Electrochemical/Fe Dual-Catalyzed Perfluoroalkylation-Thiolation of Alkenes.

A novel electrochemical/Fe dual-catalyzed perfluoroalkylation-thiolization of alkenes under mild conditions has been developed. This protocol utilizes commercially available reagents, cheap electrodes, and simple equipment. Diverse polyfunctionalized perfluoroalkyl-substituted derivatives were successfully obtained in a direct and efficient way with a broad substrate scope and excellent functional group tolerance. Notably, the gram-scale synthesis and late-stage modification of biorelevant compounds highlighted the potential application of the strategy. Mechanistic studies such as cyclic voltammetry test, free radical trapping experiments, and control experiments suggest that this strategy involves the generation of a fluorinated radical and simultaneously undergoes addition to alkenes followed by iron-mediated C-S bond formation.