palladium-catalyzed multicomponent synthesis of 2-imidazolines from imines and acid chlorides钯催化的多组分合成2-imidazolines亚胺和酸性氯化物.pdf

Molecules 2012, 17, 13759-13768; doi:10.3390/molecules171213759 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules 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; E-Mails: boran.xu@mail.mcgill.ca (B.X.); kraig.worrall@ (K.W.) * Author to whom correspondence should be addressed; E-Mail: bruce.arndtsen@mcgill.ca; Tel.: +1-514-398-6903; Fax: +1-514-398-3797. Received: 25 October 2012; in revised form: 13 November 2012 / Accepted: 14 November 2012 / Published: 22 November 2012 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 is found to result in a mixture of imidazolinium and imidazolium salts. However, 3 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 1. Introduction 2-Imidazolines, the 4,5-reduced counterpart of imidazoles, are an important class of small molec