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Amide Synthesis by Nickel/Photoredox‐Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides

Nurtalya Alandini, Luca Buzzetti, Gianfranco Favi, Tim Schulte, Lisa Candish, Karl D. Collins, Paolo Melchiorre

2020Angewandte Chemie37 citationsDOI

Abstract

Abstract Herein, we report a one‐electron strategy for catalytic amide synthesis that enables the direct carbamoylation of (hetero)aryl bromides. This radical cross‐coupling approach, which is based on the combination of nickel and photoredox catalysis, proceeds at ambient temperature and uses readily available dihydropyridines as precursors of carbamoyl radicals. The method's mild reaction conditions make it tolerant of sensitive‐functional‐group‐containing substrates and allow the installation of an amide scaffold within biologically relevant heterocycles. In addition, we installed amide functionalities bearing electron‐poor and sterically hindered amine moieties, which would be difficult to prepare with classical dehydrative condensation methods.

Topics & Concepts

AmideArylChemistryCatalysisAmine gas treatingSteric effectsCombinatorial chemistryRadicalNickelFunctional groupPhotochemistryOrganic chemistryPolymerAlkylSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions
Amide Synthesis by Nickel/Photoredox‐Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides | Litcius