有机化学 ›› 2019, Vol. 39 ›› Issue (10): 2946-2951.DOI: 10.6023/cjoc201904050 上一篇    下一篇

所属专题: 碳氢活化合辑2018-2019 镍催化有机反应合辑

研究简报

镍催化(Z)-1,2-二芳硫基-1,2-二芳基烯烃与格氏试剂偶联反应制备多取代烯烃

吴燕, 罗凡, 潘世敏, 李玉涵, 何树华*()   

  1. 长江师范学院化学化工学院 无机特种材料重庆市重点实验室 涪陵 408000
  • 收稿日期:2019-04-20 修回日期:2019-05-14 出版日期:2019-10-25 发布日期:2019-06-12
  • 通讯作者: 何树华 E-mail:thshuhua@163.com
  • 基金资助:
    重庆市基础前沿研究(Cstc2018jcyjAX0721);长江师范学院青年人才成长计划(No. 2018QNRC11)

Nickel-Catalyzed Coupling of 1,2-Diarylthio-1,2-diarylalkenes with Grignard Reagents for Synthesis of Multi-substituted Alkenes

Wu, Yan, Luo, Fan, Pan, Shimin, Li, Yuhan, He, Shuhua*()   

  1. Chongqing Key Laboratory of Inorganic Special Functional Materials, College of Chemistry and Chemical Engineering, Yangtze Normal University, Fuling 408000
  • Received:2019-04-20 Revised:2019-05-14 Online:2019-10-25 Published:2019-06-12
  • Contact: He, Shuhua E-mail:thshuhua@163.com
  • Supported by:
    Project supported by the Basic and Frontier Research Project of Chongqing City(Cstc2018jcyjAX0721);the Youth Talent Growth Plan Project of Yangtze Normal University(No. 2018QNRC11)

以5.0 mol% NiCl2(dppe)作为催化剂, 催化(Z)-1,2-二芳硫基-1,2-二芳基烯烃和格氏试剂偶联反应, 高选择性制备了一系列多取代烯烃化合物. 有机硫基团经水解、氧化后生成二芳基二硫醚, 实现了硫资源的循环利用, 符合绿色化学要求. 同时, 此方法对不同取代的(Z)-1,2-二芳硫基-1,2-二芳基烯烃和格氏试剂均具有较好的适用性, 以较高的产率获得相应的目标产物, 为多取代烯烃的制备提供了有效的路径.

关键词: 镍催化偶联反应, 多取代烯烃, (Z)-1,2-二芳硫基-1,2-二芳基烯烃, 格氏试剂

A convenient protocol for the synthesis of multi-substituted alkenes from (Z)-1,2-diarylthio-1,2-diarylalkenes with Grignard reagents was developed via the highly selective coupling of (Z)-1,2-diarylthio-1,2-diarylalkenes catalyzed by 5.0 mol% NiCl2(dppe). The leaving organosulfur group could be converted to diaryldisulfide after hydrolysis and oxidation, which realized the recycling of sulfur resources, meeting the requirements of green chemistry. This process tolerated to different (Z)-1,2-diarylthio-1,2-diarylalkenes and Grignard reagents to deliver products in good to excellent yields, providing an efficient route to multi-substituted alkenes.

Key words: nickel-catalyzed coupling, multi-substituted alkenes, (Z)-1,2-diarylthio-1,2-diarylalkenes, Grignard reagents