Asymmetric Hydrogenations of Acetophenone and Its Derivatives over RuRh/γ-Al2O3 Modified by (1S,2S)-DPEN and PPh3 |
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| Institution: | 1. Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China;2. College of Chemical and Biological Engineering, Chongqing College of Science and Technology, Chongqing 400050, P. R. China;1. Hubei Provincial Key Laboratory of Developmentally Originated Disease, State Key Laboratory of Virology, Wuhan University School of Pharmaceutical Sciences, Wuhan 430071, PR China;2. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, PR China;1. Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey;2. Department of Metallurgical and Materials Engineering, Bingöl University, 12400 Bingöl, Turkey;3. Department of Chemistry, Baku State University, Z. Khalilov, Baku, Azerbaijan;1. Joint Laboratory of Nuclear Materials and Service Safety, Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055, China;2. China Nuclear Power Engineering Co., Ltd., Shenzhen, China;3. School of Materials Science and Engineering, Tsinghua University, Beijing 100084, China;1. State Key Laboratory for Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, PR China;2. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, PR China;1. College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, People’s Republic of China;2. College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, People’s Republic of China |
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| Abstract: | The asymmetric hydrogenations of acetophenone and its derivatives over the bimetallic catalyst RuRh/γ-Al2O3 modified by PPh3 and (1S, 2S)-DPEN (1S, 2S)-1,2-diphenylethylene-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 hydrogenations 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. |
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