title: Palladium-catalyzed multicomponent synthesis of 2-imidazolines from imines and acid chlorides.
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 CHCl(3) 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.
authors.affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC H3A 2K6, Canada. boran.xu@mail.mcgill.ca
authors.forename: Boran
authors.initials: B
authors.lastname: Xu
authors.forename: Kraig
authors.initials: K
authors.lastname: Worrall
authors.forename: Bruce A
authors.initials: BA
authors.lastname: Arndtsen
mesh_terms: D002248:Carbon Monoxide; D002264:Carboxylic Acids; D002384:Catalysis; D002712:Chlorides / Q000138:chemical synthesis / Q000737:chemistry; D003653:Decarboxylation; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D002712:Chlorides; D007093:Imidazoles; D007097:Imines; D010165:Palladium; D002248:Carbon Monoxide; C017424:2-imidazoline