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

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2020 Feb 8

PMID 32030865

Citations 21

Authors

Nurtalya Alandini

Luca Buzzetti

Gianfranco Favi

Tim Schulte

Lisa Candish

Karl D Collins

Paolo Melchiorre

Affiliations

Soon will be listed here.

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.

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