Citation: Sheng Jie, Wu Na, Liu Xu, Liu Feng, Liu Shuai, Ding Weijie, Liu Chang, Cheng Xu. Electrochemical Allylic Hydrodefluorination Reaction Using Gaseous Ammonia as Hydrogen Source[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3873-3880. doi: 10.6023/cjoc202006071 shu

Electrochemical Allylic Hydrodefluorination Reaction Using Gaseous Ammonia as Hydrogen Source

Sheng Jie ^a ,
Wu Na ^a ,
Liu Xu ^a ,
Liu Feng ^a ,
Liu Shuai ^a ,
Ding Weijie ^a ,
Liu Chang ^a ,
Cheng Xu ^a,b,,

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

Corresponding author: Cheng Xu, chengxu@nju.edu.cn
Received Date: 29 June 2020
Revised Date: 23 July 2020
Available Online: 5 August 2020
Fund Project: the National Natural Science Foundation of China 22031008Project 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)the QingLan Project of Jiangsu Education Department and the National Key Research and Development Program of China 2019YFC0408303the National Natural Science Foundation of China 22071105

Figures(3)

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.
- electrochemistry,
- ammonia,
- C-F bond activation,
- graphite felt electrode
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