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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (9): 1490-1494. 上一篇    下一篇

研究简报

N,N,N,N-四[(二苯基膦)甲基]乙二胺钯配合物催化Heck反应研究

周蓉，余晓军，汪伟，付海燕，李瑞祥*，陈华，李贤均   

  1. (四川大学化学学院 教育部绿色化学与技术重点实验室 成都 610064)
  • 收稿日期:2010-11-15 修回日期:2010-03-07 发布日期:2011-04-14
  • 通讯作者: 李瑞祥 E-mail:sculiruixiang@163.com

N,N,N,N-Tetra-[(diphenylphosphino)methyl]ethylenediamine/ Palladium Catalyzed Heck Reaction

ZHOU Rong, YU Xiao-Jun, WANG Wei, FU Hai-Yan, LI Rui-Xiang, CHEN Hua, LI Xian-Jun   

  1. (Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064)
  • Received:2010-11-15 Revised:2010-03-07 Published:2011-04-14
  • Contact: LI Rui-Xiang E-mail:sculiruixiang@163.com

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以乙二胺为骨架的含氮四膦配体N,N,N,N-四[(二苯基膦)甲基]乙二胺和钯组成的催化体系用于丙烯酸酯和芳卤的Heck反应, 该催化体系对许多卤代芳烃, 尤其含吸电基的溴代芳烃显示了良好的催化活性. 对活化底物对溴苯甲醛, 即使底物与催化剂的物质的量比达到1000000, 其转化率也能达到96%|催化非活化溴代芳烃对溴苯甲醚以及难以反应的氯代芳烃, 在Pd含量为0.1 mol%时同样表现出优良催化性能.

关键词: Heck偶联反应, 四膦配体, 钯

The catalytic performance of tetraphosphine based on ethylenediamine as backbone, N,N,N,N-tetra-[(diphenylphosphino)methyl]ethylenediamine, combined with palladium for the Heck reactions of aryl halides with acrylates was investigated. The results showed that the catalytic system is highly efficient for the Heck reaction of activated aryl bromides as well as inacti-vated aryl bromides. The yield of 96% was obtained with activated 4-bromobenzaldehyde even the molar ra-tio of substrate to catalyst up to 1000000, and with inactivated 4-bromoanisole or 4-chloronitrobenzene the high conversion was obtained in the presence of 0.1 mol% Pd.

Key words: Heck coupling reaction, tetraphosphine ligand, palladium