2024-03-29T15:18:46Zhttps://uvadoc.uva.es/oai/requestoai:uvadoc.uva.es:10324/570512022-11-14T20:00:48Zcom_10324_28542com_10324_952com_10324_894col_10324_28543
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
Salamanca Verdugo, Vanesa
Lledós, Agustí
Albéniz Jiménez, Ana Carmen
Palladium
Paladio
Anilines
Anilinas
Arylation
Arilación
Pyridones
Piridonas
2303 Química Inorgánica
Producción Científica
Metal-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)
2022-11-14T14:22:31Z
2022-11-14T14:22:31Z
2022
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
https://doi.org/10.1021/acscatal.2c05206
ACS Catalysis, 2022, vol. 12. p. 14527–14532
2155-5435
https://uvadoc.uva.es/handle/10324/57051
eng
https://pubs.acs.org/doi/10.1021/acscatal.2c05206
Atribución 4.0 Internacional
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
© 2022 American Chemical Society
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American Chemical Society