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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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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. |
format | Online Article Text |
id | pubmed-7155093 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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