Direct Electrochemical Defluorinative Carboxylation of <i>gem</i>-Difluoroalkenes with Carbon Dioxide
Shi-Liang XieShanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, ChinaXiaotong GaoShanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, ChinaHaihong WuShanghai Key Laboratory of Green Chemistry and Chemical Process and Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, ChinaFeng ZhouShanghai Key Laboratory of Green Chemistry and Chemical Process and Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, ChinaJian ZhouState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, China
2020en
ABI
Аннотация
We report a facile and economical synthesis of α-fluoroacrylic acids via direct electrochemical defluorinative carboxylation of gem-difluoroalkenes with CO2. By using a platinum plate as the working cathode and a cheap nickel plate as the anode in a user-friendly undivided cell under constant current conditions, the reactions proceed smoothly under room temperature, without the use of expensive transition metal catalysts, ligands, external base or reductant, affording the desired adducts in up to 83% yield and 20:1 Z/E ratio, with good functional group tolerance. A cyclic voltammetry study was conducted and suggested a novel ECEC process.
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