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A novel palladium-mediated coupling approach to 2,3- disubstituted benzo[b]thiophenes and its application to the synthesis of tubulin binding agents

  1. Author:
    Flynn, B. L.
    Verdier-Pinard, P.
    Hamel, E.

  2. Author Address

    Australian Natl Univ, The Fac, Dept Chem, Canberra, ACT 0200, Australia. Australian Natl Univ, The Fac, Dept Chem, Canberra, ACT 0200, Australia. NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Dev Therapeut Program, Screening Technol Branch, Frederick, MD 21702 USA. Flynn BL Australian Natl Univ, The Fac, Dept Chem, Canberra, ACT 0200, Australia.
    1. Year: 2001
  2. Journal: Organic Letters
    1. 3
    2. 5
    3. Pages: 651-654
  4. Type of Article: Article
  1. Abstract:

    [GRAPHICS] Flexible, convergent access to 2,3-disubstituted benzo[b]thiophenes has been developed. The most concise approach involves sequential coupling of o-bromoiodobenzenes with benzylmercaptan and zinc acetylides to give benzyl o- ethynylphenyl sulfides which react with iodine to give 3- iodobenzo[b]thiophenes in a 5-endo-dig iodocyclization. These iodides can be further elaborated using palladium-mediated coupling and/or metalation techniques. This method has been applied to the synthesis of some novel tubulin binding agents.

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