; (2004); p. 1835 - 1840 View in Reaxys With aluminum oxide, copper in n-heptane, Time= 7h, T= 90 °C , p= 760Torr Zaccheria, Federica; Ravasio, Nicoletta; Psaro, Rinaldo; Fusi, Achille; Tetrahedron Letters; vol. 46; nb. 21; (2005); p. 3695 3697 View in Reaxys 92 % Chromat.

With triiron dodecarbonyl, sodium isopropylate, 5,15,10,20-tetraphenylporphyrin in isopropyl alcohol, Time= 7h, T= 100 °C Enthaler, Stephan; Erre, Giulia; Tse, Man Kin; Junge, Kathrin; Beller, Matthias; Tetrahedron Letters; vol. 47; nb. 46; (2006); p. 8095 - 8099 View in Reaxys

93 % Chromat.

With imidazolium ion, sodium isopropylate, Ru(COD)(methallyl)2 in isopropyl alcohol, Time= 24h, T= 100 °C Enthaler, Stephan; Jackstell, Ralf; Hagemann, Bernhard; Junge, Kathrin; Erre, Giulia; Beller, Matthias; Journal of Organometallic Chemistry; vol. 691; nb. 22; (2006); p. 4652 - 4659 View in Reaxys With tert-butyl substituted phosphine oxazoline ligand, diphenylsilane, chloro(1,5-cyclooctadiene)rhodium(I) dimer in tetrahydrofuran, Time= 72h, T= 20 °C Coyne, Anthony G.; Guiry, Patrick J.; Tetrahedron Letters; vol. 48; nb. 5; (2007); p. 747 - 750 View in Reaxys

99 % Chromat.

With potassium hydroxide, isopropyl alcohol, Ru3(CO)12 supported on Cs zeolite beta, Time= 24h, T= 82 °C Kantam, M. Lakshmi; Rao, B. Purna Chandra; Choudary; Sreedhar; Advanced Synthesis and Catalysis; vol. 348; nb. 14; (2006); p. 1970 - 1976 View in Reaxys

84 % Chromat.

With samarium, iodine, isopropyl alcohol, T= 25 °C , Meerwein-Ponndorf-Verley reduction Fukuzawa, Shin-Ichi; Nakano, Narihito; Saitoh, Takahide; European Journal of Organic Chemistry; nb. 13; (2004); p. 2863 2867 View in Reaxys

92 % Spectr.

With ammonium hydroxide, titanium(III) chloride in methanol, Time= 0.0833333h, T= 20 - 25 °C , pH= 10 - 11 Clerici, Angelo; Pastori, Nadia; Porta, Ombretta; European Journal of Organic Chemistry; nb. 19; (2002); p. 3326 - 3335 View in Reaxys With sodium tetrahydroborate

22/120

2018-07-03 17:12:41

Allan; Carnell; Journal of Organic Chemistry; vol. 66; nb. 19; (2001); p. 6495 - 6497 View in Reaxys 99 % Spectr.

With sodium isopropylate, Ru(II) aminophosphine in isopropyl alcohol, Time= 48h, T= 82 °C Standfest-Hauser; Slugovc; Mereiter; Schmid; Kirchner; Xiaoc; Weissensteiner; Journal of the Chemical Society, Dalton Transactions; nb. 20; (2001); p. 2989 - 2995 View in Reaxys With potassium hydroxide, [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, (1R,2R)-1-butylamino-3(diphenylmethoxy)-1-phenylpropan-2-ol in isopropyl alcohol, Time= 17h, T= 0 °C Pasto, Mireia; Riera, Antoni; Pericas, Miquel A.; European Journal of Organic Chemistry; nb. 14; (2002); p. 2337 - 2341 View in Reaxys

94 % Chromat.

With potassium tert-butylate, hydrogen, RuCl2(PPh3)(Me4BPPy) in isopropyl alcohol, Time= 4h, T= 25 °C , p= 15201Torr Yu; Zeng; Sun; Deng; Dong; Chen; Wang; Pei; Journal of Organometallic Chemistry; vol. 692; nb. 11; (2007); p. 2306 - 2313 View in Reaxys With sodium tetrahydroborate in methanol Mastranzo, Virginia M.; Quintero, Leticia; De Parrodi, Cecilia Anaya; Juaristi, Eusebio; Walsh, Patrick J.; Tetrahedron; vol. 60; nb. 8; (2004); p. 1781 - 1789 View in Reaxys Kodama, Koichi; Kobayashi, Yuka; Saigo, Kazuhiko; Chemistry - A European Journal; vol. 13; nb. 7; (2007); p. 2144 - 2152 View in Reaxys With ketoreductase, isopropyl alcohol in phosphate buffer, pentane, T= 24.99 °C , pH= 7.3, Equilibrium constant, Further Variations: Solvents Tewari, Yadu B.; Kishore, Nand; Rozzell, J. David; Vanderah, David J.; Schantz, Michele M.; Journal of Chemical Thermodynamics; vol. 38; nb. 10; (2006); p. 1165 - 1171 View in Reaxys Reaction Steps: 3 1: 1.) lithium diisopropylamide / 1.) THF, -78 deg C 2: H2 / rhodium cationic complex with (R)-1-<(S)-1',2-bis(diphenylphosphino)ferrocenyl>ethanol <(R)-(S)-BPPFOH> / benzene / 70 h / 30 °C / 38000 Torr 3: 1.) MeLi 2.) H3O(1+) / 1.) ether With oxonium, methyllithium, hydrogen, lithium diisopropyl amide, rhodium cationic complex with (R)-1-<(S)-1',2-bis(diphenylphosphino)ferrocenyl>ethanol <(R)-(S)-BPPFOH> in benzene Hayashi, Tamio; Kanehira, Koichi; Kumada, Makoto; Tetrahedron Letters; vol. 22; nb. 44; (1981); p. 4417 - 4420 View in Reaxys C.3 : Comparative Example 3 Comparative Example 3 Except for using RuCl2[(R)-binap][(R)-daipen] instead of RuBr2[(S,S)-Tolskewphos][(R)-daipen] as the catalyst, hydrogenation of propiophenone was carried out in the same way as Example 3 to give the product of 1-phenyl-1-propanol. The yield of the product was 99percent or higher and (R)-product was formed in 91.5percent ee. Patent; Kanto Kagaku Kabushiki Kaisha; US2003/166978; (2003); (A1) English View in Reaxys C.10 : Comparative Example 10 Comparative Example 10 Except for using RuCl2[(R)-binap][(R)-daipen] instead of RuBr2[(S,S)-Xylskewphos][(R)-daipen] as the catalyst, hydrogenation of propiophenone was carried out in the same way as Example 9 to give the product of 1-phenyl-1-propanol. The yield of the product was 99percent or higher and (R)-product was formed in 91.5percent ee. Patent; Kanto Kagaku Kabushiki Kaisha; US2003/166978; (2003); (A1) English View in Reaxys 33 : EXAMPLE 33

23/120

2018-07-03 17:12:41

EXAMPLE 33 12.2 mg (2*10-5 moles) of [Ir(PPEI)COD]+ ClO4 - (+) were suspended in 50 ml of isopropanol and oxidized with air for 4 hours. The yellow limpid solution so obtained was degasified for 20 minutes at reflux under a nitrogen stream and then treated with 2.7 ml of a deaerated isopropanol solution of KOH (2 mg of KOH). The solution was preliminarily reduced for 30 minutes in a N2 stream at reflux and then treated with 2.56 ml of deaerated propiophenone. After 60 minutes the reaction was stopped, obtaining a conversion to phenylpropanol (+) of 57.3percent with an e.e. of 30percent. Ratios: [substratum]/[cat.]=1000; [KOH]/[cat.]=1.8. With potassium hydroxide in N2, isopropyl alcohol Patent; Montedison S.p.A.; US4290961; (1981); (A) English View in Reaxys With sodium tetrahydroborate in methanol, Time= 2h Hobuss, Dennis; Baro, Angelika; Laschat, Sabine; Frey, Wolfgang; Tetrahedron; vol. 64; nb. 8; (2008); p. 1635 - 1640 View in Reaxys Stage 1: With [(Cp*)Rh(Cl)(η2-3-PiPr2-2-S-indene)], phenylsilane, lithium tetrakis(pentafluorophenyl)borate in tetrahydrofuran, Time= 5h, T= 20 °C Stage 2: With hydrogenchloride in tetrahydrofuran, water, acetone, Time= 2.5h, T= 0 - 20 °C Hesp, Kevin D.; McDonald, Robert; Ferguson, Michael J.; Stradiotto, Mark; Journal of the American Chemical Society; vol. 130; nb. 48; (2008); p. 16394 - 16406 View in Reaxys 98 %Spectr. With RuCl2(NC6H4NHCC5H3NN2C3H(CH3)2)(P(C6H5)3), potassium isopropoxide, isopropyl alcohol, Time= 0.00833333h, T= 28 °C , Air Zhao, Miao; Yu, Zhengkun; Yan, Shenggang; Li, Yang; Tetrahedron Letters; vol. 50; nb. 32; (2009); p. 4624 - 4628 View in Reaxys 5 :Examole 5: catalytic reduction of linear and cyclic dialkvl ketones, alkylaryl ketonesand diaryl ketones in presence of complex 8; Complex 8 (3.0 mg, 0.005 mmol) is suspended in 3 ml of 2-propanol in a 10mltailed tubes (Schlenk) and 2 ml of a 0.1M solution of NaOH in 2-propanol added.The complex is completely solubilised in a few minutes by stirring.Separately, in a 50ml tailed tubes (Schlenk), the necessary amount ofacetophenone (240 ul, 2 mmol) is dissolved in 19 ml of 2-propanol, the system isrefluxed and 1 ml of the previously prepared catalyst solution added (the addition of the complex is considered to be the starting time of the reaction). The molarratios between acetophenone/catalyst/NaOH are 2000/1/40; the reaction ismonitored at 1, 2, 5 minutes by collecting 0.5 ml of the solution and adding 4.5 mlof diethyl ether. This solution is passed through a silica column in order toeliminate the catalyst and sodium hydroxide, and finally analysed by gaschromatography. The gas chromatograph analysis data are reported in table 2. With sodium hydroxide, isopropyl alcohol, RuCl(CO)(CH2C6H3(CH3)(P(C6H5)2))(C5H4N(CH2NH2)), Time= 0.0833333h, Heating / reflux Patent; UNIVERSITA' DEGLI STUDI DI UDINE; WO2005/51965; (2005); (A2) English View in Reaxys With sodium hydroxide in water, isopropyl alcohol, Time= 0.5h, T= 120 - 130 °C , Microwave irradiation Gracia, Maria Jose; Campelo, Juan Manuel; Losada, Elia; Luque, Rafael; Marinas, Jose Maria; Romero, Antonio Angel; Organic and Biomolecular Chemistry; vol. 7; nb. 23; (2009); p. 4821 - 4824 View in Reaxys With C42H38ClN2OsP2, potassium tert-butylate, hydrogen in methanol, Time= 0.5h, T= 70 °C , p= 3800.26Torr , chemoselective reaction Baratta, Walter; Fanfoni, Lidia; Magnolia, Santo; Siega, Katia; Rigo, Pierluigi; European Journal of Inorganic Chemistry; nb. 9; (2010); p. 1419 - 1423 View in Reaxys With sodium tetrahydroborate

24/120

2018-07-03 17:12:41

Li, De Run; He, Anyu; Falck; Organic Letters; vol. 12; nb. 8; (2010); p. 1756 - 1759 View in Reaxys With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, C23H26N2O, potassium hydroxide in isopropyl alcohol, Time= 49h, T= 60 °C , Inert atmosphere Zhou, Zhongqiang; Bian, Yongjun; Heteroatom Chemistry; vol. 19; nb. 7; (2008); p. 682 - 687 View in Reaxys 87 %Chromat.

With ethanol, titanium(IV) oxide, Time= 8h, T= 32 °C , Inert atmosphere, UV-irradiation Kohtani, Shigeru; Yoshioka, Eito; Saito, Kenji; Kudo, Akihiko; Miyabe, Hideto; Catalysis Communications; vol. 11; nb. 13; (2010); p. 1049 - 1053 View in Reaxys With (2-((5-(tert-butyl)-2,4-dimethyl-5-imidazo[1,5-b]pyridazin-7-yl)amido)ethan-1-ol)(1,5-cyclooctadiene)iridium(I), potassium tert-butylate, hydrogen, acetone in tetrahydrofuran, Time= 48h, T= 20 °C , p= 15.0015Torr , Autoclave Irrgang, Torsten; Friedrich, Denise; Kempe, Rhett; Angewandte Chemie - International Edition; vol. 50; nb. 9; (2011); p. 2183 - 2186 View in Reaxys With sodium tetrahydroborate in methanol, Inert atmosphere Zhou, Xiao-Yu; Wang, Duo-Sheng; Bao, Ming; Zhou, Yong-Gui; Tetrahedron Letters; vol. 52; nb. 22; (2011); p. 2826 - 2829 View in Reaxys With Ru(P,O,P-xantphos)(S-dmso)Cl2, isopropyl alcohol, potassium hydroxide, Time= 12h, Reflux Kharat, Ali Nemati; Bakhoda, Abolghasem; Jahromi, Bahareh Tamaddoni; Inorganic Chemistry Communications; vol. 14; nb. 7; (2011); p. 1161 - 1164 View in Reaxys With hydrogen in tetrahydrofuran, Time= 24h, T= 39 °C , p= 15001.5Torr , Autoclave, chemoselective reaction Hermannsdoerfer, Justus; Kempe, Rhett; Chemistry - A European Journal; vol. 17; nb. 29; (2011); p. 8071 - 8077 View in Reaxys

94 %Chromat.

With C71H56N5P2Ru(1+)*Cl(1-), potassium isopropoxide, isopropyl alcohol, Time= 4.5h, T= 82 °C , Inert atmosphere Wang, Lei; Pan, Hai-Ran; Yang, Qin; Fu, Hai-Yan; Chen, Hua; Li, Rui-Xiang; Inorganic Chemistry Communications; vol. 14; nb. 9; (2011); p. 1422 - 1427 View in Reaxys 4.1. Synthesis of secondary alcohols General procedure: All racemic alcohols except for the (R,S)-1-phenylethanol were prepared using the following procedure: a mixture of ketone (5 mmol) and sodium borohydride (10 mmol) in anhydrous methanol (50 mL) was stirred at room temperature for 30 min. Next, saturated NaHCO3 (50 mL) and CH2Cl2 (100 mL) were introduced, and the mixture was stirred at room temperature for another 10 min. The organic layer was removed, and the aqueous layer was extracted twice with 25 mL CH2Cl2. The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give the corresponding crude alcohols. The crude alcohols were then chromatographed to afford pure products. The 1H NMR spectra of these products were in good agreement with the literature. Stage 1: With sodium tetrahydroborate in methanol, Time= 0.5h, T= 20 °C Stage 2: With sodium hydrogencarbonate in methanol, dichloromethane, Time= 0.166667h, T= 20 °C , Saturated solution Wang, Bo; Jiang, Ling; Wang, Jue; Ma, Jingbo; Liu, Min; Yu, Hongwei; Tetrahedron Asymmetry; vol. 22; nb. 9; (2011); p. 980 - 985 View in Reaxys

93 %Chromat.

Stage 1: With [RuCl2(η6-benzene)tris(4-methoxyphenyl)phosphane] in isopropyl alcohol, Time= 0.166667h, T= 82 °C , p= 750.075Torr , Inert atmosphere Stage 2: With potassium isopropoxide in isopropyl alcohol, Time= 8h, T= 82 °C , Inert atmosphere Wang, Lei; Yang, Qin; Fu, Hai-Yan; Chen, Hua; Yuan, Mao-Lin; Li, Rui-Xiang; Applied Organometallic Chemistry; vol. 25; nb. 8; (2011); p. 626 - 631

25/120

2018-07-03 17:12:41

View in Reaxys With [RuCl(bis(2-(dimethylamino)phenyl)amide)(PPh3)], isopropyl alcohol, potassium hydroxide, Time= 2h, T= 83 °C , Inert atmosphere Ren, Peng; Vechorkin, Oleg; Csok, Zsolt; Salihu, Isuf; Scopelliti, Rosario; Hu, Xile; Dalton Transactions; vol. 40; nb. 35; (2011); p. 8906 - 8911 View in Reaxys Kodama, Koichi; Sekine, Eriko; Hirose, Takuji; Chemistry - A European Journal; vol. 17; nb. 41; (2011); p. 11527 - 11534 View in Reaxys With sodium tetrahydroborate Li, Chengyong; Zhao, Jiangfeng; Tan, Rong; Peng, Zhigang; Luo, Rongchang; Peng, Ming; Yin, Donghong; Catalysis Communications; vol. 15; nb. 1; (2011); p. 27 - 31 View in Reaxys With [Ru(Ph2PNHCH2(C4H3O))(η6-benzene)Cl2], isopropyl alcohol, potassium hydroxide, Time= 0.333333h, T= 82 °C Aydemir, Murat; Baysal, Akin; Guemguem, Bahattin; Applied Organometallic Chemistry; vol. 26; nb. 1; (2012); p. 1 - 8 View in Reaxys With hydrogen in toluene, Time= 24h, T= 85 °C , p= 30003Torr , Autoclave Zaheer, Muhammad; Motz, Guenter; Kempe, Rhett; Journal of Materials Chemistry; vol. 21; nb. 46; (2011); p. 18825 18831 View in Reaxys With potassium tert-butylate, isopropyl alcohol, T= 39.84 °C , Inert atmosphere Yang, Yong; Weng, Zhihuan; Muratsugu, Satoshi; Ishiguro, Nozomu; Ohkoshi, Shin-Ichi; Tada, Mizuki; Chemistry - A European Journal; vol. 18; nb. 4; (2012); p. 1142 - 1153 View in Reaxys 82 %Chromat.

Stage 1: With diethylaluminum benzenethiolate, benzaldehyde in hexane, toluene, Time= 1.08333h, T= -78 °C , Inert atmosphere Stage 2: With diisobutylaluminium hydride in hexane, toluene, T= -78 °C , Inert atmosphere Stage 3: With hydrogenchloride in hexane, water, toluene, T= 0 °C , chemoselective reaction Bastug, Gulluzar; Dierick, Steve; Lebreux, Frederic; Marko, Istvan E.; Organic Letters; vol. 14; nb. 5; (2012); p. 1306 1309 View in Reaxys With sodium tetrahydroborate in ethanol, Time= 0.0166667h, T= 100 °C , Microwave irradiation Murphree, S. Shaun; Mason, Jeremy D.; Bean, Theodore G.; Perry, Michelle C.; Synthetic Communications; vol. 42; nb. 13; (2012); p. 1979 - 1986 View in Reaxys With sodium tetrahydroborate in ethanol, Inert atmosphere Zhang, Juanni; Yang, Xiangren; Zhou, Han; Li, Yanyun; Dong, Zhenrong; Gao, Jingxing; Green Chemistry; vol. 14; nb. 5; (2012); p. 1289 - 1292 View in Reaxys

98 %Chromat.

With Re(H)(NO)(PiPr3)(C5H4OH), isopropyl alcohol, Time= 1.5h, T= 120 °C , Inert atmosphere Landwehr, Anne; Dudle, Balz; Fox, Thomas; Blacque, Olivier; Berke, Heinz; Chemistry - A European Journal; vol. 18; nb. 18; (2012); p. 5701 - 5714 View in Reaxys With NADH, Time= 0.0166667h, T= 30 °C , pH= 7.5, Enzymatic reaction Cuetos, Anibal; Rioz-Martinez, Ana; Bisogno, Fabricio R.; Grischek, Barbara; Lavandera, Ivan; De Gonzalo, Gonzalo; Kroutil, Wolfgang; Gotor, Vicente; Advanced Synthesis and Catalysis; vol. 354; nb. 9; (2012); p. 1743 - 1749 View in Reaxys

26/120

2018-07-03 17:12:41

With [{(CH3)2C3HN2-C5H3N-C3H3N2}RuCl2(PPh3)], potassium isopropoxide, isopropyl alcohol, Time= 0.0166667h, T= 82 °C , Inert atmosphere Jin, Weiwei; Wang, Liandi; Yu, Zhengkun; Organometallics; vol. 31; nb. 15; (2012); p. 5664 - 5667,4 View in Reaxys Typical procedure for transfer hydrogenation of ketones General procedure: In an oven-dried round bottom flask, were placed ketone (2.4 mmol), catalyst (3 mol), base (12 mol), internal standard (m-xylene, 30 L, 0.24 mmol) and i-PrOH (5 mL) at room temperature. The reaction mixture was heated at 82 °C for the required reaction time under an atmosphere of nitrogen. Aliquots (0.2 mL) were taken at fixed time and the catalyst removed as precipitate from the reaction mixture by the addition of diethyl ether. The organic layer was neutralized with 1 N HCl, washed with water and dried over anhydrous Na2SO4. The combined organic layer passed through a short path of silica gel and then subjected to GCMS analysis. The conversions obtained are related to the residual unreacted ketone and are averages of two runs in the case of all catalytic reactions. With C55H41ClN2O3P2Ru, isopropyl alcohol, potassium hydroxide in m-xylene, Time= 4h, T= 20 - 82 °C , Inert atmosphere Prabhu, Rupesh Narayana; Ramesh, Rengan; Journal of Organometallic Chemistry; vol. 718; (2012); p. 43 - 51,9 View in Reaxys 4.3.4 General procedure for the transfer hydrogenation of ketones General procedure: Typical procedure for the catalytic hydrogen transfer reaction: a solution of complexes [C10H6N2{NHPPh2Ru(η6-benzene)Cl2}2], 1, [C10H6N2{PPh2NHRh(cod)Cl}2], 2 and [C10H6N2{NHPPh2Ir(η5-C5Me5)Cl2}2], 3 (0.005 mmol), NaOH (0.025 mmol) and the corresponding ketone (0.5 mmol) in degassed iso-PrOH (5 mL) were refluxed for 10 min for 1, 1 h for 2 and 3 h for 3. After this period a sample of the reaction mixture was taken off, diluted with acetone and analyzed immediately by GC. Conversions obtained are related to the residual unreacted ketone. With [C10H6N2{NHPPh2Ru(η6-benzene)Cl2}2], sodium hydroxide in isopropyl alcohol, Time= 0.25h, Reflux, Inert atmosphere, Reagent/catalyst, Time Aydemir, Murat; Meric, Nermin; Baysal, Akn; Journal of Organometallic Chemistry; vol. 720; (2012); p. 38 - 45,8 View in Reaxys 99 %Chromat.

With [{o-C6H4(PPh2)}2(Ph)BH]Rh(CO)(triphenylphosphine), isopropyl alcohol, Time= 40h, T= 70 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst, Time Kameo, Hajime; Nakazawa, Hiroshi; Organometallics; vol. 31; nb. 21; (2012); p. 7476 - 7484,9 View in Reaxys With borane-THF in tetrahydrofuran, T= 20 °C , Inert atmosphere Ran, De-Qiang; Shen, Tian-Hua; Zhou, Xiao-Cong; Ma, Chun-An; Song, Qing-Bao; Journal of the Chemical Society of Pakistan; vol. 35; nb. 1; (2013); p. 125 - 129 View in Reaxys With sodium tetrahydroborate Tan, Rong; Dong, Yan; Peng, Ming; Zheng, Weiguo; Yin, Donghong; Applied Catalysis A: General; vol. 458; (2013); p. 1 10 View in Reaxys

97 %Chromat.

With [(2-(benzimidazol-2-yl)-6-(benzotriazol-1-yl)pyridine)RuCl(PPh3)2]Cl, potassium isopropoxide, isopropyl alcohol, Time= 0.166667h, T= 82 °C , p= 750.075Torr , Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst, Time Du, Wangming; Wu, Ping; Wang, Qingfu; Yu, Zhengkun; Organometallics; vol. 32; nb. 10; (2013); p. 3083 - 3090 View in Reaxys With [ruthenium(II)(η6-benzene)(chloride)(S(CH2C5H4N)2)](hexafluorophosphate), potassium hydroxide in isopropyl alcohol, Time= 3h, T= 80 °C , Reflux, Reagent/catalyst, Time Prakash, Om; Sharma, Kamal Nayan; Joshi, Hemant; Gupta, Pancham Lal; Singh, Ajai K.; Dalton Transactions; vol. 42; nb. 24; (2013); p. 8736 - 8747 View in Reaxys

27/120

2018-07-03 17:12:41

> 99 %Spectr.

With chloro(η4-1,5-cyclooctadiene)[1,3-bis(2,4,6-triisopropylbenzyl)-5,6-dimethylbenzimidazol-2-ylidene]iridium(I), isopropyl alcohol, potassium hydroxide, Time= 0.0833333h, T= 82 °C , Catalytic behavior, Reagent/catalyst, Time Guelcemal, Sueleyman; Goekce, Aytac Guerhan; Cetinkaya, Bekir; Inorganic Chemistry; vol. 52; nb. 18; (2013); p. 10601 10609 View in Reaxys With hydrogen, Time= 24h, T= 50 °C , p= 15001.5Torr , Inert atmosphere, Autoclave, Schlenk technique, Glovebox Hermannsdoerfer, Justus; Friedrich, Martin; Kempe, Rhett; Chemistry - A European Journal; vol. 19; nb. 41; (2013); p. 13652 - 13657 View in Reaxys 4.4 General procedure for the transfer hydrogenation reaction General procedure: The tested complex (0.01 mmol; 1 molpercent) was dissolved in a solution of KOH (0.1 mmol) and 2-propanol (5 ml) in a two necked flask. The solution was heated to 82 °C for 30 min. Subsequently, acetophenone (1 mmol) was added. After the desired reaction time the solution was allowed to cool and quenched with 1M HCl, extracted with CH2Cl2 and the organic phase separated. The reaction progress was monitored by 1H NMR and GC the results for each experiment are averages over two runs. With C41H58ClN4Ru(1+)*Cl(1-), isopropyl alcohol, potassium hydroxide, Time= 0.5h, T= 82 °C Goek, Luetfiye; Tuerkmen, Hayati; Tetrahedron; vol. 69; nb. 49; (2013); p. 10669 - 10674 View in Reaxys

90 %Chromat.

Stage 1: With (η6-C6H6)RuCl2[μ-(PPh2CH2N)2CH2(C10H6)]RuCl2(η6-C6H6), isopropyl alcohol, Time= 0.166667h, Inert atmosphere, Schlenk technique Stage 2: With potassium isopropoxide in isopropyl alcohol, Time= 0.5h, T= 82 °C , Inert atmosphere, Schlenk technique Fu, Qi; Zhang, Lei; Yi, Tao; Zou, Mingjun; Wang, Xiaoyan; Fu, Haiyan; Li, Ruixiang; Chen, Hua; Inorganic Chemistry Communications; vol. 38; (2013); p. 28 - 32 View in Reaxys With [Rh((Ph2P)2NCH2-C4H3S)(Cp*)Cl]Cl, sodium hydroxide in isopropyl alcohol, Time= 4h, T= 82 °C , Schlenk technique, Inert atmosphere, Catalytic behavior, Reagent/catalyst Ok, Fatih; Aydemir, Murat; Durap, Feyyaz; Applied Organometallic Chemistry; vol. 28; nb. 1; (2014); p. 38 - 43 View in Reaxys Stage 1: With sodium tetrahydroborate in methanol, T= 0 °C Stage 2: With hydrogenchloride in methanol, water Rodriguez, Cristina; Borzecka, Wioleta; Sattler, Johann H.; Kroutil, Wolfgang; Lavandera, Ivan; Gotor, Vicente; Organic and Biomolecular Chemistry; vol. 12; nb. 4; (2014); p. 673 - 681 View in Reaxys With [Ru(Cy2PNHCH2-C4H3S)(η6-benzene)Cl2], isopropyl alcohol, sodium hydroxide, Time= 1h, T= 82 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst, Time Kayan, Cezmi; Meric, Nermin; Aydemir, Murat; Ocak, Yusuf Selim; Temel, Hamdi; Applied Organometallic Chemistry; vol. 28; nb. 2; (2014); p. 127 - 133 View in Reaxys With methanol in toluene, Time= 1.5h, 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

98 %Chromat.

