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• Worrall, K
• Arndtsen, BA.
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• Worrall, K
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Molecules 2012, 17(12), 13759-13768; doi:10.3390/molecules171213759

Communication

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

Boran Xu, Kraig Worrall and Bruce A. Arndtsen*

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; in revised form: 13 November 2012 / Accepted: 14 November 2012 / Published: 22 November 2012

(This article belongs to the Special Issue Transition Metals Catalysis)

Download PDF Full-Text [289 KB, uploaded 22 November 2012 14:24 CET]

Abstract: 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

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