Thio radical-induced denitrogenative annulation of 1-azido-2-isocyanoarenes to construct 2-thiolated benzimidazoles

Abstract

A method for the synthesis of 2-thiolated benzimidazoles is described starting from thiols and 1-azido-2-isocyanoarenes. The isocyano group works as an acceptor of various thio radicals, followed by denitrogenative annulation of the resulting imidoyl radical intermediates to the azido group, with nitrogen loss as the only process involving high bond-forming efficiency. The one-pot method for the synthesis of these products with high functional group tolerance in the benzimidazole-based ring is not available in previous literature.