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

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 imidazo...

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Main Authors: Boran Xu, Kraig Worrall, Bruce A. Arndtsen
Format: Article
Language:English
Published: MDPI AG 2012-11-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/17/12/13759
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author Boran Xu
Kraig Worrall
Bruce A. Arndtsen
author_facet Boran Xu
Kraig Worrall
Bruce A. Arndtsen
author_sort Boran Xu
collection DOAJ
description 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.
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spelling doaj.art-e444d559b05546c9b4b879cd94e5c15e2022-12-22T01:19:14ZengMDPI AGMolecules1420-30492012-11-011712137591376810.3390/molecules171213759Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid ChloridesBoran XuKraig WorrallBruce A. ArndtsenWe 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.http://www.mdpi.com/1420-3049/17/12/137592-imidazolinepalladiumcatalysismulticomponent synthesis
spellingShingle Boran Xu
Kraig Worrall
Bruce A. Arndtsen
Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides
Molecules
2-imidazoline
palladium
catalysis
multicomponent synthesis
title Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides
title_full Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides
title_fullStr Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides
title_full_unstemmed Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides
title_short Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides
title_sort palladium catalyzed multicomponent synthesis of 2 imidazolines from imines and acid chlorides
topic 2-imidazoline
palladium
catalysis
multicomponent synthesis
url http://www.mdpi.com/1420-3049/17/12/13759
work_keys_str_mv AT boranxu palladiumcatalyzedmulticomponentsynthesisof2imidazolinesfromiminesandacidchlorides
AT kraigworrall palladiumcatalyzedmulticomponentsynthesisof2imidazolinesfromiminesandacidchlorides
AT bruceaarndtsen palladiumcatalyzedmulticomponentsynthesisof2imidazolinesfromiminesandacidchlorides