Next Article in Journal
Red Ginseng Marc Oil Inhibits iNOS and COX-2 via NFκB and p38 Pathways in LPS-Stimulated RAW 264.7 Macrophages
Next Article in Special Issue
New Advances in Titanium-Mediated Free Radical Reactions
Previous Article in Journal
Generation of the First Structure-Based Pharmacophore Model Containing a Selective “Zinc Binding Group” Feature to Identify Potential Glyoxalase-1 Inhibitors
Previous Article in Special Issue
Azide-Alkyne Huisgen [3+2] Cycloaddition Using CuO Nanoparticles
Article Menu

Article Versions

Export Article

Open AccessCommunication
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)
Download PDF [289 KB, uploaded 18 June 2014]

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 2-imidazoline; palladium; catalysis; multicomponent synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top