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NHPI-Mediated Electrochemical α-Oxygenation of Amides to Benzimides

Fang Bai, Ning Wang, Yinshan Bai, Xiaowei Ma, Cheng‐Zhi Gu, Bin Dai, Jianpeng Chen

2023The Journal of Organic Chemistry14 citationsDOI

Abstract

This report describes a mild electrochemical α-oxygenation of a wide range of linear and cyclic benzamides mediated by N -hydroxyphthalimide (NHPI) in an undivided cell using O 2 as the oxygen source and 2,4,6-trimethylpyridine perchlorate as an electrolyte. The radical scavenger experiment and the 18 O labeling experiment were carried out, which indicated the involvement of a radical pathway and suggested O 2 as an oxygen source in the imides, respectively.

Topics & Concepts

ElectrochemistryOxygenationChemistryElectrolyteScavengerPerchlorateOxygenFree radical scavengerCombinatorial chemistryElectrodeRadicalOrganic chemistryInternal medicinePhysical chemistryMedicineAntioxidantIonRadical Photochemical ReactionsOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods
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