Silver-catalyzed Radical Cascade Arylthiodifluoromethylation/ Cyclization of Isonitriles for the Synthesis of 6-Phenanthridinyldifluoromethyl Aryl Thioethers

Abstract

An efficient method for silver-catalyzed radical cascade arylthiodifluoromethylation/cyclization of isonitriles is disclosed. The transformation comprised addition of an arylthiodifluoromethyl radical generated in situ by the oxidative decarboxylation of arylthiodifluoroacetic salts to the isonitrile functionality to construct an ArSCF₂ -C bond, followed by intramolecular cyclization to eventually afford 6-phenanthridinyldifluoromethyl aryl thioethers. The protocol provided a variety of 6-phenanthridinyldifluoromethyl aryl thioethers in medium to excellent yields with a good functional group tolerance under mild reaction conditions.

Keywords: arylthiodifluoroacetic; difluoromethylene-containing thioether; isonitrile; phenanthridine; radical cascade.