Acta Phys. -Chim. Sin. ›› 2010, Vol. 26 ›› Issue (03): 675-678.doi: 10.3866/PKU.WHXB20100225

• CATALYSIS AND SURFACE STRUCTURE • Previous Articles     Next Articles

Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by RuCl2[(S)-P-Phos]-[(S)-DAIPEN]

JIANG He, WANG Jin-Bo, XIONG Wei, JIA Yun, QIN Rui-Xiang, LIU De-Rong, CHEN Hua   

  1. College of Chemistry &Chemical Engineering, Chongqing University of Science and Technology, Chongqing 401331, P. R. China; Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
  • Received:2009-09-04 Revised:2009-10-26 Published:2010-03-03
  • Contact: WANG Jin-Bo, CHEN Hua E-mail:scuhchen@163.com; wjb76@163.com

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Abstract:

A ruthenium phosphine diamine complex RuCl2[(S)-P-Phos]-[(S)-DAIPEN] [P-Phos: 2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine, DAIPEN: 1,1'-di(4-anisyl)-2-iopropyl-1,2-ethylenediamine] for the asymmetric hydrogenation of aromatic ketones has been studied. The influences of different bases , (CH3)3COK concentration, organic solvent, and molar ratio of substrate to catalyst on activity and enantioselectivity were investigated. Under the following optimum conditions: n(ketone):n(KOH):n(catalyst)=1000:20:1, pH2=2 MPa and T=30 ℃, the conversion of acetophenone and the enantioselectivity (ee) of S-1-phenylethanol was 100% and 88.5%, respectively. Additionally, the ee value of 2'-bromophenyl ethanol was 97.1%.

Key words: Asymmetric hydrogenation, Ruthenium-phosphine complex, Chiral diamine, Aromatic ketones