Amide Synthesis by Nickel/Photoredox-Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides |
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| Authors: | Nurtalya Alandini Dr Luca Buzzetti Prof Dr Gianfranco Favi Tim Schulte Dr Lisa Candish Dr Karl D Collins Prof Dr Paolo Melchiorre |
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| Institution: | 1. ICIQ – Institute of Chemical Research of Catalonia the Barcelona Institute of Science and Technology, Avenida Països Catalans 16, 43007 Tarragona, Spain;2. Department of Biomolecular Sciences, University of Urbino “Carlo Bo”, via I. Maggetti 24, 61029 Urbino, Italy;3. Small Molecule Innovations, Bayer AG, Pharmaceuticals, Aprather Weg 18a, 42113 Wuppertal, Germany;4. ICREA, Passeig Lluís Companys 23, 08010 Barcelona, Spain |
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| 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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| Keywords: | Amide Kreuzkupplung Nickelkatalyse Photoredoxkatalyse Radikalchemie |
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