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Silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes
A silver-catalyzed three-component reaction involving alkynes, Selectfluor(®), and diethyl phosphite was employed for the one-pot formation of C(sp(2))–F and C(sp(2))–P bonds to provide an efficient access to β-fluorovinylphosphonates in a highly regio- and stereoselective manner under mild reaction...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7753110/ https://www.ncbi.nlm.nih.gov/pubmed/33414856 http://dx.doi.org/10.3762/bjoc.16.258 |
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author | Zhang, Yajing Tian, Qingshan Zhang, Guozhu Zhang, Dayong |
author_facet | Zhang, Yajing Tian, Qingshan Zhang, Guozhu Zhang, Dayong |
author_sort | Zhang, Yajing |
collection | PubMed |
description | A silver-catalyzed three-component reaction involving alkynes, Selectfluor(®), and diethyl phosphite was employed for the one-pot formation of C(sp(2))–F and C(sp(2))–P bonds to provide an efficient access to β-fluorovinylphosphonates in a highly regio- and stereoselective manner under mild reaction conditions. This reaction is operationally simple and offers an excellent functional group tolerance as well as a broad substrate scope that includes both terminal and internal alkynes. The reaction proceeded through the oxidative generation of a P-centered radical and subsequent fluorine atom transfer. |
format | Online Article Text |
id | pubmed-7753110 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-77531102021-01-06 Silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes Zhang, Yajing Tian, Qingshan Zhang, Guozhu Zhang, Dayong Beilstein J Org Chem Full Research Paper A silver-catalyzed three-component reaction involving alkynes, Selectfluor(®), and diethyl phosphite was employed for the one-pot formation of C(sp(2))–F and C(sp(2))–P bonds to provide an efficient access to β-fluorovinylphosphonates in a highly regio- and stereoselective manner under mild reaction conditions. This reaction is operationally simple and offers an excellent functional group tolerance as well as a broad substrate scope that includes both terminal and internal alkynes. The reaction proceeded through the oxidative generation of a P-centered radical and subsequent fluorine atom transfer. Beilstein-Institut 2020-12-18 /pmc/articles/PMC7753110/ /pubmed/33414856 http://dx.doi.org/10.3762/bjoc.16.258 Text en Copyright © 2020, Zhang et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms) |
spellingShingle | Full Research Paper Zhang, Yajing Tian, Qingshan Zhang, Guozhu Zhang, Dayong Silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes |
title | Silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes |
title_full | Silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes |
title_fullStr | Silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes |
title_full_unstemmed | Silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes |
title_short | Silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes |
title_sort | silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7753110/ https://www.ncbi.nlm.nih.gov/pubmed/33414856 http://dx.doi.org/10.3762/bjoc.16.258 |
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