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Electrochemical Radical–Radical Cross-Coupling Approach between Sodium Sulfinates and 2<i>H</i>-Indazoles to 3-Sulfonylated 2<i>H</i>-Indazoles

Wansoo Kim, Hun Young Kim, Kyungsoo Oh

2020Organic Letters84 citationsDOI

Abstract

A direct cross-coupling between sodium sulfinates and 2H-indazoles has been developed under electrochemical conditions. The utilization of a graphite anode and platinum cathode in an undivided cell with a constant current of 7 mA allowed the concurrent oxidations of sulfinates and 2H-indazoles to sulfonyl radical and radical cationic 2H-indazoles, facilitating the direct radical–radical coupling strategy to 3-sulfonylated 2H-indazole derivatives. The transition-metal- and redox-reagent-free synthetic approach should serve as a valuable synthetic tool to achieve heteroaromatic compounds.

Topics & Concepts

ChemistrySulfonylIndazoleElectrochemistryReagentCombinatorial chemistryAnodeRadical ionSodiumPhotochemistryOrganic chemistryElectrodePhysical chemistryIonAlkylSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
Electrochemical Radical–Radical Cross-Coupling Approach between Sodium Sulfinates and 2<i>H</i>-Indazoles to 3-Sulfonylated 2<i>H</i>-Indazoles | Litcius