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Mild Deoxygenation of Aromatic Ketones and Aldehydes over Pd/C Using Polymethylhydrosiloxane as the Reducing Agent**
Herein, a practical and mild method for the deoxygenation of a wide range of benzylic aldehydes and ketones is described, which utilizes heterogeneous Pd/C as the catalyst together with the green hydride source, polymethylhydrosiloxane. The developed catalytic protocol is scalable and robust, as exe...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
WILEY-VCH Verlag
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4471587/ https://www.ncbi.nlm.nih.gov/pubmed/25728614 http://dx.doi.org/10.1002/anie.201411059 |
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author | Volkov, Alexey Gustafson, Karl P J Tai, Cheuk-Wai Verho, Oscar Bäckvall, Jan-E Adolfsson, Hans |
author_facet | Volkov, Alexey Gustafson, Karl P J Tai, Cheuk-Wai Verho, Oscar Bäckvall, Jan-E Adolfsson, Hans |
author_sort | Volkov, Alexey |
collection | PubMed |
description | Herein, a practical and mild method for the deoxygenation of a wide range of benzylic aldehydes and ketones is described, which utilizes heterogeneous Pd/C as the catalyst together with the green hydride source, polymethylhydrosiloxane. The developed catalytic protocol is scalable and robust, as exemplified by the deoxygenation of ethyl vanillin, which was performed on a 30 mmol scale in an open-to-air setup using only 0.085 mol % Pd/C catalyst to furnish the corresponding deoxygenated product in 93 % yield within 3 hours at room temperature. Furthermore, the Pd/C catalyst was shown to be recyclable up to 6 times without any observable decrease in efficiency and it exhibited low metal leaching under the reaction conditions. |
format | Online Article Text |
id | pubmed-4471587 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | WILEY-VCH Verlag |
record_format | MEDLINE/PubMed |
spelling | pubmed-44715872015-06-23 Mild Deoxygenation of Aromatic Ketones and Aldehydes over Pd/C Using Polymethylhydrosiloxane as the Reducing Agent** Volkov, Alexey Gustafson, Karl P J Tai, Cheuk-Wai Verho, Oscar Bäckvall, Jan-E Adolfsson, Hans Angew Chem Int Ed Engl Communications Herein, a practical and mild method for the deoxygenation of a wide range of benzylic aldehydes and ketones is described, which utilizes heterogeneous Pd/C as the catalyst together with the green hydride source, polymethylhydrosiloxane. The developed catalytic protocol is scalable and robust, as exemplified by the deoxygenation of ethyl vanillin, which was performed on a 30 mmol scale in an open-to-air setup using only 0.085 mol % Pd/C catalyst to furnish the corresponding deoxygenated product in 93 % yield within 3 hours at room temperature. Furthermore, the Pd/C catalyst was shown to be recyclable up to 6 times without any observable decrease in efficiency and it exhibited low metal leaching under the reaction conditions. WILEY-VCH Verlag 2015-04-20 2015-02-26 /pmc/articles/PMC4471587/ /pubmed/25728614 http://dx.doi.org/10.1002/anie.201411059 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. http://creativecommons.org/licenses/by/3.0/ This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. |
spellingShingle | Communications Volkov, Alexey Gustafson, Karl P J Tai, Cheuk-Wai Verho, Oscar Bäckvall, Jan-E Adolfsson, Hans Mild Deoxygenation of Aromatic Ketones and Aldehydes over Pd/C Using Polymethylhydrosiloxane as the Reducing Agent** |
title | Mild Deoxygenation of Aromatic Ketones and Aldehydes over Pd/C Using Polymethylhydrosiloxane as the Reducing Agent** |
title_full | Mild Deoxygenation of Aromatic Ketones and Aldehydes over Pd/C Using Polymethylhydrosiloxane as the Reducing Agent** |
title_fullStr | Mild Deoxygenation of Aromatic Ketones and Aldehydes over Pd/C Using Polymethylhydrosiloxane as the Reducing Agent** |
title_full_unstemmed | Mild Deoxygenation of Aromatic Ketones and Aldehydes over Pd/C Using Polymethylhydrosiloxane as the Reducing Agent** |
title_short | Mild Deoxygenation of Aromatic Ketones and Aldehydes over Pd/C Using Polymethylhydrosiloxane as the Reducing Agent** |
title_sort | mild deoxygenation of aromatic ketones and aldehydes over pd/c using polymethylhydrosiloxane as the reducing agent** |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4471587/ https://www.ncbi.nlm.nih.gov/pubmed/25728614 http://dx.doi.org/10.1002/anie.201411059 |
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