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Nickel-Catalyzed Direct Sulfonylation of Styrenes and Unactivated Aliphatic Alkenes with Sulfonyl Chlorides

Wei‐Hao Rao, Ying‐Ge Li, Lili Jiang, Chang Gao, Yi-Zhuo Wang, Jiafan Liu, Fu-Yu Zhou, Guo‐Dong Zou, Xinhua Cao

2024The Journal of Organic Chemistry12 citationsDOI

Abstract

A nickel-catalyzed direct sulfonylation of alkenes with sulfonyl chlorides has been developed using 1,10-phenanthroline-5,6-dione as the ligand. Unactivated alkenes and styrenes including 1,1-, 1,2-disubstituted alkenes can be subjected to the protocol, and a wide range of vinyl sulfones was obtained in high to excellent yields with good functional group compatibility. Notably, the process did not allow the desulfonylation of sulfonyl chloride or chlorosulfonylation of alkenes. Radical-trapping experiment supported that a sulfonyl free-radical was likely produced and triggered subsequent transformation in the process.

Topics & Concepts

ChemistrySulfonylCatalysisNickelOrganic chemistryMedicinal chemistryAlkylSulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsCatalytic C–H Functionalization Methods
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