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

Mohammad Ahmad, Marie-José Tranchant, Sébastien Comesse, Nathalie Saffon-Merceron, Julien Pilmé, Sami Lakhdar, Isabelle Chataigner, Vincent Dalla () and Catherine Taillier ()
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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
Vincent Dalla: URCOM
Catherine Taillier: URCOM

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: 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.

Date: 2024
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DOI: 10.1038/s41467-024-53003-z

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