Three-Component Oxychalcogenation of Alkenes under Metal-Free Conditions: A Tetrabutylammonium Tribromide-Catalyzed System

A three-component oxychalcogenation reaction, from alkenes, diselenides/thiophenols, and H2O/alcohols, has been realized herein. Tetrabutylammonium tribromide (TBATB) and dimethylsulfoxide (DMSO) are utilized as the catalyst and the terminal oxidant, respectively, to enable this difunctionalization transformation. The metal-free reaction system shows good functional group compatibility, providing a unified and practical approach to access beta-hydroxyl or beta-alkoxy organochalcogenides.

Automated summary

A three-component oxychalcogenation reaction is achieved in this study, using alkenes, diselenides/thiophenols, and H2O/alcohols as reactants. Tetrabutylammonium tribromide (TBATB) and dimethylsulfoxide (DMSO) are employed as the catalyst and terminal oxidant, respectively, enabling the difunctionalization transformation. This metal-free reaction system shows excellent functional group compatibility and provides a unified and practical approach to access beta-hydroxyl or beta-alkoxy organochalcogenides.