Perfluorobutylation of benzo(hetero)arenes in aqueous media

Abstract

Perfluorobutylation of a series of benzo(hetero)aromatic compounds without formal leaving groups is achieved efficaciously in organic solvent-water mixtures under photostimulation. The methodology is compared with previously reported trifluoromethylation strategies of these nuclei in terms of product yields and regioselectivity. The reaction is a radical homolytic aromatic substitution process, where the perfluoroalkyl-substituted cyclohexadienyl radical intermediate is first oxidized and then a proton transfer sequence leads to the products.