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...
| Autores: | , , , , , , |
|---|---|
| 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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oai:dnet:biblosearchi::daead70ec7d1d022079821bcb5277410 |
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| spelling |
Conjugated 1,8 and 1,6 addition of bis-trimethylsilylketene acetal to activated p-quinone methides via trifluoromethanesulfonic anhydride Benitez-Puebla, Luis J. Ballinas-Indili, Ricardo Flores-Alamo, Marcos Guevara-Vela, José M. Rocha-Rinza, Tomas Rosales-Amezcua, Saulo Alvarez-Toledano, Cecilio Addition reactions para-quinone methides bis-trimethylsilylacetalketene acetals trifluoromethanesulfonic anhydride Química Física 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 Financial 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 Society https://hdl.handle.net/10486/764580 https://dx.doi.org/10.1021/acs.joc.4c02852 |
| 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 |
| 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 |
| topic |
Addition reactions para-quinone methides bis-trimethylsilylacetalketene acetals trifluoromethanesulfonic anhydride Química Física |
| topic_facet |
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 |
| format |
article |
| url |
https://hdl.handle.net/10486/764580 https://dx.doi.org/10.1021/acs.joc.4c02852 |
| language |
eng |
| eu_rights_str_mv |
openAccess |
| publisher |
American Chemical Society |
| institution |
Universidad Autónoma de Madrid |
| collection |
Biblos-e Archivo. Repositorio Institucional de la UAM |
| reponame_str |
Biblos-e Archivo. Repositorio Institucional de la UAM |
| instname_str |
Universidad Autónoma de Madrid |
| _version_ |
1878440195642097665 |
| publishDateSort |
2025 |
| author_browse |
Alvarez-Toledano, Cecilio Ballinas-Indili, Ricardo Benitez-Puebla, Luis J. Flores-Alamo, Marcos Guevara-Vela, José M. Rocha-Rinza, Tomas Rosales-Amezcua, Saulo |
| publisherStr |
American Chemical Society |
| score |
6,924472 |