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Azaphosphatrane Cations: Weak Acids, Robust Phase-transfer Catalysts

Authors

  • Dr. Pascal Dimitrov-Raytchev,

    1. Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, 46, Allée d'Italie, F-69364 Lyon (France), Fax: (+33) 4-7272-8860
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  • Dr. Jean-Pierre Dutasta,

    Corresponding author
    1. Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, 46, Allée d'Italie, F-69364 Lyon (France), Fax: (+33) 4-7272-8860
    • Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, 46, Allée d'Italie, F-69364 Lyon (France), Fax: (+33) 4-7272-8860
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  • Dr. Alexandre Martinez

    Corresponding author
    1. Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, 46, Allée d'Italie, F-69364 Lyon (France), Fax: (+33) 4-7272-8860
    • Laboratoire de Chimie, École Normale Supérieure de Lyon, CNRS, 46, Allée d'Italie, F-69364 Lyon (France), Fax: (+33) 4-7272-8860
    Search for more papers by this author

Abstract

The use of azaphosphatrane derivatives, which are the acidic counterparts of the well-known proazaphosphatrane superbases (also named Verkade’s superbases), are found to function as phase-transfer catalysts. In four representative protocols of phase-transfer catalytic reactions—two alkylations of enolates, one generation of carbene, and one oxidation of an electrophilic alkene—azaphosphatranes act as catalysts in biphasic heterogeneous media.

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