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Electrochemical Desaturative β‐Acylation of Cyclic <i>N</i>‐Aryl Amines

Tian Feng, Siyi Wang, Yin Liu, Shouzhuo Liu, Youai Qiu

2021Angewandte Chemie International Edition94 citationsDOI

Abstract

Abstract Herein, we disclose a straightforward, robust, and simple route to access β‐substituted desaturated cyclic amines via an electrochemically driven desaturative β‐functionalization of cyclic amines. This transformation is based on multiple single‐electron oxidation processes using catalytic amounts of ferrocene. The reaction proceeds in the absence of stoichiometric amounts of electrolyte under mild conditions, affording the desired products with high chemo‐ and regioselectivity. The reaction was tolerant of a broad range of substrates and also enables late‐stage β‐C(sp 3 )−H acylation of potentially valuable products. Preliminary mechanistic studies using cyclic voltammetry reveal the key role of ferrocene as a redox mediator in the reaction.

Topics & Concepts

FerroceneAcylationCyclic voltammetryChemistryElectrochemistryRedoxRegioselectivityCombinatorial chemistryStoichiometryCyclic aminesArylCatalysisSupporting electrolyteElectrolyteReactive intermediateSurface modificationOrganic chemistryElectrodePhysical chemistryAlkylCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
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