Stage 1: With C33H26Cl2F6N5PRu in isopropyl alcohol, Time= 0.166667h, T= 82 °C , Inert atmosphere Stage 2: With potassium isopropoxide in isopropyl alcohol, Time= 0.0833333h, T= 0 °C , Inert atmosphere, Catalytic behavior, Reagent/catalyst, Time Du, Wangming; Wang, Qingfu; Wang, Liandi; Yu, Zhengkun; Organometallics; vol. 33; nb. 4; (2014); p. 974 - 982 View in Reaxys

28/120

2018-07-03 17:12:41

4.2. General procedure for the transfer hydrogenation of ketones General procedure: Typical procedure for the catalytic hydrogen transfer reaction: a solution of complexes [Rh(Cy2PNHCH2C4H3O)(cod)Cl], (1),[Rh(Cy2PNHCH2-C4H3S)(cod)Cl], (2), [Ir(Cy2PNHCH2-C4H3O)(η5-C5Me5)Cl2], (3) and [Ir(Cy2PNHCH2C4H3S)(η5-C5Me5)Cl2], (4)(0.005 mmol), NaOH (0.025 mmol) and the corresponding ketone(0.5 mmol) in degassed iso-PrOH (5 mL) were refluxed until the reactions were completed. After this period a sample of the reactionmixture was taken off, diluted with acetone and analyzed immediately by GC. Conversions obtained are related to the residual unreacted ketone. With [Rh(Cy2PNHCH2-C4H3O)(cod)Cl], isopropyl alcohol, sodium hydroxide, Time= 0.333333h, T= 82 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst, Time Rafikova, Khadichakhan; Kystaubayeva, Nurzhamal; Aydemir, Murat; Kayan, Cezmi; Ocak, Yusuf Selim; Temel, Hamdi; Zazybin, Alexey; Guerbuez, Nevin; Oezdemir, Ismail; Journal of Organometallic Chemistry; vol. 758; (2014); p. 1 - 8 View in Reaxys With RuCl(CH3(C6H4)CH3CHCH3)((C5H4N)C2N3(CH3)2)(1+)*CF3SO3 (1-) = [RuCl(CH3(C6H4)C3H7)((C5H4N)C2N3(CH3)2)] (CF3SO3), potassium hydroxide in isopropyl alcohol, Time= 2h, Reflux, Time Delgado-Rebollo, Manuela; Canseco-Gonzalez, Daniel; Hollering, Manuela; Mueller-Bunz, Helge; Albrecht, Martin; Dalton Transactions; vol. 43; nb. 11; (2014); p. 4462 - 4473 View in Reaxys With C24H29ClRhSe2 (1+)*F6P(1-), potassium hydroxide in isopropyl alcohol, acetonitrile, Time= 5h, T= 80 °C , Catalytic behavior, Reagent/catalyst, Time Prakash, Om; Sharma, Kamal Nayan; Joshi, Hemant; Gupta, Pancham L.; Singh, Ajai K.; Organometallics; vol. 33; nb. 4; (2014); p. 983 - 993 View in Reaxys With ethanol, titanium(IV) oxide, T= 31.84 °C , UV-irradiation, Kinetics Kohtani, Shigeru; Kamoi, Yuna; Yoshioka, Eito; Miyabe, Hideto; Catalysis Science and Technology; vol. 4; nb. 4; (2014); p. 1084 - 1091 View in Reaxys With sodium tetrahydroborate in methanol, Time= 2.08333h, T= 0 - 20 °C Hesse, Matthew J.; Essafi, Stephanie; Watson, Charlotte G.; Harvey, Jeremy N.; Hirst, David; Willis, Christine L.; Aggarwal, Varinder K.; Angewandte Chemie - International Edition; vol. 53; nb. 24; (2014); p. 6145 - 6149; Angew. Chem.; vol. 126; nb. 24; (2014); p. 6259 - 6263,5 View in Reaxys General procedure for the transfer hydrogenation reaction#10; General procedure: Under inert atmosphere, in a vial fitted with a screw cap, an aliquot of the tested complex (1 molpercent), from a stock solution in dichloromethane was added. The solvent was removed under vacuum and solution of KOH (0.25 mmol, 5 molpercent) in 2-propanol (2.5 mL) was added. Mesitylene (0.1 mmol) was added to the solution as internal standard. The solution was heated to 82 °C for 5 min. Subsequently, cyclohexanone (0.5 mmol) was added. After the desired reaction time an aliquot (10 μL) of the mixture was taken and quenched with 2 mL of dichloromethane. The resulting solution was filtered to remove insoluble inorganic material and the reaction progress was monitored by GC. The results for each experiment are averages over two runs.#10; With C38H50ClN2Rh, potassium hydroxide in isopropyl alcohol, Time= 4h, T= 82 °C , Inert atmosphere, Schlenk technique, Time Akinci, P. Arzu; Guelcemal, Sueleyman; Kazheva, Olga N.; Alexandrov, Grigorii G.; Dyachenko, Oleg A.; Cetinkaya, Engin; Cetinkaya, Bekir; Journal of Organometallic Chemistry; vol. 765; (2014); p. 23 - 30 View in Reaxys With C27H24ClN2RuSSe(1+)*F6P(1-), isopropyl alcohol, potassium hydroxide, Time= 3h, T= 80 °C , Reagent/catalyst Sharma, Alpesh K.; Joshi, Hemant; Sharma, Kamal Nayan; Gupta, Pancham L.; Singh, Ajai K.; Organometallics; vol. 33; nb. 13; (2014); p. 3629 - 3639 View in Reaxys 3.2 Transfer hydrogenation of ketones

29/120

2018-07-03 17:12:41

General procedure: Typical procedure for the catalytic hydrogen transfer reaction: a solution of the complexes [Ru((Ph2PO)C7H14N2Cl)(η6-arene)Cl2]Cl and [Ru((Ph2PO)-C7H14N2Cl)(η6-arene)Cl2]Cl {arene: benzene 4, 5; p-cymene 6, 7} (0.005 mmol), KOH (0.025 mmol) and the corresponding ketone (0.5 mmol) in degassed 2-propanol (5 mL) was refluxed until the reactions were completed. Then, a sample of the reaction mixture was taken off, diluted with acetone and analyzed immediately by GC. The conversions are related to the residual unreacted ketone. GC analyses were performed a Shimadzu 2010 Plus Gas Chromatograph equipped with a capillary column (5 percent biphenyl, 95 percent dimethylsiloxane) (30 m×0.32 mm×0.25 μm). The GC parameters for transfer hydrogenation of the ketones were as follows: initial temperature, 50° C; initial time, hold min 1 min; solvent delay, 4.48 min; temperature ramp 15° C/min; final temperature, 270° C, hold min 5 min; final time, 20.67 min; injector port temperature, 200° C; detector temperature, 200° C, injection volume, 2.0 μL With [Ru((Cy2PO)-C7H14N2Cl)(η6-p-cymene)Cl2]Cl, potassium hydroxide in isopropyl alcohol, Time= 0.25h, T= 82 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst Aydemir, Murat; Rafikova, Khadichakhan; Kystaubayeva, Nurzhamal; Pasa, Salih; Meric, Nermin; Ocak, Yusuf Selim; Zazybin, Alexey; Temel, Hamdi; Guerbuez, Nevin; Oezdemir, Ismail; Polyhedron; vol. 81; (2014); p. 245 - 255 View in Reaxys With sodium tetrahydroborate Umeda, Rui; Takahashi, Yuuki; Nishiyama, Yutaka; Tetrahedron Letters; vol. 55; nb. 44; (2014); p. 6113 - 6116 View in Reaxys With sodium tetrahydroborate in ethanol, T= 0 - 20 °C Bigler, Raphael; Mezzetti, Antonio; Organic Letters; vol. 16; nb. 24; (2014); p. 6460 - 6463 View in Reaxys 38 %Chromat.

With C33H33Cl2N5PRu, potassium hydroxide in isopropyl alcohol, Time= 1h, T= 82 °C , Inert atmosphere, Schlenk technique, Catalytic behavior Zhu, Zhu; Zhang, Jie; Fu, Haiyan; Yuan, Maolin; Zheng, Xueli; Chen, Hua; Li, Ruixiang; RSC Advances; vol. 4; nb. 95; (2014); p. 52734 - 52739 View in Reaxys With sodium tetrahydroborate in methanol Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys With [(ruthenium(II))3(2-[(diphenylphosphanyl)({2-[(diphenylphosphanyl)oxy]ethyl})amino]-ethyldiphenylphosphinite)(η6-pcymene)3Cl6], isopropyl alcohol, sodium hydroxide, Time= 0.333333h, T= 82 °C , Reflux, Reagent/catalyst, Time Meri, Nermin; Durap, Feyyaz; Aydemir, Murat; Baysal, Akn; Journal of Pharmacy and Pharmacology; vol. 28; nb. 11; (2014); p. 803 - 808 View in Reaxys With potassium tert-butylate in isopropyl alcohol, Time= 0.533333h, T= 90 °C , Flow reactor, Inert atmosphere Rojo, Maria Victoria; Guetzoyan, Lucie; Baxendale, Ian. R.; Organic and Biomolecular Chemistry; vol. 13; nb. 6; (2015); p. 1768 - 1777 View in Reaxys

95 %Chromat.

With C27H35IrN3 (1+)*F6P(1-), sodium t-butanolate in isopropyl alcohol, Time= 2h, T= 50 °C , Schlenk technique, Inert atmosphere, Reagent/catalyst, Temperature Sabater, Sara; Baya, Miguel; Mata, Jose A.; Organometallics; vol. 33; nb. 23; (2014); p. 6830 - 6839 View in Reaxys Reaction Steps: 2 1: C59H80FeO2P4 / tetrahydrofuran / 18 h / 65 °C 2: sodium hydroxide; water / methanol With C59H80FeO2P4, water, sodium hydroxide in tetrahydrofuran, methanol Huang, Shaofeng; Zhao, Hua; Li, Xiaoyan; Wang, Lin; Sun, Hongjian; RSC Advances; vol. 5; nb. 20; (2015); p. 15660 15667

30/120

2018-07-03 17:12:41

View in Reaxys With [(ruthenium(II))3(2-[(diphenylphosphanyl)({2-[(diphenylphosphanyl)oxy]ethyl})amino]-ethyldiphenylphosphinite)(η6-pcymene)3Cl6], isopropyl alcohol, sodium hydroxide, T= 82 °C , Inert atmosphere, Schlenk technique, Catalytic behavior Meric, Nermin; Durap, Feyyaz; Aydemir, Murat; Baysal, Akin; Applied Organometallic Chemistry; vol. 28; nb. 11; (2014); p. 803 - 808 View in Reaxys With sodium tetrahydroborate in ethanol, T= 0 - 20 °C Bigler, Raphael; Huber, Raffael; Mezzetti, Antonio; Angewandte Chemie - International Edition; vol. 54; nb. 17; (2014); p. 5171 - 5174; Angew. Chem.; vol. 127; nb. 17; (2014); p. 5260 - 5263,4 View in Reaxys With sodium tetrahydroborate in methanol, T= 0 - 20 °C Kišic, Andrea; Stephan, Michel; Mohar, Barbara; Advanced Synthesis and Catalysis; vol. 357; nb. 11; (2015); p. 2540 - 2546 View in Reaxys 2.2 General procedure for the transfer hydrogenation of ketones General procedure: A typical procedure for the catalytic hydrogen transfer reaction was as follows: A solution of the complex [Ru(bpy)2L](PF6)2], NaOH (0.025mmol) and the corresponding ketone (0.5mmol) in degassed iso-Pr-OH (5mL) were refluxed until the completion of the reaction. After this period, a sample of the reaction mixture was taken, diluted with acetone and analyzed immediately by GC. Conversions obtained were related to the residual unreacted ketone. The GC parameters were as follows: initial temperature, 110°C; initial time, 1min; solvent delay, 4.48min; temperature ramp 80°C/min; final temperature, 200°C; final time, 21.13min; injector port temperature, 200°C; detector temperature, 200°C; injection volume, 2.0μL. With [Ru(2,2'-bipyridine)2(1,5-dihydro-2H-cyclopenta[1,2-b:5,4-bη]dipyridine-2-one)](PF6)2, isopropyl alcohol, sodium hydroxide, Time= 5h, T= 82 °C Baysal, Akin; Aydemir, Murat; Durap, Feyyaz; Özkar, Saim; Yildirim, Leyla Tatar; Ocak, Yusuf Selim; Polyhedron; vol. 89; (2015); p. 55 - 61 View in Reaxys > 99 %Chromat.

With C16H33Cl2CoN5P2, hydrogen, sodium t-butanolate in tert-Amyl alcohol, Time= 24h, T= 20 °C , p= 15001.5Torr , Autoclave Rösler, Sina; Obenauf, Johannes; Kempe, Rhett; Journal of the American Chemical Society; vol. 137; nb. 25; (2015); p. 7998 - 8001 View in Reaxys

96 %Chromat.

With C22H26ClIrN2O, caesium carbonate, isopropyl alcohol, Time= 24h, T= 100 °C , Sealed tube, Reagent/catalyst Iglesias, Diego; Sabater, Sara; Azua, Arturo; Mata, Jose A.; New Journal of Chemistry; vol. 39; nb. 8; (2015); p. 6437 - 6444 View in Reaxys With sodium tetrahydroborate in methanol, water, Time= 3.5h, T= 28 °C Soni, Rina; Hall, Thomas H.; Mitchell, Benjamin P.; Owen, Matthew R.; Wills, Martin; Journal of Organic Chemistry; vol. 80; nb. 13; (2015); p. 6784 - 6793 View in Reaxys

84 %Chromat.

General procedure for the catalytic transfer hydrogenation reaction General procedure: The substrate (ketone) (2.4mmol), ruthenium catalyst (2.5μmol), and propan-2-ol (5mL) were introduced into a two necked round-bottomed flask fitted with a condenser and heated at 80°C for 15–20min in an open air atmosphere. Then, a solution of KOH (0.05mmol) in 2-propanol (5mL) was introduced to initiate the reaction and it was heated at 80°C. The progress of the reaction was monitored by GC analysis of the samples. With potassium hydroxide in isopropyl alcohol, T= 80 °C , Catalytic behavior Molla, Rostam Ali; Roy, Anupam Singha; Ghosh, Kajari; Salam, Noor; Iqubal, Md Asif; Tuhina; Islam, Sk Manirul; Journal of Organometallic Chemistry; vol. 776; (2015); p. 170 - 179 View in Reaxys

31/120

2018-07-03 17:12:41

98 %Chromat.

With C31H32ClN3ORu, isopropyl alcohol, sodium hydroxide, Time= 24h, Reflux, Inert atmosphere Çalik, Hatice Selvi; Ispir, Esin; Karabuga, Şemistan; Aslantas, Mehtet; Journal of Organometallic Chemistry; vol. 801; (2016); p. 122 - 129 View in Reaxys Stage 1: With C67H59ClN7O4P2RuS2 (1+)*Cl(1-), isopropyl alcohol, Time= 0.166667h, T= 82 °C , p= 750.075Torr , Inert atmosphere Stage 2: With potassium isopropoxide, Time= 0.05h, T= 82 °C , p= 750.075Torr , Inert atmosphere, Catalytic behavior Chai, Huining; Liu, Tingting; Wang, Qingfu; Yu, Zhengkun; Organometallics; vol. 34; nb. 21; (2015); p. 5278 - 5284 View in Reaxys

18 %Spectr. Stage 1: With Triethoxysilane, C38H60FeN7PSi2 in tetrahydrofuran, Time= 22h, T= 70 °C Stage 2: With potassium hydroxide in water Metsänen, Toni T.; Gallego, Daniel; Szilvási, Tibor; Driess, Matthias; Oestreich, Martin; Chemical Science; vol. 6; nb. 12; (2015); p. 7143 - 7149 View in Reaxys With sodium tetrahydroborate in ethanol Perna; Ricci; Scilimati; Mena; Pisano; Palmieri; Agrimi; Vitale; Journal of Molecular Catalysis B: Enzymatic; vol. 124; (2016); p. 29 - 37 View in Reaxys With RuCl(4-methyl-2-aminomethylbenzo[h]quinoline-H)(1,4-bis(diphenylphosphino)butane), sodium isopropylate in propan-1-ol, Time= 0.166667h, T= 82 °C , Inert atmosphere, Reagent/catalyst Facchetti, Sarah; Jurcik, Vaclav; Baldino, Salvatore; Giboulot, Steven; Nedden, Hans Günter; Zanotti-Gerosa, Antonio; Blackaby, Andrew; Bryan, Richard; Boogaard, Adrian; McLaren, David B.; Moya, Eduardo; Reynolds, Steven; Sandham, Karl S.; Martinuzzi, Paolo; Baratta, Walter; Organometallics; vol. 35; nb. 2; (2016); p. 277 - 287 View in Reaxys With sodium tetrahydroborate in methanol, Time= 1h, T= 20 °C Renom-Carrasco, Marc; Gajewski, Piotr; Pignataro, Luca; De Vries, Johannes G.; Piarulli, Umberto; Gennari, Cesare; Lefort, Laurent; Advanced Synthesis and Catalysis; vol. 358; nb. 4; (2016); p. 515 - 519 View in Reaxys General procedure for reduction of ketones using pre-modified borohydride General procedure: Exclusive formation of premodified [10] sodium borohydride: in a precooled vessel at 0 °C, fine grained NaBH4 (10.8 mg, 0.3 mmol) was placed in a mixture of solvents CHCl3 (0.5 mL) and EtOH (0.5 mL) for 30 min.Catalytic borohydride reduction: The initially employed catalyst/imidazole/substrate/reductant molar ratio was of 1 : 35 : 50 : 150, achieved through addition of 0.10 mmol substrate, 2 μmol catalyst, and 0.07 mmol imidazole. They were added to the solution of premodified sodium borohydride and the mixture was stirred for 5 min at 0 °C. The progress of the reaction was monitored by GC. With 1H-imidazole, sodium tetrahydroborate in ethanol, chloroform, Time= 0.25h, T= 0 °C Rayati, Saeed; Bohloulbandi, Elaheh; Zakavi, Saeed; Journal of Coordination Chemistry; vol. 69; nb. 4; (2016); p. 638 - 649 View in Reaxys Stage 1: With silver tetrafluoroborate, diethoxymethylane, C30H39ClIrN3O2 in tetrahydrofuran, Time= 15h, T= 20 °C Stage 2: With potassium carbonate in tetrahydrofuran, methanol, Time= 2h, T= 20 °C Shinohara, Kanako; Kawabata, Shun; Nakamura, Hanako; Manabe, Yoshiki; Sakaguchi, Satoshi; European Journal of Organic Chemistry; vol. 2014; nb. 25; (2014); p. 5532 - 5539 View in Reaxys With C38H38IrN4S2 (1+)*F6P(1-), ammonium formate, 3-methyl-5-p-methoxyphenyl-1-hydropyrazole in tetrahydrofuran, water, T= 40 °C Tian, Cheng; Gong, Lei; Meggers, Eric; Chemical Communications; vol. 52; nb. 22; (2016); p. 4207 - 4210 View in Reaxys

32/120

2018-07-03 17:12:41

25 %Chromat.

2.3.1. Procedure using [IrCl(cod)]2as an Ir catalyst precursor General procedure: A flask was charged with azolium salt L12 (0.02 mmol, 9.1 mg),Ag2O (0.01 mmol, 2.4 mg) and CH2Cl2(1 mL). After stirring the resulting mixture at room temperature for 2 h in the dark, CH2Cl2 was removed in vacuo. Then, a THF (1 mL) solution of [IrCl(cod)]2(0.01 mmol, 6.9 mg) was added to the reaction vessel. The resulting mixture was stirred at room temperature for an additional 4 h in the dark, filtered through a membrane filter, and evaporated to dry-ness in vacuo. Subsequently, to the resulting flask containing yellow solid of the unpurified IrCl(cod)(NHC) complex, a solution of AgBF4(0.025 mmol, 4.9 mg) in CPME (2 mL) was added, and then stirred at room temperature for 1 h. Finally, propiophenone (0.5 mmol,66 mg) and (EtO)2MeSiH (2.25 mmol, 294 mg) were added to the resulting CPME solution (see Appendix A. Supplementary data fordetails). After stirring at room temperature for 20 h under open-air conditions, K2CO3(2 mg) and MeOH (2 mL) were added. Then, the resulting mixture was stirred at room temperature for 2 h. Afterevaporation of the solvents, the residue obtained was purified bycolumn chromatography on silica gel (Et2O/n-hexane = 3:7) to give(S)-1-phenyl-1-propanol (61 mg, 91percent isolated yield). The ee was measured by chiral GLC. With silver tetrafluoroborate, diethoxymethylane, C17H25N3O2*Cl(1-)*Ir(1+)*C8H12, Time= 20h, T= 20 °C Manabe, Yoshiki; Shinohara, Kanako; Nakamura, Hanako; Teramoto, Hiro; Sakaguchi, Satoshi; Journal of Molecular Catalysis A: Chemical; vol. 421; (2016); p. 138 - 145 View in Reaxys With formic acid in water, Time= 2h, T= 40 °C , pH= 3.64, Schlenk technique, Inert atmosphere, enantioselective reaction Xie, Yinzheng; Wang, Mengpan; Wu, Xiaohui; Chen, Chen; Ma, Wenbo; Dong, Qifeng; Yuan, Mingming; Hou, Zhenshan; ChemPlusChem; vol. 81; nb. 6; (2016); p. 541 - 549 View in Reaxys With 2-butanol, sodium hydroxide, Time= 3h, T= 80 °C Kim, Daeho; Kang, Hyuntae; Park, Hyesu; Park, Sungkyun; Park, Ji Chan; Park, Kang Hyun; European Journal of Inorganic Chemistry; vol. 2016; nb. 21; (2016); p. 3469 - 3473 View in Reaxys

99 %Chromat.

With trans-RuCl(2-(2-pyridyl-6-ol)-1,10-phenanthroline)(PPh3)2PF6, potassium tert-butylate, isopropyl alcohol, Time= 0.5h, T= 80 °C , Inert atmosphere, Schlenk technique Paul, Bhaskar; Chakrabarti, Kaushik; Kundu, Sabuj; Dalton Transactions; vol. 45; nb. 27; (2016); p. 11162 - 11171 View in Reaxys

97 %Chromat.

With (4-NHCpr)Triaz(NHPiPr2)2Mn(CO)2Br, potassium tert-butylate, hydrogen in toluene, Time= 4h, T= 80 °C , p= 15001.5Torr , Inert atmosphere, Autoclave Kallmeier, Fabian; Irrgang, Torsten; Dietel, Thomas; Kempe, Rhett; Angewandte Chemie - International Edition; vol. 55; nb. 39; (2016); p. 11806 - 11809; Angew. Chem.; vol. 128; nb. 39; (2016); p. 11984 - 11988,5 View in Reaxys

98 %Chromat.

With C53H44ClN5P2Ru, potassium isopropoxide, isopropyl alcohol, Time= 0.05h, T= 82 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst Chai, Huining; Wang, Qingfu; Liu, Tingting; Yu, Zhengkun; Dalton Transactions; vol. 45; nb. 44; (2016); p. 17843 - 17849 View in Reaxys 2.2 Transfer hydrogenation of ketones General procedure: Typical procedure for the catalytic hydrogen transfer reaction: a solution of cataysts (1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-yl diphenylphosphinite chloride) (chloro 4-1,5-cyclooctadiene rhodium(I))], 2 or (1-chloro-3-(3methylimidazolidin-1-yl)propan-2-yl diphenylphosphinite chloride) (dichloro 5-pentamethylcyclopentadienyl iridium(III))], 3 (0.005mmol), NaOH (0.025mmol) and the corresponding ketone (0.5mmol) in degassed 2-propanol (5mL) were refluxed until the reactions were completed. Then, a sample of the reaction mixture was taken off, diluted with acetone and analyzed immediately by GC. The conversions are related to the residual unreacted ketone. GC analyses were performed on a Shimadzu 2010 Plus Gas Chromatograph equipped with capillary column (5percent biphenyl, 95percent dimethylsiloxane) (30m×0.32mm×0.25μm). The GC parameters for transfer hydrogenation of ketones were as follows; initial temperature, 50°C; initial time, hold min 1min; solvent delay, 4.48min; temperature ramp 15 °C/min; final temperature, 270°C, hold min 5min; final time, 20.67min; injector port temperature, 200°C; detector temperature, 200°C, injection volume, 2.0μL. With C27H33Cl2N2OPRh(1+)*Cl(1-), isopropyl alcohol, sodium hydroxide, Time= 0.5h, Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst

33/120

2018-07-03 17:12:41

Elma Karakaş, Duygu; Durap, Feyyaz; Baysal, Akın; Ocak, Yusuf Selim; Rafikova, Khadichakhan; Kaya, Eda Çavuş; Zazybin, Alexey; Temel, Hamdi; Kayan, Cezmi; Meriç, Nermin; Aydemir, Murat; Journal of Organometallic Chemistry; vol. 824; (2016); p. 25 - 32 View in Reaxys 23 : Example 23 Transfer hydrogenation of ketones. The catalyst (2.5 μηη) used was dissolved in 2.5 mL of 2-propanol. The ketone (2.0 mmol) was dissolved in 2-propanol and the solution (final volume 19.4 mL) was heated under argon at reflux. By addition of 400 μ of NaO/'Pr (0.1 M, 40 μηη) in 2-propanol and 200 of the solution containing the catalyst the reduction of the ketone started immediately and the yield was determined by GC after reaction times given in the Table 1 Table 1. Catalytic transfer hydrogenation of ketones (0.1 M) with complexes 13-20 (S/C = 5000- 20000) and NaO/'Pr (2 mol percent) in 2-propanol at 82 °C. Conv. Entry Complex Ketone S (M) S/C t (min) (percent)a 1 13 23 0.1 10000 2 98 2 14 23 0.1 5000 10 99 3 14 23 0.1 10000 15 99 4 14 23 0.1 20000 15 98 5 14 23 0.2 10000 15 96 6 14 23 0.5 10000 15 93 7 15 23 0.1 10000 2 97 8 15 23 0.1 20000 10 97 9 16 23 0.1 10000 10 96 10 17 23 0.1 10000 10 95 1 1 18 23 0.1 10000 20 93 12 19 23 0.1 10000 10 97 13 20 23 0.1 10000 2 97b 14 17 24 0.1 10000 10 94 15 15 25 0.1 10000 20 99 16 15 26 0.1 10000 40 95 17 18 26 0.1 10000 20 93 18 13 27 0.1 5000 40 99 19 18 27 0.1 5000 14 h 97 20 13 28 0.1 5000 40 99 21 18 28 0.1 5000 14 h 98 22 15 29 0.1 10000 10 99 23 15 30 0.1 10000 10 98 24 17 31 0.1 10000 5 99 25 17 32 0.1 10000 5 99 a The conversion was determined by GC analysis. b ee = 85percent (S) The catalysts of this investigation reduce a wide structural variety of ketones. In 2-propanol at reflux and in the presence of NaO/'Pr (2 mol percent) the ketones in Table 1 are efficiently reduced via transfer hydrogenation with a S/C ratio up to 20000/1 . The ketones are selected to cover a broad range of structures: alkyl-arylketones 23-27, benzophenone 29 and dialkylketones 28, 30-32. Ketones 27 and 28 having bulky tertBu substituents are reduced with near complete conversion of the substrate. Reduction of C=0 bond of 5-hexen-2-one 30 is entirely chemoselective, without saturation or isomerization of the terminal C=C bond. The use of methyl-benzo[ ?]quinoline or phenyl-benzo[ ?] quinoline ligands allows a fine tuning of catalyst activity and selectivity. The chiral complex 20 containing the (S,R)-JOSIPHOS ligand reduced 23 quantitatively to (S)-1 -phenylethanol in 2 min and with 85 percent ee. With C43H41ClN2P2Ru, sodium isopropylate, isopropyl alcohol in neat (no solvent), Time= 0.166667h, T= 82 °C , Inert atmosphere, Catalytic behavior, Reagent/catalyst, Solvent, Temperature Patent; JOHNSON MATTHEY PUBLIC LIMITED COMPANY; BALDINO, Salvatore; BARATTA, Walter; BLACKABY, Andrew; BRYAN, Richard, Charles; FACCHETTI, Sarah; JURCIK, Vaclav; NEDDEN, Hans, Guenter; (112 pag.); WO2016/193761; (2016); (A1) English View in Reaxys 76 %Spectr. Stage 1: With diphenylsilane, C54H44Cl2FeN2, trimethylsilylmethyllithium in toluene, Time= 1h, T= 25 °C , Glovebox, Inert atmosphere Stage 2: With tetrabutyl ammonium fluoride in tetrahydrofuran, Time= 6h, Inert atmosphere Yu, Xun; Zhu, Feifeng; Bu, Donglei; Lei, Hao; RSC Advances; vol. 7; nb. 25; (2017); p. 15321 - 15329 View in Reaxys 2.3. Transfer hydrogenation of acetophenone by BL1 and BL2 General procedure: The common procedure for transfer hydrogenation: particular amount of (0.04 mmol) boroncomplex solutions, NaOH (0.05 mmol), and acetophenone (5 mmol) in degassed isoPrOH(5 mL) were reuxed at 82 °C. Samples from the mixture were taken, diluted with acetoneand checked for conversion at dierent time periods. The products were compared with theunreacted acetophenone. GC analyses were applied with a Shimadzu 2010 Plus GasChromatograph having a capillary column (95percent dimethyl siloxane and 5percent biphenyl)(30 m × 0.32 mm × 0.25 m). The adjusted GC parameters were: initial temperature, 50 °C;solvent delay, 4.48 min; initial time, hold 1 min; nal temperature, 270 °C; hold 5 min; temperatureramp 15 °C min−1; injector port temperature, 200 °C; detector temperature, 200 °C,nal time, 20.67 min, and injection volume, 1.5 L. With sodium hydroxide, phenylboronic acid in isopropyl alcohol, T= 82 °C , Catalytic behavior, Reagent/catalyst Pasa, Salih; Gürler, Nedim; Temel, Hamdi; Rafikova, Khadichakhan; Aydemir, Murat; Journal of Coordination Chemistry; vol. 70; nb. 8; (2017); p. 1357 - 1367 View in Reaxys 60 %Spectr. With Ni(1,3-bis(2,4,6-trimethylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)(PPh3)2, sodium t-butanolate in isopropyl alcohol, Time= 20h, Schlenk technique, Glovebox, Reflux Sabater, Sara; Page, Michael J.; Mahon, Mary F.; Whittlesey, Michael K.; Organometallics; vol. 36; nb. 9; (2017); p. 1776 1783 View in Reaxys Reaction Steps: 2

34/120

2018-07-03 17:12:41

1: sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; C24H23ClCrIrNO3 / dichloromethane / 2 h / 25 °C / Schlenk technique; Glovebox; Inert atmosphere 2: hydrogenchloride / methanol; water / 12 h / 25 °C / Inert atmosphere With hydrogenchloride, C24H23ClCrIrNO3, sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate in methanol, dichloromethane, water Corre, Yann; Rysak, Vincent; Trivelli, Xavier; Agbossou-Niedercorn, Francine; Michon, Christophe; European Journal of Organic Chemistry; vol. 2017; nb. 32; (2017); p. 4820 - 4826 View in Reaxys 97 %Chromat.

With C66H60Cl2N10P2Ru2 (2+)*2Cl(1-), potassium isopropoxide in isopropyl alcohol, Time= 0.333333h, T= 82 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst Wang, Qingfu; Chai, Huining; Yu, Zhengkun; Organometallics; vol. 36; nb. 18; (2017); p. 3638 - 3644 View in Reaxys

99 %Chromat.

