Disulfide-mediated ruthenium-catalyzed direct C–H thiolation in benzoxazinone systems: selective synthesis of ortho-thiolated 2-arylbenzoxazinones

Abstract

2-Arylbenzoxazinone undergoes direct ortho-C–H thiolation by using diaryl disulfide in the presence of a Ru(II)–phosphine catalytic system and an Ag additive. The protocol has been generalized with benzoxazinone substrates having different substituents and a series of disulfides. ortho-Selenylation has also been performed successfully using diphenyl diselenide under similar catalytic conditions. Based on control experiments and reported literature studies, a probable mechanistic pathway has been suggested.