RT info:eu-repo/semantics/article
T1 Faster palladium-catalyzed arylation of simple arenes in the presence of a methylketone: beneficial effect of an a priori interfering solvent in C–H activation
A1 Salamanca Verdugo, Vanesa
A1 Albéniz Jiménez, Ana Carmen
K1 Química
K1 C-H activation
K1 Catalysis
K1 palladium
K1 Arene functionalization
K1 reaction mechanisms
K1 2306 Química Orgánica
K1 2303 Química Inorgánica
AB The functionalization of simple arenes without coordinating directing groups is a challenge. Besides facing the task of cleaving the sluggish C-H bond, the process is hampered by the weak coordinating ability of the arene π-system to the metal, which results in reactions that need a large excess of the reactant arene. Using a well-defined palladium complex with the ligand [2, 2’-bipyridin]-6(1H)-one, we have found that the use of a moderately coordinating solvent allows a decrease of the amount of arene used. Moreover, for the least coordinating arenes, the co-solvent produces a significant accelerating effect by altering the concentration and relative stability of relevant metal species in the catalytic cycle as well as the catalyst resting state. t-Butyl methyl ketone (pinacolone) is one of the most effective co-solvents: Even if the ketone C-H bond cleaves easily, the final products are determined by the reductive elimination step (the product-forming step) so the target biaryl products are selectively observed.
YR 2021
FD 2021
LK http://uvadoc.uva.es/handle/10324/46100
UL http://uvadoc.uva.es/handle/10324/46100
LA eng
NO Org. Chem. Front. DOI: 10.1039/D1QO00236H
NO Producción Científica
DS UVaDOC
RD 27-nov-2024