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Direct Electrochemical Ritter‐Type Amination of Electron‐Deficient Arenes

Youtian Fu, Ling Zhang, Maolin Sun, Liming Cao, Lei Yang, Ruihua Cheng, Yueyue Ma, Jinxing Ye

2023European Journal of Organic Chemistry13 citationsDOI

Abstract

Abstract Due to the high oxidation potentials of electron‐deficient aromatic hydrocarbons, it is difficult to achieve the direct oxidative C(sp 2 )−H bonds functionalizations of such substrates. Herein, we develop a Ritter‐type amination of electron‐deficient aromatics by merging electricity and sulfate. This practical and straightforward method provides a series of acetanilides from simple electron‐deficient arenes, including mono‐, di‐ and tri‐substituted arenes (22 examples, up to 75 %) with moderate to good yields under mild conditions. This method is characterized by cheap and readily available regents, atom and step economy.

Topics & Concepts

ChemistryAminationAcetanilideElectrochemistryAtom economyCombinatorial chemistryRitter reactionOrganic chemistryCatalysisElectrodePhysical chemistryCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsSynthesis and Catalytic Reactions