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Synthesis 2009(10): 1647-1650  
DOI: 10.1055/s-0028-1088053
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

N′-Activation of N-Arylimidazoles: Facile Syntheses of N-Alkyl-N′-aryl­imidazolium Iodides from Less Expensive Chloro Substrates

Anna Magdalena Oertel, Vincent Ritleng, Michael J. Chetcuti*
Laboratoire de Chimie Organométallique Appliquée, UMR CNRS 7509, Université de Strasbourg, Ecole Européenne de Chimie, Polymères et Matériaux, 25 rue Becquerel, 67087 Strasbourg, France
Fax: +33(3)90242639; e-Mail: chetcuti@chimie.u-strasbg.fr;
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Publication History

Received 4 December 2008
Publication Date:
20 April 2009 (online)

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Abstract

A series of N,N′-asymmetrically substituted imidazolium iodide salts have been synthesized, starting from N-arylimidazoles and the less expensive, but less reactive, 1-chlorobutane or (3-chloropropyl)trimethoxysilane. The addition of potassium iodide and the use of 1,2-dimethoxyethane as a solvent lead to multigram quantities of these salts becoming readily available, in yields ranging from 50% to 94%. Direct combination of (3-chloropropyl)trimethoxysilane with 1-mesityl-1H-imidazole was also effected, in good yield, by using a microwave oven at 180 ˚C. The synthesis of two 1-alkyl-3-isopropylimidazolium chlorides is also presented herein.

Key words

arylimidazoles - imidazolium salts - trimethoxysilyl - chloroalkyls - N-heterocyclic carbenes

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