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Synergistic Photoredox and Iron Catalyzed 1,2-Thiosulfonylation of Alkenes with Thiophenols and Sulfonyl Chlorides

Fei Tang, Yi‐Si Feng, Wenqing Yang, Hua‐Jian Xu

2023Organic Letters17 citationsDOI

Abstract

Herein, a three-component 1,2-thiosulfonylation of alkenes with thiophenols and sulfonyl chlorides via synergistic photoredox and iron catalysis is described. Compared with previous studies, this protocol avoids tedious pre-synthesis of thiosulfonates and employs more readily accessible sulfonyl chlorides as a sulfonation reagent. Moreover, the reaction exhibits high compatibility with styrenes and unactivated alkenes as well as diverse sulfonyl chlorides, especially sulfamoyl chlorides. Preliminary mechanism investigations reveal that a radical pathway is involved in the catalytic cycle.

Topics & Concepts

SulfonylChemistryReagentCatalysisPhotoredox catalysisCombinatorial chemistryCatalytic cycleOrganic chemistryPhotocatalysisAlkylSulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsRadical Photochemical Reactions
Synergistic Photoredox and Iron Catalyzed 1,2-Thiosulfonylation of Alkenes with Thiophenols and Sulfonyl Chlorides | Litcius