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

Julien Gasnot; Clément Botella; Sébastien Comesse; Sami Lakhdar; Carole Alayrac; Annie‐claude Gaumont; Vincent Dalla; Catherine Taillier

doi:10.1002/anie.201916449

Journal articles

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

Abstract : 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

Document type :

Journal articles

Domain :

Chemical Sciences

Chemical Sciences / Organic chemistry

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https://hal-normandie-univ.archives-ouvertes.fr/hal-02899688
Contributor : Carole Witulski-Alayrac <>
Submitted on : Tuesday, December 15, 2020 - 4:02:47 PM
Last modification on : Thursday, December 17, 2020 - 3:34:02 PM
Long-term archiving on: : Tuesday, March 16, 2021 - 7:59:48 PM

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

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

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