Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2946-2951.DOI: 10.6023/cjoc201904050 Previous Articles     Next Articles

Special Issue: 碳氢活化合辑2018-2019 镍催化有机反应合辑



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 发布日期:2019-06-12
  • 通讯作者: 何树华
  • 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 Published:2019-06-12
  • Contact: He, Shuhua
  • 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)

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