Electrochemical vicinal aminotrifluoromethylation of alkenes: high regioselective acquisition of β-trifluoromethylamines

Abstract

A novel vicinal aminotrifluoromethylation of alkenes using CF₃SO₂Na as a trifluoromethyl precursor and acetonitrile as an N-nucleophile has been achieved by an electrooxidative strategy. The present electrochemical protocol achieves efficient and highly regioselective difunctionalization of CC bonds under metal-free and external oxidant-free electrolysis conditions, leading to a series of β-trifluoromethylamine compounds with good to excellent yields. It is confirmed that the reaction involves free radical processes since CF₃ radicals are trapped by scavengers and the β-trifluoromethylated radical is trapped by BHT, and the deuterium-labeling experiments prove that the oxygen in the product comes from water.