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Hydration of nitriles using a metal–ligand cooperative ruthenium pincer catalyst
Nitrile hydration provides access to amides that are important structural elements in organic chemistry. Here we report catalytic nitrile hydration using ruthenium catalysts based on a pincer scaffold with a dearomatized pyridine backbone. These complexes catalyze the nucleophilic addition of H(2)O...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7020783/ https://www.ncbi.nlm.nih.gov/pubmed/32110350 http://dx.doi.org/10.1039/c9sc04624k |
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author | Guo, Beibei de Vries, Johannes G. Otten, Edwin |
author_facet | Guo, Beibei de Vries, Johannes G. Otten, Edwin |
author_sort | Guo, Beibei |
collection | PubMed |
description | Nitrile hydration provides access to amides that are important structural elements in organic chemistry. Here we report catalytic nitrile hydration using ruthenium catalysts based on a pincer scaffold with a dearomatized pyridine backbone. These complexes catalyze the nucleophilic addition of H(2)O to a wide variety of aliphatic and (hetero)aromatic nitriles in (t)BuOH as solvent. Reactions occur under mild conditions (room temperature) in the absence of additives. A mechanism for nitrile hydration is proposed that is initiated by metal–ligand cooperative binding of the nitrile. |
format | Online Article Text |
id | pubmed-7020783 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-70207832020-02-27 Hydration of nitriles using a metal–ligand cooperative ruthenium pincer catalyst Guo, Beibei de Vries, Johannes G. Otten, Edwin Chem Sci Chemistry Nitrile hydration provides access to amides that are important structural elements in organic chemistry. Here we report catalytic nitrile hydration using ruthenium catalysts based on a pincer scaffold with a dearomatized pyridine backbone. These complexes catalyze the nucleophilic addition of H(2)O to a wide variety of aliphatic and (hetero)aromatic nitriles in (t)BuOH as solvent. Reactions occur under mild conditions (room temperature) in the absence of additives. A mechanism for nitrile hydration is proposed that is initiated by metal–ligand cooperative binding of the nitrile. Royal Society of Chemistry 2019-10-07 /pmc/articles/PMC7020783/ /pubmed/32110350 http://dx.doi.org/10.1039/c9sc04624k Text en This journal is © The Royal Society of Chemistry 2019 https://creativecommons.org/licenses/by-nc/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0) |
spellingShingle | Chemistry Guo, Beibei de Vries, Johannes G. Otten, Edwin Hydration of nitriles using a metal–ligand cooperative ruthenium pincer catalyst |
title | Hydration of nitriles using a metal–ligand cooperative ruthenium pincer catalyst
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title_full | Hydration of nitriles using a metal–ligand cooperative ruthenium pincer catalyst
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title_fullStr | Hydration of nitriles using a metal–ligand cooperative ruthenium pincer catalyst
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title_full_unstemmed | Hydration of nitriles using a metal–ligand cooperative ruthenium pincer catalyst
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title_short | Hydration of nitriles using a metal–ligand cooperative ruthenium pincer catalyst
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title_sort | hydration of nitriles using a metal–ligand cooperative ruthenium pincer catalyst |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7020783/ https://www.ncbi.nlm.nih.gov/pubmed/32110350 http://dx.doi.org/10.1039/c9sc04624k |
work_keys_str_mv | AT guobeibei hydrationofnitrilesusingametalligandcooperativerutheniumpincercatalyst AT devriesjohannesg hydrationofnitrilesusingametalligandcooperativerutheniumpincercatalyst AT ottenedwin hydrationofnitrilesusingametalligandcooperativerutheniumpincercatalyst |