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Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions
Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of ben...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6539589/ https://www.ncbi.nlm.nih.gov/pubmed/31035405 http://dx.doi.org/10.3390/molecules24091671 |
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author | Wang, Xiu Wang, Zhenhua Liu, Li Asanuma, Yuya Nishihara, Yasushi |
author_facet | Wang, Xiu Wang, Zhenhua Liu, Li Asanuma, Yuya Nishihara, Yasushi |
author_sort | Wang, Xiu |
collection | PubMed |
description | Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation of the corresponding cross-coupled products, further demonstrated the synthetic utility of the present method. This newly developed methodology with a good functional-group compatibility via C–F bond cleavage and C–Sn bond formation under nickel catalysis opens a new area for the functionalization of acyl fluorides in terms of carbon-heteroatom bond formation. |
format | Online Article Text |
id | pubmed-6539589 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-65395892019-05-31 Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions Wang, Xiu Wang, Zhenhua Liu, Li Asanuma, Yuya Nishihara, Yasushi Molecules Article Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation of the corresponding cross-coupled products, further demonstrated the synthetic utility of the present method. This newly developed methodology with a good functional-group compatibility via C–F bond cleavage and C–Sn bond formation under nickel catalysis opens a new area for the functionalization of acyl fluorides in terms of carbon-heteroatom bond formation. MDPI 2019-04-28 /pmc/articles/PMC6539589/ /pubmed/31035405 http://dx.doi.org/10.3390/molecules24091671 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Wang, Xiu Wang, Zhenhua Liu, Li Asanuma, Yuya Nishihara, Yasushi Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions |
title | Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions |
title_full | Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions |
title_fullStr | Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions |
title_full_unstemmed | Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions |
title_short | Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions |
title_sort | nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6539589/ https://www.ncbi.nlm.nih.gov/pubmed/31035405 http://dx.doi.org/10.3390/molecules24091671 |
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