Use of tunable ligands allows for intermolecular Pd-catalyzed C-O bond formation

Authors

Ryan A. Altman, Massachusetts Institute of Technology
Alan M. Hyde, Massachusetts Institute of Technology
Xiaohua Huang, Massachusetts Institute of Technology
Stephen L. Buchwald, Massachusetts Institute of Technology

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