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oai:uvadoc.uva.es:10324/461002021-06-24T07:44:28Zcom_10324_1186com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1404col_10324_28543

Salamanca Verdugo, Vanesa Albéniz Jiménez, Ana Carmen 2021-04-08T17:32:46Z 2021-04-08T17:32:46Z 2021 Org. Chem. Front. DOI: 10.1039/D1QO00236H http://uvadoc.uva.es/handle/10324/46100 10.1039/D1QO00236H Organic Chemistry Frontiers 2052-4129 Producción Científica 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. MINECO -AEI (grant CTQ2016-80913-P) MICINN-AEI (grant PID2019-111406GB-I00) Junta de Castilla y Leoń (grant VA224P20) application/pdf eng info:eu-repo/semantics/openAccess Química C-H activation Catalysis palladium Arene functionalization reaction mechanisms 2306 Química Orgánica 2303 Química Inorgánica 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 info:eu-repo/semantics/article info:eu-repo/semantics/submittedVersion https://pubs.rsc.org/en/content/articlelanding/2021/qo/d1qo00236h#!divAbstract SI