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Pairing Iron and Nickel Catalysis for Electrochemical Esterification of Aryl Halides with Carbazates

Peng Xue, Liubo Li, Niankai Fu

2022Organic Letters28 citationsDOI

Abstract

We report an electrocatalytic approach for esterification of aryl halides by pairing iron and nickel electrocatalysis. The reaction involves anodically iron-catalyzed oxidation of carbazates to produce alkoxycarbonyl radicals. The carbon-centered radicals then enter nickel catalysis that is powered by cathodic reduction to deliver the radical coupling products. Mechanistic data are consistent with arylnickel(II) species as the key intermediates enabling the desired carbon-carbon bond formation.

Topics & Concepts

ChemistryHalideNickelCatalysisArylElectrocatalystRadicalElectrochemistryCarbon fibersPhotochemistryPairingCombinatorial chemistryInorganic chemistryOrganic chemistryElectrodePhysical chemistryAlkylSuperconductivityComposite materialMaterials sciencePhysicsQuantum mechanicsComposite numberRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
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