Palladium-catalyzed ortho C–H arylation of unprotected anilines: Chemo- and regioselectivity enabled by the cooperating ligand [2,2′-bipyridin]-6(1H)-one

Producción Científica

Bibliographic Details
Authors: Pinilla Martín, Cintya, Salamanca Verdugo, Vanesa, Lledós, Agustí, Albéniz Jiménez, Ana Carmen
Format: article
Status:Published version
Publication Date:2022
Country:España
Institution:Universidad de Valladolid
Repository:UVaDOC. Repositorio Documental de la Universidad de Valladolid
OAI Identifier:oai:uvadoc.uva.es:10324/57051
Online Access:https://doi.org/10.1021/acscatal.2c05206
https://uvadoc.uva.es/handle/10324/57051
Access Level:Open access
Keyword:Palladium
Paladio
Anilines
Anilinas
Arylation
Arilación
Pyridones
Piridonas
2303 Química Inorgánica
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oai_identifier_str oai:uvadoc.uva.es:10324/57051
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spelling Palladium-catalyzed ortho C–H arylation of unprotected anilines: Chemo- and regioselectivity enabled by the cooperating ligand [2,2′-bipyridin]-6(1H)-onePinilla Martín, CintyaSalamanca Verdugo, VanesaLledós, AgustíAlbéniz Jiménez, Ana CarmenPalladiumPaladioAnilinesAnilinasArylationArilaciónPyridonesPiridonas2303 Química InorgánicaProducción CientíficaMetal-catalyzed C–H functionalizations on the aryl ring of anilines usually need cumbersome N-protection–deprotection strategies to ensure chemoselectivity. We describe here the Pd-catalyzed direct C–H arylation of unprotected anilines with no competition of the N-arylation product. The ligand [2,2′-bipyridin]-6(1H)-one drives the chemoselectivity by kinetic differentiation in the product-forming step, while playing a cooperating role in the C–H cleavage step. The latter is favored in an anionic intermediate where the NH moiety is deprotonated, driving the regioselectivity of the reaction toward ortho substitution.Ministerio de Ciencia, Innovación y Universidades (projects PID2019-111406GB-I00 and PID-2020-116861GB-I00)Junta de Castilla y Leon - Fondo Europeo de Desarrollo Regional (projects VA224P20 and VA087-18)American Chemical Society2022info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://doi.org/10.1021/acscatal.2c05206https://uvadoc.uva.es/handle/10324/57051reponame:UVaDOC. Repositorio Documental de la Universidad de Valladolidinstname:Universidad de ValladolidIngléshttps://pubs.acs.org/doi/10.1021/acscatal.2c05206info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/oai:uvadoc.uva.es:10324/570512026-06-13T12:44:47Z
dc.title.none.fl_str_mv Palladium-catalyzed ortho C–H arylation of unprotected anilines: Chemo- and regioselectivity enabled by the cooperating ligand [2,2′-bipyridin]-6(1H)-one
title Palladium-catalyzed ortho C–H arylation of unprotected anilines: Chemo- and regioselectivity enabled by the cooperating ligand [2,2′-bipyridin]-6(1H)-one
spellingShingle Palladium-catalyzed ortho C–H arylation of unprotected anilines: Chemo- and regioselectivity enabled by the cooperating ligand [2,2′-bipyridin]-6(1H)-one
Pinilla Martín, Cintya
Palladium
Paladio
Anilines
Anilinas
Arylation
Arilación
Pyridones
Piridonas
2303 Química Inorgánica
title_short Palladium-catalyzed ortho C–H arylation of unprotected anilines: Chemo- and regioselectivity enabled by the cooperating ligand [2,2′-bipyridin]-6(1H)-one
title_full Palladium-catalyzed ortho C–H arylation of unprotected anilines: Chemo- and regioselectivity enabled by the cooperating ligand [2,2′-bipyridin]-6(1H)-one
title_fullStr Palladium-catalyzed ortho C–H arylation of unprotected anilines: Chemo- and regioselectivity enabled by the cooperating ligand [2,2′-bipyridin]-6(1H)-one
title_full_unstemmed Palladium-catalyzed ortho C–H arylation of unprotected anilines: Chemo- and regioselectivity enabled by the cooperating ligand [2,2′-bipyridin]-6(1H)-one
title_sort Palladium-catalyzed ortho C–H arylation of unprotected anilines: Chemo- and regioselectivity enabled by the cooperating ligand [2,2′-bipyridin]-6(1H)-one
dc.creator.none.fl_str_mv Pinilla Martín, Cintya
Salamanca Verdugo, Vanesa
Lledós, Agustí
Albéniz Jiménez, Ana Carmen
author Pinilla Martín, Cintya
author_facet Pinilla Martín, Cintya
Salamanca Verdugo, Vanesa
Lledós, Agustí
Albéniz Jiménez, Ana Carmen
author_role author
author2 Salamanca Verdugo, Vanesa
Lledós, Agustí
Albéniz Jiménez, Ana Carmen
author2_role author
author
author
dc.subject.none.fl_str_mv Palladium
Paladio
Anilines
Anilinas
Arylation
Arilación
Pyridones
Piridonas
2303 Química Inorgánica
topic Palladium
Paladio
Anilines
Anilinas
Arylation
Arilación
Pyridones
Piridonas
2303 Química Inorgánica
description Producción Científica
publishDate 2022
dc.date.none.fl_str_mv 2022
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/10.1021/acscatal.2c05206
https://uvadoc.uva.es/handle/10324/57051
url https://doi.org/10.1021/acscatal.2c05206
https://uvadoc.uva.es/handle/10324/57051
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://pubs.acs.org/doi/10.1021/acscatal.2c05206
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
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 15,300724

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