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Electrochemical Mn-Promoted Radical Selenylation of Boronic Acids with Diselenide Reagents

Ziyue Chen, Yuan Wang, Chenjian Hu, Daoxin Wang, Peilin Lei, Hong Yi, Yong Yuan, Aiwen Lei

2022Organic Letters57 citationsDOI

Abstract

A powerful and environmentally friendly electrochemical manganese-promoted free radical selenylation reaction between boronic acids and diselenide reagents was established. This electrochemical protocol provides a practically applicable way to a series of valuable organoselenium compounds with the use of easy available materials. Mechanistic experiments implied that the seleno-radical formed via direct or indirect electrochemical oxidation of diselenide may be involved as a key species in this transformation.

Topics & Concepts

DiselenideChemistryReagentElectrochemistryDiphenyl diselenideManganeseCombinatorial chemistryBoronic acidOrganic chemistrySeleniumElectrodePhysical chemistryRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesOrganoselenium and organotellurium chemistry
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