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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...

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Detalles Bibliográficos
Autores principales: Wang, Xiu, Wang, Zhenhua, Liu, Li, Asanuma, Yuya, Nishihara, Yasushi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
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.
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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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