催化学报

催化学报 ›› 2012, Vol. 33 ›› Issue (7): 1146-1153.DOI: 10.1016/S1872-2067(11)60397-5

• 研究论文 • 上一篇    下一篇

聚乙二醇 400-水介质中水溶性钌膦二胺催化苄叉丙酮的不对称加氢反应

秦瑞香1, 王金波1,2,a, 熊伟1, 冯建1, 刘德蓉1, 陈华2,b   

  1. 1重庆科技学院化学化工学院, 重庆 401331; 2四川大学化学学院有机金属络合催化研究所, 绿色化学及技术教育部重点实验室, 四川成都 610064
  • 收稿日期:2012-03-12 修回日期:2012-04-11 出版日期:2012-06-21 发布日期:2012-06-21

Green and Recyclable Medium for Asymmetric Hydrogenation of Benzalacetone Catalyzed by RuCl2(TPPTS)2-(S,S)-DPENDS

QIN Ruixiang1, WANG Jinbo1,2,a, XIONG Wei1, FENG Jian1, LIU Derong1, CHEN Hua2,b   

  1. 1College of Chemistry and Chemical Engineering, Chongqing University of Science and Technology, Chongqing 401331, 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:2012-03-12 Revised:2012-04-11 Online:2012-06-21 Published:2012-06-21

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摘要： 在聚乙二醇 400-水绿色可循环介质中, 以手性二胺 (S,S)-1,2-二苯基乙二胺二磺酸钠 ((S,S)-DPENDS) 与非手性钌膦络合物 ([RuCl2(TPPTS)2]2) 原位生成的水溶性钌膦二胺为催化剂, 考察了苄叉丙酮的选择性不对称加氢反应. 在优化的反应条件下, 羰基加氢产物 4-苯基-3-丁烯-2-醇的化学选择性和对映选择性分别为 98.5% 和 74.3%. 经正己烷萃取后, 催化剂即可从产物中分离出来. 循环使用 5 次后, 4-苯基-3-丁烯-2-醇化学选择性和对映选择性没有明显下降.

关键词: 聚乙二醇 400, 水, 不对称加氢, 水溶性钌膦二胺, 苄叉丙酮, 循环

Abstract: PEG400-H2O was a green and recyclable reaction medium for asymmetric hydrogenation of benzalacetone catalyzed by ruthenium achiral monophosphine complex, RuCl2(TPPTS)2 (TPPTS: P(m-C6H4SO3Na)3), which was modified by (S,S)-DPENDS (disodium salt of sulfonated (S,S)-1,2-diphenyl-1,2-ethylene-diamine). Under the optimized conditions, the chemoselectivity for 4-phenyl-3-buten-2-ol was 98.5% with a corresponding ee value of 74.3%. The resulting products could easily be separated from the catalyst by extraction with n-hexane. The catalyst immobilized on PEG400-H2O could be recycled and reused at least five times without significant loss of chemoselectivity and enantioselectivity.

Key words: polyethylene glycol 400, water, asymmetric hydrogenation, water-soluble ruthenium-phosphine-diamine, benzalacetone, recycling