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Direct Copper-Catalyzed α-Arylation of Benzyl Phenyl Ketones with Aryl Iodides: Route towards Tamoxifen

Authors

  • Dr. Grégory Danoun,

    1. Institut Charles Gerhardt Montpellier, ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5 (France)
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    • These authors contributed equally to this work.

  • Dr. Anis Tlili,

    1. Institut Charles Gerhardt Montpellier, ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5 (France)
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    • These authors contributed equally to this work.

  • Dr. Florian Monnier,

    1. Institut Charles Gerhardt Montpellier, ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5 (France)
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  • Dr. Marc Taillefer

    Corresponding author
    1. Institut Charles Gerhardt Montpellier, ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5 (France)
    • Institut Charles Gerhardt Montpellier, ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5 (France)
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  • The CNRS, ENSCM, and ANR (grant ANR-07-CP2D-08, H2OFERCAT) are thanked for financial support.

Abstract

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No activation needed: The first efficient method for direct α-arylation of non-activated or non-protected family of enolizable ketones with simple aryl iodides employs a catalytic copper system. The method shows potential for the easy and step-economical synthesis of tamoxifen, the most commonly administrated drug for the management of breast cancer. R, R′, R′′ = electron-donating or electron-withdrawing groups.

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