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Electrochemical Umpolung C–H Functionalization of Oxindoles

Miryam Pastor, Marie Vayer, Harald Weinstabl, Nuno Maulide

2021The Journal of Organic Chemistry26 citationsDOIOpen Access PDF

Abstract

Herein, we present a general electrochemical method to access unsymmetrical 3,3-disubstituted oxindoles by direct C-H functionalization where the oxindole fragment behaves as an electrophile. This Umpolung approach does not rely on stoichiometric oxidants and proceeds under mild, environmentally benign conditions. Importantly, it enables the functionalization of these scaffolds through C-O, and by extension to C-C or even C-N bond formation.

Topics & Concepts

UmpolungSurface modificationChemistryElectrophileOxindoleElectrochemistryCombinatorial chemistryStoichiometryOrganic chemistryNucleophileElectrodeCatalysisPhysical chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions
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