Catalytic asymmetric hydrogenation of aromatic ketones in room temperature ionic liquids

被引：47
|
作者：
Ngo, HL [1 ]
Hu, AG [1 ]
Lin, WB [1 ]
机构：
[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 04期
基金：
美国国家科学基金会;
关键词：
ionic liquid; hydrogenation; asymmetric catalysis;
D O I：
10.1016/j.tetlet.2004.11.150
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Polar bisphosphonic acid-derived Ru(BINAP)(DPEN)Cl-2 precatalysts were synthesized and immobilized in room temperature ionic liquids (RTILs) for asymmetric hydrogenation of aromatic ketones with cc values of up to 98.7%. The performance of the Ru catalysts is highly dependent on the nature of imidazolium ILs. For the imidazolium ILs without acidic protons, both ILs and Ru catalysts were recycled by simple extraction and reused. Such a simple immobilization approach also prevented the leaching of Ru (and Ru catalysts) into the chiral secondary alcohol products, and should prove desirable for the production of pharmaceutical intermediates that are free from metal contaminants. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：595 / 597
页数：3
相关论文
共 50 条
  • [1] Catalytic asymmetric hydrogenation in room temperature ionic liquids
    Lam, KH
    Xu, LJ
    Fan, QH
    Qiu, LQ
    Wu, J
    Cheung, HY
    Lo, WH
    Chan, ASC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U118 - U118
  • [2] Catalytic asymmetric hydrogenation in room temperature ionic liquids.
    Ngo, HL
    Hu, AG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U653 - U653
  • [3] Enantioselective catalytic asymmetric hydrogenation of ethyl acetoacetate in room temperature ionic liquids
    Berthod, M
    Joerger, JM
    Mignani, G
    Vaultier, M
    Lemaire, M
    TETRAHEDRON-ASYMMETRY, 2004, 15 (14) : 2219 - 2221
  • [4] Highly enantioselective catalytic asymmetric hydrogenation of β-keto esters in room temperature ionic liquids
    Ngo, HL
    Hu, AG
    Lin, WB
    CHEMICAL COMMUNICATIONS, 2003, (15) : 1912 - 1913
  • [5] Hydrogen-Bonding-Mediated Selective Hydrogenation of Aromatic Ketones over Pd/C in Ionic Liquids at Room Temperature
    Li, Ruipeng
    Wang, Yuepeng
    Zhao, Yanfei
    Zhang, Fengtao
    Zeng, Wei
    Tang, Minhao
    Xiang, Junfeng
    Zhang, Xiaoyu
    Han, Buxing
    Liu, Zhimin
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2021, 9 (42) : 14216 - 14223
  • [6] Asymmetric hydrogenation of aromatic ketones catalyzed by achiral monophosphine TPPTS-stabilized Ru in ionic liquids
    Wang, Jinbo
    Feng, Han
    Qin, Ruixiang
    Fu, Halyan
    Yuan, Maolin
    Chen, Him
    Li, Xianlun
    TETRAHEDRON-ASYMMETRY, 2007, 18 (14) : 1643 - 1647
  • [7] Asymmetric reduction of aromatic ketones in pyridinium-based ionic liquids
    Xiao, Ying
    Malhotra, Sanjay V.
    TETRAHEDRON-ASYMMETRY, 2006, 17 (07) : 1062 - 1065
  • [8] Iridium nanoparticles prepared in ionic liquids: An efficient catalytic system for the hydrogenation of ketones
    Fonseca, GS
    Scholten, JD
    Dupont, J
    SYNLETT, 2004, (09) : 1525 - 1528
  • [9] Catalytic Hydrogenolysis of Aromatic Ketones in Mixed Choline-Betainium Ionic Liquids
    Van Doorslaer, Charlie
    Wahlen, Joos
    Mertens, Pascal G. N.
    Thijs, Ben
    Nockemann, Peter
    Binnemans, Koen
    De Vos, Dirk E.
    CHEMSUSCHEM, 2008, 1 (12) : 997 - 1005
  • [10] Thermoregulated ionic liquid-coordinating ruthenium complexes for asymmetric hydrogenation of aromatic ketones
    Tang, Guoping
    Chen, Manyu
    Fang, Jian
    Xu, Zichen
    Gong, Honghui
    Peng, Qingpo
    Hou, Zhenshan
    CATALYSIS COMMUNICATIONS, 2019, 121 : 43 - 47
12345