FeCl2/K2S2O8-mediated oxidative radical alkoxycarbonylation of trifluoromethylated N-acylhydrazones using carbazates

Abstract

A protocol for alkoxycarbonylation mediated by FeCl₂/K₂S₂O₈ has been developed for trifluoromethylated N-acylhydrazones with carbazates under mild reaction conditions. This methodology allows for the efficient synthesis of a variety of functionalized trifluoromethylated N-acylhydrazone derivatives. Mechanistic studies, including control experiments and density functional theory (DFT) calculations, indicate that the electron-withdrawing trifluoromethyl group facilitates the radical addition process, and the sulfate radical anion plays a crucial role in the oxidative dehydrogenation of intermediates.