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Molecules 2012, 17(12), 13759-13768;

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)
PDF [289 KB, uploaded 18 June 2014]


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 3.0).

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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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