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Electrochemical 1,3-Alkyloxylimidation of Arylcyclopropane Radical Cations: Four-Component Access to Imide Derivatives

Wei Zhou, Peng Chen, Zi-Qiong Li, Li-Tong Xiao, Jiang Bai, Xian‐Rong Song, Mu‐Jia Luo, Qiang Xiao

2023Organic Letters16 citationsDOI

Abstract

Herein, a general electrochemical radical-cation-mediated four-component ring-opening 1,3-alkyloxylimidation of arylcyclopropanes, acetonitrile, carboxylic acids, and alcohols is described, providing a facile and sustainable approach to quickly construct structurally diverse imide derivatives from easily available raw materials in an operationally simple undivided cell. This metal-catalyst- and oxidant-free single-electron oxidation strategy offers a green alternative for the formation of highly reactive cyclopropane-derived radical cations, and this protocol features a broad functional group tolerance.

Topics & Concepts

ChemistryImideAcetonitrileElectrochemistryCyclopropaneCatalysisRing (chemistry)Functional groupCombinatorial chemistryComponent (thermodynamics)Organic chemistryElectrodePhysicsPhysical chemistryThermodynamicsPolymerRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms
Electrochemical 1,3-Alkyloxylimidation of Arylcyclopropane Radical Cations: Four-Component Access to Imide Derivatives | Litcius