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

被引:103
作者
Alandini, Nurtalya [2 ]
Buzzetti, Luca [2 ]
Favi, Gianfranco [3 ]
Schulte, Tim [4 ]
Candish, Lisa [4 ]
Collins, Karl D. [4 ]
Melchiorre, Paolo [1 ,2 ]
机构
[1] ICREA, Passeig Lluis Co 23, Barcelona 08010, Spain
[2] Barcelona Inst Sci & Technol, ICIQ Inst Chem Res Catalonia, Ave Paisos Catalans 16, Tarragona 43007, Spain
[3] Univ Urbino Carlo Bo, Dept Biomol Sci, Via I Maggetti 24, I-61029 Urbino, Italy
[4] Bayer AG, Small Mol Innovat, Pharmaceut, Aprather Weg 18a, D-42113 Wuppertal, Germany
基金
欧盟地平线“2020”; 欧洲研究理事会;
关键词
amides; cross-coupling; nickel catalysis; photoredox catalysis; radical chemistry; CARBOXYLIC-ACIDS; AMIDATION; LIGHT; AMINOCARBONYLATION; HETEROCYCLES; PERSPECTIVE; CHLORIDES;
D O I
10.1002/anie.202000224
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:5248 / 5253
页数:6
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