Assessing the cooperating ability of 6‐hydroxypicolinic acid and pyridyl‐amide ligands in palladium‐mediated C−H activation

Producción Científica

Detalles Bibliográficos
Autores: Pinilla Martín, Cintya, Albéniz Jiménez, Ana Carmen
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2024
País:España
Institución:Universidad de Valladolid
Repositorio:UVaDOC. Repositorio Documental de la Universidad de Valladolid
OAI Identifier:oai:uvadoc.uva.es:10324/75092
Acceso en línea:https://doi.org/10.1002/ejic.202400076
https://uvadoc.uva.es/handle/10324/75092
Access Level:acceso abierto
Palabra clave:Química
C–H activation
metal-ligand cooperation
palladium
2303 Química Inorgánica
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spelling Assessing the cooperating ability of 6‐hydroxypicolinic acid and pyridyl‐amide ligands in palladium‐mediated C−H activationPinilla Martín, CintyaAlbéniz Jiménez, Ana CarmenQuímicaC–H activationmetal-ligand cooperationpalladium2303 Química InorgánicaProducción CientíficaThe behavior of 6-hydroxypicolinic acid (pic-6-OH) and pyridyl- amides as cooperating ligands in the C- H activation of arenes has been studied experimentally. When deprotonated, both compounds are chelating ligands and bear either a pyridone moiety or an N-acyl substituent that can assist the C-H cleavage in the same way as the successful bipyridone ligands and MPAAs do. In addition, they are easily available, commercially or via straightforward syntheses. Palladium complexes of formula (NBu4)[Pd(k2-O, N-pic-6-O)(C6F5)py] (2) and [Pd(k2-N, N- py-CH2N(COCF3)(C6F5)py] (6) have been synthesized and their decomposition in the presence of an arene gives the C6F5-arene coupling product, showing that the ligands enable the C-H activation of the arene (arene = pyridine, toluene, ethyl ben- zoate). The amount of C6F5-arene products observed leads to the following trend in cooperating ability: pic-6-OH > pyridyl- amide. DFT calculations on the pyridine activation are consis- tent with the experimental findings. The C-H activation does not occur for the isomeric complex (NBu4)[Pd(k2-O, N-pic-4- O)(C6F5)py] (4) with the pyridone oxygen far from the metal, showing the involvement of this moiety in the C-H cleavage. The performance of these ligands in the direct arylation of arenes has been evaluated.MICIU/AEI Grant PID2022-142100NB-I00Junta de Castilla y León-Feder Fellowship VA087-18EU/MICIN/JCyL Grant C17.I01.P01.S21, H2MetAmoWiley2024info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://doi.org/10.1002/ejic.202400076https://uvadoc.uva.es/handle/10324/75092reponame:UVaDOC. Repositorio Documental de la Universidad de Valladolidinstname:Universidad de ValladolidIngléshttps://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejic.202400076info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-nd/4.0/oai:uvadoc.uva.es:10324/750922026-06-13T12:44:47Z
dc.title.none.fl_str_mv Assessing the cooperating ability of 6‐hydroxypicolinic acid and pyridyl‐amide ligands in palladium‐mediated C−H activation
title Assessing the cooperating ability of 6‐hydroxypicolinic acid and pyridyl‐amide ligands in palladium‐mediated C−H activation
spellingShingle Assessing the cooperating ability of 6‐hydroxypicolinic acid and pyridyl‐amide ligands in palladium‐mediated C−H activation
Pinilla Martín, Cintya
Química
C–H activation
metal-ligand cooperation
palladium
2303 Química Inorgánica
title_short Assessing the cooperating ability of 6‐hydroxypicolinic acid and pyridyl‐amide ligands in palladium‐mediated C−H activation
title_full Assessing the cooperating ability of 6‐hydroxypicolinic acid and pyridyl‐amide ligands in palladium‐mediated C−H activation
title_fullStr Assessing the cooperating ability of 6‐hydroxypicolinic acid and pyridyl‐amide ligands in palladium‐mediated C−H activation
title_full_unstemmed Assessing the cooperating ability of 6‐hydroxypicolinic acid and pyridyl‐amide ligands in palladium‐mediated C−H activation
title_sort Assessing the cooperating ability of 6‐hydroxypicolinic acid and pyridyl‐amide ligands in palladium‐mediated C−H activation
dc.creator.none.fl_str_mv Pinilla Martín, Cintya
Albéniz Jiménez, Ana Carmen
author Pinilla Martín, Cintya
author_facet Pinilla Martín, Cintya
Albéniz Jiménez, Ana Carmen
author_role author
author2 Albéniz Jiménez, Ana Carmen
author2_role author
dc.subject.none.fl_str_mv Química
C–H activation
metal-ligand cooperation
palladium
2303 Química Inorgánica
topic Química
C–H activation
metal-ligand cooperation
palladium
2303 Química Inorgánica
description Producción Científica
publishDate 2024
dc.date.none.fl_str_mv 2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://doi.org/10.1002/ejic.202400076
https://uvadoc.uva.es/handle/10324/75092
url https://doi.org/10.1002/ejic.202400076
https://uvadoc.uva.es/handle/10324/75092
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejic.202400076
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:UVaDOC. Repositorio Documental de la Universidad de Valladolid
instname:Universidad de Valladolid
instname_str Universidad de Valladolid
reponame_str UVaDOC. Repositorio Documental de la Universidad de Valladolid
collection UVaDOC. Repositorio Documental de la Universidad de Valladolid
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.812429

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