Conjugated 1,8 and 1,6 addition of bis-trimethylsilylketene acetal to activated p-quinone methides via trifluoromethanesulfonic anhydride

In this work, we studied the conjugated additions of bis-trimethylsilylacetalketene acetals (bis-TMSKA) to para-quinone methides (p-QMs), which are one of the most explored molecules for the study of conjugated additions and gained significant attention in organic chemistry due to their versatile re...

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Detalles Bibliográficos
Autores: Benitez-Puebla, Luis J., Ballinas-Indili, Ricardo, Flores-Alamo, Marcos, Guevara-Vela, José M., Rocha-Rinza, Tomas, Rosales-Amezcua, Saulo, Alvarez-Toledano, Cecilio
Tipo de recurso: artículo
Fecha de publicación:2025
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:dnet:biblosearchi::daead70ec7d1d022079821bcb5277410
Acceso en línea:https://hdl.handle.net/10486/764580
https://dx.doi.org/10.1021/acs.joc.4c02852
Access Level:acceso abierto
Palabra clave:Addition reactions
para-quinone methides
bis-trimethylsilylacetalketene acetals
trifluoromethanesulfonic anhydride
Química
Física
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spelling Conjugated 1,8 and 1,6 addition of bis-trimethylsilylketene acetal to activated p-quinone methides via trifluoromethanesulfonic anhydrideBenitez-Puebla, Luis J.Ballinas-Indili, RicardoFlores-Alamo, MarcosGuevara-Vela, José M.Rocha-Rinza, TomasRosales-Amezcua, SauloAlvarez-Toledano, CecilioAddition reactionspara-quinone methidesbis-trimethylsilylacetalketene acetalstrifluoromethanesulfonic anhydrideQuímicaFísicaIn this work, we studied the conjugated additions of bis-trimethylsilylacetalketene acetals (bis-TMSKA) to para-quinone methides (p-QMs), which are one of the most explored molecules for the study of conjugated additions and gained significant attention in organic chemistry due to their versatile reactivity, particularly in Michael addition reactions. In this study, trifluoromethanesulfonic anhydride (Tf2O) was used as an activating agent for p-QMs, aiming to achieve 1,6-Michael addition products and the least reported 1,8-Michael addition with pyridine substituents. The reactivity of p-QMs derived from pyridine demonstrated distinct reaction pathways, leading to the formation of δ and γ lactones. The investigation also involved synthesizing a 1-indanone derived from the carboxylic acids obtained from the 1,6-additionFinancial support was gratefully received from PAPIIT IN213523 (C. Alvarez), Consejo Nacional de Humanidades, Ciencia y Tecnología (CONAHCyT) postdoctoral scholarship No. 481594 (L.J.B.P)American Chemical SocietyFacultad de CienciasDepartamento de Química Física Aplicada20252025-03-31research articlehttp://purl.org/coar/resource_type/c_2df8fbb1VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10486/764580https://dx.doi.org/10.1021/acs.joc.4c02852reponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengopen accesshttp://purl.org/coar/access_right/c_abf2Attribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:dnet:biblosearchi::daead70ec7d1d022079821bcb52774102026-06-23T12:46:27Z
dc.title.none.fl_str_mv Conjugated 1,8 and 1,6 addition of bis-trimethylsilylketene acetal to activated p-quinone methides via trifluoromethanesulfonic anhydride
title Conjugated 1,8 and 1,6 addition of bis-trimethylsilylketene acetal to activated p-quinone methides via trifluoromethanesulfonic anhydride
spellingShingle Conjugated 1,8 and 1,6 addition of bis-trimethylsilylketene acetal to activated p-quinone methides via trifluoromethanesulfonic anhydride
Benitez-Puebla, Luis J.
Addition reactions
para-quinone methides
bis-trimethylsilylacetalketene acetals
trifluoromethanesulfonic anhydride
Química
Física
title_short Conjugated 1,8 and 1,6 addition of bis-trimethylsilylketene acetal to activated p-quinone methides via trifluoromethanesulfonic anhydride
title_full Conjugated 1,8 and 1,6 addition of bis-trimethylsilylketene acetal to activated p-quinone methides via trifluoromethanesulfonic anhydride
title_fullStr Conjugated 1,8 and 1,6 addition of bis-trimethylsilylketene acetal to activated p-quinone methides via trifluoromethanesulfonic anhydride
title_full_unstemmed Conjugated 1,8 and 1,6 addition of bis-trimethylsilylketene acetal to activated p-quinone methides via trifluoromethanesulfonic anhydride
title_sort Conjugated 1,8 and 1,6 addition of bis-trimethylsilylketene acetal to activated p-quinone methides via trifluoromethanesulfonic anhydride
dc.creator.none.fl_str_mv Benitez-Puebla, Luis J.
Ballinas-Indili, Ricardo
Flores-Alamo, Marcos
Guevara-Vela, José M.
Rocha-Rinza, Tomas
Rosales-Amezcua, Saulo
Alvarez-Toledano, Cecilio
author Benitez-Puebla, Luis J.
author_facet Benitez-Puebla, Luis J.
Ballinas-Indili, Ricardo
Flores-Alamo, Marcos
Guevara-Vela, José M.
Rocha-Rinza, Tomas
Rosales-Amezcua, Saulo
Alvarez-Toledano, Cecilio
author_role author
author2 Ballinas-Indili, Ricardo
Flores-Alamo, Marcos
Guevara-Vela, José M.
Rocha-Rinza, Tomas
Rosales-Amezcua, Saulo
Alvarez-Toledano, Cecilio
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Facultad de Ciencias
Departamento de Química Física Aplicada
dc.subject.none.fl_str_mv Addition reactions
para-quinone methides
bis-trimethylsilylacetalketene acetals
trifluoromethanesulfonic anhydride
Química
Física
topic Addition reactions
para-quinone methides
bis-trimethylsilylacetalketene acetals
trifluoromethanesulfonic anhydride
Química
Física
description In this work, we studied the conjugated additions of bis-trimethylsilylacetalketene acetals (bis-TMSKA) to para-quinone methides (p-QMs), which are one of the most explored molecules for the study of conjugated additions and gained significant attention in organic chemistry due to their versatile reactivity, particularly in Michael addition reactions. In this study, trifluoromethanesulfonic anhydride (Tf2O) was used as an activating agent for p-QMs, aiming to achieve 1,6-Michael addition products and the least reported 1,8-Michael addition with pyridine substituents. The reactivity of p-QMs derived from pyridine demonstrated distinct reaction pathways, leading to the formation of δ and γ lactones. The investigation also involved synthesizing a 1-indanone derived from the carboxylic acids obtained from the 1,6-addition
publishDate 2025
dc.date.none.fl_str_mv 2025
2025-03-31
dc.type.none.fl_str_mv research article
http://purl.org/coar/resource_type/c_2df8fbb1
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/10486/764580
https://dx.doi.org/10.1021/acs.joc.4c02852
url https://hdl.handle.net/10486/764580
https://dx.doi.org/10.1021/acs.joc.4c02852
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:Biblos-e Archivo. Repositorio Institucional de la UAM
instname:Universidad Autónoma de Madrid
instname_str Universidad Autónoma de Madrid
reponame_str Biblos-e Archivo. Repositorio Institucional de la UAM
collection Biblos-e Archivo. Repositorio Institucional de la UAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.812455

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