[2,2′-Bipyridin]-6(1H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C–H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine

Producción Científica

Detalles Bibliográficos
Autores: Salamanca Verdugo, Vanesa, Toledo Pérez, Alberto, Albéniz Jiménez, Ana Carmen
Tipo de recurso: artículo
Estado:Versión enviada para evaluación y publicación
Fecha de publicación:2018
País:España
Institución:Universidad de Valladolid
Repositorio:UVaDOC. Repositorio Documental de la Universidad de Valladolid
OAI Identifier:oai:uvadoc.uva.es:10324/37805
Acceso en línea:https://doi.org/10.1021/jacs.8b10680
http://uvadoc.uva.es/handle/10324/37805
Access Level:acceso abierto
Palabra clave:Química
2303 Química Inorgánica
2306 Química Orgánica
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spelling [2,2′-Bipyridin]-6(1H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C–H Activation Step: Experimental Evidence in the Direct C-3 Arylation of PyridineSalamanca Verdugo, VanesaToledo Pérez, AlbertoAlbéniz Jiménez, Ana CarmenQuímica2303 Química Inorgánica2306 Química OrgánicaProducción CientíficaThe ligand [2,2′-bipyridin]-6(1H)-one (bipy-6-OH) has a strong accelerating effect on the Pd- catalyzed direct arylation of pyridine or arenes. The isolation of relevant intermediates and the study of their decomposition unequivocally show that the deprotonated coordinated ligand acts as a base and assists the cleavage of the C−H bond. Mechanistic work indicates that the direct arylation of pyridine with this ligand occurs through a Pd(0)/Pd(II) cycle. Because of this dual ligand− intramolecular base role, there is no need for an available coordination site on the metal for an external base, a difficulty encountered when chelating ligands are used in coupling reactions that involve a C−H cleavage step.MINECO (SGPI, grant CTQ2016-80913-P, BES-2014- 067770 fellowship to A.T.)Junta de Castilla y Leoń (grants VA062G18 and VA051P17)Universidad de Valladolid (fellowship to V.S.).American Chemical Society2018info:eu-repo/semantics/articleinfo:eu-repo/semantics/submittedVersionapplication/pdfhttps://doi.org/10.1021/jacs.8b10680http://uvadoc.uva.es/handle/10324/37805reponame:UVaDOC. Repositorio Documental de la Universidad de Valladolidinstname:Universidad de ValladolidInglésinfo:eu-repo/semantics/openAccessoai:uvadoc.uva.es:10324/378052026-06-13T12:44:47Z
dc.title.none.fl_str_mv [2,2′-Bipyridin]-6(1H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C–H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine
title [2,2′-Bipyridin]-6(1H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C–H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine
spellingShingle [2,2′-Bipyridin]-6(1H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C–H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine
Salamanca Verdugo, Vanesa
Química
2303 Química Inorgánica
2306 Química Orgánica
title_short [2,2′-Bipyridin]-6(1H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C–H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine
title_full [2,2′-Bipyridin]-6(1H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C–H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine
title_fullStr [2,2′-Bipyridin]-6(1H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C–H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine
title_full_unstemmed [2,2′-Bipyridin]-6(1H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C–H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine
title_sort [2,2′-Bipyridin]-6(1H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C–H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine
dc.creator.none.fl_str_mv Salamanca Verdugo, Vanesa
Toledo Pérez, Alberto
Albéniz Jiménez, Ana Carmen
author Salamanca Verdugo, Vanesa
author_facet Salamanca Verdugo, Vanesa
Toledo Pérez, Alberto
Albéniz Jiménez, Ana Carmen
author_role author
author2 Toledo Pérez, Alberto
Albéniz Jiménez, Ana Carmen
author2_role author
author
dc.subject.none.fl_str_mv Química
2303 Química Inorgánica
2306 Química Orgánica
topic Química
2303 Química Inorgánica
2306 Química Orgánica
description Producción Científica
publishDate 2018
dc.date.none.fl_str_mv 2018
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/submittedVersion
format article
status_str submittedVersion
dc.identifier.none.fl_str_mv https://doi.org/10.1021/jacs.8b10680
http://uvadoc.uva.es/handle/10324/37805
url https://doi.org/10.1021/jacs.8b10680
http://uvadoc.uva.es/handle/10324/37805
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
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: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 15.301603

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