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Electrochemical synthesis of sulfonated benzothiophenes using 2-alkynylthioanisoles and sodium sulfinates

Mingming Zhang, Yu Sun, Wanwan Wang, Kangkang Chen, Wenchao Yang, Lei Wang

2021Organic & Biomolecular Chemistry59 citationsDOI

Abstract

Electrochemical sulfonylation/cyclization of 2-alkynylthioanisoles with sodium sulfinates was developed under catalyst-, external oxidant- and metal-free conditions. The electrosynthesis provides sustainable and efficient access to 3-sulfonated benzothiophenes with good substrate scope and functional group tolerance. This cascade radical process has been triggered through a sulfonyl radical addition to alkynes using sodium sulfinates under electrochemical conditions.

Topics & Concepts

ChemistryElectrosynthesisSulfonylElectrochemistryCatalysisSodiumSubstrate (aquarium)Combinatorial chemistryOrganic chemistryElectrodeGeologyOceanographyAlkylPhysical chemistrySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods