Electrochemical Hydrotrifluoromethylation of Fumaronitrile

Article abstract of DOI:10.1021/jo00299a039

Electrooxidation of trifluoroacetic acid in the presence of fumaronitrile (1) in an MeCN-H2O-(Pt) system provides 2-(trifluoromethyl)succinonitrile (2) in a 65percent yield.The electrochemical reaction is remarkably affected by the reaction temperature.That is, at the ice-cooling temperature, a simple hydrogenation of 1 predominates, while at 50-55 deg C, the desired hydrotrifluoromethylation proceeds exclusively.The anodically generated trifluoromethyl radicals recombine with the succinonitrile radicals produced at the cathode, leading to the formation of 2.