Additive-free four-component radical selenosulfonylation of alkenes

Abstract

While multicomponent tandem reactions offer an efficient platform for the difunctionalization of alkenes, the precise regulation of component ordering in reaction systems remains a persistent challenge. Herein, we present an additive-free method to achieve the radical selenosulfonylation of alkenes through four-component sequential participation, enabled by the precise regulation of equilibria among multiple components and the ingenious utilization of radical-polarity matching effects between the intermediates and alkenes. Moreover, this strategy overcomes the limitations of the cumbersome presynthesis of selenosulfonates and successfully extends the substrate scope to unactivated alkenes. Simultaneously, C–S and C–Se bonds can be constructed under mild conditions without any additives, achieving the highly selective conversion of difunctionalized alkenes with the introduction of bis-heteroatoms. Through systematic controlled experiments and mechanistic studies, the radical tandem reaction pathway and polarity matching regulation mechanism were revealed.