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Amide Synthesis by Nickel/Photoredox‐Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides
Author(s) -
Alandini Nurtalya,
Buzzetti Luca,
Favi Gianfranco,
Schulte Tim,
Candish Lisa,
Collins Karl D.,
Melchiorre Paolo
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202000224
Subject(s) - amide , chemistry , aryl , catalysis , amine gas treating , steric effects , combinatorial chemistry , radical , nickel , functional group , photoredox catalysis , photochemistry , organic chemistry , photocatalysis , alkyl , polymer
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.