One‐Pot Synthesis of β‐Bromo Sulfones and Vinyl Sulfones via Different Column Chromatography

Abstract An unusual halosulfonylation of olefins, p ‐tosylhydrazones, and NBS without the need for any additional base or catalyst has been successfully discovered via the elimination of diazo compound intermediate. This reaction produces two classes of compounds, namely β‐bromo sulfones and vinyl sulfones, with entirely distinct structures under different column chromatography conditions. A free radical‐type mechanism of this unusual halosulfonylation is proposed based on control experiments and HRMS analysis. This is an easy, eco‐friendly, and effective synthetic method to synthesize vinyl sulfones and β‐halo sulfones from the same reaction system.