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 applicability 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-heteroatom. Through systematic controlled experiments and mechanistic studies, the radical tandem reaction pathway and polarity matching regulation mechanism were revealed.