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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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Detalles Bibliográficos
Autores principales: Tjutrins, Jevgenijs, Arndtsen, Bruce A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
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.
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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
title_full A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide
title_fullStr A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide
title_full_unstemmed A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide
title_short A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide
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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