Stage 1: With C83H72Cl2N12P2Ru2, isopropyl alcohol, Time= 0.166667h, T= 82 °C , Inert atmosphere, Schlenk technique Stage 2: With potassium isopropoxide, Time= 0.0166667h, T= 82 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst Liu, Tingting; Chai, Huining; Wang, Liandi; Yu, Zhengkun; Organometallics; vol. 36; nb. 15; (2017); p. 2914 - 2921 View in Reaxys Screening of substrates General procedure: A general procedure was applied depending on the physical state of the substrate, as follows: a. For solid ketones: The catalyst (3, 9µmol) and the ketone (1.85mmol) were added to a Schlenk flask. Air was purged by three vacuum/gas (N2) cycles. Degassed iPrOH (3.3mL) was added, followed by base from a freshly prepared stock solution of KOH in iPrOH (90µmol, 200µL from stock solution 0.45mol/L). A reflux condenser was connected to the Schlenk and the system was heated to 80°C in an oil bath. After the reaction time (24h) the heating was stopped and the yield was determined by 1H NMR. b. For liquid ketones: The catalyst (3, 9µmol) was added to a Schlenk flask. Air was purged by three vacuum/gas (N2) cycles. Then, the ketone (1.85mmol), iPrOH (3.3mL), and KOH (90µmol, 200µL from stock iPrOH solution 0.45mol/L) were added with a syringe. A reflux condenser was connected to the Schlenk and the system was heated to 80°C in an oil bath. After the reaction time (24h) the heating was stopped and the yield was determined by 1H NMR With C50H54IrO3P2 (1+)*F6P(1-), isopropyl alcohol, potassium hydroxide, Time= 24h, T= 80 °C , Schlenk technique, Inert atmosphere Landaeta, Vanessa R.; Rosa, Abel D. Salazar-La; Rodríguez-Lugo, Rafael E.; Inorganica Chimica Acta; vol. 470; (2018); p. 303 - 311 View in Reaxys Stage 1: With diethoxymethylane, phosphoric acid triphenyl ester, diethylzinc in tetrahydrofuran, hexane, Time= 16h, T= 20 °C , Inert atmosphere Stage 2: With sodium hydroxide in methanol, water, Time= 12h, Inert atmosphere Bouhachicha; Ngo Ndimba; Roisnel; Lalli; Argouarch; New Journal of Chemistry; vol. 41; nb. 12; (2017); p. 4767 - 4770 View in Reaxys With C19H33ClIrN3O, sodium isopropylate in isopropyl alcohol, Time= 0.25h, Inert atmosphere, Reflux, Catalytic behavior Mazloomi, Zahra; Pretorius, René; Pàmies, Oscar; Albrecht, Martin; Diéguez, Montserrat; Inorganic Chemistry; vol. 56; nb. 18; (2017); p. 11282 - 11298 View in Reaxys

93 %Chromat.

2.3. General procedure for TH of ketones catalyzed by 3 General procedure: Under a nitrogen atmosphere, a mixture of ketone (2 mmol),catalyst 3 (0.01 mmol), and 2-propanol (18 mL) was stirred at 82 °C for 10 min. Then, iPrOK solution in 2-propanol (2.0 mL,0.1 mol/L, 0.2 mmol) was introduced to initiate the reaction.The reaction mixture was stirred at reflux. After the statedtime, 0.1 mL of the reaction mixture was sampled and immediatelydiluted with 0.5 mL of 2-propanol precooled to 0 °C, andfiltered through a short pad of celite to quench the reaction byremoving the complex catalyst. The resultant filtrate was usedfor GC analysis. After the reaction was finished, the mixture wascondensed under reduced pressure and subjected to flash silicagel column chromatography to afford the alcohol product. The alcohol products were identified by comparison with authenticsamples using NMR and GC analyses.

35/120

2018-07-03 17:12:41

Stage 1: With C49H44Cl2N9P2Ru(1+)*Cl(1-), isopropyl alcohol, Time= 0.166667h, T= 82 °C , Inert atmosphere, Schlenk technique Stage 2: With potassium isopropoxide, isopropyl alcohol, Time= 2h, Reflux, Inert atmosphere, Schlenk technique Wang, Liandi; Liu, Tingting; Chinese Journal of Catalysis; vol. 39; nb. 2; (2018); p. 327 - 333 View in Reaxys With methanol, sodium tetrahydroborate, T= 20 °C Liu, Sensheng; Liu, Huan; Zhou, Haifeng; Liu, Qixing; Lv, Jinliang; Organic Letters; vol. 20; nb. 4; (2018); p. 1110 - 1113 View in Reaxys With isopropyl alcohol, potassium hydroxide, Time= 24h, T= 60 °C , Inert atmosphere, Catalytic behavior Wisser, Florian M.; Mohr, Yorck; Quadrelli, Elsje Alessandra; Farrusseng, David; Canivet, Jérôme; ChemCatChem; vol. 10; nb. 8; (2018); p. 1778 - 1782 View in Reaxys

Rx-ID: 1548719 View in Reaxys 4/280 Yield

Conditions & References With borane, dihydrogen peroxide, 1.) THF, 4 h, Multistep reaction Medlik-Balan, A.; Klein, J.; Tetrahedron; vol. 36; nb. 2; (1980); p. 299 - 304 View in Reaxys Reaction Steps: 2 1: trifluorormethanesulfonic acid; water / 2,2,2-trifluoroethanol / 48 h / 40 °C / Inert atmosphere 2: sodium tetrahydroborate; methanol / 20 °C With methanol, sodium tetrahydroborate, trifluorormethanesulfonic acid, water in 2,2,2-trifluoroethanol Liu, Sensheng; Liu, Huan; Zhou, Haifeng; Liu, Qixing; Lv, Jinliang; Organic Letters; vol. 20; nb. 4; (2018); p. 1110 - 1113 View in Reaxys O

Rx-ID: 40471831 View in Reaxys 5/280 Yield

Conditions & References With C31H47ClNRh, hydrogen in ethyl acetate, Time= 24h, T= 20 °C , p= 3750.38Torr , Autoclave, Molecular sieve Wei, Yu; Rao, Bin; Cong, Xuefeng; Zeng, Xiaoming; Journal of the American Chemical Society; vol. 137; nb. 29; (2015); p. 9250 - 9253 View in Reaxys With iridium, hydrogen, Time= 10h, T= 75 °C , p= 22502.3Torr , Autoclave, Sealed tube, Ionic liquid, Overall yield = 17.7 percent; chemoselective reaction Jiang, He-Yan; Xu, Jie; Sun, Bin; Applied Organometallic Chemistry; vol. 32; nb. 4; (2018); Art.No: E4260 View in Reaxys HO

Rx-ID: 2059287 View in Reaxys 6/280 Yield 100 %

Conditions & References 2.3. General procedure for the 1-phenyl-2-propene-1-ol allylic isomerization in THF General procedure: A solution containing 6.4 × 10−3mmol of precatalyst and0.13 mmol of substrate (20 equiv.) in 2 mL of THF was transferred into a 5 mL glass vial which was then placed under argon into a stainless steel autoclave equipped with a mag-

36/120

2018-07-03 17:12:41

netic stirring bar. The reaction vessel was pressurized with H2 to 30 bar and stirred for the desired time at room temperature. Then pressure was released andthe reaction vessel was stirred for the desired time at controlledtemperature under a dihydrogen atmosphere at 1 bar. Alterna-tively, after venting the H2pressure used for the catalyst activation,the residual H2was purged with argon by continuous flushingbefore continuing the reaction. The pure products were obtainedby chromatography of the reaction mixture on silica gel using dichloromethane as eluent and then analyzed by NMR spectrosopyand chiral GC for the determination of the yields and enantiomeric excesses. With C35H41ClFeIrPS, hydrogen, sodium methylate in tetrahydrofuran, Time= 2h, T= 25 °C , p= 22502.3Torr , Autoclave, Inert atmosphere, Reagent/catalyst Titova, Ekaterina M.; Rahaman, S.M. Wahidur; Shubina, Elena S.; Poli, Rinaldo; Belkova, Natalia V.; Manoury, Eric; Journal of Molecular Catalysis A: Chemical; vol. 426; (2017); p. 376 - 380 View in Reaxys 92 %

With 1, 1'-bis (diphenylphosphino)-ferrocene, [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, Butane-1,4-diol, potassium tert-butylate, Time= 24h, T= 110 °C , Inert atmosphere Maytum, Hannah C.; Francos, Javier; Whatrup, David J.; Williams, Jonathan M. J.; Chemistry - An Asian Journal; vol. 5; nb. 3; (2010); p. 538 - 542 View in Reaxys

90 %

With isopropyl alcohol, [{RuCl(μ-Cl)(η6-C6Me6)}2], Time= 15h, T= 82 °C Cadierno, Victorio; Francos, Javier; Gimeno, Jose; Nebra, Noel; Chemical Communications; nb. 24; (2007); p. 2536 - 2538 View in Reaxys

90 %

With [RuCl2(hexamethylbenzene)]2, caesium carbonate, isopropyl alcohol, Time= 15h, T= 82 °C , Inert atmosphere Cadierno, Victorio; Crochet, Pascale; Francos, Javier; Garcia-Garrido, Sergio E.; Gimeno, Jose; Nebra, Noel; Green Chemistry; vol. 11; nb. 12; (2009); p. 1992 - 2000 View in Reaxys

72 %

With hydrogenchloride, lithium aluminium tetrahydride, zirconium(IV) chloride in tetrahydrofuran, T= 30 °C , further allyl alcohols; further zirconium catalyst; deuterium labelling experiments, Mechanism Sato, Fumie; Tomuro, Yasuji; Ishikawa, Hiroaki; Sato, Masao; Chemistry Letters; (1980); p. 99 - 102 View in Reaxys With hydrogenchloride, lithium aluminium tetrahydride, zirconium(IV) chloride, 1.) THF, 30 deg C, 3 h, Yield given. Multistep reaction Sato, Fumie; Tomuro, Yasuji; Ishikawa, Hiroaki; Sato, Masao; Chemistry Letters; (1980); p. 99 - 102 View in Reaxys

85 %Chromat.

With isopropyl alcohol, Time= 2h, p= 760.051Torr , Inert atmosphere, Heating Kim, Jung Won; Koike, Takeshi; Kotani, Miyuki; Yamaguchi, Kazuya; Mizuno, Noritaka; Chemistry - A European Journal; vol. 14; nb. 13; (2008); p. 4104 - 4109 View in Reaxys

76 %Chromat.

With isopropyl alcohol, Time= 2h, T= 89.84 °C , p= 760.051Torr , Inert atmosphere Yamaguchi, Kazuya; Koike, Takeshi; Kim, Jung Won; Ogasawara, Yoshiyuki; Mizuno, Noritaka; Chemistry - A European Journal; vol. 14; nb. 36; (2008); p. 11480 - 11487 View in Reaxys With C19H33ClIrN3O, sodium isopropylate in isopropyl alcohol, Time= 1h, Inert atmosphere, Reflux, Catalytic behavior Mazloomi, Zahra; Pretorius, René; Pàmies, Oscar; Albrecht, Martin; Diéguez, Montserrat; Inorganic Chemistry; vol. 56; nb. 18; (2017); p. 11282 - 11298 View in Reaxys

37/120

2018-07-03 17:12:41

Rx-ID: 7159158 View in Reaxys 7/280 Yield 100 %

Conditions & References 49 Patent; SOLVIAS AG; WO2004/50585; (2004); (A1) English View in Reaxys

99 %

47 Patent; SOLVIAS AG; WO2004/50585; (2004); (A1) English View in Reaxys

98 %

51 Patent; SOLVIAS AG; WO2004/50585; (2004); (A1) English View in Reaxys

97 %

48 Patent; SOLVIAS AG; WO2004/50585; (2004); (A1) English View in Reaxys

97 %

Patent; Agency for Science, Technology and Research; US2012/136164; (2012); (A1) English View in Reaxys

94 %

52 Patent; SOLVIAS AG; WO2004/50585; (2004); (A1) English View in Reaxys

92 %

2 : General Procedure for the Reduction of Ketones General procedure: To a 25 ml round bottom flask containing 5 ml N,N-dimethylformamide, was added 1-hydrosilatrane (0.263 g, 2.0 mmol), and ketone (1.0 mmol). The resulting solution was stirred for 1 minute, after which 1 M t-BuOK in THF (1.0 mmol, 1.0 ml) was added. Reaction mixture was allowed to stir for 30 min. Reaction was quenched with 25 ml 3 M HCl, and extracted with 30 mL ethyl acetate. Organic layer was washed with brine (50 ml×3), and dried with anhydrous sodium sulphate. After filtration, the solvent was removed under vacuum to yield product. With potassium tert-butylate, 1-hydrosilatrane in tetrahydrofuran, N,N-dimethyl-formamide, Time= 0.5h Patent; Board of Trustees of Northern Illinois University; Adler, Marc J.; Gilbert, Thomas M.; Varjosaari, Sami E.; Skrypai, Vladislav; (22 pag.); US2017/362151; (2017); (A1) English View in Reaxys

80 %

50 Patent; SOLVIAS AG; WO2004/50585; (2004); (A1) English View in Reaxys

80 %

53 Patent; SOLVIAS AG; WO2004/50585; (2004); (A1) English View in Reaxys

56 %

54 Patent; SOLVIAS AG; WO2004/50585; (2004); (A1) English View in Reaxys

48 %

56 Patent; SOLVIAS AG; WO2004/50585; (2004); (A1) English View in Reaxys

45 %

38/120

2018-07-03 17:12:41

Patent; SOLVIAS AG; WO2004/50585; (2004); (A1) English View in Reaxys 14 %

57 Patent; SOLVIAS AG; WO2004/50585; (2004); (A1) English View in Reaxys Cervinka,O.; Fusek,J.; Collection of Czechoslovak Chemical Communications; vol. 38; (1973); p. 441 - 446 View in Reaxys Kuchar; Brunova; Rejholec; et al.; Collection of Czechoslovak Chemical Communications; vol. 41; nb. 2; (1976); p. 633 - 646 View in Reaxys Weinges,K. et al.; Chemische Berichte; vol. 104; (1971); p. 3594 - 3606 View in Reaxys Ford,W.T.; Pietsek,D.J.J.; Journal of the American Chemical Society; vol. 97; (1975); p. 2194 - 2198 View in Reaxys Mamalis,P. et al.; Journal of Medicinal Chemistry; vol. 8; (1965); p. 684 - 691 View in Reaxys Schulz; Jassmann; Bekker; Die Pharmazie; vol. 26; nb. 8; (1971); p. 477 - 481 View in Reaxys Risaliti,A. et al.; Tetrahedron; vol. 25; (1969); p. 143 - 148 View in Reaxys Gaudemar,M.; Bulletin de la Societe Chimique de France; (1962); p. 974 - 987 View in Reaxys Gocmen,M. et al.; Bulletin de la Societe Chimique de France; (1973); p. 1310 - 1317 View in Reaxys Traynelis,V.J. et al.; Journal of Organic Chemistry; vol. 27; (1962); p. 2377 - 2383 View in Reaxys Giacomelli,G. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 2370 - 2376 View in Reaxys Giacomelli,G. et al.; Journal of Organic Chemistry; vol. 43; nb. 9; (1978); p. 1790 - 1793 View in Reaxys Harnden,M.R. et al.; Journal of the Chemical Society [Section] C: Organic; (1968); p. 2095 - 2096 View in Reaxys Blomberg,C.; Coops,J.; Recueil des Travaux Chimiques des Pays-Bas; vol. 83; (1964); p. 1083 - 1095 View in Reaxys Schaap,A.; Arense,J.F.; Recueil des Travaux Chimiques des Pays-Bas; vol. 87; (1968); p. 1249 - 1263 View in Reaxys Blomberg,C.; Hartog,F.A.; Synthesis; (1977); p. 18 - 30 View in Reaxys Meyers,A.I.; Kendall,P.M.; Tetrahedron Letters; nb. 14; (1974); p. 1337 - 1340 View in Reaxys Acker,R.-D.; Tetrahedron Letters; nb. 39; (1977); p. 3407 - 3410 View in Reaxys Mamedov,S. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 2877 - 2881,2910 - 2913 View in Reaxys Hayashi,T. et al.; Journal of Organometallic Chemistry; vol. 112; (1976); p. 253 - 262 View in Reaxys Brown; Zweifel; Journal of the American Chemical Society; vol. 82; (1960); p. 4708,4709 View in Reaxys Asami et al.; Bulletin of the Chemical Society of Japan; vol. 51; (1978); p. 1869 View in Reaxys Meyers; Comins; Tetrahedron Letters; (1978); p. 5179 View in Reaxys Rand; Dolinski; Journal of Organic Chemistry; vol. 31; (1966); p. 4061,4066 View in Reaxys Seyden-Penne; Schaal; Bulletin de la Societe Chimique de France; (1969); p. 3653 View in Reaxys Lange et al.; Roczniki Chemii; vol. 35; (1961); p. 1645,1648 View in Reaxys Cervinka; Collection of Czechoslovak Chemical Communications; vol. 27; (1962); p. 567,571, 572 View in Reaxys

39/120

2018-07-03 17:12:41

Almasi et al.; Revue Roumaine de Chimie; vol. 9; (1964); p. 531,538 View in Reaxys Kikugawa; Chemical and Pharmaceutical Bulletin; vol. 24; (1976); p. 1059,1060, 1062 View in Reaxys Mukaiyama et al.; Journal of the American Chemical Society; vol. 101; (1979); p. 1455,1459 View in Reaxys Nakagawa; Minami; Tetrahedron Letters; (1972); p. 343,345 View in Reaxys Bavin; Journal of Medicinal Chemistry; vol. 9; (1966); p. 52 View in Reaxys Nefedow et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 35; (1965); p. 509,509 View in Reaxys Henry-Basch et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 260; (1965); p. 3694 View in Reaxys Thakar; Rao; Journal of Scientific and Industrial Research, Section B: Physical Sciences; vol. 21; (1962); p. 583,586 View in Reaxys Vigneron; Jacquet; Tetrahedron; vol. 32; (1976); p. 939,944 View in Reaxys Huet et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 262; (1966); p. 1328 View in Reaxys Nasipuri; Sarker; Journal of the Indian Chemical Society; vol. 44; (1967); p. 165 View in Reaxys Yamaguchi et al.; Journal of Organic Chemistry; vol. 42; (1977); p. 1578 View in Reaxys Giacomelli et al.; Tetrahedron Letters; (1971); p. 4135 View in Reaxys Saigo et al.; Chemistry Letters; (1979); p. 545 View in Reaxys Bogat-skii et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 47; (1977); p. 2297,2095,2099 View in Reaxys Baba; Yuki Gosei Kagaku Kyokaishi; vol. 27; (1969); p. 264,265, 266; ; vol. 71; nb. 13166 View in Reaxys Battioni; Chodkiewicz; Bulletin de la Societe Chimique de France; (1972); p. 2068 View in Reaxys Doiuchi; Minoura; Israel Journal of Chemistry; vol. 15; (1976); p. 84,85,87 View in Reaxys Shorygina; Elkin; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); (1970); p. 1052,1055; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1970); p. 1114 View in Reaxys Felkin et al.; Journal of Organometallic Chemistry; vol. 134; (1977); p. 265,266-270, 274,277-278 View in Reaxys Noyori et al.; Journal of the American Chemical Society; vol. 101; (1979); p. 3129 View in Reaxys Ojima; Chemistry Letters; (1974); p. 223,224 View in Reaxys Line't et al.; Arzneimittel Forschung; vol. 12; (1962); p. 347,348 View in Reaxys Dimmel et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 3092 View in Reaxys Pepin et al.; Canadian Journal of Chemistry; vol. 56; (1978); p. 41,43 View in Reaxys Jacquet; Vigneron; Tetrahedron Letters; (1974); p. 2065 View in Reaxys Mukaiyama et al.; Chemistry Letters; (1978); p. 219,220,221 View in Reaxys Pines; Schappell; Journal of Organic Chemistry; vol. 29; (1964); p. 1503,1507 View in Reaxys Christol et al.; Bulletin de la Societe Chimique de France; (1961); p. 2317 View in Reaxys Gelli et al.; Annali di Chimica (Rome, Italy); vol. 54; (1964); p. 1143,1146 View in Reaxys

40/120

2018-07-03 17:12:41

Kropf et al.; Tetrahedron Letters; (1969); p. 3427,3428 View in Reaxys Freidlin et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); (1969); p. 2137; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1969); p. 2290 View in Reaxys Sano et al.; Nippon Kagaku Kaishi; (1972); p. 1699,1700,1701 View in Reaxys Schostakowskii et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 2620,2641 View in Reaxys Mori et al.; Tetrahedron Letters; (1973); p. 4951,4953, 4954 View in Reaxys Henry-Basch et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 262; (1966); p. 598 View in Reaxys Laurent et al.; Bulletin de la Societe Chimique de France; (1967); p. 1995 View in Reaxys Ashby; Walker; Journal of Organic Chemistry; vol. 33; (1968); p. 3821 View in Reaxys Schaal; Seyden-Penne; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 266; (1968); p. 217 View in Reaxys Ivanov et al.; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 2120,2069 View in Reaxys Felkin; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 266; (1968); p. 1611 View in Reaxys Piekarski et al.; Bulletin de la Societe Chimique de France; (1968); p. 4063 View in Reaxys Patent; UNIVERSITY OF NOTTINGHAM; WO2006/79819; (2006); (A2) English View in Reaxys Patent; Lin, Wenbin; Hu, Aiguo; Ngo, Helen L.; US2004/192543; (2004); (A1) English View in Reaxys 17 Patent; TAKASAGO INTERNATIONAL CORPORATION; TOUGE, Taichiro; NARA, Hideki; HAKAMADA, Tomohiko; WO2012/26201; (2012); (A1) English View in Reaxys Banthorpe,D.V. et al.; Journal of the Chemical Society; (1960); p. 4054 - 4087 View in Reaxys

O HO

Rx-ID: 8694459 View in Reaxys 8/280 Yield 87 %

Conditions & References Stage 1: With lithium tri-n-butylmagnesiate in tetrahydrofuran, hexane, T= -78 °C , Metallation Stage 2: in tetrahydrofuran, hexane, Time= 0.5h, T= 0 °C , Addition Kitagawa, Kazuya; Inoue, Atsushi; Shinokubo, Hiroshi; Oshima, Koichiro; Angewandte Chemie - International Edition; vol. 39; nb. 14; (2000); p. 2481 - 2483 View in Reaxys With n-butyllithium Hu, Bin; Meng, Meng; Jiang, Shanshan; Deng, Weiping; Chinese Journal of Chemistry; vol. 30; nb. 6; (2012); p. 1289 - 1294 View in Reaxys Stage 1: With iodine, magnesium in tetrahydrofuran, Time= 0.5h, Inert atmosphere, Grignard Reaction Stage 2: in tetrahydrofuran, T= 0 °C , Inert atmosphere

41/120

2018-07-03 17:12:41

Guha, Somraj; Rajeshkumar, Venkatachalam; Kotha, Surya Srinivas; Sekar, Govindasamy; Organic Letters; vol. 17; nb. 3; (2015); p. 406 - 409 View in Reaxys Stage 1: With iodine, magnesium in tetrahydrofuran, Time= 0.5h, Inert atmosphere Stage 2: in tetrahydrofuran, T= 0 °C , Inert atmosphere Guha, Somraj; Kazi, Imran; Mukherjee, Pranamita; Sekar, Govindasamy; Chemical Communications; vol. 53; nb. 79; (2017); p. 10942 - 10945 View in Reaxys HO

Rx-ID: 11207938 View in Reaxys 9/280 Yield

Conditions & References

7 %, 93 %

2.3. General procedure for the 1-phenyl-2-propene-1-ol allylic isomerization in THF General procedure: A solution containing 6.4 × 10−3mmol of precatalyst and0.13 mmol of substrate (20 equiv.) in 2 mL of THF was transferred into a 5 mL glass vial which was then placed under argon into a stainless steel autoclave equipped with a magnetic stirring bar. The reaction vessel was pressurized with H2 to 30 bar and stirred for the desired time at room temperature. Then pressure was released andthe reaction vessel was stirred for the desired time at controlledtemperature under a dihydrogen atmosphere at 1 bar. Alterna-tively, after venting the H2pressure used for the catalyst activation,the residual H2was purged with argon by continuous flushingbefore continuing the reaction. The pure products were obtainedby chromatography of the reaction mixture on silica gel using dichloromethane as eluent and then analyzed by NMR spectrosopyand chiral GC for the determination of the yields and enantiomeric excesses. With C35H41FePRhS, hydrogen, sodium methylate in tetrahydrofuran, Time= 16h, T= 82 °C , p= 22502.3Torr , Autoclave, Inert atmosphere Titova, Ekaterina M.; Rahaman, S.M. Wahidur; Shubina, Elena S.; Poli, Rinaldo; Belkova, Natalia V.; Manoury, Eric; Journal of Molecular Catalysis A: Chemical; vol. 426; (2017); p. 376 - 380 View in Reaxys

5 % Spectr., With triethylamine, 10 wt. % palladium on activated carbon in toluene, Time= 3h, T= 150 °C 91 % Coquerel, Yoann; Bremond, Paul; Rodriguez, Jean; Journal of Organometallic Chemistry; vol. 692; nb. 22; (2007); p. 4805 Spectr. 4808 View in Reaxys 82 %Chromat.

With {(η3:η2:η3-C12H18)RuCl2}, water, sodium formate, Time= 24h, T= 100 °C , Inert atmosphere Cadierno, Victorio; Crochet, Pascale; Francos, Javier; Garcia-Garrido, Sergio E.; Gimeno, Jose; Nebra, Noel; Green Chemistry; vol. 11; nb. 12; (2009); p. 1992 - 2000 View in Reaxys

Rx-ID: 46099048 View in Reaxys 10/280 Yield

Conditions & References With hydrogenchloride in methanol, water, Time= 12h, T= 25 °C , Inert atmosphere Corre, Yann; Rysak, Vincent; Trivelli, Xavier; Agbossou-Niedercorn, Francine; Michon, Christophe; European Journal of Organic Chemistry; vol. 2017; nb. 32; (2017); p. 4820 - 4826 View in Reaxys

42/120

2018-07-03 17:12:41

Rx-ID: 46287995 View in Reaxys 11/280 Yield

Conditions & References

14 %Chromat., 38 %Chromat., 44 %Chromat.

With C21H17ClN5ORu(1+)*Cl(1-), caesium carbonate, Time= 24h, T= 85 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst Chakrabarti, Kaushik; Maji, Milan; Panja, Dibyajyoti; Paul, Bhaskar; Shee, Sujan; Das, Gourab Kanti; Kundu, Sabuj; Organic Letters; vol. 19; nb. 18; (2017); p. 4750 - 4753 View in Reaxys O

O HO HO

Rx-ID: 46287996 View in Reaxys 12/280 Yield

Conditions & References

64 %Chromat., 35 %Chromat.

With C21H17ClN5ORu(1+)*Cl(1-), sodium methylate, Time= 24h, T= 85 °C , Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst Chakrabarti, Kaushik; Maji, Milan; Panja, Dibyajyoti; Paul, Bhaskar; Shee, Sujan; Das, Gourab Kanti; Kundu, Sabuj; Organic Letters; vol. 19; nb. 18; (2017); p. 4750 - 4753 View in Reaxys

H Al

Rx-ID: 8566456 View in Reaxys 13/280 Yield 85 %

Conditions & References With titanium(IV) isopropylate in tetrahydrofuran, T= 0 °C Liu, Dacai; Ouyang, Kunbing; Yang, Nianfa; Tetrahedron; vol. 72; nb. 7; (2016); p. 1018 - 1023 View in Reaxys

94 % Chromat.

With Hexamethylphosphorous triamide in hexane, toluene, Time= 3h, T= -78 °C , Addition Schneider, Christoph; Brauner, Joerg; Tetrahedron Letters; vol. 41; nb. 17; (2000); p. 3043 - 3046 View in Reaxys Stage 1: With titanium(IV) isopropylate, (S)-4,4',6,6'-tetraperfluorooctyl-1,1'-binaphthyl-2,2'-diol in hexane, Time= 0.25h, T= 53 °C Stage 2: in hexane, T= 53 °C Tian, Yuan; Yang, Qing Chuan; Mak, Thomas C.W.; Chan, Kin Shing; Tetrahedron; vol. 58; nb. 20; (2002); p. 3951 - 3961 View in Reaxys With titanium(IV) isopropylate in tetrahydrofuran, Time= 6h, T= 0 °C Chen, Qian; Ou, Jun; Chen, Guo-Shu; Liu, Tian-Hui; Xie, Bin; Liang, Hai-Bo; Xie, Li-Qiong; Chen, Yi-Xin; Chirality; vol. 26; nb. 5; (2014); p. 268 - 271 View in Reaxys O

Rx-ID: 28530071 View in Reaxys 14/280

43/120

2018-07-03 17:12:41

Yield

Conditions & References With tert.-butylhydroperoxide, [(pymox-Me2)2RuCl2]+BF4- in water, T= 20 °C Yi, Chae S.; Kwon, Ki-Hyeok; Lee, Do W.; Organic Letters; vol. 11; nb. 7; (2009); p. 1567 - 1569 View in Reaxys

6 %Chromat., 94 %Chromat.

