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Unlocking the C-centered ring-opening of phosphiranium ions for a straightforward entry to functionalized phosphines

Author

Listed:
  • Mohammad Ahmad

    (URCOM)

  • Marie-José Tranchant

    (URCOM)

  • Sébastien Comesse

    (URCOM)

  • Nathalie Saffon-Merceron

    (Université de Toulouse III Paul Sabatier)

  • Julien Pilmé

    (LCT UMR7616)

  • Sami Lakhdar

    (UMR5069))

  • Isabelle Chataigner

    (LCT UMR7616
    COBRA)

  • Vincent Dalla

    (URCOM)

  • Catherine Taillier

    (URCOM)

Abstract

Phosphorus chemistry occupies a pivotal position in contemporary organic chemistry but significant synthetic challenges still endure. In this report, a class of electrophilic phosphiranium salts, bearing fluorinated benzyl quaternizing groups, is introduced for the direct synthesis of diversely β-functionalized phosphines. We show that, in comparison with regular quaternary phosphiranium salts, these species display the sought balance of excellent stability and high electrophilic reactivity that allow the unlocking of the C-centered ring-opening reactions with different classes of weak nitrogen-, sulfur- and oxygen protic nucleophiles.

Suggested Citation

  • Mohammad Ahmad & Marie-José Tranchant & Sébastien Comesse & Nathalie Saffon-Merceron & Julien Pilmé & Sami Lakhdar & Isabelle Chataigner & Vincent Dalla & Catherine Taillier, 2024. "Unlocking the C-centered ring-opening of phosphiranium ions for a straightforward entry to functionalized phosphines," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-53003-z
    DOI: 10.1038/s41467-024-53003-z
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