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Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Polysilane/SiO(2)‐Supported Palladium Catalyst under Continuous‐Flow Conditions

Hydrogenation of nitriles to primary amines with heterogeneous catalysts under liquid‐phase continuous‐flow conditions is described. Newly developed polysilane/SiO(2)‐supported Pd was found to be an effective catalyst and various nitriles were converted into primary amine salts in almost quantitativ...

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Detalles Bibliográficos
Autores principales: Saito, Yuki, Ishitani, Haruro, Ueno, Masaharu, Kobayashi, Shū
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5390790/
https://www.ncbi.nlm.nih.gov/pubmed/28413753
http://dx.doi.org/10.1002/open.201600166
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author Saito, Yuki
Ishitani, Haruro
Ueno, Masaharu
Kobayashi, Shū
author_facet Saito, Yuki
Ishitani, Haruro
Ueno, Masaharu
Kobayashi, Shū
author_sort Saito, Yuki
collection PubMed
description Hydrogenation of nitriles to primary amines with heterogeneous catalysts under liquid‐phase continuous‐flow conditions is described. Newly developed polysilane/SiO(2)‐supported Pd was found to be an effective catalyst and various nitriles were converted into primary amine salts in almost quantitative yields under mild reaction conditions. Interestingly, a complex mixture was obtained under batch conditions. Lifetime experiments showed that this catalyst remained active for more than 300 h (TON≥10 000) without loss of selectivity and no metal leaching from the catalyst occurred. By using this continuous‐flow hydrogenation, synthesis of venlafaxine, an antidepressant drug, has been accomplished.
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spelling pubmed-53907902017-04-14 Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Polysilane/SiO(2)‐Supported Palladium Catalyst under Continuous‐Flow Conditions Saito, Yuki Ishitani, Haruro Ueno, Masaharu Kobayashi, Shū ChemistryOpen Communications Hydrogenation of nitriles to primary amines with heterogeneous catalysts under liquid‐phase continuous‐flow conditions is described. Newly developed polysilane/SiO(2)‐supported Pd was found to be an effective catalyst and various nitriles were converted into primary amine salts in almost quantitative yields under mild reaction conditions. Interestingly, a complex mixture was obtained under batch conditions. Lifetime experiments showed that this catalyst remained active for more than 300 h (TON≥10 000) without loss of selectivity and no metal leaching from the catalyst occurred. By using this continuous‐flow hydrogenation, synthesis of venlafaxine, an antidepressant drug, has been accomplished. John Wiley and Sons Inc. 2017-01-23 /pmc/articles/PMC5390790/ /pubmed/28413753 http://dx.doi.org/10.1002/open.201600166 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) 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
Saito, Yuki
Ishitani, Haruro
Ueno, Masaharu
Kobayashi, Shū
Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Polysilane/SiO(2)‐Supported Palladium Catalyst under Continuous‐Flow Conditions
title Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Polysilane/SiO(2)‐Supported Palladium Catalyst under Continuous‐Flow Conditions
title_full Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Polysilane/SiO(2)‐Supported Palladium Catalyst under Continuous‐Flow Conditions
title_fullStr Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Polysilane/SiO(2)‐Supported Palladium Catalyst under Continuous‐Flow Conditions
title_full_unstemmed Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Polysilane/SiO(2)‐Supported Palladium Catalyst under Continuous‐Flow Conditions
title_short Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Polysilane/SiO(2)‐Supported Palladium Catalyst under Continuous‐Flow Conditions
title_sort selective hydrogenation of nitriles to primary amines catalyzed by a polysilane/sio(2)‐supported palladium catalyst under continuous‐flow conditions
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5390790/
https://www.ncbi.nlm.nih.gov/pubmed/28413753
http://dx.doi.org/10.1002/open.201600166
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