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

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 availa...

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Detalles Bibliográficos
Autores principales: Alandini, Nurtalya, Buzzetti, Luca, Favi, Gianfranco, Schulte, Tim, Candish, Lisa, Collins, Karl D., Melchiorre, Paolo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155093/
https://www.ncbi.nlm.nih.gov/pubmed/32030865
http://dx.doi.org/10.1002/anie.202000224
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author Alandini, Nurtalya
Buzzetti, Luca
Favi, Gianfranco
Schulte, Tim
Candish, Lisa
Collins, Karl D.
Melchiorre, Paolo
author_facet Alandini, Nurtalya
Buzzetti, Luca
Favi, Gianfranco
Schulte, Tim
Candish, Lisa
Collins, Karl D.
Melchiorre, Paolo
author_sort Alandini, Nurtalya
collection PubMed
description 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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spelling pubmed-71550932020-04-15 Amide Synthesis by Nickel/Photoredox‐Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides Alandini, Nurtalya Buzzetti, Luca Favi, Gianfranco Schulte, Tim Candish, Lisa Collins, Karl D. Melchiorre, Paolo Angew Chem Int Ed Engl Research Articles 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. John Wiley and Sons Inc. 2020-02-25 2020-03-23 /pmc/articles/PMC7155093/ /pubmed/32030865 http://dx.doi.org/10.1002/anie.202000224 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Research Articles
Alandini, Nurtalya
Buzzetti, Luca
Favi, Gianfranco
Schulte, Tim
Candish, Lisa
Collins, Karl D.
Melchiorre, Paolo
Amide Synthesis by Nickel/Photoredox‐Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides
title Amide Synthesis by Nickel/Photoredox‐Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides
title_full Amide Synthesis by Nickel/Photoredox‐Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides
title_fullStr Amide Synthesis by Nickel/Photoredox‐Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides
title_full_unstemmed Amide Synthesis by Nickel/Photoredox‐Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides
title_short Amide Synthesis by Nickel/Photoredox‐Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides
title_sort amide synthesis by nickel/photoredox‐catalyzed direct carbamoylation of (hetero)aryl bromides
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155093/
https://www.ncbi.nlm.nih.gov/pubmed/32030865
http://dx.doi.org/10.1002/anie.202000224
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