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Annulation Cascades of Cyclosulfonium Salts and Alkenes towards <scp>Sulfur‐Containing <i>N</i>‐Heterocycles</scp> by Visible Light/Copper Catalysis

Jie Ma, Xufeng Li, Yuqing Chen, Yongjia Shi, Xiuyan Song, Jian Lv, Daoshan Yang

2024Chinese Journal of Chemistry26 citationsDOI

Abstract

Comprehensive Summary Although, great achievements have been made in the synthesis of heterocycles using radical addition/cyclization strategy, developing versatile alkyl radical precursors, especially the non‐stabilized long chain alkyl radicals for this strategy still remains a huge challenge. Herein, we report an efficient annulation cascade reaction between cyclosulfonium salts and alkenes for the synthesis of sulfur‐containing N ‐heterocycles by visible light/copper catalysis under mild conditions. The C—S bond cleavage/radical cascade reaction delivers a variety of corresponding N ‐heterocycles containing aryl alkyl thioether motifs with good functional group tolerance. Significantly, the current system could be used for the late‐stage functionalization of complex bioactive molecules.

Topics & Concepts

ChemistryAnnulationCatalysisCopperSulfurVisible spectrumOrganic chemistryPhotochemistryCombinatorial chemistryPhysicsOptoelectronicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods