Taming the Reactivity of Phosphiranium Salts: Site‐Selective C‐Centered Ring Opening for Direct Synthesis of Phosphinoethylamines

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

Advances in the field of phosphorus chemistry are documented, by revealing the synthetic utility of previously underutilized quaternary phosphiranium salts (QPrS) as three-chain-atom electrophilic building blocks. Notably, control of their challenging C-centered electrophilicity is disclosed with an expedient synthesis of tertiary beta-anilino phosphines as a proof-of-concept.

Keywords: nucleophilic ring opening; phosphinoethyl amines; phosphiranium ions; selectivity; steric protection

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry

Julien Gasnot, Clément Botella, Sébastien Comesse, Sami Lakhdar, Carole Alayrac, et al.. Taming the Reactivity of Phosphiranium Salts: Site‐Selective C‐Centered Ring Opening for Direct Synthesis of Phosphinoethylamines. Angewandte Chemie International Edition, 2020, 59 (29), pp.11769-11773. ⟨10.1002/anie.201916449⟩. ⟨hal-02899688⟩