Visible-light-promoted S-trifluoromethylation of thiophenols with trifluoromethyl phenyl sulfone

Abstract

Trifluoromethyl phenyl sulfone is traditionally a nucleophilic trifluoromethylating agent. Herein, we report the first example of the use of trifluoromethyl phenyl sulfone as a trifluoromethyl radical precursor. Arylthiolate anions can form electron donor-acceptor (EDA) complexes with trifluoromethyl phenyl sulfone, which can undergo an intramolecular single electron transfer (SET) reaction under visible light irradiation, thus realizing the S-trifluoromethylation of thiophenols under photoredox catalyst-free conditions. Similar S-perfluoroethylation and S-perfluoro-iso-propylation of thiophenols are also achieved using the corresponding perfluoroalkyl phenyl sulfones.