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Electrochemical‐induced 1,3‐oxohydroxylation of arylcyclopropanes

Xuejin Huang, Jianhua Cai, Ye Zheng, Chunlan Song, Jiakun Li

2023Advanced Synthesis & Catalysis10 citationsDOI

Abstract

Abstract Herein, we present a method for electrochemical‐induced 1,3‐oxohydroxylation of arylcyclopropanes with H 2 O as the green oxygen source. This transformation offers a regioselective route to highly functionalized β‐hydroxy ketones under oxidant‐ and metal‐free conditions. Notably, this electrochemical approach features simple operation, good regioselectivity, high functional group tolerance, and easy derivatization of the products. Mechanistic studies have provided solid evidences that 1,3‐diol acts as the crucial intermediate in this reaction, leading to the observed regioselectivity.

Topics & Concepts

RegioselectivityChemistryDerivatizationElectrochemistryDiolCombinatorial chemistryFunctional groupReaction conditionsOrganic chemistryElectrodeCatalysisHigh-performance liquid chromatographyPhysical chemistryPolymerCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques