Synthesis of Polysubstituted Vinyl Sulfones by Direct C-S Cross-Coupling.

Abstract

Vinyl sulfones are valued for their unique chemical properties and bioactivity, but creating a wide range of different analogs remains a challenge. To address this limitation, we have developed a novel approach that facilitates the synthesis of polysubstituted vinyl sulfones. This method utilizes the dual functionality of NIS as a promoter that enables sulfonation and elimination in the synthesis of vinyl sulfones. We used the broad applicability, efficiency, selectivity, and functional group tolerance of this approach to synthesize more than 70 examples. Additionally, competition experiments have provided insights into the reactivity and selectivity of the transient sulfonyl radical towards various C-C multiple bonds. Herein, we describe using this mild protocol in the late-stage vinyl sulfonation of complex molecules to simplify the synthesis of specific targets and enable the modification of complex natural products and advanced materials.