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Dearomatization‐Enabled Visible‐Light‐Induced 1,2‐Alkylsulfonylation of Alkenes Using Sodium Sulfinates and Pyridinium Salts

Yuan Yang, Chong‐Hui Xu, Fan Teng, Jin‐Heng Li

2020Advanced Synthesis & Catalysis26 citationsDOI

Abstract

Abstract We demonstrate a three‐component 1,2‐alkylsulfonylation of alkenes using sodium sulfinates and pyridinium salts through visible light photoredox catalysis, wherein heteroarenium salts are harnessed as radical acceptors via dearomatization. This reaction allows the simultaneous incorporation of sulfonyl and 1,4‐dihydropyridine groups across the C=C bonds to access various sulfonyl‐containing 1,4‐dihydropyridine derivatives with a broad substrate scope and represents a mechanistically distinct approach to achieve alkene difunctionalization through reductive single‐electron transfer. magnified image

Topics & Concepts

ChemistryPyridiniumSulfonylAlkenePhotoredox catalysisDihydropyridineCatalysisCombinatorial chemistrySubstrate (aquarium)SodiumPhotochemistryAlkylOrganic chemistryPhotocatalysisGeologyOceanographyCalciumSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
Dearomatization‐Enabled Visible‐Light‐Induced 1,2‐Alkylsulfonylation of Alkenes Using Sodium Sulfinates and Pyridinium Salts | Litcius