2.1.4. General procedure for the oxidation of ethyl benzenes General procedure: A mixture containing substrate (0.5 mmol), t-butyl hydroperox-ide (TBHP) (1 mmol) and Au/rGO (15 mg) was mixed in acetonitrile(5 mL). The resulting mixture was stirred at 70C for 24 h. Progressof the reaction was monitored by TLC (silica gel; n-hexane/ethylacetate). After desired time, the crude material was extracted withethyl acetate and the extract concentrated under reduced pressure.The obtained material was analyzed by gas chromatography usingdodecane as internal standard. With tert.-butylhydroperoxide in acetonitrile, Time= 24h, T= 70 °C , Catalytic behavior, Reagent/catalyst Pocklanova, Radka; Gawande, Manoj B.; Rathi, Anuj K.; Datta, Kasibhatta Kumara Ramanatha; Ranc, Vaclav; Cepe, Klara; Petr, Martin; Varma, Rajender S.; Kvitek, Libor; Zboril, Radek; Journal of Molecular Catalysis A: Chemical; vol. 424; (2016); p. 121 - 127 View in Reaxys

HO O

Rx-ID: 41526500 View in Reaxys 15/280 Yield

Conditions & References 4 : Enzyme-Catalysed Kinetic Resolution of Chiral Esters General procedure: Preparative enzymatic conversions of racemic chiral esters were performed on a 10 ml scale with 0.25-0.3 mmol substrate and 1-2 ml enzyme preparation (50 U/ml based on p-nitrophenyl butyrate assay) in 50 mM phosphate-buffer pH 7.5. The reaction was stirred in a water bath at 37° C. up to a conversion of 50percent. After addition of the same volume A. dest educts and/or products were extracted as follows: ethylesters were acidified with HCl (aq. 10percent, 10 ml) and afterwards extracted with 4×20 ml diethylether. Methylesters were extracted first using a neutral to slight alkaline pH, afterwards the reaction was acidified to extract the reaction products. Acetylated substrates were extracted with 4×20 ml methylen chloride. In each case the organic phases were pooled, dried with Na2SO4 and afterwards evaporated. Reaction educts and products were separated by chromatography and analysed by NMR, polarimetric and GC-analysis to determine the grade of purity, the degree and sense of optical rotation and the enantiomeric excess. With MetProLeuAspGlnProThrAlaAlaPheLeuAspPheLeuArgSerSerGlyGlyLysProLeuTyrGluLeuProLeuAlaGluAlaArgAlaAlaMetAlaMetGlySerGlnLeuGlyAlaProProAlaAspValGlyArgIleValAspArgSerIleAspValProGlyGlyAlaValAlaLeuArgIleTyrThrProAlaThrThrLysAlaGlyGlyLeuLeuProAlaIleLeuGlnTyrHisGlyGlyGlyPheValLeuGlyAsnLeuAspThrHisGluSerIleAlaArgPheTyrCysAlaHisAlaGlyAlaValValIleSerValAspTyrArgLeuAlaProGluHisArgPheProThrGlnValGluAspSerPheAlaAlaLeuThrTrpValSerGluHisAlaSerGluLeuGlyValAspProAlaArgValAlaValAlaGlyAspSerAlaGlyGlyAsnLeuAlaThrValMetCysLeuLeuAlaLysAlaArgGlyGlyProArgIleAlaCysGlnAlaLeuLeuTyrProValAlaAspPheArgProGluGlnValTyrAlaSerHisAlaGlnPheGlyAspGlySerTyrPheLeuSerSerLysAspMetAspTrpPheArgAlaSerTyrPheThrAspValAlaSerGlnAlaAlaGluProThrAlaSerProMetAlaThrThrAspLeuSerGlyLeuProProAlaLeuValThrThrAlaGlyCysAspProLeuLeuAspGluGlyArgAlaTyrAlaAspArgLeuLysAlaAlaGlyValProValAspTyrArgCysPheGluThrThrIleHisAlaCysAlaSerPheAlaGlyThrIleProAlaGlyLeuAspMetLeuGlyPheValAlaAspTrpLeuAlaAlaHisThrLys in aq. phosphate buffer, T= 37 °C , pH= 7.5, Enzymatic reaction, Reagent/catalyst, enantioselective reaction Patent; B.R.A.I.N. AG; Liebeton, Klaus; Eck, Jürgen; Bornscheuer, Uwe; Böttcher, Dominique; Langer, Peter; Bellur, Esen; US9193961; (2015); (B2) English View in Reaxys With Fusarium proliferatum mycelia in aq. phosphate buffer, pH= 7.2, Microbiological reaction Jadhav, Dipesh D.; Patil, Harshal S.; Chaya, Patil S.; Thulasiram, Hirekodathakallu V.; Tetrahedron Letters; vol. 57; nb. 41; (2016); p. 4563 - 4567 View in Reaxys With Sulfolobus tokodaii esterase ST0071, G274W mutant in aq. buffer, Time= 1.5h, T= 50 °C , pH= 8, Enzymatic reaction, Reagent/catalyst, Temperature, Time

44/120

2018-07-03 17:12:41

Ozaki, Masanaru; Kawakami, Norifumi; Ohta, Hiromichi; Miyamoto, Kenji; Biocatalysis and Biotransformation; vol. 34; nb. 5; (2016); p. 249 - 252 View in Reaxys

Rx-ID: 42519710 View in Reaxys 16/280 Yield

Conditions & References Peroxidation of n-propylbenzene under air saturated conditions In a 50 mL, two-neck round bottom flask, catalyst (100 mg) and cumene hydroperoxide (140 mmol) were added to 10 mL of npropylbenzene and the reaction was heated to 40 or 80 °C. An aliquot was taken from thereaction mixture every hour, centrifuged and subsequently analyzed by HPLC. Control reactions were carried out using the support itself and in the absence of catalyst. With Cumene hydroperoxide, T= 40 °C , Temperature Crites, Charles-Oneil L.; Netto-Ferreira, José Carlos; Hallett-Tapley, Geniece L.; Scaiano, Juan Cesar; Journal of the Brazilian Chemical Society; vol. 27; nb. 2; (2016); p. 334 - 340 View in Reaxys H 2N

Rx-ID: 42865451 View in Reaxys 17/280 Yield

Conditions & References 6 : example 6 General procedure: A vial containing a solution of 1 (0.2 mmol, 1.0 equiv.), HC02NH4(37.8 mg, 2 mmol, 10.0 equiv.) and Pd°nanocatalyst (Pd°-AmP-MFC, 2.68 mg, 0.002 mmol, 8 wtpercent, 1 molpercent) in MeOH (0.3 mL) under ISb atmosphere was stirred at 70°C for the time shown in table 4. Next, the solvent was evaporated and a solution of DIPEA (N,N-Diisopropylethylamine, 0.052 mL, 0.3 mmol, 1.5 equiv.) in dry dichloromethane (2.0 ml_) followed by the addition of methoxy acetylchloride (0.4 mL, 0.51 mmol/mL, 1 equiv.) were added to the vial, which was flushed with Ar. After stirring overnight at room temperature, reaction mixture was filtered through Celite with CH2CI2 (2.5 mL) and the solvent was removed under reduced pressure. The racemic a-methoxy-acetamides 3 were next isolated by silica gel flash column chromatography. With ammonium formate in methanol, Time= 1.5h, T= 70 °C , Inert atmosphere Patent; CÓRDOVA, Armando; PALO-NIETO, Carlos; AFEWERKI, Samson; (46 pag.); WO2016/96905; (2016); (A1) English View in Reaxys O

H 2N

Rx-ID: 42997005 View in Reaxys 18/280 Yield

Conditions & References With ammonium formate in methanol, Time= 1.5h, T= 70 °C , Inert atmosphere Palo-Nieto, Carlos; Afewerki, Samson; Anderson, Mattias; Tai, Cheuk-Wai; Berglund, Per; Córdova, Armando; ACS Catalysis; vol. 6; nb. 6; (2016); p. 3932 - 3940 View in Reaxys

45/120

2018-07-03 17:12:41

HO O

Rx-ID: 43213216 View in Reaxys 19/280 Yield

Conditions & References

63 %

Stage 1: With dipotassium hydrogenphosphate, oxygen, 9-mesityl-10-methylacridinium perchlorate in chloroform, Time= 24h, T= 20 °C , Schlenk technique, Irradiation, Green chemistry Stage 2: With sodium tetrahydroborate in methanol, chloroform, Time= 0.5h, Green chemistry Song, Hai-Tao; Ding, Wei; Zhou, Quan-Quan; Liu, Jing; Lu, Liang-Qiu; Xiao, Wen-Jing; Journal of Organic Chemistry; vol. 81; nb. 16; (2016); p. 7250 - 7255 View in Reaxys HO

Rx-ID: 44450833 View in Reaxys 20/280 Yield

Conditions & References With [RuHCl(CO)(NH(C2H4PPh2)2)], potassium tert-butylate in tert-butyl methyl ether, Time= 0.25h, T= 50 °C , Inert atmosphere Bornschein, Christoph; Gustafson, Karl P. J.; Verho, Oscar; Beller, Matthias; Bäckvall, Jan-E.; Chemistry - A European Journal; vol. 22; nb. 33; (2016); p. 11583 - 11586 View in Reaxys

O O

Si O O

Rx-ID: 39941308 View in Reaxys 21/280 Yield

Conditions & References With water, sodium hydroxide in methanol Huang, Shaofeng; Zhao, Hua; Li, Xiaoyan; Wang, Lin; Sun, Hongjian; RSC Advances; vol. 5; nb. 20; (2015); p. 15660 15667 View in Reaxys

Rx-ID: 39986859 View in Reaxys 22/280 Yield

Conditions & References Reaction Steps: 2 1: hydrogenchloride / ethanol; water / Heating 2: 10% palladium on activated carbon; Degussa type; hydrogen / ethanol / 12 h / 20 °C With hydrogenchloride, 10% palladium on activated carbon; Degussa type, hydrogen in ethanol, water Borah, Ashwini; Goswami, Limi; Neog, Kashmiri; Gogoi, Pranjal; Journal of Organic Chemistry; vol. 80; nb. 9; (2015); p. 4722 - 4728 View in Reaxys Reaction Steps: 2 1: N,N-dimethyl acetamide / 24 h / 120 °C

46/120

2018-07-03 17:12:41

2: 10% palladium on activated carbon; Degussa type; hydrogen / ethanol / 12 h / 20 °C With 10% palladium on activated carbon; Degussa type, hydrogen in ethanol, N,N-dimethyl acetamide Borah, Ashwini; Goswami, Limi; Neog, Kashmiri; Gogoi, Pranjal; Journal of Organic Chemistry; vol. 80; nb. 9; (2015); p. 4722 - 4728 View in Reaxys O

Rx-ID: 39986863 View in Reaxys 23/280 Yield

Conditions & References Reaction Steps: 2 1: N,N-dimethyl acetamide / 24 h / 120 °C 2: hydrogen; 5% Rh/C / ethanol / 12 h / 20 °C With 5% Rh/C, hydrogen in ethanol, N,N-dimethyl acetamide Borah, Ashwini; Goswami, Limi; Neog, Kashmiri; Gogoi, Pranjal; Journal of Organic Chemistry; vol. 80; nb. 9; (2015); p. 4722 - 4728 View in Reaxys O

Rx-ID: 39986873 View in Reaxys 24/280 Yield

Conditions & References

107 mg

With 10% palladium on activated carbon; Degussa type, hydrogen in ethanol, Time= 12h, T= 20 °C , Reagent/catalyst, Temperature Borah, Ashwini; Goswami, Limi; Neog, Kashmiri; Gogoi, Pranjal; Journal of Organic Chemistry; vol. 80; nb. 9; (2015); p. 4722 - 4728 View in Reaxys O

O N

Rx-ID: 39986874 View in Reaxys 25/280 Yield

Conditions & References With 5% Rh/C, hydrogen in ethanol, Time= 12h, T= 20 °C , Reagent/catalyst Borah, Ashwini; Goswami, Limi; Neog, Kashmiri; Gogoi, Pranjal; Journal of Organic Chemistry; vol. 80; nb. 9; (2015); p. 4722 - 4728 View in Reaxys O

Rx-ID: 39986912 View in Reaxys 26/280 Yield 88 %

Conditions & References With 10% palladium on activated carbon; Degussa type, hydrogen in ethanol, Time= 12h, T= 20 °C , Reagent/catalyst, Temperature

47/120

2018-07-03 17:12:41

Borah, Ashwini; Goswami, Limi; Neog, Kashmiri; Gogoi, Pranjal; Journal of Organic Chemistry; vol. 80; nb. 9; (2015); p. 4722 - 4728 View in Reaxys O

Rx-ID: 39986914 View in Reaxys 27/280 Yield

Conditions & References

92 %

HO O

Rx-ID: 39991833 View in Reaxys 28/280 Yield 72 %

Conditions & References With sodium tetrahydroborate, nickel(II) chloride hexahydrate in methanol, Time= 24h, Reflux, chemoselective reaction Khurana, Jitender M.; Dawra, Kiran; Sharma, Purnima; RSC Advances; vol. 5; nb. 16; (2015); p. 12048 - 12051 View in Reaxys

Rx-ID: 40406122 View in Reaxys 29/280 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide; potassium hydroxide / 12 h / 60 °C / Inert atmosphere With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide, potassium hydroxide in tetrahydrofuran, 1: |Grignard Reaction Shoola, Christopher O.; DelMastro, Thomas; Wu, Ruoqiu; Sowa, John R.; European Journal of Organic Chemistry; vol. 2015; nb. 8; (2015); p. 1670 - 1673 View in Reaxys

O O

Rx-ID: 40406124 View in Reaxys 30/280 Yield

48/120

2018-07-03 17:12:41

With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide, potassium hydroxide in tetrahydrofuran, 1: |Grignard Reaction Shoola, Christopher O.; DelMastro, Thomas; Wu, Ruoqiu; Sowa, John R.; European Journal of Organic Chemistry; vol. 2015; nb. 8; (2015); p. 1670 - 1673 View in Reaxys F F

Rx-ID: 40406126 View in Reaxys 31/280 Yield

Rx-ID: 40406128 View in Reaxys 32/280 Yield

Conditions & References With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide, potassium hydroxide, Time= 12h, T= 60 °C , Inert atmosphere Shoola, Christopher O.; DelMastro, Thomas; Wu, Ruoqiu; Sowa, John R.; European Journal of Organic Chemistry; vol. 2015; nb. 8; (2015); p. 1670 - 1673 View in Reaxys HO

Rx-ID: 40406129 View in Reaxys 33/280 Yield

Rx-ID: 40406130 View in Reaxys 34/280 Yield

49/120

2018-07-03 17:12:41

View in Reaxys O

Rx-ID: 40445136 View in Reaxys 35/280 Yield

Conditions & References With 3-butyl-1,2-dimethyl-1H-imidazol-3-ium hydroxide, hydrogen, Time= 15h, T= 30 °C , p= 37503.8Torr , Autoclave, chemoselective reaction Jiang, He-Yan; Zheng, Xu-Xu; Catalysis Science and Technology; vol. 5; nb. 7; (2015); p. 3728 - 3734 View in Reaxys With C31H47ClNRh, hydrogen in ethylene dibromide, Time= 24h, T= 20 °C , p= 3750.38Torr , Autoclave, Molecular sieve Wei, Yu; Rao, Bin; Cong, Xuefeng; Zeng, Xiaoming; Journal of the American Chemical Society; vol. 137; nb. 29; (2015); p. 9250 - 9253 View in Reaxys O

Rx-ID: 40471824 View in Reaxys 36/280 Yield

Conditions & References With C31H47ClNRh, hydrogen in tert-Amyl alcohol, Time= 24h, T= 20 °C , p= 3750.38Torr , Autoclave, Molecular sieve Wei, Yu; Rao, Bin; Cong, Xuefeng; Zeng, Xiaoming; Journal of the American Chemical Society; vol. 137; nb. 29; (2015); p. 9250 - 9253 View in Reaxys O

Rx-ID: 40471826 View in Reaxys 37/280 Yield

Conditions & References With chloro(1,5-cyclooctadiene)rhodium(I) dimer, hydrogen, 1,3-bis(2,4,6-trimethylphenyl)4,5-dihydroimidazolium, sodium tbutanolate in 2,2,2-trifluoroethanol, Time= 12h, T= 70 °C , p= 3750.38Torr , Molecular sieve Wei, Yu; Rao, Bin; Cong, Xuefeng; Zeng, Xiaoming; Journal of the American Chemical Society; vol. 137; nb. 29; (2015); p. 9250 - 9253 View in Reaxys With chloro(1,5-cyclooctadiene)rhodium(I) dimer, hydrogen in 2,2,2-trifluoroethanol, Time= 24h, T= 20 °C , p= 3750.38Torr , Molecular sieve Wei, Yu; Rao, Bin; Cong, Xuefeng; Zeng, Xiaoming; Journal of the American Chemical Society; vol. 137; nb. 29; (2015); p. 9250 - 9253 View in Reaxys

HO HO

Rx-ID: 41066143 View in Reaxys 38/280

50/120

2018-07-03 17:12:41

Yield

Conditions & References With [(4-(4-CF3)-Ph)Tr(NP(iPr)2)(NHP(iPr)2)Ir(cod)], potassium tert-butylate in 1,4-dioxane, Time= 4h, T= 125 °C , Inert atmosphere, Sealed tube Deibl, Nicklas; Ament, Kevin; Kempe, Rhett; Journal of the American Chemical Society; vol. 137; nb. 40; (2015); p. 12804 12807 View in Reaxys O

Rx-ID: 37443697 View in Reaxys 39/280 Yield

Conditions & References With sodium tetrahydroborate Coronel, Camila; Arce, Gabriel; Iglesias, Cesar; Noguera, Cynthia Magallanes; Bonnecarrere, Paula Rodriguez; Giordano, Sonia Rodriguez; Gonzalez, David; Journal of Molecular Catalysis B: Enzymatic; vol. 102; (2014); p. 94 - 98 View in Reaxys OH

O N N

Rx-ID: 37443702 View in Reaxys 40/280 Yield

Rx-ID: 38141961 View in Reaxys 41/280 Yield

Conditions & References 2.4 Oxidation of styrene The selective oxidation of styrene was carried out in a round bottom flask (25 mL) equipped with Teflon coated magnetic stirrer and a reflux condenser. In a typical procedure, 3.0 mg of catalyst, 2.0 mL (17.4 mmol) of styrene, 5.0 mL of water and 4.5 mL of hydrogen peroxide (30percent) were added successively into the flask. The flask is then immersed in an oil bath at desired temperature for reaction. The products were identified by GC–MS and quantified by GC. Hydrogen peroxide utilization efficiency is defined as molar ratio of H2O2 utilized to produce benzaldehyde, phenylacetaldehyde and styrene oxide. With dihydrogen peroxide in water, Time= 6h, T= 80 °C , Catalytic behavior, Reagent/catalyst, Temperature, Time, Solvent Tong, Jinhui; Cai, Xiaodong; Wang, Haiyan; Zhang, Qianping; Materials Research Bulletin; vol. 55; (2014); p. 205 - 211 View in Reaxys

51/120

2018-07-03 17:12:41

Rx-ID: 38141962 View in Reaxys 42/280 Yield

Conditions & References 2.4 Oxidation of styrene The selective oxidation of styrene was carried out in a round bottom flask (25 mL) equipped with Teflon coated magnetic stirrer and a reflux condenser. In a typical procedure, 3.0 mg of catalyst, 2.0 mL (17.4 mmol) of styrene, 5.0 mL of water and 4.5 mL of hydrogen peroxide (30percent) were added successively into the flask. The flask is then immersed in an oil bath at desired temperature for reaction. The products were identified by GC–MS and quantified by GC. Hydrogen peroxide utilization efficiency is defined as molar ratio of H2O2 utilized to produce benzaldehyde, phenylacetaldehyde and styrene oxide. With dihydrogen peroxide in water, Time= 6h, T= 80 °C , Catalytic behavior, Reagent/catalyst, Temperature, Time Tong, Jinhui; Cai, Xiaodong; Wang, Haiyan; Zhang, Qianping; Materials Research Bulletin; vol. 55; (2014); p. 205 - 211 View in Reaxys

O O H

Rx-ID: 38141963 View in Reaxys 43/280 Yield

Conditions & References 2.4 Oxidation of styrene The selective oxidation of styrene was carried out in a round bottom flask (25 mL) equipped with Teflon coated magnetic stirrer and a reflux condenser. In a typical procedure, 3.0 mg of catalyst, 2.0 mL (17.4 mmol) of styrene, 5.0 mL of water and 4.5 mL of hydrogen peroxide (30percent) were added successively into the flask. The flask is then immersed in an oil bath at desired temperature for reaction. The products were identified by GC–MS and quantified by GC. Hydrogen peroxide utilization efficiency is defined as molar ratio of H2O2 utilized to produce benzaldehyde, phenylacetaldehyde and styrene oxide. With dihydrogen peroxide in ethanol, Time= 6h, T= 80 °C , Catalytic behavior Tong, Jinhui; Cai, Xiaodong; Wang, Haiyan; Zhang, Qianping; Materials Research Bulletin; vol. 55; (2014); p. 205 - 211 View in Reaxys

O H

Rx-ID: 38141964 View in Reaxys 44/280 Yield

52/120

2018-07-03 17:12:41

Tong, Jinhui; Cai, Xiaodong; Wang, Haiyan; Zhang, Qianping; Materials Research Bulletin; vol. 55; (2014); p. 205 - 211 View in Reaxys O

Rx-ID: 39115182 View in Reaxys 45/280 Yield

Conditions & References Reaction Steps: 2 1: yeast culture of Candida viswanathii KCh 120 / acetone / 144 h / 25 °C / Microbiological reaction 2: sodium tetrahydroborate / methanol With sodium tetrahydroborate in methanol, acetone Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys Reaction Steps: 2 1: yeast culture of Candida viswanathii KCh 120 / acetone / 6 h / 25 °C / Microbiological reaction 2: sodium tetrahydroborate / methanol With sodium tetrahydroborate in methanol, acetone Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys Reaction Steps: 2 1: yeast culture of Rhodotorula glutinis KCh 242 / acetone / 6 h / 25 °C / Microbiological reaction 2: sodium tetrahydroborate / methanol With sodium tetrahydroborate in methanol, acetone Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys Reaction Steps: 2 1: yeast culture of Rhodotorula rubra KCh 4 / acetone / 24 h / 25 °C / Microbiological reaction 2: sodium tetrahydroborate / methanol With sodium tetrahydroborate in methanol, acetone Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys Reaction Steps: 2 1: yeast culture of Rhodotorula rubra KCh 82 / acetone / 24 h / 25 °C / Microbiological reaction 2: sodium tetrahydroborate / methanol With sodium tetrahydroborate in methanol, acetone Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys Reaction Steps: 2 1: yeast culture of Rhodotorula rubra KCh 82 / acetone / 6 h / 25 °C / Microbiological reaction 2: sodium tetrahydroborate / methanol With sodium tetrahydroborate in methanol, acetone Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys Reaction Steps: 2 1: yeast culture of Saccharomyces brasiliensis KCh 905 / acetone / 24 h / 25 °C / Microbiological reaction 2: sodium tetrahydroborate / methanol With sodium tetrahydroborate in methanol, acetone Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269

53/120

2018-07-03 17:12:41

View in Reaxys Reaction Steps: 2 1: yeast culture of Saccharomyces cerevisiae KCh 464 / acetone / 144 h / 25 °C / Microbiological reaction 2: sodium tetrahydroborate / methanol With sodium tetrahydroborate in methanol, acetone Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys Reaction Steps: 2 1: yeast culture of Yarrowia lipolytica ATCC 32-338 A / acetone / 72 h / 25 °C / Microbiological reaction 2: sodium tetrahydroborate / methanol With sodium tetrahydroborate in methanol, acetone Janeczko, Tomasz; Kostrzewa-Suslow, Edyta; Tetrahedron Asymmetry; vol. 25; nb. 18-19; (2014); p. 1264 - 1269 View in Reaxys H (v2)

Rx-ID: 9014907 View in Reaxys 46/280 Yield 11 %

Conditions & References 4.5 General procedure for enantioselective addition of alkynylzinc compounds to aldehydes General procedure: To a solution of the corresponding ligand 16a or 17a (0.3equiv) in toluene, Et2Zn (2equiv of 1M solution in hexane) and Lewis base (Et3N, 2equiv) were added under an Ar atmosphere at room temperature. After 1h of stirring, the corresponding alkyne (1.5equiv) was added. The mixture was cooled to 0°C and the aldehyde (1equiv) was added. The reaction was stirred at rt and monitored by TLC (hexane/MTBE=5:1) until the aldehyde was consumed. The mixture was quenched (aq. NH4Cl), extracted with Et2O (3×20ml), and dried. After evaporation of the solvent the crude product was purified by column chromatography (hexane/MTBE=5:1). The enantiomeric excess was determinated by HPLC (chiral columns). Stage 1: With 1-((S)-(((S)-1-phenylethyl)amino)(m-tolyl)methyl)naphthalen-2-ol in hexane, toluene, Time= 1h, T= 20 °C , Schlenk technique, Inert atmosphere Stage 2: in hexane, toluene, T= 0 - 20 °C , Schlenk technique, Inert atmosphere, enantioselective reaction Marinova, Maya; Kostova, Kalina; Tzvetkova, Pavleta; Tavlinova-Kirilova, Maya; Chimov, Angel; Nikolova, Rosica; Shivachev, Boris; Dimitrov, Vladimir; Tetrahedron Asymmetry; vol. 24; nb. 23; (2013); p. 1453 - 1466 View in Reaxys With (S)-2-(methanesulfonylamino)-1,1-diethyl-3-phenyl-1-propanol, titanium(IV) isopropylate in toluene, T= 0 - 20 °C , Product distribution, Further Variations: Reagents, Solvents, Temperatures, with additive Xu, Zhaoqing; Lin, Li; Xu, Jiangke; Yan, Wenjin; Wang, Rui; Advanced Synthesis and Catalysis; vol. 348; nb. 4-5; (2006); p. 506 - 514 View in Reaxys Stage 1: With 1,1'-bi-2-naphthol in toluene, T= 20 °C Stage 2: With titanium(IV) isopropylate, 1,1'-bi-2-naphthol in toluene, T= 20 °C , Further stages. Moore, David; Pu, Lin; Organic letters; vol. 4; nb. 11; (2002); p. 1855 - 1857 View in Reaxys

54/120

2018-07-03 17:12:41

Rx-ID: 11013728 View in Reaxys 47/280 Yield

Conditions & References

100 % Chromat.

With potassium hydroxide, RuCl2(PPh3)(iBu-BTP), Time= 4h, T= 82 °C , p= 750.075Torr Yu; Zeng; Sun; Deng; Dong; Chen; Wang; Pei; Journal of Organometallic Chemistry; vol. 692; nb. 11; (2007); p. 2306 - 2313 View in Reaxys With C58H49ClN5P2Ru(1+)*Cl(1-), potassium isopropoxide, Time= 0.166667h, T= 82 °C , Inert atmosphere

98 %Chromat.

Ye, Wenjing; Zhao, Miao; Du, Wangming; Jiang, Quanbin; Wu, Kaikai; Wu, Ping; Yu, Zhengkun; Chemistry - A European Journal; vol. 17; nb. 17; (2011); p. 4737 - 4741 View in Reaxys With (thiophene-2-(N-diphenylphosphino)methylamine)(1,5-cyclooctadiene)chlororhodium(I), potassium hydroxide, Time= 5h, T= 82 °C , Inert atmosphere Aydemir, Murat; Baysal, Akin; Turgut, Yilmaz; Applied Organometallic Chemistry; vol. 25; nb. 4; (2011); p. 270 - 275 View in Reaxys General procedure for the transfer hydrogenation of ketones General procedure: Typical procedure for the catalytic hydrogen transfer reaction: asolution of ruthenium complexes the [Rh((Ph2P)2NCH2-C4H3S)2]-BF4, 5, [Rh((Ph2P)2NCH2-C4H3O)2]BF4, 6, Rh((Ph2P)2N-C6H4-2-CH(CH3)2)(cod)]BF4, 7, [Rh((Ph2P)2N-C6H4-4-CH(CH3)2)(cod)]BF4,8, [Rh((Ph2P)2N-C6H4-2-CH(CH3)2)2]BF4, 9 or [Rh((Ph2P)2N-C6H4-4CH(CH3)2)2]BF4, 10, NaOH (0.025 mmol) and the corresponding ketone (0.5 mmol) in degassed iso-PrOH (5 mL) were refluxed until the reactions were completed. After this period a sample of the reaction mixture was taken off, diluted with acetone and analyzed immediately by GC. Conversions obtained are related to the residual unreacted ketone. With [rhodium(I)((Ph2P)2N-C6H4-4-CH(CH3)2)(1,5-cyclooctadiene)](tetrafluoroborate), sodium hydroxide, Time= 0.166667h, T= 82 °C , Reflux, Inert atmosphere, Schlenk technique, Reagent/catalyst, Time Aydemir, Murat; Meric, Nermin; Kayan, Cezmi; Ok, Fatih; Baysal, Akin; Inorganica Chimica Acta; vol. 398; (2013); p. 1 10 View in Reaxys

O H 2N

Rx-ID: 35454734 View in Reaxys 48/280 Yield

Conditions & References

74 %Spectr., 64 %

With dichlorobis(dicyclohexylphosphinomethylpyridine)-ruthenium (II), potassium tert-butylate in neat (no solvent), Time= 24h, T= 165 °C , Inert atmosphere, Concentration, Time Iida, Kazuki; Miura, Takashi; Ando, Junki; Saito, Susumu; Organic Letters; vol. 15; nb. 7; (2013); p. 1436 - 1439 View in Reaxys

HO NH 2

Rx-ID: 35454742 View in Reaxys 49/280

55/120

2018-07-03 17:12:41

Yield

Conditions & References Stage 1: With dichlorobis(dicyclohexylphosphinomethylpyridine)-ruthenium (II), potassium tert-butylate, Time= 24h, T= 165 °C , Inert atmosphere Stage 2: With sodium tetrahydroborate in methanol, T= 20 °C , Inert atmosphere

56 %, 88 %Spectr.

Iida, Kazuki; Miura, Takashi; Ando, Junki; Saito, Susumu; Organic Letters; vol. 15; nb. 7; (2013); p. 1436 - 1439 View in Reaxys

O NH H

NH 2

Rx-ID: 35454744 View in Reaxys 50/280 Yield

80 %Spectr., 74 %

Iida, Kazuki; Miura, Takashi; Ando, Junki; Saito, Susumu; Organic Letters; vol. 15; nb. 7; (2013); p. 1436 - 1439 View in Reaxys

O H 2N

Rx-ID: 35454747 View in Reaxys 51/280 Yield

Conditions & References

80 %Spectr., 51 %

Stage 1: With dichlorobis(dicyclohexylphosphinomethylpyridine)-ruthenium (II), potassium tert-butylate, Time= 24h, T= 165 °C , Inert atmosphere Stage 2: With sodium tetrahydroborate in methanol, T= 20 °C , Inert atmosphere Iida, Kazuki; Miura, Takashi; Ando, Junki; Saito, Susumu; Organic Letters; vol. 15; nb. 7; (2013); p. 1436 - 1439 View in Reaxys

ruthenium-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine copolymer (PCP-TsDPEN-Ru)

Rx-ID: 36452761 View in Reaxys 52/280 Yield

Conditions & References Catalytic tests General procedure: In the asymmetric transfer hydrogenation of aromatic ketones, all reactions were carried out under a nitrogen atmosphere by using standard Schlenk-type techniques. As a typical run, a desired amount of PCP-TsDPEN-Ru, HCOONa·2H2O (2.5mmol) and ketones (0.5mmol, S/C=100) were added into degassed water (5mL) in a Schlenk tube and the mixture was stirred at 40°C for a desired time. After the reaction, the mixture was extracted with ethyl acetate and catalyst was taken out from the system by centrifugation and the liquid was passed through a short column before analyzed by gas chromatography

56/120

2018-07-03 17:12:41

(GC-1690 Kexiao Co. equipped with a flame ionization detector and a Supelco η-DEX 225 capillary column). Dodecane was added as internal standard. With sodium formate dihydrate in water, Time= 1.5h, T= 40 °C , Inert atmosphere, Schlenk technique Sun, Qi; Jin, Yinying; Zhu, Longfeng; Wang, Liang; Meng, Xiangju; Xiao, Feng-Shou; Nano Today; vol. 8; nb. 4; (2013); p. 342 - 350 View in Reaxys H (v2)

Cl O

Rx-ID: 36746447 View in Reaxys 53/280 Yield 40 %

Rx-ID: 36978607 View in Reaxys 54/280 Yield 69 %Spectr., 6.6 %Chromat.

