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

Jiawei Huang, Xiaoman Li, Liang Xu and Yu Wei*

*School of Chemistry and Chemical Engineering, Shihezi University, Shihezi 832003, China, Email:

J. Huang, X. Li, L. Xu, Y. Wei, J. Org. Chem., 2023, 88, 3054-3067.

DOI: 10.1021/acs.joc.2c02856

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A convenient and metal-free three-component oxychalcogenation reaction of alkenes, diselenides/thiophenols, and H2O/alcohols provides β-hydroxyl or β-alkoxy organochalcogenides in very good yields. Tetrabutylammonium tribromide (TBATB) and dimethylsulfoxide (DMSO) are utilized as the catalyst and the terminal oxidant, respectively.

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proposed mechanism

Key Words

benzylic alcohols, aryl sulfides, DMSO, multicomponent reactions

ID: J42-Y2023