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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, France, Email:

A. M. Oertel, V. Ritleng, M. J. Chetcuti, Synthesis, 2009, 1647-1650.

DOI: 10.1055/s-0028-1088053

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A series of N,N′-asymmetrically substituted imidazolium iodides 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 allowed the synthesis of multigram quantities of these salts.

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Key Words

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

ID: J66-Y2009-1540