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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
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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

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LCMT | URCOM | INSA-GROUPE | UNILEHAVRE | INSA-ROUEN | UNIROUEN | COMUE-NORMANDIE | UNICAEN | ENSICAEN | CNRS

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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, Wiley-VCH Verlag, 2020, 59 (29), pp.11769-11773. ⟨10.1002/anie.201916449⟩. ⟨hal-02899688⟩

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