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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...

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Autores principales: Volkov, Alexey, Gustafson, Karl P J, Tai, Cheuk-Wai, Verho, Oscar, Bäckvall, Jan-E, Adolfsson, Hans
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2015
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.
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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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