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Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes

We describe a nickel-catalyzed highly regio- and stereoselective migratory fluoro-alkenylation of unactivated alkyl bromides. A unique catalytic cycle merging alkyl nickel chain-walking and defluorinative coupling enables the introduction of a broad array of fluoroalkenyl moieties into carbon chains...

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Detalles Bibliográficos
Autores principales: Zhou, Lu, Zhu, Chuan, Bi, Peijia, Feng, Chao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6349022/
https://www.ncbi.nlm.nih.gov/pubmed/30774912
http://dx.doi.org/10.1039/c8sc04162h
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author Zhou, Lu
Zhu, Chuan
Bi, Peijia
Feng, Chao
author_facet Zhou, Lu
Zhu, Chuan
Bi, Peijia
Feng, Chao
author_sort Zhou, Lu
collection PubMed
description We describe a nickel-catalyzed highly regio- and stereoselective migratory fluoro-alkenylation of unactivated alkyl bromides. A unique catalytic cycle merging alkyl nickel chain-walking and defluorinative coupling enables the introduction of a broad array of fluoroalkenyl moieties into carbon chains. Control experiments with other halogenated alkenes demonstrated the essential role of fluorine atoms in this reaction. Notably, the reaction proceeds under mild conditions and allows for the synthesis of a variety of valuable monofluoroalkenes.
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spelling pubmed-63490222019-02-15 Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes Zhou, Lu Zhu, Chuan Bi, Peijia Feng, Chao Chem Sci Chemistry We describe a nickel-catalyzed highly regio- and stereoselective migratory fluoro-alkenylation of unactivated alkyl bromides. A unique catalytic cycle merging alkyl nickel chain-walking and defluorinative coupling enables the introduction of a broad array of fluoroalkenyl moieties into carbon chains. Control experiments with other halogenated alkenes demonstrated the essential role of fluorine atoms in this reaction. Notably, the reaction proceeds under mild conditions and allows for the synthesis of a variety of valuable monofluoroalkenes. Royal Society of Chemistry 2018-11-09 /pmc/articles/PMC6349022/ /pubmed/30774912 http://dx.doi.org/10.1039/c8sc04162h Text en This journal is © The Royal Society of Chemistry 2019 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Zhou, Lu
Zhu, Chuan
Bi, Peijia
Feng, Chao
Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes
title Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes
title_full Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes
title_fullStr Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes
title_full_unstemmed Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes
title_short Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes
title_sort ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6349022/
https://www.ncbi.nlm.nih.gov/pubmed/30774912
http://dx.doi.org/10.1039/c8sc04162h
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