Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles

first_page settings Open AccessArticle Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles by Nerea Conde , María Teresa Herrero , Garazi Urgoitia and Raul SanMartin * [ORCID] Department of Organic and Inorganic Chemistry, Faculty of Science and...

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Autores: Conde García, Nerea, Herrero Corral, María Teresa, Urgoitia Gabikaetxebarria, Garazi, San Martín Faces, Raúl
Tipo de documento: artigo
Data de publicação:2022
País:España
Recursos:Universidad del País Vasco
Repositório:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/55607
Acesso em linha:http://hdl.handle.net/10810/55607
Access Level:Acceso aberto
Palavra-chave:palladium
domino reactions
alkynes
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spelling Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with DinucleophilesConde García, NereaHerrero Corral, María TeresaUrgoitia Gabikaetxebarria, GaraziSan Martín Faces, Raúlpalladiumdomino reactionsalkynesfirst_page settings Open AccessArticle Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles by Nerea Conde , María Teresa Herrero , Garazi Urgoitia and Raul SanMartin * [ORCID] Department of Organic and Inorganic Chemistry, Faculty of Science and Technology, University of the Basque Country (UPV/EHU), 48940 Leioa, Spain * Author to whom correspondence should be addressed. Academic Editors: Thomas J. J. Müller and Eelco Ruijter Catalysts 2022, 12(2), 127; https://doi.org/10.3390/catal12020127 Received: 18 December 2021 / Revised: 13 January 2022 / Accepted: 17 January 2022 / Published: 21 January 2022 (This article belongs to the Special Issue Metal-Catalyzed Processes in One-Pot Syntheses of Heterocycles) Download PDF Browse Figures Citation Export Abstract Metal-catalyzed cascade processes based on hydrofunctionalization of alkynes are receiving much more attention because of their potential to provide advantageous approaches to otherwise synthetically challenging compounds. An alternative catalyst system has been found for the domino cycloisomerization/cyclocondensation reaction involving acetylenic acids and heterodinucleophiles. A CNN pincer palladium(II) complex, acting as a homogeneous catalyst, provides the corresponding polyheterocycles with a higher substrate/catalyst ratio. Other palladium sources were also tested and discarded, and a number of mechanistic studies including poisoning assays, kinetic plots, TEM images, XRD spectra and UPLC-MS analysis of reaction intermediates were conducted in order to shed light on the role of this pincer catalyst and the catalytic cycle involved in the cascade reaction. As a result, a more nuanced mechanism is tentatively proposed.This research was funded by the Basque Government (IT1405-19) and the Spanish Ministry of Economy and Competitiveness (CTQ2017-86630-P).MDPI2022202220222022info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/55607reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/MINECO/CTQ2017-86630-P/https://www.mdpi.com/2073-4344/12/2/127/htminfo:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/3.0/es/2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).oai:addi.ehu.eus:10810/556072026-06-18T09:23:17Z
dc.title.none.fl_str_mv Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles
title Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles
spellingShingle Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles
Conde García, Nerea
palladium
domino reactions
alkynes
title_short Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles
title_full Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles
title_fullStr Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles
title_full_unstemmed Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles
title_sort Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles
dc.creator.none.fl_str_mv Conde García, Nerea
Herrero Corral, María Teresa
Urgoitia Gabikaetxebarria, Garazi
San Martín Faces, Raúl
author Conde García, Nerea
author_facet Conde García, Nerea
Herrero Corral, María Teresa
Urgoitia Gabikaetxebarria, Garazi
San Martín Faces, Raúl
author_role author
author2 Herrero Corral, María Teresa
Urgoitia Gabikaetxebarria, Garazi
San Martín Faces, Raúl
author2_role author
author
author
dc.subject.none.fl_str_mv palladium
domino reactions
alkynes
topic palladium
domino reactions
alkynes
description first_page settings Open AccessArticle Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles by Nerea Conde , María Teresa Herrero , Garazi Urgoitia and Raul SanMartin * [ORCID] Department of Organic and Inorganic Chemistry, Faculty of Science and Technology, University of the Basque Country (UPV/EHU), 48940 Leioa, Spain * Author to whom correspondence should be addressed. Academic Editors: Thomas J. J. Müller and Eelco Ruijter Catalysts 2022, 12(2), 127; https://doi.org/10.3390/catal12020127 Received: 18 December 2021 / Revised: 13 January 2022 / Accepted: 17 January 2022 / Published: 21 January 2022 (This article belongs to the Special Issue Metal-Catalyzed Processes in One-Pot Syntheses of Heterocycles) Download PDF Browse Figures Citation Export Abstract Metal-catalyzed cascade processes based on hydrofunctionalization of alkynes are receiving much more attention because of their potential to provide advantageous approaches to otherwise synthetically challenging compounds. An alternative catalyst system has been found for the domino cycloisomerization/cyclocondensation reaction involving acetylenic acids and heterodinucleophiles. A CNN pincer palladium(II) complex, acting as a homogeneous catalyst, provides the corresponding polyheterocycles with a higher substrate/catalyst ratio. Other palladium sources were also tested and discarded, and a number of mechanistic studies including poisoning assays, kinetic plots, TEM images, XRD spectra and UPLC-MS analysis of reaction intermediates were conducted in order to shed light on the role of this pincer catalyst and the catalytic cycle involved in the cascade reaction. As a result, a more nuanced mechanism is tentatively proposed.
publishDate 2022
dc.date.none.fl_str_mv 2022
2022
2022
2022
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/55607
url http://hdl.handle.net/10810/55607
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/MINECO/CTQ2017-86630-P/
https://www.mdpi.com/2073-4344/12/2/127/htm
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/3.0/es/
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/3.0/es/
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv reponame:Addi. Archivo Digital para la Docencia y la Investigación
instname:Universidad del País Vasco
instname_str Universidad del País Vasco
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collection Addi. Archivo Digital para la Docencia y la Investigación
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