有机化学 ›› 2017, Vol. 37 ›› Issue (5): 1273-1277.DOI: 10.6023/cjoc201612015 上一篇    下一篇

研究论文

铜催化的乙腈为氰源的芳基碘化物的氰化(英文)

俞峥炜, 李林奕, 沈增明   

  1. 上海交通大学化学化工学院 上海 200240
  • 收稿日期:2016-12-06 修回日期:2017-01-05 发布日期:2017-01-17
  • 通讯作者: 沈增明 E-mail:shenzengming@sjtu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21272001,21672144)及上海教育委员会(No.13ZZ014)资助项目.

Cu-Catalyzed Cyanation of Aryl Iodides with Acetonitrile as Cyano Source

Yu Zhengwei, Li Linyi, Shen Zengming   

  1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
  • Received:2016-12-06 Revised:2017-01-05 Published:2017-01-17
  • Contact: 10.6023/cjoc201612015 E-mail:shenzengming@sjtu.edu.cn
  • Supported by:

    Project supported by the National Natural Sciences Foundation of China (Nos. 21272001, 21672144) and the Shanghai Education Committee (No. 13ZZ014).

利用低毒廉价的乙腈溶剂作为新型“CN”源,开发了铜催化下芳基碘化物氰化反应.其中六甲基二硅烷可以促进铜盐对乙腈C-CN键的断裂,而2,2,6,6-四甲基哌啶-氮-氧化物(TEMPO)作为温和的氧化剂,对产率的提高至关重要.在Cu/TEMPO/Si体系下显示出了底物良好的兼容性和反应性.无论是富电子或缺电子取代基的底物都能够兼容.最后根据反应结果和文献推测了反应机理.

关键词: 铜催化, 氰化, 乙腈, 芳基碘化物, TEMPO

A Cu-catalyzed protocol for the cyanation of aryl iodides by using acetonitrile as the “CN” source has been developed, in which the Cu(cat.)/2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)/Si system shows good reactivity and generality. Both electron-rich and electron-deficient functional groups can be tolerated in this system.

Key words: Cu catalyst, cyanation, acetonitrile, aryl iodide, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)