A Rh(II)-catalyzed formal 1,3-dichalcogenation of vinyl carbenes is described using stable hydrazones as carbene precursors and disulfides and diselenides as chalcogen sources. The reaction proceeds with excellent regio- and stereoselectivities under mild conditions, with the 1,4-sigmatropic migration of an ylidic intermediate being a key step. Mechanistic studies support a concerted pathway of chalcogen migration.
Wang et al. (Mon,) studied this question.