Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3873-3880.DOI: 10.6023/cjoc202006071 Previous Articles     Next Articles

Special Issue: 创刊四十周年专辑


盛杰a, 吴娜a, 刘旭a, 刘峰a, 刘帅a, 丁伟杰a, 刘畅a, 程旭a,b   

  1. a 南京大学化学化工学院 江苏省先进有机材料重点实验室 化学与生物医学科学研究所 南京 210023;
    b 南开大学 元素有机化学国家重点实验室 天津 30071
  • 收稿日期:2020-06-29 修回日期:2020-07-23 发布日期:2020-08-06
  • 通讯作者: 程旭
  • 基金资助:

Electrochemical Allylic Hydrodefluorination Reaction Using Gaseous Ammonia as Hydrogen Source

Sheng Jiea, Wu Naa, Liu Xua, Liu Fenga, Liu Shuaia, Ding Weijiea, Liu Changa, Cheng Xua,b   

  1. a Institute of Chemical and Biomedical Science, Jiangsu Advanced Organic Material Laboratory, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023;
    b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071
  • Received:2020-06-29 Revised:2020-07-23 Published:2020-08-06
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 22071105, 22031008), the QingLan Project of Jiangsu Education Department and the National Key Research and Development Program of China (No. 2019YFC0408303).

gem-Difluoroalkenes have wide applications in the drug designs and act as the synthon of molecules containing fluoride. The current researches on the electrochemical syntheses of gem-difluoroalkenes are limited to the silylation of enolated trifluoromethyl ketones. Herein, by using graphite felt as electrodes, the electrochemical allylic hydrodefluorination of α-trifluoromethyl cinnamates is realized using gaseous ammonia as hydrogen source, giving gem-difluorostyrenes in moderate to good yields. The usage of ammonia and graphite felt cathode is important to inhibit the cathodic hydrogen evolution, keeping the electron transfer from cathode to substrate with high selectivity. The cyclic voltammetry (CV) and square wave voltammetry (SWV) analyses support a stepwise electron transfer process to achieve the C—H bond formation and C—F bond cleavage.

Key words: electrochemistry, ammonia, C-F bond activation, graphite felt electrode