Amide Synthesis by Nickel/Photoredox‐Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides. (25th February 2020)

• Record Type: Journal Article
• Authors: Alandini, Nurtalya; Buzzetti, Luca; Favi, Gianfranco; Schulte, Tim; Candish, Lisa; Collins, Karl D.; Melchiorre, Paolo
• Is Part Of: Angewandte Chemie. Volume 132:Number 13(2020)
• Page Start: 5286
• Page End: 5291
• Publication Date: 2020-02-25
• Subjects: Amide -- Kreuzkupplung -- Nickelkatalyse -- Photoredoxkatalyse -- Radikalchemie; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202000224
• Languages: English
• ISSNs: 0044-8249

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. Abstract : Amidsynthese im Team : Eine katalytische Methode für die Amidsynthese wird beschrieben, die bei Umgebungstemperatur abläuft und die direkte Carbamoylierung von (Hetero)Arylbromiden ermöglicht. Die Methode basiert auf der Kombination von Nickel‐ und Photoredox‐Katalyse und verwendet leicht verfügbare Dihydropyridine als Vorläufer von Carbamoyl‐Radikalen.