Conditions & References With acetylacetonatodicarbonylrhodium(l), 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II), carbon monoxide, C70H72O2P2, hydrogen in 1,4-dioxane, Time= 36h, T= 120 °C , p= 3750.38Torr , Inert atmosphere, Autoclave Yuki, Yamato; Takahashi, Kohei; Tanaka, Yoshiyuki; Nozaki, Kyoko; Journal of the American Chemical Society; vol. 135; nb. 46; (2013); p. 17393 - 17400 View in Reaxys

57/120

2018-07-03 17:12:41

OH H

Rx-ID: 436579 View in Reaxys 55/280 Yield

Conditions & References

98 %

With hydrogen, TMSB, palladium in ethanol, Time= 20h, T= 20 °C , p= 760Torr Belotti, Damien; Cantagrel, Guillaume; Combellas, Catherine; Cossy, Janine; Kanoufi, Frederic; Nunige, Sandra; New Journal of Chemistry; vol. 29; nb. 6; (2005); p. 761 - 764 View in Reaxys

92 %

With riboflavin tetrabutyrate, oxygen, hydrazine hydrate in acetonitrile, Time= 30h, 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

92 %

With oxygen, hydrazine hydrate, riboflavin tetrabutyrate in acetonitrile, Time= 30h, T= 25 - 30 °C , chemoselective reaction Imada, Yasushi; Iida, Hiroki; Kitagawa, Takahiro; Naota, Takeshi; Chemistry - A European Journal; vol. 17; nb. 21; (2011); p. 5908 - 5920 View in Reaxys

80 %

With oxygen, guanidine nitrate, hydrazine hydrate in ethanol, Time= 24h, 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 ethyl acetate, platinum, Hydrogenation Cymerman-Craig et al.; Australian Journal of Chemistry; vol. 9; (1956); p. 397,402 View in Reaxys With methanol, nickel, Hydrogenation Hirao; Yakugaku Zasshi; vol. 73; (1953); p. 1224; ; (1954); p. 12702 View in Reaxys

H 2N

NH 2 H

Rx-ID: 32991144 View in Reaxys 56/280 Yield 16 %Chromat., 75 %

Conditions & References With ammonia-borane, water in dimethyl sulfoxide, Time= 18h, T= 30 °C , pH= 7, aq. phosphate buffer, Enzymatic reaction, optical yield given as percent ee Leisch, Hannes; Grosse, Stephan; Iwaki, Hiroaki; Hasegawa, Yoshie; Lau, Peter C.K.; Canadian Journal of Chemistry; vol. 90; nb. 1; (2012); p. 39 - 45 View in Reaxys H

Rx-ID: 33825518 View in Reaxys 57/280 Yield

Conditions & References in tetrahydrofuran, T= 0 °C , Inert atmosphere

58/120

2018-07-03 17:12:41

Fernandez-Mateos, Emilio; MacIa, Beatriz; Yus, Miguel; European Journal of Organic Chemistry; nb. 20; (2012); p. 3732 3736 View in Reaxys

Rx-ID: 33951186 View in Reaxys 58/280 Yield 4 %, 13 %, 56 %

Conditions & References Stage 1: With (1,3-dimethylimidazol-2-ylidene)borane, bis(trifluoromethanesulfonyl)amide in 1,2-dichloro-ethane, Time= 3h, T= 25 °C , Inert atmosphere Stage 2: With dihydrogen peroxide, sodium hydroxide in methanol, water, 1,2-dichloro-ethane, Time= 16h, T= 25 °C Prokofjevs, Aleksandrs; Boussonniere, Anne; Li, Linfeng; Bonin, Helene; Lacote, Emmanuel; Curran, Dennis P.; Vedejs, Edwin; Journal of the American Chemical Society; vol. 134; nb. 29; (2012); p. 12281 - 12288 View in Reaxys

Rx-ID: 34305092 View in Reaxys 59/280 Yield

Conditions & References Stage 1: With iron(III)-acetylacetonate, ethylmagnesium bromide in diethyl ether, Time= 0.25h, T= 20 °C Stage 2: in diethyl ether, Time= 2.5h, T= 20 °C Ilies, Laurean; Yoshida, Takumi; Nakamura, Eiichi; Journal of the American Chemical Society; vol. 134; nb. 41; (2012); p. 16951 - 16954,4 View in Reaxys

Rx-ID: 2007961 View in Reaxys 60/280 Yield

Conditions & References With lithium aluminium tetrahydride, 2,2'-azobis(isobutyronitrile), oxygen, relative chain propagation rates, Kinetics Pritzkow, Wilhelm; Thomas, Gerda; Willecke, Lothar; Journal fuer Praktische Chemie (Leipzig); vol. 327; nb. 6; (1985); p. 945 - 952 View in Reaxys

99 % Chromat.

With NADPH in dimethyl sulfoxide, T= 30 °C , pH= 7.4, Product distribution, Further Variations: Reagents Whitehouse, Christopher J. C.; Bell, Stephen G.; Tufton, Henry G.; Kenny, Richard J. P.; Ogilvie, Lydia C. I.; Wong, Luet-Lok; Chemical Communications; nb. 8; (2008); p. 966 - 968 View in Reaxys

98.7 %Chromat.

With cytochrome P450BM3 CYP102A1 monooxygenase, NADPH, bovine liver catalase in dimethyl sulfoxide, T= 30 °C , pH= 7.4, aq. buffer, Enzymatic reaction Whitehouse, Christopher J.C.; Bell, Stephen G.; Wong, Luet-Lok; Chemistry - A European Journal; vol. 14; nb. 35; (2008); p. 10905 - 10908 View in Reaxys With Aspergillus niger MTCC-404, Microbiological reaction

59/120

2018-07-03 17:12:41

Yadav, Saroj; Yadav, Rama S.S.; Yadava, Sudha; Yadav, Kapil D.S.; Catalysis Communications; vol. 12; nb. 9; (2011); p. 781 - 784 View in Reaxys Cl

Rx-ID: 2950969 View in Reaxys 61/280 Yield

Conditions & References

96 %

With iron(III) sulfate, water in toluene, Time= 1h, T= 110 °C , Ionic liquid Hu, Yu Lin; Jiang, Hui; Zhu, Jie; Lu, Ming; New Journal of Chemistry; vol. 35; nb. 2; (2011); p. 292 - 298 View in Reaxys in ethanol, T= 25 °C , ΔH(excit.), ΔS(excit.), Rate constant, Kinetics, Thermodynamic data Orlovic, Mirko; Kronja, Olga; Humski, Kresimir; Borcic, Stanko; Polla, Eugenio; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3253 - 3256 View in Reaxys O

Rx-ID: 3399321 View in Reaxys 62/280 Yield

Conditions & References

90 %, 7 % Chromat.

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 With sodium tetrahydroborate, aluminium trichloride in tetrahydrofuran, Time= 2h, Ambient temperature, Yield given. Yields of byproduct given Ono, Aoi; Maruyama, Tamiko; Suzuki, Nobuko; Synthetic Communications; vol. 17; nb. 8; (1987); p. 1001 - 1006 View in Reaxys With hydrogen in toluene, Time= 24h, T= 80 °C , p= 15001.5Torr , Autoclave, chemoselective reaction Hermannsdoerfer, Justus; Kempe, Rhett; Chemistry - A European Journal; vol. 17; nb. 29; (2011); p. 8071 - 8077 View in Reaxys With hydrogen in tetrahydrofuran, Time= 24h, T= 50 °C , p= 15001.5Torr , Autoclave, chemoselective reaction Hermannsdoerfer, Justus; Kempe, Rhett; Chemistry - A European Journal; vol. 17; nb. 29; (2011); p. 8071 - 8077 View in Reaxys

HO O

Rx-ID: 4886109 View in Reaxys 63/280 Yield 13 %, 85 %

Conditions & References With potassium superoxide, 2-Nitrobenzenesulfonyl chloride in acetonitrile, Time= 5h, T= -20 °C Kim II, Yong; Kim, Yong Hae; Tetrahedron Letters; vol. 39; nb. 7; (1998); p. 639 - 642 View in Reaxys

15 %Chromat., 79 %

With dihydrogen peroxide in water, acetonitrile, Time= 10h, T= 25 °C , UV-irradiation Farhadi, Saeid; Zabardasti, Abedien; Rahmati, Mohammad Hosien; Journal of Chemical Research; vol. 35; nb. 3; (2011); p. 157 - 160

60/120

2018-07-03 17:12:41

View in Reaxys OH

O HO O

Rx-ID: 30282725 View in Reaxys 64/280 Yield

Conditions & References

9 %Spectr., 23 %Spectr., 63 %Spectr.

4 :In a vacuum-sealed tube and a final reaction volume of 0.50 ml in toluene, 1- phenylpropan-l,3-diol (0.225 mmol), was heated to 175 0C with carbonyl- Ws(trifluoroacetato)Ms(triphenylphosphino)rathenium(II) (0.0112 mmol) and (9,9- dimethylxanthene-4,5-diyl)Ms(diphenylphosphine) (0.0112 mmol). After 17 h, full consumption of the starting material yielded propiophenone (0.142 mmol, 63percent), 1-phenylpropan-l-ol (0.0203 mmol, 9percent), and acetophenone (0.0518 mmol, 23percent) as determined by 1H NMR integration relative to an external capillary standard. Product identification was further confirmed by GC- MS for propiophenone (134 m/z), 1-phenylpropan-l-ol (136 m/z), and acetophenone (120 m/z). With carbonyl-bis(trifluoroacetato)bis(triphenylphosphino)ruthenium(II), 4,5-bis(diphenylphosphino)-9 ,9-dimethylxanthene in toluene, Time= 17h, T= 175 °C , vacuum-sealed tube, Product distribution / selectivity Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BERGMAN, Robert; ELLMAN, Jonathan; NICHOLS, Jason; BISHOP, Lee; VOLKMAN, Jerome; TOSTE, Dean; SON, Sunghee; HARTWIG, John; SERGEEV, Alexey; WO2011/3029; (2011); (A2) English View in Reaxys H

Mg Br

Rx-ID: 30449251 View in Reaxys 65/280 Yield

Conditions & References

48 %, 35 %

in diethyl ether, Time= 16h, T= 80 °C , Ionic liquid, Grignard reaction Ford, Leigh; Atefi, Farzad; Singer, Robert D.; Scammells, Peter J.; European Journal of Organic Chemistry; nb. 5; (2011); p. 942 - 950 View in Reaxys

(v2)

Rx-ID: 31086722 View in Reaxys 66/280 Yield 44 %, 32 %

Conditions & References Stage 1: With (S)-bis(3,5-dimethylphenyl)(1-methylpyrrolidin-2-yl)methanol in hexane, toluene, Time= 10h, T= 20 °C , Inert atmosphere Stage 2: With ammonium chloride in hexane, toluene, optical yield given as percent ee, enantioselective reaction Kojima, Naoto; Nishijima, Shogo; Tsuge, Kaoru; Tanaka, Tetsuaki; Organic and Biomolecular Chemistry; vol. 9; nb. 12; (2011); p. 4425 - 4428 View in Reaxys

61/120

2018-07-03 17:12:41

Mg Br

Rx-ID: 32044622 View in Reaxys 67/280 Yield

Conditions & References

11 %, 25 %, Stage 1: With zinc(II) chloride in tetrahydrofuran, Time= 1h, T= 0 - 20 °C 25 % Stage 2: in tetrahydrofuran, Time= 8h, T= 0 °C Jagtap; Joshi; Tetrahedron Letters; vol. 52; nb. 48; (2011); p. 6501 - 6503 View in Reaxys H

Rx-ID: 597380 View in Reaxys 68/280 Yield

Conditions & References With diethyl ether, sodium Morton; Stevens; Journal of the American Chemical Society; vol. 53; (1931); p. 2247 View in Reaxys With magnesium, Multistep reaction Eichinger, Peter C. H.; Bowie, John H.; Blumenthal Thomas; Journal of Organic Chemistry; vol. 51; nb. 26; (1986); p. 5078 - 5082 View in Reaxys With 18-crown-6 ether, calcium, 1.) toluene, heating 2.) 40-60 deg C, Yield given. Multistep reaction Bogatskii, A. V.; Luk'yanenko, N. G.; Lyamtseva, L. N.; Doklady Chemistry; vol. 259; (1981); p. 349 - 350; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 259; nb. 4; (1981); p. 851 - 853 View in Reaxys With magnesium, 1.) Et2O, 0 deg C, 2.) Et2O, 0 deg C, 20 min, Yield given. Multistep reaction Maguire, Anita R.; Buckley, N. Rachael; O'Leary, Patrick; Ferguson, George; Journal of the Chemical Society - Perkin Transactions 1; nb. 24; (1998); p. 4077 - 4091 View in Reaxys Stage 1: With iodine, magnesium in diethyl ether, Inert atmosphere, Reflux Stage 2: in diethyl ether, T= 0 °C , Inert atmosphere Stage 3: With water, ammonium chloride in diethyl ether, T= 0 °C , Inert atmosphere Chang, Lu; Kuang, Yulong; Qin, Bo; Zhou, Xin; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; Organic Letters; vol. 12; nb. 10; (2010); p. 2214 - 2217 View in Reaxys HO

Rx-ID: 29526783 View in Reaxys 69/280 Yield 80 %

Conditions & References With 1, 1'-bis (diphenylphosphino)-ferrocene, [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, Butane-1,4-diol, potassium tert-butylate, Time= 48h, T= 110 °C , Inert atmosphere Maytum, Hannah C.; Francos, Javier; Whatrup, David J.; Williams, Jonathan M. J.; Chemistry - An Asian Journal; vol. 5; nb. 3; (2010); p. 538 - 542 View in Reaxys

62/120

2018-07-03 17:12:41

Br HO

Rx-ID: 29583980 View in Reaxys 70/280 Yield

Conditions & References

17 %, 36 %

in tetrahydrofuran, T= 0 °C , Grignard addition Hatano, Manabu; Ito, Orie; Suzuki, Shinji; Ishihara, Kazuaki; Chemical Communications; vol. 46; nb. 15; (2010); p. 2674 2676 View in Reaxys

Br B

Rx-ID: 29676954 View in Reaxys 71/280 Yield

Conditions & References

58 %

Stage 1: With magnesium in tetrahydrofuran, N,N-dimethyl acetamide, T= 27 °C Stage 2: in tetrahydrofuran, N,N-dimethyl acetamide, T= 27 °C Stage 3: With dihydrogen peroxide, sodium hydroxide in tetrahydrofuran, N,N-dimethyl acetamide, water Condon, Sylvie; Nedelec, Jean-Yves; Journal of Organometallic Chemistry; vol. 695; nb. 1; (2010); p. 32 - 35 View in Reaxys

Rx-ID: 29676961 View in Reaxys 72/280 Yield

Conditions & References With dihydrogen peroxide, sodium hydroxide in water Condon, Sylvie; Nedelec, Jean-Yves; Journal of Organometallic Chemistry; vol. 695; nb. 1; (2010); p. 32 - 35 View in Reaxys

O O S HS

S S

Rx-ID: 29758043 View in Reaxys 73/280 Yield 76 %

Conditions & References Stage 1: With sodium methylate in N,N-dimethyl-formamide, Inert atmosphere, Cooling with ice Stage 2: in N,N-dimethyl-formamide, T= -4 - 80 °C , Inert atmosphere, optical yield given as percent ee Scholz, Roland; Hellmann, Gunther; Rohs, Susanne; Oezdemir, Diana; Raabe, Gerhard; Vermeeren, Cornelia; Gais, Hans-Joachim; European Journal of Organic Chemistry; nb. 24; (2010); p. 4588 - 4616

63/120

2018-07-03 17:12:41

View in Reaxys

Rx-ID: 29790631 View in Reaxys 74/280 Yield

Conditions & References Stage 1: With CF3O3S(1-)*C45H36F3N2PRh(1+), benzo[1,3,2]dioxaborole in tetrahydrofuran, T= 0 °C , Inert atmosphere Stage 2: With dihydrogen peroxide, sodium hydroxide in ethanol, water, T= 0 - 20 °C Maxwell, Aoife C.; Flanagan, Susan P.; Goddard, Richard; Guiry, Patrick J.; Tetrahedron Asymmetry; vol. 21; nb. 11-12; (2010); p. 1458 - 1473 View in Reaxys

Si O

Rx-ID: 30028614 View in Reaxys 75/280 Yield

Conditions & References With potassium fluoride, C46H34I4O6 in 1,4-dioxane, Time= 144h, T= 20 °C , optical yield given as percent ee, enantioselective reaction Yan, Hailong; Jang, Hyeong Bin; Lee, Ji-Woong; Kim, Hong Ki; Lee, Soon Won; Yang, Jung Woon; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 49; nb. 47; (2010); p. 8915 - 8917 View in Reaxys OH

Rx-ID: 31574924 View in Reaxys 76/280 Yield

Conditions & References With NADPH, Enzymatic reaction Whitehouse, Christopher J. C.; Yang, Wen; Yorke, Jake A.; Rowlatt, Benjamin C.; Strong, Anthony J. F.; Blanford, Christopher F.; Bell, Stephen G.; Bartlam, Mark; Wong, Luet-Lok; Rao, Zihe; ChemBioChem; vol. 11; nb. 18; (2010); p. 2549 - 2556 View in Reaxys

O Br

Rx-ID: 28884931 View in Reaxys 77/280 Yield 11 %, 85 %

Conditions & References Stage 1: With magnesium, ethylene dibromide in 2-methyltetrahydrofuran, T= 20 °C , Inert atmosphere Stage 2: in 2-methyltetrahydrofuran, Time= 1.25h, T= 0 - 20 °C , Inert atmosphere, Grignard reaction, chemoselective reaction

64/120

2018-07-03 17:12:41

Zhong, Weihui; Wu, Yaotiao; Zhang, Xingxian; Journal of Chemical Research; nb. 6; (2009); p. 370 - 373 View in Reaxys

Rx-ID: 1839908 View in Reaxys 78/280 Yield

Conditions & References With sodium hydroxide, diphenylamine borane, dihydrogen peroxide, 1.) THF, 0 deg C, 1 h; 20 deg C, 1 h, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Camacho, Carlos; Uribe, Guillermo; Contreras, Rosalinda; Synthesis; nb. 12; (1982); p. 1027 - 1030 View in Reaxys Stage 1: With C6H14BN, iodine in dichloromethane, T= 20 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in methanol, water Scheideman, Matthew; Wang, Guoqiang; Vedejs, Edwin; Journal of the American Chemical Society; vol. 130; nb. 27; (2008); p. 8669 - 8676 View in Reaxys

Rx-ID: 11041557 View in Reaxys 79/280 Yield 95 %

Conditions & References With silica triflate in methanol, Time= 0.0666667h, Heating Shirini; Marjani; Nahzomi, H. Taherpour; Zolfigol; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 183; nb. 1; (2008); p. 168 - 177 View in Reaxys

94 %

With 1-butyl-3-methylimidazolium chloride, Time= 1.33h, T= 20 °C Shaabani, Ahmad; Rezayan, Ali Hossein; Heidary, Marjan; Sarvary, Afshin; Monatshefte fur Chemie; vol. 139; nb. 12; (2008); p. 1471 - 1474 View in Reaxys

90 %

With silica gel, iodic acid in water, Time= 0.00833333h, microwave irradiation Hashemi; Bakhtiari; Karimi-Jaberi; Russian Journal of Organic Chemistry; vol. 43; nb. 4; (2007); p. 621 - 622 View in Reaxys OH H

Mg Br

Rx-ID: 11110898 View in Reaxys 80/280 Yield 83 %, 6 %

Conditions & References Stage 1: With tetradecyl(trihexyl)phosphonium decanoate in tetrahydrofuran, Time= 6h, Grignard reaction Stage 2: in tetrahydrofuran, Time= 16h, Further stages. Ramnial, Taramatee; Taylor, Stephanie A.; Clyburne, Jason A. C.; Walsby, Charles J.; Chemical Communications; nb. 20; (2007); p. 2066 - 2068 View in Reaxys

83 %, 8 %

Stage 1: in tetrahydrofuran

65/120

2018-07-03 17:12:41

Stage 2:Time= 16h, Further stages. Ramnial, Taramatee; Taylor, Stephanie A.; Bender, Marissa L.; Gorodetsky, Brian; Lee, Peter T. K.; Dickie, Diane A.; McCollum, Brett M.; Pye, Cory C.; Walsby, Charles J.; Clyburne, Jason A. C.; Journal of Organic Chemistry; vol. 73; nb. 3; (2008); p. 801 - 812 View in Reaxys H

diethylzinc O

Rx-ID: 25942555 View in Reaxys 81/280 Yield 35 %

Conditions & References With chiral 2,2'-bipyridinemonosulfoxide in benzene, Time= 120h, T= 20 °C Lawecka, Justyna; Bujnicki, Bogdan; Drabowicz, Jozef; Rykowski, Andrzej; Tetrahedron Letters; vol. 49; nb. 4; (2008); p. 719 - 722 View in Reaxys

OH HO

Rx-ID: 26049093 View in Reaxys 82/280 Yield 5 % Chromat., 65 % Chromat.

Conditions & References With NADPH in dimethyl sulfoxide, T= 30 °C , pH= 7.4, Product distribution Whitehouse, Christopher J. C.; Bell, Stephen G.; Tufton, Henry G.; Kenny, Richard J. P.; Ogilvie, Lydia C. I.; Wong, Luet-Lok; Chemical Communications; nb. 8; (2008); p. 966 - 968 View in Reaxys OH HO

Rx-ID: 26049094 View in Reaxys 83/280 Yield 30 % Chromat., 2 % Chromat., 68 % Chromat. 7.8 %Chromat., 14.4 %Chromat., 77.2 %Chromat.

Conditions & References With NADPH in dimethyl sulfoxide, T= 30 °C , pH= 7.4, Product distribution, Further Variations: Reagents Whitehouse, Christopher J. C.; Bell, Stephen G.; Tufton, Henry G.; Kenny, Richard J. P.; Ogilvie, Lydia C. I.; Wong, Luet-Lok; Chemical Communications; nb. 8; (2008); p. 966 - 968 View in Reaxys With cytochrome P450BM3 CYP102A1 variant GVQ (A74G/F87V/L188Q) monooxygenase, NADPH, bovine liver catalase in dimethyl sulfoxide, T= 30 °C , pH= 7.4, aq. buffer, Enzymatic reaction Whitehouse, Christopher J.C.; Bell, Stephen G.; Wong, Luet-Lok; Chemistry - A European Journal; vol. 14; nb. 35; (2008); p. 10905 - 10908 View in Reaxys

66/120

2018-07-03 17:12:41

Rx-ID: 26049095 View in Reaxys 84/280 Yield

Conditions & References

53 % Chromat., 46 % Chromat.

46.5 With cytochrome P450BM3 CYP102A1 variant KSK19 (F87A/H171L/Q307H/N319Y) monooxygenase, NADPH, bovine liver catalase %Chromat., in dimethyl sulfoxide, T= 30 °C , pH= 7.4, aq. buffer, Enzymatic reaction 53.1 %Chromat. Whitehouse, Christopher J.C.; Bell, Stephen G.; Wong, Luet-Lok; Chemistry - A European Journal; vol. 14; nb. 35; (2008); p. 10905 - 10908 View in Reaxys 78.3 With cytochrome P450BM3 CYP102A1 variant KT5 (F87A/A330P/E377A/D425N) monooxygenase, NADPH, bovine liver catalase in %Chromat., dimethyl sulfoxide, T= 30 °C , pH= 7.4, aq. buffer, Enzymatic reaction 20.3 %Chromat. Whitehouse, Christopher J.C.; Bell, Stephen G.; Wong, Luet-Lok; Chemistry - A European Journal; vol. 14; nb. 35; (2008); p. 10905 - 10908 View in Reaxys

H 2N

Rx-ID: 28157771 View in Reaxys 85/280 Yield

Conditions & References Stage 1: in dichloromethane Stage 2: With iodine in dichloromethane, Time= 5h, T= 20 °C Stage 3: With sodium hydroxide, dihydrogen peroxide in methanol, water Scheideman, Matthew; Wang, Guoqiang; Vedejs, Edwin; Journal of the American Chemical Society; vol. 130; nb. 27; (2008); p. 8669 - 8676 View in Reaxys

O B

S+

S O–

Rx-ID: 28163640 View in Reaxys 86/280 Yield 70 %

Conditions & References Stage 1: With lithium hexamethyldisilazane in tetrahydrofuran, Time= 0.333333h, T= -78 °C Stage 2: With triphenylborane in tetrahydrofuran, T= -105 - 20 °C Stage 3: With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran, water, T= 0 - 20 °C Howells, Dean; Robiette, Raphael; Fang, Guang Y.; Knowles, Luke S.; Woodrow, Michael D.; Harvey, Jeremy N.; Aggarwal, Varinder K.; Organic and Biomolecular Chemistry; vol. 6; nb. 7; (2008); p. 1185 - 1189 View in Reaxys

67/120

2018-07-03 17:12:41

Rx-ID: 28764096 View in Reaxys 87/280 Yield

Conditions & References

30.4 With cytochrome P450BM3 CYP102A1 variant A330P monooxygenase, NADPH, bovine liver catalase in dimethyl sulfoxide, T= %Chromat., 30 °C , pH= 7.4, aq. buffer, Enzymatic reaction 67.7 %Chromat. Whitehouse, Christopher J.C.; Bell, Stephen G.; Wong, Luet-Lok; Chemistry - A European Journal; vol. 14; nb. 35; (2008); p. 10905 - 10908 View in Reaxys

Rx-ID: 8968911 View in Reaxys 88/280 Yield 99.6 %

Conditions & References With silica-supported prop-1-ylsulfonic acid in methanol Wiles, Charlotte; Watts, Paul; Chemical Communications; nb. 46; (2007); p. 4928 - 4930 View in Reaxys

97 %

With tetra-N-butylammonium tribromide in methanol, Time= 1h, T= 20 °C Naik, Sarala; Gopinath, Rangam; Patel, Bhisma K; Tetrahedron Letters; vol. 42; nb. 43; (2001); p. 7679 - 7681 View in Reaxys

97 %

With tetra-N-butylammonium tribromide in methanol, Time= 1.2h Gopinath, Rangam; Patel, Bhisma K.; Organic Letters; vol. 2; nb. 26; (2000); p. 4177 - 4180 View in Reaxys

92 %

With trichloroisocyanuric acid in methanol, Time= 4h, T= 20 °C Firouzabadi, Habib; Iranpoor, Nasser; Hazarkhani, Hassan; Synthetic Communications; vol. 34; nb. 19; (2004); p. 3623 3630 View in Reaxys

Rx-ID: 9941118 View in Reaxys 89/280 Yield

Conditions & References Stage 1: With iodine, borane pyridine complex in dichloromethane, Time= 2h, T= 20 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in methanol, dichloromethane, T= 0 - 20 °C , Title compound not separated from byproducts Clay, Julia M.; Vedejs, Edwin; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5766 - 5767 View in Reaxys With benzo[1,3,2]dioxaborole, 1,3-dibutyl-4,5-dichloro-imidazole-1,3-divinylsiloxane Pt(0) in tetrahydrofuran, Time= 3h, T= 25 °C

68/120

2018-07-03 17:12:41

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, 1,3-dibutyl-triazole-1,3-divinylsiloxane Pt(0) 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 H I

Rx-ID: 600374 View in Reaxys 90/280 Yield

Conditions & References

94 %

Stage 1: With 1-butylpyridinium bromide, N-butylpyridinium tetrafluoroborate, zinc, Time= 1h, T= 50 °C Stage 2:Time= 12h, T= 20 °C Law, Man Chun; Wong, Kwok-Yin; Chan, Tak Hang; Journal of Organic Chemistry; vol. 70; nb. 25; (2005); p. 10434 10439 View in Reaxys

83 %

Stage 1: With N-butylpyridinium tetrafluoroborate, Time= 1h, T= 20 °C Stage 2: With pyridine, Time= 12h, T= 20 °C , Further stages. Law, Man Chun; Wong, Kwok-Yin; Chan, Tak Hang; Chemical Communications; nb. 23; (2006); p. 2457 - 2459 View in Reaxys With diethyl ether, calcium Glacet; Bulletin de la Societe Chimique de France; vol. <5> 5; (1938); p. 895,898 View in Reaxys

H B

Rx-ID: 5002752 View in Reaxys 91/280 Yield 93 %

Conditions & References With bis(1,5-cyclooctadiene)nickel (0), tri-tert-butyl phosphine, 1-(Prop-2-enyl)-1,2,3,4,5-pentamethylcyclopenta-2,4-dien in hexane, toluene, Time= 24h, T= 0 °C Hirano, Koji; Yorimitsu, Hideki; Oshima, Koichiro; Organic Letters; vol. 7; nb. 21; (2005); p. 4689 - 4691 View in Reaxys

81 %

With tri-tert-butyl phosphine, bis(1,5-cyclooctadiene)nickel (0) in hexane, water, Time= 20h, T= 20 °C , Product distribution, Further Variations: Catalysts, Reagents, Solvents Hirano, Koji; Yorimitsu, Hideki; Oshima, Koichiro; Advanced Synthesis and Catalysis; vol. 348; nb. 12-13; (2006); p. 1543 1546 View in Reaxys

74 %

With tetra-(n-butyl)ammonium iodide in tetrahydrofuran, N,N-dimethyl-formamide, Time= 7h, Ambient temperature, electrolysis with Pt/Cu electrodes Choi, Jung Hoon; Youm, Jong Sung; Cho, Cheon-Gyu; Czae, Myung-Zoon; Hwang, Book Kee; Kim, Jung Sung; Tetrahedron Letters; vol. 39; nb. 27; (1998); p. 4835 - 4838 View in Reaxys

69/120

2018-07-03 17:12:41

Rx-ID: 10306973 View in Reaxys 92/280 Yield

Conditions & References

16 %

With bis(acetylacetonate)nickel(II), diethylzinc in tetrahydrofuran, hexane, Time= 1h, T= 0 °C , Title compound not separated from byproducts Kimura, Masanari; Ezoe, Akihiro; Mori, Masahiko; Iwata, Keisuke; Tamaru, Yoshinao; Journal of the American Chemical Society; vol. 128; nb. 26; (2006); p. 8559 - 8568 View in Reaxys

O HO

Rx-ID: 10319352 View in Reaxys 93/280 Yield

Conditions & References

38 %, 56 %

Stage 1: in tetrahydrofuran, Time= 1h, T= 20 °C Stage 2: in tetrahydrofuran, Time= 2h, T= 0 °C Hatano, Manabu; Suzuki, Shinji; Ishihara, Kazuaki; Journal of the American Chemical Society; vol. 128; nb. 31; (2006); p. 9998 - 9999 View in Reaxys H

(v2)

OH OH

Rx-ID: 10417650 View in Reaxys 94/280 Yield

Conditions & References Stage 1: in tetrahydrofuran, hexane, Time= 1h Stage 2: in tetrahydrofuran, hexane, Time= 20h, T= 0 °C , Title compound not separated from byproducts Scarpi, Dina; Galbo, Fabrizio Lo; Guarna, Antonio; Tetrahedron Asymmetry; vol. 17; nb. 9; (2006); p. 1409 - 1414 View in Reaxys H (v2)

70/120

2018-07-03 17:12:41

OH Cl

Rx-ID: 10523232 View in Reaxys 95/280 Yield

Conditions & References

77 %

Stage 1: With zirconocene hydrochloride in dichloromethane, Time= 0.25h, T= 20 °C Stage 2: With (Rp)-[2.2]paracyclophane, 4-OH-5-(S)-[CyCH(Me)-N=CMe-] in hexane, toluene, Time= 2h, T= -65 - -20 °C Stage 3: in hexane, toluene, T= -20 °C Lauterwasser, Frank; Gall, Julia; Hoefener, Sebastian; Braese, Stefan; Advanced Synthesis and Catalysis; vol. 348; nb. 15; (2006); p. 2068 - 2074 View in Reaxys

H O

(v2)

OH O

Rx-ID: 10523268 View in Reaxys 96/280 Yield 88 %

Conditions & References Stage 1: With zirconocene hydrochloride in dichloromethane, Time= 0.25h, T= 20 °C Stage 2: With (Rp)-[2.2]paracyclophane, 4-OH-5-(S)-[CyCH(Me)-N=CMe-] in hexane, toluene, Time= 2h, T= -65 - -20 °C Stage 3: in hexane, toluene, T= -20 °C Lauterwasser, Frank; Gall, Julia; Hoefener, Sebastian; Braese, Stefan; Advanced Synthesis and Catalysis; vol. 348; nb. 15; (2006); p. 2068 - 2074 View in Reaxys

H (v2)

HO OH

Rx-ID: 10523286 View in Reaxys 97/280 Yield 54 %

71/120

2018-07-03 17:12:41

View in Reaxys

(v2)

OH O

Rx-ID: 10523310 View in Reaxys 98/280 Yield

Conditions & References

64 %

O O

Rx-ID: 25990499 View in Reaxys 99/280 Yield 78 % Spectr.

