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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.
Molecules 2012, 17(12), 13759-13768;
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)
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. View Full-Text
Keywords: 2-imidazoline; palladium; catalysis; multicomponent synthesis 2-imidazoline; palladium; catalysis; multicomponent synthesis
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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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