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DOI: 10.1055/s-0028-1088053
N′-Activation of N-Arylimidazoles: Facile Syntheses of N-Alkyl-N′-arylimidazolium Iodides from Less Expensive Chloro Substrates
Publication History
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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