Use of tunable ligands allows for intermolecular Pd-catalyzed C-O bond formation
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. © 2008 American Chemical Society.
Publication Title
Journal of the American Chemical Society
Recommended Citation
Altman, R., Hyde, A., Huang, X., & Buchwald, S. (2005). Use of tunable ligands allows for intermolecular Pd-catalyzed C-O bond formation. Journal of the American Chemical Society, 127 (22), 8146-8149. https://doi.org/10.1021/ja050471r
