Asymmetric Hydrogenation of Acetophenone and Its derivatives Catalyzed by (1S,2S)-DPEN Modified Ir/γ-Al2O3

doi:10.7503/cjcu20130013

Chem. J. Chinese Universities ›› 2013, Vol. 34 ›› Issue (7): 1679.doi: 10.7503/cjcu20130013

• Physical Chemistry • Previous Articles Next Articles

Asymmetric Hydrogenation of Acetophenone and Its derivatives Catalyzed by (1S,2S)-DPEN Modified Ir/γ-Al₂O₃

YANG Jun^1,2, ZHAO Wen-Bo¹, YANG Chao-Fen², SUN Xiao-Dong², WANG Qi², ZHU Yan-Qing², CHEN Hua³

1. College of Chemistry and Engineering, Kunming University of Science and Technology, Kunming 650500, China;
2. Research Center for Analysis and Measurement, Kunming University of Science and Technology, Kunming 650093, China;
3. Key Laboratory of Green Chemistry and Technology, Ministry of Education, Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, Chengdu 610064, China

Received:2013-01-05 Online:2013-07-10 Published:2013-06-21
Contact: yang caofeng E-mail:wenshuixing@126.com;yangmlh@163.com

Abstract

Abstract:

Under the basic conditions, an efficient catalyst without any stabilizer was prepared and applied in the asymmetric hydrogenation of acetophenone and its derivatives. The effects of different base, concentration of (1S,2S)-diphenylethylenediamine[(1S,2S)-DPEN] and base, reaction temperature and pressure of hydrogen on the asymmetric hydrogenation of acetophenone were investigated in detail. The results showed that this catalytic system had high activity and moderate enantioselectivity for the asymmetric hydrogenation of acetophenone and its derivatives. Under the optimum conditions, a good enantiomeric excess(e.e.) value of 80.3% was obtained for asymmetric hydrogenation of isobutyrophenone. Especially, the catalyst preparation is simple and no stabilizer was applied. The catalyst performance is steady and the catalyst can be reused several times through the facilitative separation of the catalyst from the reaction medium.

Key words: (1S,2S)-Diphenylethylenediamine, Ir/Al₂O₃ catalyst, Acetophenone, Asymmetric hydrogenation

CLC Number:

O643

TrendMD:

YANG Jun, ZHAO Wen-Bo, YANG Chao-Fen, SUN Xiao-Dong, WANG Qi, ZHU Yan-Qing, CHEN Hua. Asymmetric Hydrogenation of Acetophenone and Its derivatives Catalyzed by (1S,2S)-DPEN Modified Ir/γ-Al₂O₃[J]. Chem. J. Chinese Universities, 2013, 34(7): 1679.

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Asymmetric Hydrogenation of Acetophenone and Its derivatives Catalyzed by (1S,2S)-DPEN Modified Ir/γ-Al₂O₃

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