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An efficient protocol for the preparation of pyridinium and imidazolium salts based on the Mitsunobu reaction

Sylvain Petit 1 Rabah Azzouz 2 Corinne Fruit 2 Laurent Bischoff 2 Francis Marsais 3 
1 GDI - Gouvernance et développement insulaire
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
3 IRCOF - Institut de Chimie Organique Fine
Abstract : We report herein that, in the absence of any nucleophilic counterions, tertiary nitrogen nucleophiles such as pyridines and imidazoles can be alkylated with alcohols, by simply using their ammonium form as the acidic component of the Mitsunobu reaction. This led to efficient preparation of ionic liquids under mild conditions, avoiding the usual anion exchange step.
Keywords : Mitsunobu Pyridinium Imidazolium Ionic liquid Alkylation
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02384999
Contributor : Laurent Bischoff Connect in order to contact the contributor
Submitted on : Thursday, November 28, 2019 - 3:58:05 PM
Last modification on : Saturday, June 25, 2022 - 9:54:46 AM

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CNRS | INSA-ROUEN | COMUE-NORMANDIE | INC-CNRS | UPF | 251167 | UNIROUEN | ENSICAEN | UNILEHAVRE | UNICAEN | COBRA | INSA-GROUPE

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Sylvain Petit, Rabah Azzouz, Corinne Fruit, Laurent Bischoff, Francis Marsais. An efficient protocol for the preparation of pyridinium and imidazolium salts based on the Mitsunobu reaction. Tetrahedron Letters, Elsevier, 2008, 49 (22), pp.3663-3665. ⟨10.1016/j.tetlet.2008.03.146⟩. ⟨hal-02384999⟩

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