Copper-Catalyzed Radical N-Demethylation of Amides Using <i>N</i>-Fluorobenzenesulfonimide as an Oxidant
Xue-Wen Yi, Siyu Lei, Wangsheng Liu, Fengrui Che, Chunzheng Yu, Xuesong Liu, Zonghua Wang, Xin Zhou, Yuexia Zhang
Abstract
An unprecedented N-demethylation of N-methyl amides has been developed by use of N-fluorobenzenesulfonimide as an oxidant with the aid of a copper catalyst. The conversion of amides to carbinolamines involves successive single-electron transfer, hydrogen-atom transfer, and hydrolysis, and is accompanied by formation of N-(phenylsulfonyl)benzenesulfonamide. Carbinolamines spontaneously decompose to N-demethylated amides and formaldehyde, because of their inherent instability.
Topics & Concepts
ChemistryDemethylationCatalysisCopperFormaldehydeHydrogen atomMedicinal chemistryOrganic chemistryCombinatorial chemistryAlkylDNA methylationGene expressionGeneBiochemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsAdvanced Synthetic Organic Chemistry