Orthogonal Pd- and Cu-Based Catalyst Systems for C- and N-Arylation of Oxindoles
Journal of the American Chemical Society2008Vol. 130(29), pp. 9613–9620
Citations Over TimeTop 1% of 2008 papers
Abstract
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.
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