Litcius/Paper detail

Direct Amino-α-C–H Heteroarylation of Amides under Electrochemical Conditions

Congcong Qiang, Tan Zhang, Zhaoyue Feng, Ping Liu, Peipei Sun

2024Organic Letters21 citationsDOI

Abstract

An electrochemical hydrogen atom transfer (HAT) strategy for the direct amino-α-C–H heteroarylation of amides is described. The cheap TMSN 3 acts as a hydrogen atom transfer reagent. A series of heteroarenes including quinoxalin-2(1 H )-ones, 4-methylquinoline, isoquinoline, 2-methylquinoxaline, benzothiazole, etc., and various readily available amides/lactams were suitable. The reaction has the characteristics of a wide range of substrates, good regioselectivity, chemical oxidant-free conditions, etc.

Topics & Concepts

BenzothiazoleChemistryReagentRegioselectivityHydrogen atomIsoquinolineElectrochemistryCombinatorial chemistryOrganic chemistryCatalysisGroup (periodic table)Physical chemistryElectrodeCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsAsymmetric Hydrogenation and Catalysis