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Discloses the first palladium catalyst system for the Suzuki-Miyaura coupling of unactivated aryl tosylates. Aryl benzenesulfonates as substrates in the arylation of enolates derived from cyclic and acyclic ketones, β-dicarbonyl compounds and ester.

In the cross-coupling reactions of unprotected oxindoles with aryl halides, Pd- and Cu-based catalyst systems displayed orthogonal chemoselectivity. A Pd-dialkylbiarylphosphine-based catalyst system chemoselectively arylated oxindole at the 3 position, while arylation occurred exclusively at the nitrogen using a Cu-diamine-based catalyst system. Computational examination of the relevant L1Pd(Ar)(oxindolate) and diamine-Cu(oxindolate) species was performed to gain mechanistic insight into the controlling features of the observed chemoselectivity. [ABSTRACT FROM AUTHOR]