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

Author

Alandini, Nurtalya

Buzzetti, Luca

Favi, Gianfranco

Schulte, Tim

Candish, Lisa

Collins, Karl D.

Melchiorre, Paolo

Publication date

2020-03-23



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 ap- proach, 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 sub- strates 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.

Document Type

Article
Accepted version

Language

English

Subject

54

Pages

5248 p.

Grant Agreement Number

MICIU (CTQ2016-75520- P)

AGAUR (Grant 2017 SGR 981)

ERC-2015-CoG 681840 – CATA-LUX

H2020-MSCA-ITN-2016

722591 – PHOTO- TRAIN

CTQ2013-45938-P

Documents

20_Amide Synthesis by Nickel_Photoredox‐Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides.pdf

4.955Mb

 

Rights

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