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Photoredox-Catalyzed Tandem Cyclization of Enaminones with <i>N</i>-Sulfonylaminopyridinium Salts toward the Synthesis of 3-Sulfonaminated Chromones

Wenyu Hu, Xiaoqiong Diao, Jinwei Yuan, Wei Liang, Wan Yang, Liangru Yang, Ji Ma, Shouren Zhang

2023The Journal of Organic Chemistry27 citationsDOI

Abstract

A photoredox-catalyzed intermolecular tandem sulfonamination/cyclization of enaminones was realized by using N -aminopyridinium salts as the sulfonaminated reagents without transition-metal catalysts or bases. The reaction exhibits a broad scope and good functional group tolerance, good yields, and regioselectivity. Preliminary mechanistic studies support the radical property of the reaction and the involvement of N -centered radical intermediates.

Topics & Concepts

TandemChemistryRegioselectivityCatalysisReagentFunctional groupIntermolecular forceCombinatorial chemistryPhotoredox catalysisScope (computer science)RadicalPhotochemistryMedicinal chemistryOrganic chemistryPhotocatalysisMoleculeMaterials scienceComputer scienceProgramming languagePolymerComposite materialSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions