RT info:eu-repo/semantics/article
T1 Palladium-catalyzed ortho C–H arylation of unprotected anilines: Chemo- and regioselectivity enabled by the cooperating ligand [2,2′-bipyridin]-6(1H)-one
A1 Pinilla Martín, Cintya
A1 Salamanca Verdugo, Vanesa
A1 Lledós, Agustí
A1 Albéniz Jiménez, Ana Carmen
K1 Palladium
K1 Paladio
K1 Anilines
K1 Anilinas
K1 Arylation
K1 Arilación
K1 Pyridones
K1 Piridonas
K1 2303 Química Inorgánica
AB 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.
PB American Chemical Society
SN 2155-5435
YR 2022
FD 2022
LK https://uvadoc.uva.es/handle/10324/57051
UL https://uvadoc.uva.es/handle/10324/57051
LA eng
NO ACS Catalysis, 2022, vol. 12. p. 14527–14532
NO Producción Científica
DS UVaDOC
RD 12-nov-2024