Synthesis of Substituted Oxindoles from α-Chloroacetanilides via Palladium-Catalyzed C−H Functionalization

Edward J. Hennessy and Stephen L. Buchwald*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
J. Am. Chem. Soc., 2003, 125 (40), pp 12084–12085
DOI: 10.1021/ja037546g
Publication Date (Web): September 13, 2003
Copyright © 2003 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sbuchwal@mit.edu

Abstract

Abstract Image

A novel method for the synthesis of oxindoles is described. In the presence of catalytic palladium acetate and 2-(di-tert-butylphosphino)biphenyl, α-chloroacetanilides are converted to oxindoles in good to excellent yields with high functional group compatibility using triethylamine as a stoichiometric base. The cyclization is highly regioselective, obviating the need for prefunctionalized arenes. Plausible mechanistic pathways for the reaction are discussed.

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History

  • Published In Issue October 08, 2003
  • Received July 25, 2003

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