Trichloroacetonitrile-Mediated Oxidation of Sulfides and Benzylic C–H Bonds via Photoexcited Radical Reactions under Clean Conditions

The protocol using only trichloroacetonitrile (CCl₃CN) or CCl₃CN/methanol to achieve oxidation of sulfides and benzylic C-H bonds in open air was established. Highly selective oxidation of sulfides to sulfoxides and efficient oxidation of benzylic C-H bonds were realized under clean and mild conditions, respectively. The main features of this protocol are a wide substrate scope, high yields, gram-scale preparation, and efficient conversion of various pharmaceutical molecules. The reactions were performed in air under light irradiation, and the mechanism was demonstrated to involve a radical process. This protocol provides a sustainable and straightforward method for the oxidation of sulfides and benzylic C-H bonds.