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Molecules 2012, 17(12), 13759-13768; doi:10.3390/molecules171213759

Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides

Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC H3A 2K6, Canada
* Author to whom correspondence should be addressed.
Received: 25 October 2012 / Revised: 13 November 2012 / Accepted: 14 November 2012 / Published: 22 November 2012
(This article belongs to the Special Issue Transition Metals Catalysis)
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We describe the palladium-catalyzed multicomponent synthesis of 2-imidazolines. This reaction proceeds via the coupling of imines, acid chlorides and carbon monoxide to form imidazolinium carboxylates, followed by a decarboxylation. Decarboxylation in CHCl3 is found to result in a mixture of imidazolinium and imidazolium salts. However, the addition of benzoic acid suppresses aromatization, and generates the trans-disubstituted imidazolines in good yield. Combining this reaction with subsequent nitrogen deprotection provides an overall synthesis of imidazolines from multiple available building blocks.
Keywords: 2-imidazoline; palladium; catalysis; multicomponent synthesis 2-imidazoline; palladium; catalysis; multicomponent synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Xu, B.; Worrall, K.; Arndtsen, B.A. Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides. Molecules 2012, 17, 13759-13768.

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