A Formal Exchange Reaction between Ketones and Vinyl Ethers with Solid Catalysts

The formal exchange of functional groups in internal positions of two different molecules is of interest in synthetic chemistry, as a simple retrosynthetic strategy. Here the formal exchange reaction between internal α-methylene ketones and vinyl ethers, retaining the original C–O bonds is presented...

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Autores: Mingueza-Verdejo, Paloma, Cerón-Carrasco, Jose Pedro, Oliver Meseguer, Judit, Leyva, Antonio
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2023
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/364624
Acceso en línea:http://hdl.handle.net/10261/364624
Access Level:acceso abierto
Palabra clave:solid catalyst
vinyl ether
ketone
exchange reaction
reaction in flow
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spelling A Formal Exchange Reaction between Ketones and Vinyl Ethers with Solid CatalystsMingueza-Verdejo, PalomaCerón-Carrasco, Jose PedroOliver Meseguer, JuditLeyva, Antoniosolid catalystvinyl etherketoneexchange reactionreaction in flowThe formal exchange of functional groups in internal positions of two different molecules is of interest in synthetic chemistry, as a simple retrosynthetic strategy. Here the formal exchange reaction between internal α-methylene ketones and vinyl ethers, retaining the original C–O bonds is presented. This process offers a new route for the synthesis of vinyl ethers in one step from ketones, including 1,3-diketones, under mild reaction conditions. Besides, the reaction is catalyzed by reusable cheap solids and can be carried out in flow for 20 days without signs of catalyst depletion. Combined experimental and computational mechanistic studies unveil the key role of carbonyl–enol equilibria.Financial support by Severo Ochoa centre of excellence program (CEX2021-001230-S) is gratefully acknowledged. Financial support by Spanish MICIIN (project code PID2020-115100GB-I00) and Generalitat Valenciana (GV/2021/138) are also acknowledged.With funding from the Spanish government through the ‘Severo Ochoa Centre of Excellence’ accreditation (CEX2021-001230-S).Peer reviewedGeorg Thieme VerlagMinisterio de Ciencia e Innovación (España)Ministerio de Ciencia, Innovación y Universidades (España)Agencia Estatal de Investigación (España)Generalitat ValencianaConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202420242023info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/364624reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/CEX2021-001230-Sinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-115100GB-I00https://www.thieme-connect.de/products/ejournals/abstract/10.1055/a-2204-2801Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3646242026-05-22T06:33:51Z
dc.title.none.fl_str_mv A Formal Exchange Reaction between Ketones and Vinyl Ethers with Solid Catalysts
title A Formal Exchange Reaction between Ketones and Vinyl Ethers with Solid Catalysts
spellingShingle A Formal Exchange Reaction between Ketones and Vinyl Ethers with Solid Catalysts
Mingueza-Verdejo, Paloma
solid catalyst
vinyl ether
ketone
exchange reaction
reaction in flow
title_short A Formal Exchange Reaction between Ketones and Vinyl Ethers with Solid Catalysts
title_full A Formal Exchange Reaction between Ketones and Vinyl Ethers with Solid Catalysts
title_fullStr A Formal Exchange Reaction between Ketones and Vinyl Ethers with Solid Catalysts
title_full_unstemmed A Formal Exchange Reaction between Ketones and Vinyl Ethers with Solid Catalysts
title_sort A Formal Exchange Reaction between Ketones and Vinyl Ethers with Solid Catalysts
dc.creator.none.fl_str_mv Mingueza-Verdejo, Paloma
Cerón-Carrasco, Jose Pedro
Oliver Meseguer, Judit
Leyva, Antonio
author Mingueza-Verdejo, Paloma
author_facet Mingueza-Verdejo, Paloma
Cerón-Carrasco, Jose Pedro
Oliver Meseguer, Judit
Leyva, Antonio
author_role author
author2 Cerón-Carrasco, Jose Pedro
Oliver Meseguer, Judit
Leyva, Antonio
author2_role author
author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (España)
Ministerio de Ciencia, Innovación y Universidades (España)
Agencia Estatal de Investigación (España)
Generalitat Valenciana
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv solid catalyst
vinyl ether
ketone
exchange reaction
reaction in flow
topic solid catalyst
vinyl ether
ketone
exchange reaction
reaction in flow
description The formal exchange of functional groups in internal positions of two different molecules is of interest in synthetic chemistry, as a simple retrosynthetic strategy. Here the formal exchange reaction between internal α-methylene ketones and vinyl ethers, retaining the original C–O bonds is presented. This process offers a new route for the synthesis of vinyl ethers in one step from ketones, including 1,3-diketones, under mild reaction conditions. Besides, the reaction is catalyzed by reusable cheap solids and can be carried out in flow for 20 days without signs of catalyst depletion. Combined experimental and computational mechanistic studies unveil the key role of carbonyl–enol equilibria.
publishDate 2023
dc.date.none.fl_str_mv 2023
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/364624
url http://hdl.handle.net/10261/364624
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/CEX2021-001230-S
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-115100GB-I00
https://www.thieme-connect.de/products/ejournals/abstract/10.1055/a-2204-2801
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Georg Thieme Verlag
publisher.none.fl_str_mv Georg Thieme Verlag
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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