催化学报

催化学报 ›› 2012, Vol. 33 ›› Issue (7): 1154-1160.DOI: 10.1016/S1872-2067(11)60403-8

• 研究论文 • 上一篇    下一篇

(1S,2S)-1,2-二苯基乙二胺修饰 Ir/SiO2 催化苯乙酮及其衍生物不对称加氢

杨朝芬1, 杨俊1, 孙晓东1, 朱艳琴1, 王齐1, 陈华2,*   

  1. 1昆明理工大学分析测试研究中心, 云南昆明 650093; 2四川大学化学学院有机金属络合催化研究所, 绿色化学与技术教育部重点实验室, 四川成都 610064
  • 收稿日期:2012-02-28 修回日期:2012-04-12 出版日期:2012-06-21 发布日期:2012-06-21

(1S,2S)-Diphenylethylenediamine Modified Ir/SiO2 Catalyst for Asymmetric Hydrogenation of Acetophenone and Its Derivatives

YANG Chaofen1, YANG Jun1, SUN Xiaodong1, ZHU Yanqin1, WANG Qi1, CHEN Hua2,*   

  1. 1Research Center for Analysis and Measurement, Kunming University of Science and Technology, Kunming 650093, Yunnan, China; 2Key Laboratory of Green Chemistry and Technology, Ministry of Education, Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, Chengdu 610064, Sichuan, China
  • Received:2012-02-28 Revised:2012-04-12 Online:2012-06-21 Published:2012-06-21

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摘要： 不添加任何稳定剂, 在碱性条件下制备了 5%Ir/SiO2 催化剂, 并用于催化苯乙酮的不对称加氢反应中, 详细考察了碱和手性修饰剂种类、氢气压力、反应温度、(1S,2S)-1,2-二苯基乙二胺 ((1S,2S)-DPEN) 浓度对反应的影响. 在优化反应条件下, 5%Ir/SiO2 催化剂表现出较好的反应活性和对映选择性. 其中, 苯乙酮不对称加氢反应的对映选择性达 70%. 该催化剂不需要任何稳定剂, 制备方法简单, 催化性能稳定, 通过简单的离心分离即可循环使用.

关键词: 铱, 苯乙酮, 多相不对称加氢, (1S,2S)-1,2-二苯基乙二胺, 对映选择性

Abstract: An efficient and highly dispersed 5%Ir/SiO2 catalyst for the asymmetric hydrogenation of acetophenone and its derivatives were prepared under basic conditions without the use of any stabilizer. The effects of different reaction parameters, namely, catalyst preparation, base used, chiral modifier, and concentration of (1S,2S)-diphenylethylenediamine ((1S,2S)-DPEN), were evaluated. Under optimum conditions with 5%Ir/SiO2 modified by (1S,2S)-DPEN, a high ee value of 70.0% was obtained for the asymmetric hydrogenation of acetophenone. It is noteworthy that this highest ee value was obtained with a supported metal catalyst without any stabilizer. The catalyst preparation is simple and there was no loss of enantioselectivity when the catalyst was reused several times.

Key words: iridium, acetophenone, heterogeneous asymmetric hydrogenation, (1S,2S)-diphenylethylenediamine, enantioselectivity