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

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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 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. 2022-11-14 2022-11-14 2022 info:eu-repo/semantics/article ACS Catalysis, 2022, vol. 12. p. 14527–14532 2155-5435 https://uvadoc.uva.es/handle/10324/57051 10.1021/acscatal.2c05206 eng https://pubs.acs.org/doi/10.1021/acscatal.2c05206 info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/4.0/ © 2022 American Chemical Society Atribución 4.0 Internacional American Chemical Society