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A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide
We describe here a tandem catalytic route to prepare imidazoles in a single operation from aryl iodides, imines and CO. The reaction involves a catalytic carbonylation of aryl halides with imines to form 1,3-dipoles, which undergo spontaneous 1,3-dipolar cycloaddition. Overall, this offers an altern...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Royal Society of Chemistry
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5354067/ https://www.ncbi.nlm.nih.gov/pubmed/28451237 http://dx.doi.org/10.1039/c6sc04371b |
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author | Tjutrins, Jevgenijs Arndtsen, Bruce A. |
author_facet | Tjutrins, Jevgenijs Arndtsen, Bruce A. |
author_sort | Tjutrins, Jevgenijs |
collection | PubMed |
description | We describe here a tandem catalytic route to prepare imidazoles in a single operation from aryl iodides, imines and CO. The reaction involves a catalytic carbonylation of aryl halides with imines to form 1,3-dipoles, which undergo spontaneous 1,3-dipolar cycloaddition. Overall, this offers an alternative to coupling reactions to construct the (hetero)aryl-imidazole motif, where variation of the building blocks can allow the synthesis of broad families of imidazoles with independent control of all substituents. |
format | Online Article Text |
id | pubmed-5354067 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-53540672017-04-27 A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide Tjutrins, Jevgenijs Arndtsen, Bruce A. Chem Sci Chemistry We describe here a tandem catalytic route to prepare imidazoles in a single operation from aryl iodides, imines and CO. The reaction involves a catalytic carbonylation of aryl halides with imines to form 1,3-dipoles, which undergo spontaneous 1,3-dipolar cycloaddition. Overall, this offers an alternative to coupling reactions to construct the (hetero)aryl-imidazole motif, where variation of the building blocks can allow the synthesis of broad families of imidazoles with independent control of all substituents. Royal Society of Chemistry 2017-02-01 2016-11-03 /pmc/articles/PMC5354067/ /pubmed/28451237 http://dx.doi.org/10.1039/c6sc04371b Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Chemistry Tjutrins, Jevgenijs Arndtsen, Bruce A. A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide |
title | A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide
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title_full | A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide
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title_fullStr | A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide
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title_full_unstemmed | A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide
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title_short | A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide
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title_sort | palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5354067/ https://www.ncbi.nlm.nih.gov/pubmed/28451237 http://dx.doi.org/10.1039/c6sc04371b |
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