Conditions & References Stage 1: With t-Bu-N=P[N=P(NMe)3]3 in tetrahydrofuran, hexane, Time= 5h, T= 20 °C Stage 2: in tetrahydrofuran, hexane, Time= 17h, T= -40 - 20 °C , Further stages. Title compound not separated from byproducts. Ueno, Masahiro; Wheatley, Andrew E. H.; Kondo, Yoshinori; Chemical Communications; nb. 33; (2006); p. 3549 - 3550 View in Reaxys H

Mg I

Rx-ID: 597285 View in Reaxys 100/280 Yield 96 %

Conditions & References in diethyl ether, Heating Hatzakis, Nikos S.; Smonou, Ioulia; Bioorganic Chemistry; vol. 33; nb. 4; (2005); p. 325 - 337 View in Reaxys With diethyl ether Klages; Chemische Berichte; vol. 36; (1903); p. 621 View in Reaxys With 2,3-Dimethylaniline, benzene Tschelinzew; Chemische Berichte; vol. 37; (1904); p. 4539 View in Reaxys

72/120

2018-07-03 17:12:41

Si O

Rx-ID: 3230830 View in Reaxys 101/280 Yield

Conditions & References

98 %

With tetra-N-butylammonium tribromide in methanol, Time= 7h Gopinath, Rangam; Patel, Bhisma K.; Organic Letters; vol. 2; nb. 26; (2000); p. 4177 - 4180 View in Reaxys

95 %

With N-iodo-succinimide in methanol, Time= 19h, T= 20 °C Karimi, Babak; Zamani, Asghar; Zareyee, Daryoush; Tetrahedron Letters; vol. 45; nb. 49; (2004); p. 9139 - 9141 View in Reaxys

87 %

With sulfonic acid functionalized nanoporous silica in methanol, Time= 12h, T= 35 °C Karimi, Babak; Zareyee, Daryoush; Tetrahedron Letters; vol. 46; nb. 27; (2005); p. 4661 - 4665 View in Reaxys With tetrabutyl ammonium fluoride Shinokubo, Hiroshi; Miura, Katsukiyo; Oshima, Koichiro; Utimoto, Kiitiro; Tetrahedron Letters; vol. 34; nb. 12; (1993); p. 1951 - 1954 View in Reaxys Shinokubo, Hiroshi; Miura, Katsukiyo; Oshima, Koichiro; Utimoto, Kiitiro; Tetrahedron; vol. 52; nb. 2; (1996); p. 503 514 View in Reaxys -1 F (v4)

B FF

S+

Rx-ID: 9775480 View in Reaxys 102/280 Yield

Conditions & References

76 %

Stage 1: With lithium hexamethyldisilazane in tetrahydrofuran, 1,4-dioxane, Time= 5h, T= 5 °C Stage 2: With sodium hydroxide, dihydrogen peroxide Aggarwal, Varinder K.; Guang, Yu Fang; Schmidt, Andreas T.; Journal of the American Chemical Society; vol. 127; nb. 6; (2005); p. 1642 - 1643 View in Reaxys OH

H (v2)

Rx-ID: 9885843 View in Reaxys 103/280 Yield 81 %, 12 %

Conditions & References With palladium diacetate, tributylphosphine in hexane, toluene, Time= 6h, T= 20 °C Kimura, Masanari; Shimizu, Masamichi; Tanaka, Shuji; Tamaru, Yoshinao; Tetrahedron; vol. 61; nb. 15; (2005); p. 3709 3718 View in Reaxys

73/120

2018-07-03 17:12:41

SiH

Rx-ID: 9955261 View in Reaxys 104/280 Yield

Conditions & References With potassium carbonate in methanol, Time= 1h Kromm, Klemenz; Eichenseher, Sandra; Prommesberger, Markus; Hampel, Frank; Gladysz; European Journal of Inorganic Chemistry; nb. 15; (2005); p. 2983 - 2998 View in Reaxys O

Rx-ID: 10070514 View in Reaxys 105/280 Yield

Conditions & References

6 %, 79 %, 3 %, 7 %

With samarium diiodide, water in tetrahydrofuran, Time= 0.166667h, T= 20 °C , Further byproducts given Kamochi, Yasuko; Kudo, Tadahiro; Masuda, Toshinobu; Takadate, Akira; Chemical and Pharmaceutical Bulletin; vol. 53; nb. 8; (2005); p. 1017 - 1020 View in Reaxys

bis<chloro(η3-1,3-diphenylallyl)palladium> HO

Rx-ID: 13054234 View in Reaxys 106/280 Yield

Conditions & References Reaction Steps: 2 1: Rh chelate of chiral Re diphosphane / tetrahydrofuran / 336 h / 20 °C 2: K2CO3 / methanol / 1 h With potassium carbonate, Rh chelate of chiral Re diphosphane in tetrahydrofuran, methanol Kromm, Klemenz; Eichenseher, Sandra; Prommesberger, Markus; Hampel, Frank; Gladysz; European Journal of Inorganic Chemistry; nb. 15; (2005); p. 2983 - 2998 View in Reaxys

(1R,2R)-O-Merrifield bound N-(2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-2'-phenylacetamide

Rx-ID: 13209935 View in Reaxys 107/280 Yield

Conditions & References Reaction Steps: 2 1.1: 96 percent / aq. NaBF4 / CH2Cl2 / 48 h 2.1: LiHMDS / tetrahydrofuran; dioxane / 5 h / 5 °C 2.2: 76 percent / aq. NaOH; H2O2 With sodium tetrafluoroborate, lithium hexamethyldisilazane in tetrahydrofuran, 1,4-dioxane, dichloromethane

74/120

2018-07-03 17:12:41

Aggarwal, Varinder K.; Guang, Yu Fang; Schmidt, Andreas T.; Journal of the American Chemical Society; vol. 127; nb. 6; (2005); p. 1642 - 1643 View in Reaxys

Rx-ID: 9327810 View in Reaxys 108/280 Yield

Conditions & References Stage 1: With naphthalene, lithium in tetrahydrofuran, Time= 0.75h, T= -78 °C Stage 2: in tetrahydrofuran, Time= 0.5h Yus, Miguel; Ramon, Diego J.; Gomez, Inmaculada; Tetrahedron; vol. 59; nb. 18; (2003); p. 3219 - 3225 View in Reaxys

SiH

Rx-ID: 9334599 View in Reaxys 109/280 Yield

Conditions & References

7 % Spectr., With chloro(1,5-cyclooctadiene)rhodium(I) dimer, (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl in benzene-d6, T= 63 °C 4 % Spectr., Reyes, Clementina; Prock, Alfred; Giering, Warren P.; Journal of Organometallic Chemistry; vol. 671; nb. 1-2; (2003); p. 13 83 % - 26 Spectr. View in Reaxys

SiH O

Si O

Rx-ID: 9334609 View in Reaxys 110/280 Yield

Conditions & References

1 % Spectr., With chloro(1,5-cyclooctadiene)rhodium(I) dimer, (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl in benzene-d6, T= 63 °C 4 % Spectr., Reyes, Clementina; Prock, Alfred; Giering, Warren P.; Journal of Organometallic Chemistry; vol. 671; nb. 1-2; (2003); p. 13 92 % - 26 Spectr. View in Reaxys

SiH

Rx-ID: 9334611 View in Reaxys 111/280

75/120

2018-07-03 17:12:41

Yield

Conditions & References

4 % Spectr., With chloro(1,5-cyclooctadiene)rhodium(I) dimer, (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl in benzene-d6, T= 63 °C 88 % Spectr., 4 % Reyes, Clementina; Prock, Alfred; Giering, Warren P.; Journal of Organometallic Chemistry; vol. 671; nb. 1-2; (2003); p. 13 - 26 Spectr. View in Reaxys

SiH

Si O

Rx-ID: 9334613 View in Reaxys 112/280 Yield

Conditions & References

10 % With chloro(1,5-cyclooctadiene)rhodium(I) dimer, (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl in benzene-d6, T= 63 °C Spectr., 83 % Spectr., 6 Reyes, Clementina; Prock, Alfred; Giering, Warren P.; Journal of Organometallic Chemistry; vol. 671; nb. 1-2; (2003); p. 13 - 26 % Spectr. View in Reaxys

SiH

Si O

Rx-ID: 9334618 View in Reaxys 113/280 Yield

Conditions & References

5 % Spectr., With chloro(1,5-cyclooctadiene)rhodium(I) dimer, (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl in benzene-d6, T= 63 °C 74 % Spectr., 5 % Reyes, Clementina; Prock, Alfred; Giering, Warren P.; Journal of Organometallic Chemistry; vol. 671; nb. 1-2; (2003); p. 13 - 26 Spectr. View in Reaxys

SiH

Rx-ID: 9334626 View in Reaxys 114/280

76/120

2018-07-03 17:12:41

Yield

Conditions & References

1 % Spectr., With chloro(1,5-cyclooctadiene)rhodium(I) dimer, (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl in benzene-d6, T= 63 °C 7 % Spectr., Reyes, Clementina; Prock, Alfred; Giering, Warren P.; Journal of Organometallic Chemistry; vol. 671; nb. 1-2; (2003); p. 13 90 % - 26 Spectr. View in Reaxys

SiH

Si O

Rx-ID: 9334636 View in Reaxys 115/280 Yield

Conditions & References

4 % Spectr., With chloro(1,5-cyclooctadiene)rhodium(I) dimer, (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl in benzene-d6, T= 63 °C 80 % Reyes, Clementina; Prock, Alfred; Giering, Warren P.; Journal of Organometallic Chemistry; vol. 671; nb. 1-2; (2003); p. 13 Spectr. - 26 View in Reaxys

SiH

Rx-ID: 9334676 View in Reaxys 116/280

77/120

2018-07-03 17:12:41

Yield

Conditions & References

Rx-ID: 9507371 View in Reaxys 117/280 Yield 21 %, 69 %

Conditions & References Stage 1: With titanium(IV) isopropylate in diethyl ether, Time= 0.5h, T= -78 °C , p= 2068.65Torr Stage 2: With isopropylmagnesium chloride in diethyl ether, Time= 0.5h, T= -78 °C , Further stages. Eisch, John J.; Adeosun, Adetenu A.; Gitua, John N.; European Journal of Organic Chemistry; nb. 24; (2003); p. 4721 - 4727 View in Reaxys O

RuBr2[(S,S)-Tolskewphos][(S)-daipen] HO

Rx-ID: 23925727 View in Reaxys 118/280 Yield

Conditions & References C.4 : Comparative Example 4 Comparative Example 4 Except for using RuBr2[(S,S)-Tolskewphos][(S)-daipen] instead of RuBr2[(S,S)-Tolskewphos][(R)-daipen] as the catalyst, hydrogenation of propiophenone was carried out in the same way as Example 3 to give the product of 1-phenyl-1-propanol. The yield of the product was 99percent or higher and (R)-product was formed in 93.2percent ee. Patent; Kanto Kagaku Kabushiki Kaisha; US2003/166978; (2003); (A1) English View in Reaxys O

RuBr2[(S,S)-Xylskewphos][(S)-daipen] HO

Rx-ID: 23925728 View in Reaxys 119/280 Yield

Conditions & References C.11 : Comparative Example 11 Comparative Example 11 Except for using RuBr2[(S,S)-Xylskewphos][(S)-daipen] instead of RuBr2[(S,S)-Xylskewphos][(R)-daipen] as the catalyst, hydrogenation of propiophenone was carried out in the same way as Example 9 to give the product of 1-phenyl-1-propanol. The yield of the product was 99percent or higher and (R)-product was formed in 88.7percent ee. Patent; Kanto Kagaku Kabushiki Kaisha; US2003/166978; (2003); (A1) English View in Reaxys

Rx-ID: 1763944 View in Reaxys 120/280 Yield 48 %

Conditions & References With oxygen, tetraethylammonium borohydride, 5,10,15,20-tetraphenyl-21H,23H-porphine cobalt(II) in 1,2-dimethoxyethane, isopropyl alcohol, Time= 240h, Ambient temperature Okamoto, Tadashi; Oka, Shinzaburo; Journal of Organic Chemistry; vol. 49; nb. 9; (1984); p. 1589 - 1594 View in Reaxys

78/120

2018-07-03 17:12:41

With sodium tetrahydroborate, oxygen, [CoIII(dimethylglyoximate)2pyridineCl] in 1,2-dimethoxyethane, Time= 20h

Okamoto, Tadashi; Oka, Shinzaburo; Tetrahedron Letters; vol. 22; nb. 23; (1981); p. 2191 - 2194 View in Reaxys With sodium hydroxide, bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, dihydrogen peroxide, 1,4-di(diphenylphosphino)butane, benzo[1,3,2]dioxaborole, 1.) THF, 25 deg C, 15 h, 2.) THF, RT, 3 h, Yield given. Multistep reaction Hayashi; Matsumoto; Ito; Tetrahedron Asymmetry; vol. 2; nb. 7; (1991); p. 601 - 612 View in Reaxys With perchloric acid, T= 25 °C , Equilibrium constant Dey, Joykrishna; O'Donoghue, AnnMarie C.; More O'Ferrall, Rory A.; Journal of the American Chemical Society; vol. 124; nb. 29; (2002); p. 8561 - 8574 View in Reaxys

Rx-ID: 9060431 View in Reaxys 121/280 Yield

Conditions & References

9.9 %

Stage 1: With rhodium(III) chloride, THF·BF3 in tetrahydrofuran, Time= 2h, T= 20 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in water Morrill, Terence C.; D'Souza, Christopher A.; Yang, Lu; Sampognaro, Anthony J.; Journal of Organic Chemistry; vol. 67; nb. 8; (2002); p. 2481 - 2484 View in Reaxys

9.9 %

Stage 1: With rhodium(III) chloride, THF·BF3 in tetrahydrofuran, Time= 2h, T= 24 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran, water, T= 24 °C Morrill, Terence C.; D'Souza, Christopher A.; Yang, Lu; Sampognaro, Anthony J.; Journal of Organic Chemistry; vol. 67; nb. 8; (2002); p. 2481 - 2484 View in Reaxys HO

(v2)

N O

HO O

Rx-ID: 9256541 View in Reaxys 122/280 Yield

Conditions & References Stage 1: With 2-(N,N-dimethylamino)athanol in hexane, toluene, Time= 0.5h, T= 0 °C Stage 2: in hexane, toluene, Time= 48h, T= 0 °C Klein, Guenter; Pandiaraju, Subramaniam; Reiser, Oliver; Tetrahedron Letters; vol. 43; nb. 42; (2002); p. 7503 - 7506 View in Reaxys Br Mg

Rx-ID: 24094805 View in Reaxys 123/280 Yield

Conditions & References 3.A : Step A:

79/120

2018-07-03 17:12:41

Step A: Preparation of 3-(3-methoxypheny)-1-phenylpropanol To a solution of benzaldehyde (920 μl, 9 mmol) in dry THF (20 mL) was added slowly a solution of 2-(3-methoxyphenyl) ethylmagnesium bromide prepared from 2-(3-methoxyphenyl) ethyl bromide (2.1 g. 9.77 mmol) and magnesium (300 mg, 12 mmol). The mixture was stirred at room temperature for 1/2 hour then quenched with saturated NH4Cl. The mixture was then extracted into EtOAc, washed with H2O, dried (Na2SO4), filtered and concentrated in vacuo, then purified by silica gel chromatography (30percent EtOAc/Hexane) to provide the desired product as a colorless viscous oil. Patent; Merck and Co., Inc.; US6358985; (2002); (B1) English View in Reaxys

Br–

+Mg

O HO

Rx-ID: 643502 View in Reaxys 124/280 Yield

Conditions & References

88 %

in diethyl ether, T= -78 - 20 °C Soloshonok; Tang; Hruby; Van Meervelt; Organic letters; vol. 3; nb. 3; (2001); p. 341 - 343 View in Reaxys With diethyl ether Meisenheimer; Justus Liebigs Annalen der Chemie; vol. 442; (1925); p. 200; Justus Liebigs Annalen der Chemie; vol. 446; (1926); p. 84 View in Reaxys Addition Huang, Wei-Sheng; Hu, Qiao-Sheng; Pu, Lin; Journal of Organic Chemistry; vol. 64; nb. 21; (1999); p. 7940 - 7956 View in Reaxys OH

Rx-ID: 2138470 View in Reaxys 125/280 Yield

Conditions & References

89 %

With n-butyllithium, naphthalene, lithium in tetrahydrofuran, Time= 1.5h, T= -78 °C Yus, Miguel; Ramon, Diego J.; Journal of the Chemical Society, Chemical Communications; nb. 6; (1991); p. 398 - 400 View in Reaxys

77 %

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 3h, T= 0 - 63 °C Yasuda; Onishi; Ueba; Miyai; Baba; Journal of Organic Chemistry; vol. 66; nb. 23; (2001); p. 7741 - 7744 View in Reaxys

O OH HO

Rx-ID: 8768836 View in Reaxys 126/280 Yield 2%

Conditions & References With hydrogenchloride, samarium in tetrahydrofuran, T= 20 °C , Title compound not separated from byproducts Talukdar; Fang; Journal of Organic Chemistry; vol. 66; nb. 1; (2001); p. 330 - 333

80/120

2018-07-03 17:12:41

View in Reaxys O

O Cl

Rx-ID: 8813269 View in Reaxys 127/280 Yield

Conditions & References With Merulius tremellosus ono991 in acetone, Time= 72h, T= 28 °C , Title compound not separated from byproducts Hage, Annemarie; Petra, Danielle G.I.; Field, Jim A.; Schipper, Dick; Wijnberg, Joannes B.P.A.; Kamer, Paul C.J.; Reek, Joost N.H.; Van Leeuwen, Piet W.N.M.; Wever, Ron; Schoemaker, Hans E.; Tetrahedron Asymmetry; vol. 12; nb. 7; (2001); p. 1025 - 1034 View in Reaxys

Mg– Br

Li+

Rx-ID: 8825206 View in Reaxys 128/280 Yield 87 %

Conditions & References Stage 1: in tetrahydrofuran, hexane, Time= 0.5h, T= 0 °C Stage 2: in tetrahydrofuran, hexane, Time= 0.5h, T= -78 °C , Further stages. Inoue; Kitagawa; Shinokubo; Oshima; Journal of Organic Chemistry; vol. 66; nb. 12; (2001); p. 4333 - 4339 View in Reaxys

Rx-ID: 8913407 View in Reaxys 129/280 Yield 80 %

Conditions & References With cerium(IV) triflate, water in acetonitrile, Time= 1.5h, T= 25 °C Khalafi-Nezhad, Ali; Fareghi Alamdari, Reza; Tetrahedron; vol. 57; nb. 31; (2001); p. 6805 - 6807 View in Reaxys

81/120

2018-07-03 17:12:41

HO O

Rx-ID: 4952761 View in Reaxys 130/280 Yield

Conditions & References With η-cyclodextrin in water, T= 25 °C , acid and base hydrolysis of alkyl nitrites in the presence of η-cyclodextrin (CD); kinetics; effect of CD on the hydrolysis rate; CD catalysis of basic hydrolysis; complexation of alkyl nitrites with CD, Rate constant Iglesias, Emilia; Fernandez, Aurora; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 7; (1998); p. 1691 - 1700 View in Reaxys With acetate buffer, acetic acid, T= 25 °C , also in the presence of η-cyclodextrin; also basic hydrolysis, Rate constant Iglesias, Emilia; Journal of the American Chemical Society; vol. 120; nb. 50; (1998); p. 13057 - 13069 View in Reaxys With pyrrolidine, water in 1,4-dioxane, alkaline aq. solution, T= 25 °C , Kinetics, Further Variations: Reagents Iglesias; New Journal of Chemistry; vol. 24; nb. 12; (2000); p. 1025 - 1035 View in Reaxys With water, dodecyltrimethylammonium bromide, η-cyclodextrin in 1,4-dioxane, alkaline aq. solution, T= 25 °C , Kinetics, Further Variations: Reagents Iglesias; New Journal of Chemistry; vol. 24; nb. 12; (2000); p. 1025 - 1035 View in Reaxys O

H Mg Br

Rx-ID: 5330099 View in Reaxys 131/280 Yield

Conditions & References in diethyl ether, Addition, Product distribution Holm, Torkil; Journal of Organic Chemistry; vol. 65; nb. 4; (2000); p. 1188 - 1192 View in Reaxys H (v2)

Rx-ID: 8691281 View in Reaxys 132/280 Yield 87 %, 12 %

Conditions & References in toluene, Time= 0.166667h, Alkylation, reduction, Title compound not separated from byproducts. Musser; Richey Jr.; Journal of Organic Chemistry; vol. 65; nb. 23; (2000); p. 7750 - 7756 View in Reaxys

82/120

2018-07-03 17:12:41

H (v2)

Rx-ID: 8691282 View in Reaxys 133/280 Yield 97 %, 2 %

H (v2)

Rx-ID: 8691471 View in Reaxys 134/280 Yield 97 %, 2 %

Conditions & References in toluene, Time= 24h, Alkylation, reduction, Title compound not separated from byproducts. Musser; Richey Jr.; Journal of Organic Chemistry; vol. 65; nb. 23; (2000); p. 7750 - 7756 View in Reaxys

(v2)

H –O

HO K+

Rx-ID: 8691531 View in Reaxys 135/280 Yield 94 %

Conditions & References in toluene, Time= 0.25h, Alkylation Musser; Richey Jr.; Journal of Organic Chemistry; vol. 65; nb. 23; (2000); p. 7750 - 7756 View in Reaxys

(v2)

H –O

HO Li+

Rx-ID: 8691532 View in Reaxys 136/280 Yield 34 %, 6 %

Conditions & References in toluene, Time= 0.25h, Alkylation, reduction, Title compound not separated from byproducts. Musser; Richey Jr.; Journal of Organic Chemistry; vol. 65; nb. 23; (2000); p. 7750 - 7756 View in Reaxys

(v2)

Zn Br–

N+

Rx-ID: 8691545 View in Reaxys 137/280 Yield 38 %

Conditions & References in toluene, Time= 1h, Alkylation Musser; Richey Jr.; Journal of Organic Chemistry; vol. 65; nb. 23; (2000); p. 7750 - 7756

83/120

2018-07-03 17:12:41

View in Reaxys O Cl

Rx-ID: 5136643 View in Reaxys 138/280 Yield

Conditions & References

6 % Chromat., 11 % Chromat., 31 % Chromat., 1 % Chromat., 51 % Chromat.

With potassium hydroxide, hydrogen, 10% platinum on carbon in 2,2,4-trimethylpentane, water, Time= 0.283333h, T= 50 °C , p= 760Torr , Product distribution Perosa, Alvise; Selva, Maurizio; Tundo, Pietro; Journal of Organic Chemistry; vol. 64; nb. 11; (1999); p. 3934 - 3939 View in Reaxys

O Cl

Rx-ID: 5136644 View in Reaxys 139/280 Yield

Conditions & References

85 % Chromat., 1 % Chromat., 2 % Chromat., 12 % Chromat.

With potassium hydroxide, hydrogen, 10% platinum on carbon in 2,2,4-trimethylpentane, water, Time= 6h, T= 50 °C , p= 760Torr , other reagent, reaction time, various KOH concentrations, pH effect, Product distribution Perosa, Alvise; Selva, Maurizio; Tundo, Pietro; Journal of Organic Chemistry; vol. 64; nb. 11; (1999); p. 3934 - 3939 View in Reaxys

H (v2)

Rx-ID: 5151804 View in Reaxys 140/280 Yield 16 %

Conditions & References With isoprene, bis(acetylacetonate)nickel(II) in tetrahydrofuran, hexane, Time= 4h, Ambient temperature, Yields of byproduct given Kimura, Masanari; Fujimatsu, Hidetaka; Ezoe, Akihiro; Shibata, Kazufumi; Shimizu, Masamichi; Matsumoto, Satoru; Tamaru, Yoshinao; Angewandte Chemie - International Edition; vol. 38; nb. 3; (1999); p. 397 - 400 View in Reaxys

Li O HO

Rx-ID: 1569281 View in Reaxys 141/280

84/120

2018-07-03 17:12:41

Yield

Conditions & References

0.1 %, 73 % With bis(trimethylsilyl)amide yttrium(III) in diethyl ether, Time= 2h, T= 25 °C Mukerji, Ishita; Wayda, Andrea L.; Dabbagh, Gary; Bertz, Steven H.; Angewandte Chemie; vol. 98; nb. 8; (1986); p. 756 757 View in Reaxys With zinc(II) chloride, 1.) Et2O, THF, 0 deg C, 30 min, 2.) Et2O, THF, RT, 4 h, Yield given. Multistep reaction. Yields of byproduct given Uchiyama, Masanobu; Kameda, Mitsuyoshi; Mishima, Osamu; Yokoyama, Nobuko; Koike, Minako; Kondo, Yoshinori; Sakamoto, Takao; Journal of the American Chemical Society; vol. 120; nb. 20; (1998); p. 4934 - 4946 View in Reaxys O Cl

Rx-ID: 4859444 View in Reaxys 142/280 Yield

Conditions & References

11 % Chromat., 18 % Chromat., 10 % Chromat., 17 % Chromat., 44 % Chromat.

With hydrogen, Aliquat 336, 10% platinum on carbon in 2,2,4-trimethylpentane, Time= 6h, T= 50 °C , reaction in multiphase conditions (aq. KOH); different ionic and nonionic phase-transfer agents; hydrodehalogenation of halogenated aryl ketones and benzyl alcohols under phase-transfer conditions; chemoselectivity toward aryl alcohols, Product distribution Selva, Maurizio; Tundo, Pietro; Perosa, Alvise; Journal of Organic Chemistry; vol. 63; nb. 10; (1998); p. 3266 - 3271 View in Reaxys

O Cl

Rx-ID: 4859445 View in Reaxys 143/280 Yield

Conditions & References

95 % Chromat.

With potassium hydroxide, hydrogen, Aliquat 336, 10% platinum on carbon in 2,2,4-trimethylpentane, Time= 2h, T= 50 °C Selva, Maurizio; Tundo, Pietro; Perosa, Alvise; Journal of Organic Chemistry; vol. 63; nb. 10; (1998); p. 3266 - 3271 View in Reaxys

HO Cl

Rx-ID: 4869518 View in Reaxys 144/280 Yield

Conditions & References

96 % Chromat.

