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First C-H activation route to oxindoles using copper catalysis

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

Organic letters, 06 August 2010, Vol.12(15), pp.3446-9 [Peer Reviewed Journal]

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  • Title:
    First C-H activation route to oxindoles using copper catalysis
  • Author: Klein, Johannes E M N ; Perry, Alexis ; Pugh, David S ; Taylor, Richard J K
  • Description: 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(2)O 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.
  • Is Part Of: Organic letters, 06 August 2010, Vol.12(15), pp.3446-9
  • Identifier: E-ISSN: 1523-7052 ; PMID: 20670011 Version:1 ; DOI: 10.1021/ol1012668
  • Subjects: Anilides -- Chemistry ; Copper -- Chemistry ; Indoles -- Chemical Synthesis
  • Language: English

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