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

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.

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Publication Details

Journal
Nature Communications
Published
2024-10-03
DOI
https://doi.org/10.1038/s41467-024-53003-z
Citations
1
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.25

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article

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

Marie‐José Tranchant, Isabelle Chataigner, Catherine Taillier, Nathalie Saffon‐Merceron et al.
1 citations
Nature Communications
Sulfur-Based Synthesis Techniques
0.25
article

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

Marie‐José Tranchant, Isabelle Chataigner, Catherine Taillier, Nathalie Saffon‐Merceron, Vincent Dalla, Sébastien Comesse, Julien Pilmé, Sami Lakhdar, Mohammad Ahmad
article en
1 citations

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.

Nature CommunicationsVol. 15(1)
Centre National de la Recherche Scientifique (FR), Université Toulouse III - Paul Sabatier (FR), Université Le Havre Normandie (FR), University of Kentucky (US), Commissariat à l'Énergie Atomique et aux Énergies Alternatives (FR), CEA Grenoble (FR), Sorbonne Université (FR), Laboratoire de Chimie Théorique (FR), Normandie Université (FR), CEA Cadarache (FR), Laboratoire Hétérochimie Fondamentale et Appliquée (FR), Laboratoire de Chimie Organique (FR), Laboratoire COBRA (FR), Unité de Recherche en Chimie Organique et Macromoléculaire (FR), Université de Rouen Normandie (FR), Institut National des Sciences Appliquées Rouen Normandie (FR), Université de Reims Champagne-Ardenne (FR)
Agence Nationale de la Recherche
Openalex Percentile: Top 48%
Sulfur-Based Synthesis Techniques
0.25
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