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Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers

A new method for the preparation of α-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynyl sulfides with 3HF·Et(3)N, a process that requires Lewis acid activation using BF(3)·Et(2)O and TiF(4). The method gives access to a range of α-fluorovinyl thioethers, some in high...

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Autores principales: Bello, Davide, O'Hagan, David
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4661019/
https://www.ncbi.nlm.nih.gov/pubmed/26664609
http://dx.doi.org/10.3762/bjoc.11.205
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author Bello, Davide
O'Hagan, David
author_facet Bello, Davide
O'Hagan, David
author_sort Bello, Davide
collection PubMed
description A new method for the preparation of α-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynyl sulfides with 3HF·Et(3)N, a process that requires Lewis acid activation using BF(3)·Et(2)O and TiF(4). The method gives access to a range of α-fluorovinyl thioethers, some in high stereoselectivity with the Z-isomer predominating over the E-isomer. The α-fluorovinyl thioether motif has prospects as a steric and electronic mimetic of thioester enols and enolates, important intermediates in enzymatic C–C bond forming reactions. The method opens access to appropriate analogues for investigations in this direction.
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spelling pubmed-46610192015-12-09 Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers Bello, Davide O'Hagan, David Beilstein J Org Chem Full Research Paper A new method for the preparation of α-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynyl sulfides with 3HF·Et(3)N, a process that requires Lewis acid activation using BF(3)·Et(2)O and TiF(4). The method gives access to a range of α-fluorovinyl thioethers, some in high stereoselectivity with the Z-isomer predominating over the E-isomer. The α-fluorovinyl thioether motif has prospects as a steric and electronic mimetic of thioester enols and enolates, important intermediates in enzymatic C–C bond forming reactions. The method opens access to appropriate analogues for investigations in this direction. Beilstein-Institut 2015-10-14 /pmc/articles/PMC4661019/ /pubmed/26664609 http://dx.doi.org/10.3762/bjoc.11.205 Text en Copyright © 2015, Bello and O'Hagan https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Bello, Davide
O'Hagan, David
Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers
title Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers
title_full Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers
title_fullStr Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers
title_full_unstemmed Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers
title_short Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers
title_sort lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4661019/
https://www.ncbi.nlm.nih.gov/pubmed/26664609
http://dx.doi.org/10.3762/bjoc.11.205
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