Publication | Open Access
Amide Synthesis by Nickel/Photoredox‐Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides
123
Citations
46
References
2020
Year
Photoredox CatalysisCross-coupling ReactionBioorganic ChemistryNickel/photoredox‐catalyzed Direct CarbamoylationBiochemistryCatalytic Amide SynthesisNatural SciencesEngineeringPhotoredox ProcessOrganic ChemistryCatalysisChemistryAmide ScaffoldAsymmetric CatalysisEnantioselective Synthesis
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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