Sodium perfluoroalkane carboxylates as sources of perfluoroalkyl groups

Abstract

Sodium trifluoroacetate, in the presence of copper(I) iodide, is used as a source of trifluoromethyl to replace halogen by trifluoromethyl in benzenoid and heterocyclic aromatic systems, as well as in alkenyl and alkyl halogen compounds. The mechanism of this interesting copper-assisted process has been explored and an intermediate of the form [CF₃Cul]^– is proposed. Introduction of higher perfluoroalkyl groups from their respective sodium perfluoroalkane carboxylates has been demonstrated and the mechanistic features are compared with those of the trifluoromethylation process.