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Electrochemical Lactonization Enabled by Unusual Shono-Type Oxidation from Functionalized Benzoic Acids

Chen Liu, Yunge Liu, Shurui Yang, Bing Zheng, Yunfei Zhang

2024Organic Letters17 citationsDOI

Abstract

)-H functionalization was developed. This metal- and oxidant-free strategy enabled the efficient synthesis of various lactones. Gram-scale reaction and derivatization of the lactone product demonstrated the synthetic utility of this methodology. Mechanistic studies using control experiments and CV curves elucidated the proposed intramolecular HAT and the oxidative cyclization pathway. An unusual Shono-type oxidation was realized through this electrochemical approach, proceeding without a traditional nucleophilic addition process.

Topics & Concepts

ChemistryElectrochemistryBenzoic acidCombinatorial chemistryType (biology)StereochemistryOrganic chemistryElectrodeEcologyPhysical chemistryBiologyRadical Photochemical ReactionsOxidative Organic Chemistry ReactionsPolyoxometalates: Synthesis and Applications