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oai:uvadoc.uva.es:10324/570512025-02-20T07:18:41Zcom_10324_28542com_10324_952com_10324_894col_10324_28543

Pinilla Martín, Cintya Salamanca Verdugo, Vanesa Lledós, Agustí Albéniz Jiménez, Ana Carmen 2022-11-14T14:22:31Z 2022-11-14T14:22:31Z 2022 ACS Catalysis, 2022, vol. 12. p. 14527–14532 2155-5435 https://uvadoc.uva.es/handle/10324/57051 10.1021/acscatal.2c05206 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) application/pdf eng American Chemical Society info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/4.0/ © 2022 American Chemical Society Atribución 4.0 Internacional Palladium Paladio Anilines Anilinas Arylation Arilación Pyridones Piridonas 2303 Química Inorgánica Palladium-catalyzed ortho C–H arylation of unprotected anilines: Chemo- and regioselectivity enabled by the cooperating ligand [2,2′-bipyridin]-6(1H)-one info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion https://pubs.acs.org/doi/10.1021/acscatal.2c05206 SI