Asymmetric hydrogenations of acetophenone and its derivatives over RuRh/γ-Al2O3 modified by (1S, 2S)-DPEN and PPh3

被引:9
|
作者
Liu De-Rong
Xiong Wei
Yang Chao-Fen
Wang Jin-Bo
Chen Hua
Li Rui-Xiang [1 ]
Li Xian-Jun
机构
[1] Sichuan Univ, Coll Chem, Minist Educ, Keu Lab Green Chem & Technol, Chengdu 610064, Peoples R China
[2] Chongqing Coll Sci & Technol, Coll Chem & Biol Engn, Chongqing 400050, Peoples R China
关键词
ruthenium; rhodium; bimetallic catalyst; acetophenone; asymmetric hydrogenation;
D O I
10.1016/S1872-1508(07)60031-X
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The asymmetric hydrogenations of acetophenone and its derivatives over the bimetallic catalyst RuRh/gamma-Al2O3 modified by PPh3 and (1S, 2S)-DPEN [(1S, 2S)-1,2-diphenylethane-1,2-diamine] were studied. The effects of the concentration of KOH, temperature, ratio of ruthenium to rhodium, and the concentration of diamine on the asymmetric hydrogenation of acetophenone were investigated in detail. The results showed that this catalyst system had high activity and moderate enantioselectivity for the asymmetric hydrogenation of acetophenone and its derivatives. Under the optimum conditions, the conversions of acetophenone, ethylphenylketone, and isopropylphenylketone were up to 92.5%, 95.9%, and 100%, and the enantioselectivities for the formation of (R)-aromatic alcohols were 79.6%, 81.2%, and 81.4%, respectively.
引用
收藏
页码:479 / 483
页数:5
相关论文
共 31 条
  • [1] A succession of isomers of ruthenium dihydride complexes. Which one is the ketone hydrogenation catalyst?
    Abbel, R
    Abdur-Rashid, K
    Faatz, M
    Hadzovic, A
    Lough, AJ
    Morris, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (06) : 1870 - 1882
  • [2] Mechanism of the hydrogenation of ketones catalyzed by trans-dihydrido(diamine)ruthenium(II) complexes
    Abdur-Rashid, K
    Clapham, SE
    Hadzovic, A
    Harvey, JN
    Lough, AJ
    Morris, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) : 15104 - 15118
  • [3] Ruthenium dihydride RuH2(PPh3)2((R,R)-cyclohexyldiamine) and ruthenium monohydride RuHCl(PPh3)2((R,R)-cyclohexyldiamine):: Active catalyst and catalyst precursor for the hydrogenation of ketones and imines
    Abdur-Rashid, K
    Lough, AJ
    Morris, RH
    [J]. ORGANOMETALLICS, 2000, 19 (14) : 2655 - 2657
  • [4] Catalytic cycle for the asymmetric hydrogenation of prochiral ketones to chiral alcohols:: Direct hydride and proton transfer from chiral catalysts trans-Ru(H)2(diphosphine)(diamine) to ketones and direct addition of dihydrogen to the resulting hydridoamido complexes
    Abdur-Rashid, K
    Faatz, M
    Lough, AJ
    Morris, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) : 7473 - 7474
  • [5] Doucet H, 1998, ANGEW CHEM INT EDIT, V37, P1703, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1703::AID-ANIE1703>3.0.CO
  • [6] 2-I
  • [7] Fehring V, 1998, ANGEW CHEM INT EDIT, V37, P1827, DOI 10.1002/(SICI)1521-3773(19980803)37:13/14<1827::AID-ANIE1827>3.0.CO
  • [8] 2-C
  • [9] Hartmann R, 2001, ANGEW CHEM INT EDIT, V40, P3581, DOI 10.1002/1521-3773(20011001)40:19<3581::AID-ANIE3581>3.0.CO
  • [10] 2-7