Access to Stable Quaternary Phosphiranium Salts by P-Alkylation and P-Arylation of Phosphiranes

Julien Gasnot (1) , Clément Botella (1) , Sébastien Comesse (1) , Sami Lakhdar (2) , Carole Alayrac (2) , Annie-Claude Gaumont (2) , Vincent Dalla (1) , Catherine Taillier (1)

1 URCOM - Unité de Recherche en Chimie Organique et Macromoléculaire
2 LCMT - Laboratoire de chimie moléculaire et thioorganique

We report the preparation of phosphiranium salts by quaternarization of phosphiranes, a class of sensitive, highly strained and poorly nucleophilic cyclic phosphines. High yielding introduction of a varied set of alkyl groups including methylene ester arms was accomplished under mild conditions. A Cu-catalyzed electrophilic arylation of phosphiranes using diaryl iodonium reagents was also achieved to yield unprecedented P,P diaryl phosphiraniums salts with good efficiency.

Keywords: Alkylation; Arylation; Phosphirane; Phosphiranium salt; Alkylating agent; Diaryliodonium salt

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry

Julien Gasnot, Clément Botella, Sébastien Comesse, Sami Lakhdar, Carole Alayrac, et al.. Access to Stable Quaternary Phosphiranium Salts by P-Alkylation and P-Arylation of Phosphiranes. SYNLETT, 2020, 31 (09), pp.883-888. ⟨10.1055/s-0040-1708000⟩. ⟨hal-02899695⟩