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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 CHCl(3) is found to result in a mixture of imida...

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Autores principales: Xu, Boran, Worrall, Kraig, Arndtsen, Bruce A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6269033/
https://www.ncbi.nlm.nih.gov/pubmed/23174894
http://dx.doi.org/10.3390/molecules171213759
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author Xu, Boran
Worrall, Kraig
Arndtsen, Bruce A.
author_facet Xu, Boran
Worrall, Kraig
Arndtsen, Bruce A.
author_sort Xu, Boran
collection PubMed
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 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.
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spelling pubmed-62690332018-12-14 Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides Xu, Boran Worrall, Kraig Arndtsen, Bruce A. Molecules Communication 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. MDPI 2012-11-22 /pmc/articles/PMC6269033/ /pubmed/23174894 http://dx.doi.org/10.3390/molecules171213759 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Communication
Xu, Boran
Worrall, Kraig
Arndtsen, Bruce A.
Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides
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 Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6269033/
https://www.ncbi.nlm.nih.gov/pubmed/23174894
http://dx.doi.org/10.3390/molecules171213759
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