1042159-64-7Relevant articles and documents
Orthogonal Pd- and Cu-based catalyst systems for C- and N-arylation of oxindoles
Altman, Ryan A.,Hyde, Alan M.,Huang, Xiaohua,Buchwald, Stephen L.
supporting information; scheme or table, p. 9613 - 9620 (2009/02/02)
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.