Orthogonal Pd-and Cu-based catalyst systems for C-and N-arylation of oxindoles

…, AM Hyde, X Huang, SL Buchwald

Index: Altman, Ryan A.; Hyde, Alan M.; Huang, Xiaohua; Buchwald, Stephen L. Journal of the American Chemical Society, 2008 , vol. 130, # 29 p. 9613 - 9620

Full Text: HTML

Citation Number: 117

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 ( ...