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

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

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry; Chemical Sciences; Medicinal Chemistry; Chemical Sciences; Radiochemistry; Chemical Sciences; Material chemistry; Chemical Sciences; Inorganic chemistry; Chemical Sciences; Catalysis

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, 2008, 49 (22), pp.3663-3665. ⟨10.1016/j.tetlet.2008.03.146⟩. ⟨hal-02384999⟩