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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...

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Autores principales: Zhang, Yajing, Tian, Qingshan, Zhang, Guozhu, Zhang, Dayong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
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.
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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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