With potassium hydroxide, hydrogen, Aliquat 336, 10% platinum on carbon in 2,2,4-trimethylpentane, Time= 7h, T= 50 °C Selva, Maurizio; Tundo, Pietro; Perosa, Alvise; Journal of Organic Chemistry; vol. 63; nb. 10; (1998); p. 3266 - 3271 View in Reaxys

Li O

HO HO

Rx-ID: 4937613 View in Reaxys 145/280

85/120

2018-07-03 17:12:41

Yield

Conditions & References

75 %

With boron trifluoride diethyl etherate in tetrahydrofuran, Time= 0.25h Botuha, Candice; Haddad, Mansour; Larcheveque, Marc; Tetrahedron Asymmetry; vol. 9; nb. 11; (1998); p. 1929 - 1931 View in Reaxys

O Al

Rx-ID: 4942865 View in Reaxys 146/280 Yield

Conditions & References

10 %, 2 %

in dichloromethane, Time= 1h, T= -40 °C Ooi, Takashi; Takahashi, Makoto; Maruoka, Keiji; Angewandte Chemie - International Edition; vol. 37; nb. 6; (1998); p. 835 - 837 View in Reaxys

(v3)

Al+

(v2) –

(v3)

Al+

(v2) O–

Rx-ID: 4942917 View in Reaxys 147/280 Yield

Conditions & References

71 %, 11 %

in dichloromethane, Time= 1h, T= -78 °C Ooi, Takashi; Takahashi, Makoto; Maruoka, Keiji; Angewandte Chemie - International Edition; vol. 37; nb. 6; (1998); p. 835 - 837 View in Reaxys 2H

O O HO

Rx-ID: 4992216 View in Reaxys 148/280 Yield 13 % Chromat., 30 % Chromat., 57 % Chromat.

Conditions & References With n-butyllithium in tetrahydrofuran, Time= 1h, T= -40 °C , Title compound not separated from byproducts Azzena, Ugo; Pilo, Luciano; Sechi, Alessandra; Tetrahedron; vol. 54; nb. 40; (1998); p. 12389 - 12398 View in Reaxys

With n-butyllithium, water-d2 in tetrahydrofuran, T= -80 - -40 °C , Product distribution Azzena, Ugo; Pilo, Luciano; Sechi, Alessandra; Tetrahedron; vol. 54; nb. 40; (1998); p. 12389 - 12398 View in Reaxys H

O O

Rx-ID: 5002912 View in Reaxys 149/280

86/120

2018-07-03 17:12:41

Yield

Conditions & References With 4,4'-di-tert-butylbiphenyl, lithium, 1.) THF, RT, 1.5 h; 2.) THF, -40 deg C to 0 deg C, Yield given. Multistep reaction Bachki, Abderrazak; Foubelo, Francisco; Yus, Miguel; Tetrahedron Letters; vol. 39; nb. 42; (1998); p. 7759 - 7762 View in Reaxys

HO O

Rx-ID: 4795654 View in Reaxys 150/280 Yield

Conditions & References

61 %

With dimethylsulfide, magnesium bromide in dichloromethane, Time= 94h, Ambient temperature Onoda, Toshihiko; Shirai, Ryuichi; Iwasaki, Shigeo; Tetrahedron Letters; vol. 38; nb. 8; (1997); p. 1443 - 1446 View in Reaxys

H HO

HO H

Rx-ID: 4423737 View in Reaxys 151/280 Yield

Conditions & References

3 %, 3 %, 2 %

With (S)-2-[3]pyridyl-pyrrolidine-1-carboxylic acid amide, sodium phosphate buffer, η-D-glucose 6-phosphate, NADP, magnesium chloride in water, Time= 1h, T= 37 °C , biotransformation with phenobarbital-pretreated rat liver (S-9); ee measured; further substrate investigated, Product distribution Takeshita, Mitsuhiro; Miura, Masatomo; Unuma, Yukiko; Iwai, Sakiko; Sato, Izumi; Hongo, Takahiko; Arai, Toshie; Kosaka, Kazuhiro; Heterocycles; vol. 42; nb. 2; (1996); p. 831 - 836 View in Reaxys

O Cl

Rx-ID: 4509723 View in Reaxys 152/280 Yield

Conditions & References With hydrogen, 10 wt. % palladium on activated carbon in 2,2,4-trimethylpentane, water, T= 50 °C , Product distribution Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro; Gazzetta Chimica Italiana; vol. 126; nb. 6; (1996); p. 317 - 328 View in Reaxys O

O Cl

Rx-ID: 4509724 View in Reaxys 153/280 Yield

Conditions & References With hydrogen, Aliquat 336, 10 wt. % palladium on activated carbon in 2,2,4-trimethylpentane, T= 50 °C , Product distribution

87/120

2018-07-03 17:12:41

Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro; Gazzetta Chimica Italiana; vol. 126; nb. 6; (1996); p. 317 - 328 View in Reaxys O Cl

Rx-ID: 4517719 View in Reaxys 154/280 Yield

Conditions & References

98 % Chromat., 6 % Chromat.

With potassium hydroxide, hydrogen, 10 wt. % palladium on activated carbon in 2,2,4-trimethylpentane, Time= 30h, T= 50 °C , Product distribution Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro; Gazzetta Chimica Italiana; vol. 126; nb. 6; (1996); p. 317 - 328 View in Reaxys

Rx-ID: 4517720 View in Reaxys 155/280 Yield

Conditions & References

2 % Chromat., 98 % Chromat.

With potassium hydroxide, hydrogen, Aliquat 336, 10 wt. % palladium on activated carbon in 2,2,4-trimethylpentane, Time= 20h, T= 50 °C , Product distribution Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro; Gazzetta Chimica Italiana; vol. 126; nb. 6; (1996); p. 317 - 328 View in Reaxys

O HO

Rx-ID: 4556800 View in Reaxys 156/280 Yield

Conditions & References With lithium trimethyl zincate in tetrahydrofuran, Time= 4h, Ambient temperature, other metal reagents, other aromatic compounds, Product distribution Uchiyama, Masanobu; Koike, Minako; Kameda, Mitsuyoshi; Kondo, Yoshinori; Sakamoto, Takao; Journal of the American Chemical Society; vol. 118; nb. 36; (1996); p. 8733 - 8734 View in Reaxys

O F

S O

Rx-ID: 4573207 View in Reaxys 157/280 Yield 61 %

Conditions & References With naphthalene, lithium in tetrahydrofuran, Time= 2h, T= -78 - 0 °C Alonso, Emma; Ramon, Diego J.; Yus, Miguel; Tetrahedron; vol. 52; nb. 45; (1996); p. 14341 - 14348 View in Reaxys

sodium cyanate O

88/120

2018-07-03 17:12:41

pig's pancreas-dry powder HO

Rx-ID: 17846193 View in Reaxys 158/280 Yield

Conditions & References Reaction Steps: 3 1: 1.) LDA, 3.) HMPA 2: 1.) n-Bu3SnH, Et3B, 2.) aq. KF / 1.) hexane, 80 deg C, 24 h, 2.) CH2Cl2, 25 deg C, 15 h 3: n-Bu4NF With N,N,N,N,N,N-hexamethylphosphoric triamide, potassium fluoride, triethyl borane, tetrabutyl ammonium fluoride, tri-nbutyl-tin hydride, lithium diisopropyl amide Shinokubo, Hiroshi; Miura, Katsukiyo; Oshima, Koichiro; Utimoto, Kiitiro; Tetrahedron; vol. 52; nb. 2; (1996); p. 503 514 View in Reaxys

pig's pancreas-dry powder

O HO

Rx-ID: 17850012 View in Reaxys 159/280 Yield

Conditions & References Reaction Steps: 2 1: 1.) n-Bu3SnH, Et3B, 2.) aq. KF / 1.) hexane, 80 deg C, 24 h, 2.) CH2Cl2, 25 deg C, 15 h 2: n-Bu4NF With potassium fluoride, triethyl borane, tetrabutyl ammonium fluoride, tri-n-butyl-tin hydride Shinokubo, Hiroshi; Miura, Katsukiyo; Oshima, Koichiro; Utimoto, Kiitiro; Tetrahedron; vol. 52; nb. 2; (1996); p. 503 514 View in Reaxys O

S O

Rx-ID: 2680109 View in Reaxys 160/280 Yield

Conditions & References

61 %

With naphthalene, boron trifluoride diethyl etherate, lithium in tetrahydrofuran, Time= 5h, T= -78 - 20 °C Guijaro, David; Yus, Miguel; Tetrahedron Letters; vol. 35; nb. 18; (1994); p. 2965 - 2968 View in Reaxys

61 %

With naphthalene, boron trifluoride diethyl etherate, lithium in tetrahydrofuran, Time= 5h, T= -78 - 20 °C Alonso, Emma; Guijarro, David; Yus, Miguel; Tetrahedron; vol. 51; nb. 9; (1995); p. 2699 - 2708 View in Reaxys

61 %

With naphthalene, lithium in tetrahydrofuran, Time= 5h, T= -78 - 20 °C , var. alkyl phenyl sulfone, carbonyl compound, temp., cat., Mechanism, Product distribution Alonso, Emma; Guijarro, David; Yus, Miguel; Tetrahedron; vol. 51; nb. 9; (1995); p. 2699 - 2708 View in Reaxys O

O Cl

Rx-ID: 4149432 View in Reaxys 161/280

89/120

2018-07-03 17:12:41

Yield

Conditions & References

72 %, 25 %, With potassium hydroxide, hydrogen, Aliquat 336, 10 wt. % palladium on activated carbon in pentane, Time= 0.166667h, T= 3% 30 °C , various solvents, time, temp.; also in the absence of Aliquat 336; further aromatic ketones, Product distribution Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro; Journal of Organic Chemistry; vol. 60; nb. 8; (1995); p. 2430 2435 View in Reaxys HO Cl

Rx-ID: 4160371 View in Reaxys 162/280 Yield

Conditions & References

96 %, 4 %

With potassium hydroxide, hydrogen, Aliquat 336, 10 wt. % palladium on activated carbon in 2,2,4-trimethylpentane, Time= 0.833333h, T= 50 °C , various time, solvents; also in the presence of various aromatic halides as promoters; further benzylic alcohols, Product distribution Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro; Journal of Organic Chemistry; vol. 60; nb. 8; (1995); p. 2430 2435 View in Reaxys O Se

Rx-ID: 4162686 View in Reaxys 163/280 Yield

Conditions & References

88 % Chromat.

With potassium tri-sec-butyl-borohydride in tetrahydrofuran, Time= 3h, T= 0 °C Aoki, Ikuo; Nishibayashi; Uemura, Sakae; Bulletin of the Chemical Society of Japan; vol. 68; nb. 1; (1995); p. 337 - 340 View in Reaxys O Se

Rx-ID: 4162687 View in Reaxys 164/280 Yield

Conditions & References With sodium tetrahydroborate in methanol, Time= 1h, T= 0 °C , other η-seleno ketones; var. reducing agents, solvents, temp., times; also in the presence of CaCl2 and CeCl3, Product distribution Aoki, Ikuo; Nishibayashi; Uemura, Sakae; Bulletin of the Chemical Society of Japan; vol. 68; nb. 1; (1995); p. 337 - 340 View in Reaxys

18 % Chromat.

With sodium tetrahydroborate in methanol, Time= 1h, T= -78 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Aoki, Ikuo; Nishibayashi; Uemura, Sakae; Bulletin of the Chemical Society of Japan; vol. 68; nb. 1; (1995); p. 337 - 340 View in Reaxys

90/120

2018-07-03 17:12:41

5 % Chromat.

With zinc(II) tetrahydroborate in diethyl ether, Time= 24h, T= 0 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Aoki, Ikuo; Nishibayashi; Uemura, Sakae; Bulletin of the Chemical Society of Japan; vol. 68; nb. 1; (1995); p. 337 - 340 View in Reaxys O

Rx-ID: 4185166 View in Reaxys 165/280 Yield

Conditions & References

61 % Chromat.

With sodium tetrahydroborate in methanol, Time= 1h, T= 0 °C , Yields of byproduct given Aoki, Ikuo; Nishibayashi; Uemura, Sakae; Bulletin of the Chemical Society of Japan; vol. 68; nb. 1; (1995); p. 337 - 340 View in Reaxys

8 % Chromat.

With zinc(II) tetrahydroborate in diethyl ether, Time= 24h, T= 0 °C , Yield given. Yields of byproduct given Aoki, Ikuo; Nishibayashi; Uemura, Sakae; Bulletin of the Chemical Society of Japan; vol. 68; nb. 1; (1995); p. 337 - 340 View in Reaxys

8 % Chromat.

Rx-ID: 4252910 View in Reaxys 166/280 Yield

Conditions & References With n-butyllithium, water, 1.) hexane/THF, -40 degC, 1 h, Yield given. Multistep reaction Azzena, Ugo; Demartis, Salvatore; Fiori, Maria Giovanna; Melloni, Giovanni; Pisano, Luisa; Tetrahedron Letters; vol. 36; nb. 31; (1995); p. 5641 - 5644 View in Reaxys

Rx-ID: 1548715 View in Reaxys 167/280 Yield

Conditions & References With zinc borohydride, silica gel in N,N-dimethyl-formamide, Time= 1.5h, Ambient temperature, Yield given. Yields of byproduct given Ranu, Brindaban C.; Sarkar, Arunkanti; Saha, Manika; Chakraborty, Rupak; Tetrahedron; vol. 50; nb. 22; (1994); p. 6579 - 6584 View in Reaxys O

S O

Rx-ID: 2677961 View in Reaxys 168/280

91/120

2018-07-03 17:12:41

Yield

Conditions & References With lithium, naphthalene, 1) THF, -78 deg C, 1 h, 2) THF, -78 to 20 deg C, 5 h, Yield given. Multistep reaction Guijarro; Mancheno; Yus; Tetrahedron Letters; vol. 33; nb. 38; (1992); p. 5597 - 5600 View in Reaxys With naphthalene, lithium, 1) THF, -78 deg C, 75 min, 2) THF, -78 to 20 deg C, 5 h, Yield given. Multistep reaction Guijarro, David; Guillena, Gabricia; Mancheno, Balbino; Yus, Miguel; Tetrahedron; vol. 50; nb. 11; (1994); p. 3427 - 3436 View in Reaxys

H O

O P

Rx-ID: 2678631 View in Reaxys 169/280 Yield

Conditions & References

90 %

With lithium in tetrahydrofuran, Time= 0.25h, T= -30 °C Guijarro, David; Mancheno, Balbino; Yus, Miguel; Tetrahedron; vol. 50; nb. 28; (1994); p. 8551 - 8558 View in Reaxys HO

O P

Rx-ID: 2678637 View in Reaxys 170/280 Yield

Conditions & References With lithium in tetrahydrofuran, Time= 0.25h, T= -30 °C , Yield given. Yields of byproduct given Guijarro, David; Mancheno, Balbino; Yus, Miguel; Tetrahedron; vol. 50; nb. 28; (1994); p. 8551 - 8558 View in Reaxys OH

O P

Rx-ID: 2678640 View in Reaxys 171/280 Yield

P O

Rx-ID: 2679612 View in Reaxys 172/280 Yield

92/120

2018-07-03 17:12:41

OH O

P O

Rx-ID: 2679631 View in Reaxys 173/280 Yield

Rx-ID: 2681326 View in Reaxys 174/280 Yield

Conditions & References With hydrogenchloride, 1.) THF, rt, 2 h, 2.) toluene, Yield given. Multistep reaction Bogdanovic, Borislav; Bons, Peter; Konstantinovic, Stanimir; Schwickardi, Manfred; Westeppe, Uwe; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1371 - 1384 View in Reaxys With (5aS,10aS)-(-)-Octahydro-5H,10H-dipyrrolo<1,2-a:1',2'-d>pyrazin in tetrahydrofuran, toluene, Time= 5h, T= -100 °C , Yield given Zadel, Guido; Breitmaier, Eberhard; Chemische Berichte; vol. 127; nb. 7; (1994); p. 1323 - 1326 View in Reaxys H

Mg O

Rx-ID: 2682399 View in Reaxys 175/280 Yield 60 %

Conditions & References in 1,4-dioxane, benzene, magnetic field B0 1.2 Zadel, Guido; Eisenbraun, Catja; Wolff, Gerd-Joachim; Breitmaier, Eberhard; Angewandte Chemie; vol. 106; nb. 4; (1994); p. 460 - 463 View in Reaxys

H (v2)

Rx-ID: 2689803 View in Reaxys 176/280 Yield

Conditions & References in tetrahydrofuran, diethyl ether, T= 0 °C , Yield given. Yields of byproduct given Laloe, Eric; Srebnik, Morris; Tetrahedron Letters; vol. 35; nb. 31; (1994); p. 5587 - 5590 View in Reaxys OH

H Zn

(v2)

Rx-ID: 2689807 View in Reaxys 177/280

93/120

2018-07-03 17:12:41

Yield

Conditions & References in diethyl ether, T= 0 °C , Yield given. Yields of byproduct given Laloe, Eric; Srebnik, Morris; Tetrahedron Letters; vol. 35; nb. 31; (1994); p. 5587 - 5590 View in Reaxys Li

H B

Rx-ID: 2683996 View in Reaxys 178/280 Yield

Conditions & References 1.) THF, -78 deg C, 22 h, r.t., 16 h; 2.) CHCl3, reflux, 12 h, Yield given. Multistep reaction. Yields of byproduct given Pelter; Buss; Colclough; Singaram; Tetrahedron; vol. 49; nb. 32; (1993); p. 7077 - 7103 View in Reaxys OH

HO OH

Rx-ID: 3399074 View in Reaxys 179/280 Yield

Conditions & References in benzene, Ambient temperature, Irradiation, varying concentration of initial compounds; varying irradiation intensity, Quantum yield, Rate constant Wagner, Peter J.; Zhang, Yuanda; Puchalski, Allen E.; Journal of Physical Chemistry; vol. 97; (1993); p. 13368 - 13374 View in Reaxys

Et4(PrO)4(μ-PrO)2W2 O

Rx-ID: 7912766 View in Reaxys 180/280 Yield 3%

Conditions & References in tetrahydrofuran, Yield given. Yields of byproduct given. Title compound not separated from byproducts Kauffmann, Thomas; Jordan, Jan; Voss, Karl-Uwe; Wilde, Heinz-Wilhelm; Chemische Berichte; vol. 126; nb. 9; (1993); p. 2083 - 2092

94/120

2018-07-03 17:12:41

View in Reaxys H

aminoguanidine salt O

Rx-ID: 19573981 View in Reaxys 181/280 Yield

Conditions & References Reaction Steps: 3 2: 97 percent / n-Bu3SnH, Et3B / hexane / 80 °C 3: n-Bu4NF With triethyl borane, tetrabutyl ammonium fluoride, tri-n-butyl-tin hydride in hexane Shinokubo, Hiroshi; Miura, Katsukiyo; Oshima, Koichiro; Utimoto, Kiitiro; Tetrahedron Letters; vol. 34; nb. 12; (1993); p. 1951 - 1954 View in Reaxys

Si O HO

Rx-ID: 19577781 View in Reaxys 182/280 Yield

Conditions & References Reaction Steps: 2 1: 97 percent / n-Bu3SnH, Et3B / hexane / 80 °C 2: n-Bu4NF With triethyl borane, tetrabutyl ammonium fluoride, tri-n-butyl-tin hydride in hexane Shinokubo, Hiroshi; Miura, Katsukiyo; Oshima, Koichiro; Utimoto, Kiitiro; Tetrahedron Letters; vol. 34; nb. 12; (1993); p. 1951 - 1954 View in Reaxys 2 (v3)

Cu 2-

Li+

O HO

Rx-ID: 1569433 View in Reaxys 183/280 Yield

Conditions & References With water, 1) THF, -78 deg C to 20 deg C, 18 h, Yield given. Multistep reaction. Yields of byproduct given Kauffmann, Thomas; Neiteler, Christel; Robbe, Sonja; Chemische Berichte; vol. 125; nb. 11; (1992); p. 2409 - 2418 View in Reaxys

N N

HO O

Rx-ID: 2154657 View in Reaxys 184/280 Yield

Conditions & References With 9,10-Dicyanoanthracene in acetonitrile, T= 20 °C , Irradiation

95/120

2018-07-03 17:12:41

Ishiguro, Katsuya; Ikeda, Masatoshi; Sawaki, Yasuhiko; Journal of Organic Chemistry; vol. 57; nb. 11; (1992); p. 3057 3066 View in Reaxys

H Pb

Rx-ID: 2682232 View in Reaxys 185/280 Yield

Conditions & References

15 %, 71 %

With titanium tetrachloride in dichloromethane, T= -78 - -30 °C Yamamoto, Yoshinori; Yamada, Jun-Ichi; Asano, Tetsuya; Tetrahedron; vol. 48; nb. 27; (1992); p. 5587 - 5596 View in Reaxys H

Rx-ID: 2682286 View in Reaxys 186/280 Yield

Conditions & References

62 %, 11 %

With titanium tetrachloride in dichloromethane, T= -78 - -30 °C Yamamoto, Yoshinori; Yamada, Jun-Ichi; Asano, Tetsuya; Tetrahedron; vol. 48; nb. 27; (1992); p. 5587 - 5596 View in Reaxys H

Rx-ID: 2682287 View in Reaxys 187/280 Yield

Conditions & References

62 %, 11 %, With titanium tetrachloride in dichloromethane, T= -78 - -30 °C 5% Yamamoto, Yoshinori; Yamada, Jun-Ichi; Asano, Tetsuya; Tetrahedron; vol. 48; nb. 27; (1992); p. 5587 - 5596 View in Reaxys

Rx-ID: 2682288 View in Reaxys 188/280 Yield 98 %

Conditions & References With titanium tetrachloride in dichloromethane, T= -78 - -30 °C , further aldehydes and tetraalkylleads; reaction with mixed tetraalkylleads; other conditions, Product distribution Yamamoto, Yoshinori; Yamada, Jun-Ichi; Asano, Tetsuya; Tetrahedron; vol. 48; nb. 27; (1992); p. 5587 - 5596 View in Reaxys

98 %

With titanium tetrachloride in dichloromethane, T= -78 - -30 °C Yamamoto, Yoshinori; Yamada, Jun-Ichi; Asano, Tetsuya; Tetrahedron; vol. 48; nb. 27; (1992); p. 5587 - 5596 View in Reaxys

96 %

With titanium tetrachloride in dichloromethane, T= -78 - -30 °C Yamamoto, Yoshinori; Yamada, Jun-ichi; Journal of the American Chemical Society; vol. 109; nb. 14; (1987); p. 4395 - 4396 View in Reaxys

96/120

2018-07-03 17:12:41

OH H

Pb O

Rx-ID: 2682289 View in Reaxys 189/280 Yield

Conditions & References

98 %, 1.7 % With titanium tetrachloride in dichloromethane, T= -78 - -30 °C Yamamoto, Yoshinori; Yamada, Jun-Ichi; Asano, Tetsuya; Tetrahedron; vol. 48; nb. 27; (1992); p. 5587 - 5596 View in Reaxys H

Cp2Zr(CH2=CH2)(PMePh2) O

Rx-ID: 7159160 View in Reaxys 190/280 Yield

Conditions & References

95 % Chromat.

in tetrahydrofuran, Time= 2h, Ambient temperature Takahashi, Tamotsu; Suzuki, Noriyuki; Hasegawa, Maki; Nitto, Yu; Aoyagi, Ko-ichiro; Saburi, Masahiko; Chemistry Letters; (1992); p. 331 - 334 View in Reaxys

HO O

Rx-ID: 2899598 View in Reaxys 191/280 Yield

Conditions & References

85.7 %, 14.0 %

With NaHB4, Time= 15h, Heating Rao; Nambudiry; Synthetic Communications; vol. 21; nb. 17; (1991); p. 1721 - 1727 View in Reaxys

85.7 %, 14 %

With NaHB4, Time= 15h, Heating Rao; Nambudiry; Synthetic Communications; vol. 21; nb. 17; (1991); p. 1721 - 1727 View in Reaxys

HO HO

Rx-ID: 5249047 View in Reaxys 192/280 Yield

Conditions & References With lithium aluminium tetrahydride, zirconium(IV) chloride in diethyl ether, Time= 12h, T= 30 °C , Reduction Shaozu, Wu; Tianhui, Ren; Ning, Chen; Yulan, Zhang; Organic Preparations and Procedures International; vol. 23; nb. 4; (1991); p. 427 - 431 View in Reaxys

97/120

2018-07-03 17:12:41

Rx-ID: 2040359 View in Reaxys 193/280 Yield

Conditions & References

42 % Chromat., 31 % Chromat.

With potassium in tetrahydrofuran, Time= 24h, T= 20 °C Azzena, Ugo; Denurra, Teresa; Melloni, Giovanni; Piroddi, Anna Maria; Journal of Organic Chemistry; vol. 55; nb. 20; (1990); p. 5532 - 5535 View in Reaxys

O O Cl

Rx-ID: 3399348 View in Reaxys 194/280 Yield 9%

Conditions & References With sodium tetrahydroborate, l-tartaric acid in tetrahydrofuran, Time= 120h, Ambient temperature, Yields of byproduct given. Title compound not separated from byproducts Yatagai, Masanobu; Ohnuki, Takashi; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 6; (1990); p. 1826 - 1828 View in Reaxys

Rx-ID: 2007647 View in Reaxys 195/280 Yield

Conditions & References With lithium aluminium tetrahydride, oxygen, dibenzoyl peroxide, 1.) 150 deg C, 2.) ether, reflux, 30 min, Yield given. Multistep reaction. Yields of byproduct given Batke, Birgit; Lauterbach, Gerlinde; Pritzkow, Wilhelm; Voerckel, Volkmar; Belyakov, Vladimir A.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 3; (1989); p. 424 - 430 View in Reaxys

41 % Chromat., 49 % Chromat.

With lithium aluminium tetrahydride, oxygen, dibenzoyl peroxide, chain termination and propagation constants, oxidabilities; multistep reaction, Product distribution Batke, Birgit; Lauterbach, Gerlinde; Pritzkow, Wilhelm; Voerckel, Volkmar; Belyakov, Vladimir A.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 3; (1989); p. 424 - 430 View in Reaxys

H 2

Rx-ID: 2686335 View in Reaxys 196/280 Yield 90 %

Conditions & References in tetrahydrofuran, Time= 0.0833333h, T= 20 °C

98/120

2018-07-03 17:12:41

Boudin, Alain; Cerveau, Genevieve; Chuit, Claude; Corriu, Robert J.P.; Reye, Catherine; Tetrahedron; vol. 45; nb. 1; (1989); p. 171 - 180 View in Reaxys 90 %

in tetrahydrofuran, T= 20 °C , further carbonyl compounds, further solvents, further Grignard/TDA-1 complexes Boudin, Alain; Cerveau, Genevieve; Chuit, Claude; Corriu, Robert J.P.; Reye, Catherine; Tetrahedron; vol. 45; nb. 1; (1989); p. 171 - 180 View in Reaxys O

Rx-ID: 3383841 View in Reaxys 197/280 Yield

Conditions & References With bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum, diisobutylaluminium hydride, T= -78 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Maruoka, Keiji; Araki, Yoshitaka; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 110; nb. 8; (1988); p. 2650 - 2652 View in Reaxys O

Rx-ID: 3384110 View in Reaxys 198/280 Yield

Conditions & References With dichloroaluminum hydride, bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum, T= -78 °C , studies of the selective carbonyl reduction, Product distribution Maruoka, Keiji; Araki, Yoshitaka; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 110; nb. 8; (1988); p. 2650 - 2652 View in Reaxys

Rx-ID: 3821290 View in Reaxys 199/280 Yield

Conditions & References With sodium tetrahydroborate in isopropyl alcohol, Time= 7h, Heating, Yields of byproduct given Ookawa, Atsuhiro; Kitade, Masaya; Soai, Kenso; Heterocycles; vol. 27; nb. 1; (1988); p. 213 - 216 View in Reaxys With sodium tetrahydroborate in methanol, tert-butyl alcohol, Time= 4h, Yield given. Yields of byproduct given Ookawa, Atsuhiro; Hiratsuka, Hiroshi; Soai, Kenso; Bulletin of the Chemical Society of Japan; vol. 60; (1987); p. 1813 1818 View in Reaxys With sodium tetrahydroborate in methanol, tert-butyl alcohol, Time= 4h, Yield given Ookawa, Atsuhiro; Hiratsuka, Hiroshi; Soai, Kenso; Bulletin of the Chemical Society of Japan; vol. 60; (1987); p. 1813 1818 View in Reaxys

99/120

2018-07-03 17:12:41

N N N

N N

HO O

Rx-ID: 3738203 View in Reaxys 200/280 Yield

Conditions & References

14 % Chromat., 2 % Chromat., 60 % Chromat., 2 %

With copper(II) perchlorate, Ambient temperature, Further byproducts given

15 % Chromat., 19 % Chromat., 5 % Chromat., 25 % Chromat.

With lithium perchlorate, anodic oxidation, Further byproducts given

Ishiguro, Katsuya; Sawaki, Yasuhiko; Iwamura, Hiizu; Chemistry Letters; (1987); p. 1853 - 1856 View in Reaxys

N N

HO N

N N

NH O

Rx-ID: 3738204 View in Reaxys 201/280 Yield

Conditions & References

2 % Chromat., 60 % Chromat., 5 % Chromat., 2 % Chromat.

With copper(II) perchlorate, Ambient temperature, Further byproducts given Ishiguro, Katsuya; Sawaki, Yasuhiko; Iwamura, Hiizu; Chemistry Letters; (1987); p. 1853 - 1856 View in Reaxys

N N N

Cl N N

Rx-ID: 3738205 View in Reaxys 202/280

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

100/120

2018-07-03 17:12:41

Yield

Conditions & References

12 % Chromat., 5 % Chromat., 22 % Chromat., 34 % Chromat.

