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Late‐Stage Heteroarylation of Hetero(aryl)sulfonium Salts Activated by α‐Amino Alkyl Radicals

Eva Maria Alvarez, Teresa M. Karl, Florian Berger, Luca Torkowski, Tobias Ritter

2021Angewandte Chemie15 citationsDOIOpen Access PDF

Abstract

Abstract We report a late‐stage heteroarylation of aryl sulfonium salts through activation with α‐amino alkyl radicals in a mechanistically distinct approach from previously reported halogen‐atom transfer (XAT). The new mode of activation of aryl sulfonium salts proceeds in the absence of light and photoredox catalysts, engaging a wide range of hetarenes. Furthermore, we demonstrate the applicability of this methodology in synthetically useful cross‐coupling transformations.

Topics & Concepts

SulfoniumArylChemistryRadicalHalogenAlkylPhotoredox catalysisCatalysisCombinatorial chemistryPhotochemistrySalt (chemistry)Organic chemistryPhotocatalysisSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsE-Government and Public Services
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