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Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling
In the presence of simple iron salts, 2‐pyridone derivatives react with Grignard reagents under mild conditions to give the corresponding 1,6‐addition products; if the reaction medium is supplemented with an aprotic dipolar cosolvent after the actual addition step, the intermediates primarily formed...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7687238/ https://www.ncbi.nlm.nih.gov/pubmed/31274217 http://dx.doi.org/10.1002/asia.201900865 |
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author | Huang, Lin Gu, Yiting Fürstner, Alois |
author_facet | Huang, Lin Gu, Yiting Fürstner, Alois |
author_sort | Huang, Lin |
collection | PubMed |
description | In the presence of simple iron salts, 2‐pyridone derivatives react with Grignard reagents under mild conditions to give the corresponding 1,6‐addition products; if the reaction medium is supplemented with an aprotic dipolar cosolvent after the actual addition step, the intermediates primarily formed succumb to ring opening, giving rise to non‐thermodynamic Z,E‐configured dienoic acid amide derivatives which are difficult to make otherwise. Control experiments as well as the isolation and crystallographic characterization of a (tricarbonyl)iron pyridone complex suggest that the active iron catalyst generated in situ exhibits high affinity to the polarized diene system embedded into the heterocyclic ring system of the substrates, which likely serves as the actual recognition element. |
format | Online Article Text |
id | pubmed-7687238 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-76872382020-12-05 Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling Huang, Lin Gu, Yiting Fürstner, Alois Chem Asian J Communications In the presence of simple iron salts, 2‐pyridone derivatives react with Grignard reagents under mild conditions to give the corresponding 1,6‐addition products; if the reaction medium is supplemented with an aprotic dipolar cosolvent after the actual addition step, the intermediates primarily formed succumb to ring opening, giving rise to non‐thermodynamic Z,E‐configured dienoic acid amide derivatives which are difficult to make otherwise. Control experiments as well as the isolation and crystallographic characterization of a (tricarbonyl)iron pyridone complex suggest that the active iron catalyst generated in situ exhibits high affinity to the polarized diene system embedded into the heterocyclic ring system of the substrates, which likely serves as the actual recognition element. John Wiley and Sons Inc. 2019-07-31 2019-11-18 /pmc/articles/PMC7687238/ /pubmed/31274217 http://dx.doi.org/10.1002/asia.201900865 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Huang, Lin Gu, Yiting Fürstner, Alois Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling |
title | Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling |
title_full | Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling |
title_fullStr | Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling |
title_full_unstemmed | Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling |
title_short | Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling |
title_sort | iron‐catalyzed reactions of 2‐pyridone derivatives: 1,6‐addition and formal ring opening/cross coupling |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7687238/ https://www.ncbi.nlm.nih.gov/pubmed/31274217 http://dx.doi.org/10.1002/asia.201900865 |
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