Unlocking the C-centered ring-opening of phosphiranium ions for a straightforward entry to functionalized phosphines
Year: 2024
Type: article
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. In the arena of strained heterocyclic chemistry, phosphacycles as appealing electrophilic P-containing building blocks are underestimated. Here, the authors report a class of electrophilic phosphiranium salts bearing fluorinated benzyl quaternizing groups for the direct synthesis of diverselyβ-functionalized phosphines.
Source: Nature Communications
Institutions: Centre National de la Recherche Scientifique, Unité de Recherche en Chimie Organique et Macromoléculaire, University of Kentucky, Commissariat à l'Énergie Atomique et aux Énergies Alternatives, CEA Paris-Saclay - Etablissement de Saclay, CEA Cadarache, Université Pierre-et-Marie-Curie, Université de Reims Champagne-Ardenne, Université Toulouse III - Paul Sabatier, Université de Toulouse, Institut de Chimie de Toulouse, Sorbonne Université, Laboratoire de Chimie Théorique, Laboratoire Hétérochimie Fondamentale et Appliquée, Laboratoire COBRA, Institut National des Sciences Appliquées Rouen Normandie
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $6,136
Funder: Agence Nationale de la Recherche
OpenAlex ID: W4403083366