With tris(p-bromophenylammoniumyl) hexachloroantimonate, Ambient temperature, Further byproducts given Ishiguro, Katsuya; Sawaki, Yasuhiko; Iwamura, Hiizu; Chemistry Letters; (1987); p. 1853 - 1856 View in Reaxys

HO HO

Rx-ID: 3840953 View in Reaxys 203/280 Yield

Conditions & References With lithium aluminium tetrahydride, oxygen, T= 110 °C , p= 759.8Torr , 1.) oxidation, 2.) reductiv reactions of different ηdiketones to different products, Product distribution Rao, T. S. S.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 329; nb. 3; (1987); p. 474 - 482 View in Reaxys

(v2)

Cu –

Li+

O ILi

Rx-ID: 1569414 View in Reaxys 204/280 Yield 44 %, 19 %

Conditions & References Product distribution Mukerji, Ishita; Wayda, Andrea L.; Dabbagh, Gary; Bertz, Steven H.; Angewandte Chemie; vol. 98; nb. 8; (1986); p. 756 757 View in Reaxys

O NH N

Rx-ID: 2685739 View in Reaxys 205/280 Yield

Conditions & References Yield given. Multistep reaction

101/120

2018-07-03 17:12:41

Baldwin, Jack E.; Adlington, Robert M.; Bottaro, Jeffrey C.; Kolhe, Jayant N.; Newington, Ian M.; Perry, Matthew W. D.; Tetrahedron; vol. 42; nb. 15; (1986); p. 4235 - 4246 View in Reaxys

O OH

Rx-ID: 3399320 View in Reaxys 206/280 Yield 75 %

Conditions & References With 2-amino-4-methylpyridine borane in acetic acid, Time= 24h, Ambient temperature Okamoto, Yoshihisa; Osawa, Toshimitsu; Kurasawa, Yoshihisa; Kinoshita, Toshio; Takagi, Kaname; Journal of Heterocyclic Chemistry; vol. 23; (1986); p. 1383 - 1385 View in Reaxys

Rx-ID: 1764011 View in Reaxys 207/280 Yield 61 %, 15 %

Conditions & References With sodium tetrahydroborate, oxygen, meso-tetraphenylporphyrin iron(III) chloride in methanol, benzene, Ambient temperature Santa; Mori; Hirobe; Chemical and pharmaceutical bulletin; vol. 33; nb. 5; (1985); p. 2175 - 2178 View in Reaxys

Rx-ID: 2007959 View in Reaxys 208/280 Yield

Conditions & References With lithium aluminium tetrahydride, Perbenzoic acid, 2.) ether, 30 min, reflux; study of the regioselectivity of autoxidation by reduction of the corresponding oxidation-mixture, Mechanism, Product distribution Pritzkow, Wilhelm; Thomas, Gerda; Willecke, Lothar; Journal fuer Praktische Chemie (Leipzig); vol. 327; nb. 5; (1985); p. 847 - 851 View in Reaxys

Rx-ID: 2058132 View in Reaxys 209/280 Yield

Conditions & References With lithium aluminium tetrahydride, 2,2'-azobis(isobutyronitrile), oxygen, Kinetics Pritzkow, Wilhelm; Thomas, Gerda; Willecke, Lothar; Journal fuer Praktische Chemie (Leipzig); vol. 327; nb. 6; (1985); p. 945 - 952 View in Reaxys

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

102/120

2018-07-03 17:12:41

Rx-ID: 2058133 View in Reaxys 210/280 Yield

Ti (v4)

O O

Rx-ID: 2687054 View in Reaxys 211/280 Yield 69 %

Conditions & References in diethyl ether, Time= 6h, -30 deg C to 22 deg C Reetz, Manfred T.; Westermann, Juergen; Steinbach, Rainer; Wenderoth, Bernd; Peter, Roland; et al.; Chemische Berichte; vol. 118; nb. 4; (1985); p. 1421 - 1440 View in Reaxys

Rx-ID: 3821326 View in Reaxys 212/280 Yield

Conditions & References With alkaline hydrogen peroxide, lithium triethylborohydride in tetrahydrofuran, Time= 1h, T= 0 °C , var. time, var. reducing agent, isotope effect, Rate constant, Product distribution, Mechanism Brown, Herbert C.; Narasimhan, S.; Somayaji, Vishwanatha; Journal of Organic Chemistry; vol. 48; nb. 18; (1983); p. 3091 - 3096 View in Reaxys With sodium tert-pentoxide, sodium hydride, nickel dichloride in 1,2-dimethoxyethane, Time= 18h, T= 65 °C , Yield given. Yields of byproduct given Fort, Yves; Vanderesse, Regis; Caubere, Paul; Tetrahedron Letters; vol. 26; nb. 26; (1985); p. 3111 - 3114 View in Reaxys

Rx-ID: 3821327 View in Reaxys 213/280 Yield 95 %

Conditions & References With sodium tert-pentoxide, sodium hydride, zinc(II) chloride in 1,2-dimethoxyethane, Time= 6h, T= 65 °C Fort, Yves; Vanderesse, Regis; Caubere, Paul; Tetrahedron Letters; vol. 26; nb. 26; (1985); p. 3111 - 3114 View in Reaxys

103/120

2018-07-03 17:12:41

Rx-ID: 3952119 View in Reaxys 214/280 Yield

Conditions & References

25 %, 64 %

With triphenylphosphine, bis-triphenylphosphine-palladium(II) chloride in 1,2-dimethoxyethane, toluene, Time= 7h, T= 50 °C Wakita, Yoshiaki; Yasunaga, Tomoyuki; Kojima, Masaharu; Journal of Organometallic Chemistry; vol. 288; (1985); p. 261 268 View in Reaxys

O HO

Rx-ID: 3952120 View in Reaxys 215/280 Yield

Conditions & References

10 %, 17 %, With triphenylphosphine, bis-triphenylphosphine-palladium(II) chloride in 1,2-dimethoxyethane, toluene, Time= 20h, T= 50 °C 61 % Wakita, Yoshiaki; Yasunaga, Tomoyuki; Kojima, Masaharu; Journal of Organometallic Chemistry; vol. 288; (1985); p. 261 268 View in Reaxys 25 %, 45 %, With triphenylphosphine, bis-triphenylphosphine-palladium(II) chloride in 1,2-dimethoxyethane, toluene, Time= 25h, T= 50 30 % °C , different quantity of the aluminum reagent; further aluminum reagent, Product distribution Wakita, Yoshiaki; Yasunaga, Tomoyuki; Kojima, Masaharu; Journal of Organometallic Chemistry; vol. 288; (1985); p. 261 268 View in Reaxys

Rx-ID: 1763942 View in Reaxys 216/280 Yield 10 % Chromat., 82 % Chromat.

Conditions & References 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

HO HO

Rx-ID: 2008658 View in Reaxys 217/280

104/120

2018-07-03 17:12:41

Yield

Conditions & References

5.7 % Turnov., 3.2 % Turnov., 39.1 % Turnov., 4.7 % Turnov., 11.5 % Turnov., 34.1 % Turnov.

With lithium aluminium tetrahydride, oxygen, Time= 16h, T= 90 °C , p= 759.8Torr , autoxidation, Product distribution Dao, Le Thi Anh; Blau, Karla; Pritzkow, Wilhelm; Schmidt-Renner, Wolfgang; Voerckel, Volkmar; Willecke, Lothar; Journal fuer Praktische Chemie (Leipzig); vol. 326; nb. 1; (1984); p. 73 - 80 View in Reaxys

O NH N

Rx-ID: 2689505 View in Reaxys 218/280 Yield

Conditions & References With methyllithium, acetic acid, ethanethiol, 1) THF, -40 deg C to -25 deg C, 2) THF, -25 deg C to 20 deg C, Yield given. Multistep reaction Baldwin, Jack E.; Bottaro, Jeffrey C.; Kolhe, Jayant N.; Adlington, Robert M.; Journal of the Chemical Society, Chemical Communications; nb. 1; (1984); p. 22 - 23 View in Reaxys

Rx-ID: 2130817 View in Reaxys 219/280 Yield

Conditions & References

43 % Chro- With lithium triethylborohydride in tetrahydrofuran, T= 65 °C , Product distribution mat., 55 % Chromat., 2 Brandaenge, Svante; Dahlman, Olof; Oelund, Jonas; Acta Chemica Scandinavica, Series B: Organic Chemistry and Bio% Chromat. chemistry; vol. 37; nb. 2; (1983); p. 141 - 146 View in Reaxys

Rx-ID: 2970742 View in Reaxys 220/280 Yield

Conditions & References With sodium persulfate, sulfuric acid, silver nitrate, copper(II) sulfate, 1.) water, reflux, 2.) 5 min, reflux, Yield given. Multistep reaction. Yields of byproduct given Fristad, William E.; Fry, Melisa A.; Klang, Jeffrey A.; Journal of Organic Chemistry; vol. 48; nb. 20; (1983); p. 3575 - 3577 View in Reaxys

105/120

2018-07-03 17:12:41

O O HO

Rx-ID: 3195517 View in Reaxys 221/280 Yield 45 % Chromat., 60 % Chromat., 77 % Chromat.

Conditions & References With lithium aluminium tetrahydride in diethyl ether, Time= 2h Yoshida; Miura; Nojima; Kusabayashi; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6279 - 6285 View in Reaxys

O O HO

Rx-ID: 3195520 View in Reaxys 222/280 Yield 9 % Chromat., 13 % Chromat., 81 % Chromat.

Conditions & References With lithium aluminium tetrahydride in diethyl ether, Time= 2h, Heating Yoshida; Miura; Nojima; Kusabayashi; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6279 - 6285 View in Reaxys

Rx-ID: 3821343 View in Reaxys 223/280 Yield

Conditions & References With alkaline hydrogen peroxide, lithium triethylborohydride in tetrahydrofuran, Time= 1h, T= 0 Â°C , var. time, var. reducing agent, isotope effect, Rate constant, Product distribution, Mechanism Brown, Herbert C.; Narasimhan, S.; Somayaji, Vishwanatha; Journal of Organic Chemistry; vol. 48; nb. 18; (1983); p. 3091 - 3096 View in Reaxys

Rx-ID: 3821344 View in Reaxys 224/280 Yield 92 %

Conditions & References With alkaline hydrogen peroxide, lithium triethylborohydride in tetrahydrofuran, Time= 1h

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

106/120

2018-07-03 17:12:41

Brown, Herbert C.; Narasimhan, S.; Somayaji, Vishwanatha; Journal of Organic Chemistry; vol. 48; nb. 18; (1983); p. 3091 - 3096 View in Reaxys

O O

Rx-ID: 19880615 View in Reaxys 225/280 Yield

Conditions & References Reaction Steps: 2 1: boron trifluoride-diethyl ether / CH2Cl2 / 0.33 h / 0 °C 2: 60 percent Chromat. / lithium aluminum hydride / diethyl ether / 2 h With lithium aluminium tetrahydride, boron trifluoride diethyl etherate in diethyl ether, dichloromethane Yoshida; Miura; Nojima; Kusabayashi; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6279 - 6285 View in Reaxys Reaction Steps: 2 1: boron trifluoride-diethyl ether / CH2Cl2 / 0.33 h / 0 °C 2: 13 percent Chromat. / lithium aluminum hydride / diethyl ether / 2 h / Heating With lithium aluminium tetrahydride, boron trifluoride diethyl etherate in diethyl ether, dichloromethane Yoshida; Miura; Nojima; Kusabayashi; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6279 - 6285 View in Reaxys

OH O O

HO OH

Rx-ID: 19887079 View in Reaxys 226/280 Yield

107/120

2018-07-03 17:12:41

O HO O

HO HO

Rx-ID: 2155427 View in Reaxys 227/280 Yield

Conditions & References

73 % Chromat., 1 % Chromat., 12 % Chromat.

in n-heptane, T= 98 °C , Further byproducts given Lefort, D.; Nedelec, J. Y.; Tetrahedron; vol. 38; nb. 17; (1982); p. 2681 - 2686 View in Reaxys

O O

HO O

Rx-ID: 4066682 View in Reaxys 228/280 Yield

Conditions & References Yield given. Multistep reaction Bloodworth, A. J.; Courtneidge, J. L.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 8; (1982); p. 1807 - 1810 View in Reaxys

O HO

hydrocarbures (yield: 14percent)

Rx-ID: 7923329 View in Reaxys 229/280 Yield 73 % Chromat., 1 % Chromat., 12 % Chromat.

Conditions & References in n-heptane, T= 98 °C , Mechanism, Product distribution Lefort, D.; Nedelec, J. Y.; Tetrahedron; vol. 38; nb. 17; (1982); p. 2681 - 2686 View in Reaxys

Rx-ID: 1763984 View in Reaxys 230/280 Yield

Conditions & References With air, tetrabutylammonium borohydride, (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride, 1) CH2Cl2, 2) CH2Cl2, r.t., 24 h, Yield given. Multistep reaction. Yields of byproduct given Perree-Fauvet, M.; Gaudemer, A.; Journal of the Chemical Society, Chemical Communications; nb. 17; (1981); p. 874 - 875 View in Reaxys

108/120

2018-07-03 17:12:41

P O O

Rx-ID: 2587288 View in Reaxys 231/280 Yield

Conditions & References With oxonium, methyllithium, 1.) ether, Yield given. Multistep reaction Hayashi, Tamio; Kanehira, Koichi; Kumada, Makoto; Tetrahedron Letters; vol. 22; nb. 44; (1981); p. 4417 - 4420 View in Reaxys

N N

H N

Br–

+Mg

Rx-ID: 2731189 View in Reaxys 232/280 Yield

Conditions & References 1.) tetrahydrofuran, 0 deg C, few minutes 2) reflux, 3 h, THF, 65 deg C, Yield given. Multistep reaction Comins, Daniel L.; Dernell, William; Tetrahedron Letters; vol. 22; (1981); p. 1085 - 1088 View in Reaxys

O HO

Rx-ID: 2886328 View in Reaxys 233/280 Yield

Conditions & References With ytterbium, 1.) THF, -20 deg C; 2.) rt, overnight, reflux, 2 h, Yield given. Multistep reaction Fukagawa, Toshihiro; Fujiwara, Yuzo; Yokoo, Kazuhiro; Taniguchi, Hiroshi; Chemistry Letters; (1981); p. 1771 - 1774 View in Reaxys

P O O

Rx-ID: 21570652 View in Reaxys 234/280 Yield

Conditions & References Reaction Steps: 2 1: H2 / rhodium cationic complex with (R)-1-<(S)-1',2-bis(diphenylphosphino)ferrocenyl>ethanol <(R)-(S)-BPPFOH> / benzene / 70 h / 30 °C / 38000 Torr 2: 1.) MeLi 2.) H3O(1+) / 1.) ether With oxonium, methyllithium, hydrogen, rhodium cationic complex with (R)-1-<(S)-1',2-bis(diphenylphosphino)ferrocenyl>ethanol <(R)-(S)-BPPFOH> in benzene

109/120

2018-07-03 17:12:41

Hayashi, Tamio; Kanehira, Koichi; Kumada, Makoto; Tetrahedron Letters; vol. 22; nb. 44; (1981); p. 4417 - 4420 View in Reaxys

HO Br OH

+Mg

Cl –

Rx-ID: 1904128 View in Reaxys 235/280 Yield

Conditions & References in tetrahydrofuran, Time= 4h, T= -40 - 20 °C , Yield given. Yields of byproduct given Bourgain-Commercon, Monique; Normant, Jean F.; Bulletin de la Societe Chimique de France; vol. 2; nb. 5-6; (1980); p. 289 - 294 View in Reaxys

H HO

H 2N

Rx-ID: 2198132 View in Reaxys 236/280 Yield

Conditions & References With sodium nitrite in perchloric acid, water, Product distribution, Mechanism Kirmse, Wolfgang; Guenther, Bernd-Rainer; Loosen, Karin; Chemische Berichte; vol. 113; nb. 6; (1980); p. 2140 - 2153 View in Reaxys H

Ca Br

Rx-ID: 2682392 View in Reaxys 237/280 Yield

Conditions & References

65 %

With dibenzo-18-crown-6 in diethyl ether, benzene Bogatskii, A. V.; Chumachenko, T. K.; Luk'yanenko, N. G.; Lyamtseva, L. N.; Starovoit, I. A.; Doklady Chemistry; vol. 251; (1980); p. 105 - 107; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 251; nb. 1; (1980); p. 113 - 115 View in Reaxys O

lithium alanate O

Rx-ID: 5475045 View in Reaxys 238/280 Yield

Conditions & References Searles et al.; Journal of the American Chemical Society; vol. 79; (1957); p. 948,950 View in Reaxys

lithium alanate

Rx-ID: 5475046 View in Reaxys 239/280 Yield

Conditions & References Searles et al.; Journal of the American Chemical Society; vol. 79; (1957); p. 948,950

110/120

2018-07-03 17:12:41

View in Reaxys

lithium borate

O O

Rx-ID: 5475047 View in Reaxys 240/280 Yield

Conditions & References T= 125 °C Searles et al.; Journal of the American Chemical Society; vol. 79; (1957); p. 948,950 View in Reaxys

(+-)-1-phenyl-prop-2-en-1-ol HO

Rx-ID: 7159159 View in Reaxys 241/280 Yield

Conditions & References With diethyl ether, platinum, Hydrogenation Drumheller; Andrews; Journal of the American Chemical Society; vol. 77; (1955); p. 3290,3292 View in Reaxys

buten-(2)-yl magnesium bromide O

Rx-ID: 22403800 View in Reaxys 242/280 Yield

Conditions & References Reaction Steps: 2 1: copper acetylenide 2: Raney nickel; methanol / Hydrogenation With methanol, copper(I) monacetylide, nickel Hirao; Yakugaku Zasshi; vol. 73; (1953); p. 1224; ; (1954); p. 12702 View in Reaxys O

Rx-ID: 597607 View in Reaxys 243/280 Yield

Conditions & References anschliessendes Behandeln mit wss. NaOBr-Loesung Palfray; Metayer; Panouse; Bulletin de la Societe Chimique de France; (1947); p. 766,770 View in Reaxys

copper oxide-aluminium oxide catalyst HO

Rx-ID: 5807138 View in Reaxys 244/280 Yield

Conditions & References T= 115 °C , p= 100Torr

111/120

2018-07-03 17:12:41

Ipatieff; Haensel; Journal of the American Chemical Society; vol. 64; (1942); p. 520 View in Reaxys O

–

Na +

HO HO

Rx-ID: 269556 View in Reaxys 245/280 Yield

Conditions & References T= 180 °C Adickes; v. Muellenheim; Simson; Chemische Berichte; vol. 66; (1933); p. 1904,1907 View in Reaxys Magnani; McElvain; Journal of the American Chemical Society; vol. 60; (1938); p. 813,819 View in Reaxys O OH

Raney nickel HO

Rx-ID: 5807141 View in Reaxys 246/280 Yield

Conditions & References Hydrogenation Delepine; Horeau; Bulletin de la Societe Chimique de France; vol. <5> 4; (1937); p. 31,41 View in Reaxys O OH

aqueous NaOH

Raney nickel

Rx-ID: 5807142 View in Reaxys 247/280 Yield

Conditions & References Hydrogenation Delepine; Horeau; Bulletin de la Societe Chimique de France; vol. <5> 4; (1937); p. 31,41 View in Reaxys

Al O O

Rx-ID: 600112 View in Reaxys 248/280 Yield

Conditions & References T= 80 °C Meerwein et al.; Journal fuer Praktische Chemie (Leipzig); vol. <2> 147; (1936); p. 226,239 View in Reaxys T= 80 °C Meerwein et al.; Journal fuer Praktische Chemie (Leipzig); vol. <2> 147; (1936); p. 226,239

112/120

2018-07-03 17:12:41

View in Reaxys O

sodium

Rx-ID: 5807978 View in Reaxys 249/280 Yield

Conditions & References anschliessedes Behandeln mit Wasser Nasarow; Zhurnal Obshchei Khimii; vol. 4; (1934); p. 790,795; Chem. Zentralbl.; vol. 106; nb. II; (1935); p. 3905 View in Reaxys O OH

nickel /kieselguhr HO

Rx-ID: 5807140 View in Reaxys 250/280 Yield

Conditions & References T= 125 °C , p= 125036Torr , Hydrogenation Adkins; Cramer; Journal of the American Chemical Society; vol. 52; (1930); p. 3449,3454 View in Reaxys

Cl Al

petroleum ether

HO HO

Rx-ID: 6676559 View in Reaxys 251/280 Yield

Conditions & References Huston; Lewis; Grotemut; Journal of the American Chemical Society; vol. 49; (1927); p. 1367 View in Reaxys H

Mg+

Br– O

η.η-dibenzen-ethane HO

Rx-ID: 8263487 View in Reaxys 252/280 Yield

Conditions & References nebeneinander wechselnde Mengen;Produkt5:Aethan;Pr.6:1.3-Dioxy-2-methyl-1.3-diphenyl-propan;Pr.7:Benzylbenzoat Terentjew; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 159; (1927); p. 226; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 58; (1926); p. 1265,1268 View in Reaxys

113/120

2018-07-03 17:12:41

nebeneinander wechselnde Mengen; Produkt5:Aethan; Produkt6:1.3-Dioxy-2-methyl-1.3-diphenyl-propan Terentjew; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 159; (1927); p. 226; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 58; (1926); p. 1265,1268 View in Reaxys Meisenheimer; Justus Liebigs Annalen der Chemie; vol. 442; (1925); p. 200; Justus Liebigs Annalen der Chemie; vol. 446; (1926); p. 84 View in Reaxys Hess; Rheinboldt; Chemische Berichte; vol. 54; (1921); p. 2055 View in Reaxys H

O HO

Rx-ID: 597609 View in Reaxys 253/280 Yield

Conditions & References Terentjew; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 159; (1926); p. 1268,229 View in Reaxys H

Rx-ID: 597610 View in Reaxys 254/280 Yield

Conditions & References Meisenheimer; Justus Liebigs Annalen der Chemie; vol. 446; (1926); p. 85 View in Reaxys

O O

O HO

Rx-ID: 273471 View in Reaxys 255/280 Yield

Conditions & References Rheinboldt; Roleff; Journal fuer Praktische Chemie (Leipzig); vol. <2> 109; (1925); p. 188 View in Reaxys H

ethyl magnesium halide

Rx-ID: 5711602 View in Reaxys 256/280

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

114/120

2018-07-03 17:12:41

Yield

Conditions & References Meisenheimer; Justus Liebigs Annalen der Chemie; vol. 442; (1925); p. 200; Justus Liebigs Annalen der Chemie; vol. 446; (1926); p. 84 View in Reaxys Hess; Rheinboldt; Chemische Berichte; vol. 54; (1921); p. 2055 View in Reaxys Rheinboldt; Roleff; Journal fuer Praktische Chemie (Leipzig); vol. <2> 109; (1925); p. 188 View in Reaxys

ethyl magnesium halide O

Rx-ID: 5711603 View in Reaxys 257/280 Yield

ethyl magnesium halide O

Rx-ID: 5807139 View in Reaxys 258/280 Yield

Conditions & References Grignard; Annales de Chimie (Cachan, France); vol. <7> 24; (1901); p. 468; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys Tschelinzew; Chemische Berichte; vol. 37; (1904); p. 4539 View in Reaxys Klages; Chemische Berichte; vol. 36; (1903); p. 621 View in Reaxys Meisenheimer; Justus Liebigs Annalen der Chemie; vol. 442; (1925); p. 200; Justus Liebigs Annalen der Chemie; vol. 446; (1926); p. 84 View in Reaxys Hess; Rheinboldt; Chemische Berichte; vol. 54; (1921); p. 2055 View in Reaxys

HO OH

Rx-ID: 364346 View in Reaxys 259/280 Yield

Conditions & References With sodium, T= 130 - 210 Â°C Schorigin; Chemische Berichte; vol. 57; (1924); p. 1633; Chemische Berichte; vol. 56; (1923); p. 186 View in Reaxys

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

115/120

2018-07-03 17:12:41

sodium

Rx-ID: 7448927 View in Reaxys 260/280 Yield

Conditions & References T= 130 - 210 °C Schorigin; Chemische Berichte; vol. 57; (1924); p. 1633; Chemische Berichte; vol. 56; (1923); p. 186 View in Reaxys Schorigin; Chemische Berichte; vol. 56; (1923); p. 184; Chemische Berichte; vol. 57; (1924); p. 1629,1630 Anm. 6 View in Reaxys H Na

Rx-ID: 600169 View in Reaxys 261/280 Yield

Conditions & References Schlubach; Goes; Chemische Berichte; vol. 55; (1922); p. 2898 View in Reaxys With toluene, Zersetzen des Reaktionsprodukts mit Wasser Schlubach; Goes; Chemische Berichte; vol. 55; (1922); p. 2898 View in Reaxys H Na

Rx-ID: 601063 View in Reaxys 262/280 Yield

Conditions & References und Zersetzen der Reaktionsprodukts mit Wasser Schlubach; Goes; Chemische Berichte; vol. 55; (1922); p. 2898 View in Reaxys H

Mg+

I–

Rx-ID: 597616 View in Reaxys 263/280 Yield

Conditions & References und Zersetzen des Reaktionsproduktes mit verd.Schwefelsaeure Marshall; Journal of the Chemical Society; vol. 107; (1915); p. 521 View in Reaxys

116/120

2018-07-03 17:12:41

Rx-ID: 664609 View in Reaxys 264/280 Yield

Conditions & References With potassium hydroxide Kishner; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 45; (1913); p. 953; Chem. Zentralbl.; vol. 84; nb. II; (1913); p. 2129 View in Reaxys Br

KOH-solution

dimer(ic) phenylcyclopropane HO

Rx-ID: 6213035 View in Reaxys 265/280 Yield

Conditions & References Kishner; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 45; (1913); p. 953; Chem. Zentralbl.; vol. 84; nb. II; (1913); p. 2129 View in Reaxys

Rx-ID: 22125231 View in Reaxys 266/280 Yield

Conditions & References Reaction Steps: 2 1: glacial acetic acid; HBr / 20 °C 2: KOH-solution With potassium hydroxide, hydrogen bromide, acetic acid Kishner; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 45; (1913); p. 953; Chem. Zentralbl.; vol. 84; nb. II; (1913); p. 2129 View in Reaxys

NH HN

Rx-ID: 22150255 View in Reaxys 267/280 Yield

Conditions & References Reaction Steps: 3 1: potassium hydroxide; platinized fired clay 2: glacial acetic acid; HBr / 20 °C 3: KOH-solution With potassium hydroxide, platinized fired clay, hydrogen bromide, acetic acid Kishner; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 45; (1913); p. 953; Chem. Zentralbl.; vol. 84; nb. II; (1913); p. 2129 View in Reaxys

117/120

2018-07-03 17:12:41

Mg I

Rx-ID: 601591 View in Reaxys 268/280 Yield

Conditions & References Oddo; Gazzetta Chimica Italiana; vol. 41 I; (1911); p. 271 View in Reaxys

Mg+

I–

O O

Rx-ID: 601605 View in Reaxys 269/280 Yield

Conditions & References Abwesenheit von Aether Oddo; Gazzetta Chimica Italiana; vol. 41 I; (1911); p. 271 View in Reaxys H

ligroine

Mg I

Rx-ID: 5807970 View in Reaxys 270/280 Yield

Conditions & References Oddo; Gazzetta Chimica Italiana; vol. 41 I; (1911); p. 271 View in Reaxys

H (v2)

Rx-ID: 600170 View in Reaxys 271/280 Yield

Conditions & References With diethyl ether, sodium Schorigin; Chemische Berichte; vol. 41; (1908); p. 2717,2723; Chemische Berichte; vol. 43; (1910); p. 1931 View in Reaxys H

Mg+

I– O

Rx-ID: 600178 View in Reaxys 272/280 Yield

118/120

2018-07-03 17:12:41

View in Reaxys Klages; Chemische Berichte; vol. 36; (1903); p. 621 View in Reaxys Schorigin; Chemische Berichte; vol. 41; (1908); p. 2717,2723; Chemische Berichte; vol. 43; (1910); p. 1931 View in Reaxys H

Mg+

Brâ&#x20AC;&#x201C;

Rx-ID: 600179 View in Reaxys 273/280 Yield

Conditions & References Grignard; Annales de Chimie (Cachan, France); vol. <7> 24; (1901); p. 468; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys Grignard; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys Klages; Chemische Berichte; vol. 36; (1903); p. 621 View in Reaxys Schorigin; Chemische Berichte; vol. 41; (1908); p. 2717,2723; Chemische Berichte; vol. 43; (1910); p. 1931 View in Reaxys

Hg(C2H5)2

sodium

hydrogen

Rx-ID: 5807145 View in Reaxys 274/280 Yield

Conditions & References weitere Verbindung: Aether Schorigin; Chemische Berichte; vol. 41; (1908); p. 2717,2723; Chemische Berichte; vol. 43; (1910); p. 1931 View in Reaxys

Hg(C2H5)2

sodium

nitrogen

Rx-ID: 5807146 View in Reaxys 275/280 Yield

Conditions & References weitere Verbindung: Aether Schorigin; Chemische Berichte; vol. 41; (1908); p. 2717,2723; Chemische Berichte; vol. 43; (1910); p. 1931 View in Reaxys

H (v2)

sodium

Rx-ID: 7981231 View in Reaxys 276/280 Yield

Conditions & References Schorigin; Chemische Berichte; vol. 41; (1908); p. 2717,2723; Chemische Berichte; vol. 43; (1910); p. 1931 View in Reaxys O

sodium

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

K2CO3-solution

119/120

2018-07-03 17:12:41

Rx-ID: 5807979 View in Reaxys 277/280 Yield

Conditions & References Stern; Monatshefte fuer Chemie; vol. 26; (1905); p. 1559 View in Reaxys

Mg+

I–

N O

Rx-ID: 600592 View in Reaxys 278/280 Yield

Conditions & References Tschelinzew; Chemische Berichte; vol. 37; (1904); p. 4539 View in Reaxys O OH

sodium HO

Rx-ID: 5807144 View in Reaxys 279/280 Yield

Conditions & References Klages; Chemische Berichte; vol. 35; (1902); p. 2263; Chemische Berichte; vol. 38; (1905); p. 913 View in Reaxys O OH

sodium amalgam

Rx-ID: 5807143 View in Reaxys 280/280 Yield

Conditions & References Errera; Gazzetta Chimica Italiana; vol. 16; (1886); p. 322 View in Reaxys Barry; Chemische Berichte; vol. 6; (1873); p. 1008 View in Reaxys

120/120

2018-07-03 17:12:41