高等学校化学学报

高等学校化学学报 ›› 2013, Vol. 34 ›› Issue (7): 1679.doi: 10.7503/cjcu20130013

• 物理化学 • 上一篇    下一篇

(1S,2S)-DPEN修饰的Ir/Al2O3催化苯乙酮及其衍生物的不对称加氢反应

杨俊1,2, 赵文波1, 杨朝芬2, 孙晓东2, 王齐2, 朱艳琴2, 陈华3   

  1. 1. 昆明理工大学化学工程学院, 昆明 650500;
    2. 昆明理工大学分析测试研究中心, 昆明 650093;
    3. 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, 成都 610064
  • 收稿日期:2013-01-05 出版日期:2013-07-10 发布日期:2013-06-21
  • 通讯作者: 赵文波, 男, 博士, 副教授, 主要从事活性金属催化机理方面的研究. E-mail: wenshuixing@126.com;杨朝芬, 女, 博士, 讲师, 主要从事有机金属络合催化方面的研究. E-mail: yangmlh@163.com E-mail:wenshuixing@126.com;yangmlh@163.com
  • 基金资助:

    云南省应用基础研究基金(批准号: 2010ZC039)和云南省教育厅科研基金(批准号: KKJA201032009)资助.

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

YANG Jun1,2, ZHAO Wen-Bo1, YANG Chao-Fen2, SUN Xiao-Dong2, WANG Qi2, ZHU Yan-Qing2, CHEN Hua3   

  1. 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

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摘要：

在碱性条件下制备了三氧化二铝负载的铱(Ir/γ-Al2O3)催化剂, 并用于苯乙酮及其衍生物的不对称催化加氢反应. 考察了不同的碱, 碱浓度、手性二胺(1S,2S)-1,2-二苯基乙二胺[(1S,2S)-DPEN]浓度、反应温度和反应压力对催化剂及反应的影响. 结果显示, 在优化反应条件下, 该催化剂表现出较高的催化活性和良好的对映选择性, 其中异丁酰苯不对称催化加氢反应的对映选择性达到了80.3%. 该催化剂不需要使用任何稳定剂, 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: (1S,2S)-1,2-二苯基乙二胺, Ir/Al2O3催化剂, 苯乙酮, 不对称加氢反应

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

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