Litcius/Paper detail

Electrochemical Ni‐Catalyzed Decarboxylative C(sp<sup>3</sup>)−N Cross‐Electrophile Coupling

Ming Cai, X. Liu, Lin‐Lin Xu, Ming Shan

2024Angewandte Chemie International Edition32 citationsDOIOpen Access PDF

Abstract

Abstract A new electrochemical transformation is presented that enables chemists to couple simple alkyl carboxylic acid derivatives with an electrophilic amine reagent to construct C(sp 3 )−N bond. The success of this reaction hinges on the merging of cooperative electrochemical reduction with nickel catalysis. The chemistry exhibits a high degree of practicality, showcasing its wide applicability with 1°, 2°, 3° carboxylic acids and remarkable compatibility with diverse functional groups, even in the realm of late‐stage functionalization. Furthermore, extensive mechanistic studies have unveiled the engagement of alkyl radicals and iminyl radicals; and elucidated the multifaceted roles played by i Pr 2 O, Ni catalyst, and electricity.

Topics & Concepts

ElectrophileCatalysisElectrochemistryChemistryRadicalReagentCarboxylic acidAlkylCombinatorial chemistryOrganic chemistryPhysical chemistryElectrodeRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques