Hydrogenation of Quinolines Using a Recyclable Phosphine-Free Chiral Cationic Ruthenium Catalyst: Enhancement of Catalyst Stability and Selectivity in an Ionic Liquid

Liquid assets: The catalyst (S,S)‐1 exhibits an unprecedented reactivity and excellent enantioselectivity for the title reaction when it is carried out in neat ionic liquid (see scheme; BMIM=1‐n‐butyl‐3‐methylimidazolium, Tf=trifluoromethanesulfonyl, Ts=4‐toluenesulfonyl). The ionic liquid facilitat...

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Published inAngewandte Chemie (International ed.) Vol. 47; no. 44; pp. 8464 - 8467
Main Authors Zhou, Haifeng, Li, Zhiwei, Wang, Zhijian, Wang, Tianli, Xu, Lijin, He, Yanmei, Fan, Qing-Hua, Pan, Jie, Gu, Lianquan, Chan, Albert S.C
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2008
WILEY‐VCH Verlag
Wiley
Subjects
asymmetric catalysis
Catalysis
Chemistry
Chemistry, Multidisciplinary
Hydrogenation
ionic liquids
Ionic Liquids - chemistry
Phosphines - chemistry
Physical Sciences
quinolines
Quinolines - chemistry
Ruthenium - chemistry
Science & Technology
DRAMATIC ENHANCEMENT
MECHANISM
IMINES
COMPLEXES
asymmetric catalysis
hydrogenation
IMMOBILIZATION
KETONES
LIGANDS
ENANTIOSELECTIVE HYDROGENATION
OLEFINS
ionic liquids
ASYMMETRIC HYDROGENATION
quinolines
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Summary:Liquid assets: The catalyst (S,S)‐1 exhibits an unprecedented reactivity and excellent enantioselectivity for the title reaction when it is carried out in neat ionic liquid (see scheme; BMIM=1‐n‐butyl‐3‐methylimidazolium, Tf=trifluoromethanesulfonyl, Ts=4‐toluenesulfonyl). The ionic liquid facilitates the catalyst recycling and enhances its stability and selectivity.
Bibliography:http://dx.doi.org/10.1002/anie.200802237
Financial support from the National Natural Science Foundation of China (grant no. 20325209, 20418002 and 20532010), the Major State Basic Research Development Program of China (grant no. 2005CCA06600), the Chinese Academy of Sciences, the National Natural Science Foundation/Hong Kong Research Grants Council Joint Research Scheme (N_PolyU506/04), and Hong Kong UGC Areas of Excellence Scheme (AOE/P‐10/01) is greatly appreciated.
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content type line 23
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.200802237