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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Language: | English |
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MDPI AG
2012-11-01
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Series: | Molecules |
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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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format | Article |
id | doaj.art-e444d559b05546c9b4b879cd94e5c15e |
institution | Directory Open Access Journal |
issn | 1420-3049 |
language | English |
last_indexed | 2024-12-11T05:37:34Z |
publishDate | 2012-11-01 |
publisher | MDPI AG |
record_format | Article |
series | Molecules |
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 |