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Direct C–H Thiolation for Selective Cross-Coupling of Arenes with Thiophenols via Aerobic Visible-Light Catalysis

Liang Ge, Jing‐Hao Wang, Tao Lei, Yuanyuan Cheng, Chao Zhou, Yajing Chen, Chen Ye, Bin Chen, Chen‐Ho Tung, Li‐Zhu Wu

2021Organic Letters37 citationsDOI

Abstract

An aerobic metal-free, visible-light-induced regioselective thiolation of phenols with thiophenols is reported. The cross-coupling protocol exhibits great functional group tolerance and high regioselectivity. Mechanistic studies reveal that the disulfide radical cation plays a crucial role in the visible-light catalysis of aerobic thiolation. Simply controlling the equivalent ratio of substrates enables the selective formation of sulfide or sulfoxide products with high activity in a one-pot reaction.

Topics & Concepts

ChemistryRegioselectivityCatalysisVisible spectrumFunctional groupSulfidePhotochemistrySulfoxideCombinatorial chemistryCoupling reactionOrganic chemistryPolymerPhysicsOptoelectronicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsAdvanced Photocatalysis Techniques
Direct C–H Thiolation for Selective Cross-Coupling of Arenes with Thiophenols via Aerobic Visible-Light Catalysis | Litcius