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Organoboron-Promoted Electrochemical Chlorosulfonylation of Alkenes with Sulfonyl Chlorides

Xi Peng, Shaokun Tao, Weichao Xue, Haiyan Fu, Jiaqi Xu, Ruixiang Li, Hua Chen, Xueli Zheng

2024Organic Letters9 citationsDOI

Abstract

Although extraordinary advances have been achieved by the transition-metal catalysis system, there is an urgent need to explore and develop alternative methodologies that are more environmentally friendly. Herein, we report an electrochemical chlorosulfonylation of alkenes using a wide range of sulfonyl chlorides with an inexpensive, degradable, and commercially available organoboron as a promoter. Furthermore, this protocol employs convergent paired electrolysis, reducing the need for sacrificial anodes and minimizing the extent of hydrogen evolution.

Topics & Concepts

SulfonylChemistryEnvironmentally friendlyElectrochemistryCombinatorial chemistryElectrolysisCatalysisAnodeOrganoboron compoundsOrganic chemistryElectrolyteAlkylBiologyPhysical chemistryElectrodeEcologySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods