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Palladium-Catalyzed Direct Benzylation of Xanthines

Authors

  • Sophian Sahnoun,

    1. Université Paris-Sud, CNRS, BioCIS-UMR 8076 Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, 92296 (France), Fax: (+33) 146-83-58-28
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  • Dr. Samir Messaoudi,

    Corresponding author
    1. Université Paris-Sud, CNRS, BioCIS-UMR 8076 Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, 92296 (France), Fax: (+33) 146-83-58-28
    • Université Paris-Sud, CNRS, BioCIS-UMR 8076 Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, 92296 (France), Fax: (+33) 146-83-58-28
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  • Prof. Jean-Daniel Brion,

    1. Université Paris-Sud, CNRS, BioCIS-UMR 8076 Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, 92296 (France), Fax: (+33) 146-83-58-28
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  • Dr. Mouâd Alami

    Corresponding author
    1. Université Paris-Sud, CNRS, BioCIS-UMR 8076 Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, 92296 (France), Fax: (+33) 146-83-58-28
    • Université Paris-Sud, CNRS, BioCIS-UMR 8076 Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, 92296 (France), Fax: (+33) 146-83-58-28
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Abstract

An efficient and versatile synthetic palladium-catalyzed sp2 C[BOND]H bond activation approach for the preparation of a series of C8-benzyl xanthines has been developed using benzyl chlorides as coupling partners. The reactions take place rapidly in 1,4-dioxane and proceed in the presence of [PdCl2(MeCN)2]/P(o-tolyl)3 as a catalyst system and Cs2CO3 as a base to afford good to excellent yields of the corresponding C8-benzylated xanthines of biological interest.

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