First C-H activation route to oxindoles using copper catalysis

Johannes E.M.N. Klein, Alexis Perry, David S. Pugh, Richard J.K. Taylor

Research output: Contribution to journalArticlepeer-review

150 Scopus citations

Abstract

(Equation Presented). The preparation of 3,3-disubstituted oxindoles by a formal C-H, Ar-H coupling of anilides is described. Highly efficient conditions have been identified using catalytic (5 mol %) Cu(OAc)2·H 2O with atmospheric oxygen as the reoxidant; no additional base is required, and the reaction can be run in toluene or mesitylene. Optimization studies are reported together with a scope and limitation investigation based on variation of the anilide precursors. The application of this methodology to prepare a key intermediate for the total synthesis of the anticancer, analgesic oxindole alkaloid Horsfiline is also described.

Original languageEnglish (US)
Pages (from-to)3446-3449
Number of pages4
JournalOrganic Letters
Volume12
Issue number15
DOIs
StatePublished - Aug 6 2010

Fingerprint Dive into the research topics of 'First C-H activation route to oxindoles using copper catalysis'. Together they form a unique fingerprint.

Cite this