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Platinum-Based Heterogeneous Catalysts for Nitrile Synthesis via Aerobic Oxidative Coupling of Alcohols and Ammonia

[Image: see text] Transition-metal-catalyzed aerobic oxidative coupling of alcohols and ammonia represents an attractive atom-economical synthetic route to prepare nitriles. Heterogeneous platinum catalysts have been widely used for aerobic alcohol oxidation to aldehydes and carboxylic acids but hav...

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Autores principales: Preger, Yuliya, Root, Thatcher W., Stahl, Shannon S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644636/
https://www.ncbi.nlm.nih.gov/pubmed/31458796
http://dx.doi.org/10.1021/acsomega.8b00911
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author Preger, Yuliya
Root, Thatcher W.
Stahl, Shannon S.
author_facet Preger, Yuliya
Root, Thatcher W.
Stahl, Shannon S.
author_sort Preger, Yuliya
collection PubMed
description [Image: see text] Transition-metal-catalyzed aerobic oxidative coupling of alcohols and ammonia represents an attractive atom-economical synthetic route to prepare nitriles. Heterogeneous platinum catalysts have been widely used for aerobic alcohol oxidation to aldehydes and carboxylic acids but have not been applied to nitrile synthesis. In this work, we show that carbon-supported Pt catalysts are effective for this transformation. Unpromoted Pt is competent with benzylic substrates bearing either electron-donating or electron-withdrawing substituents. Use of both K(2)CO(3) and Bi additives accelerates the rate of alcohol oxidation and affords high yields with challenging heterocyclic alcohols.
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spelling pubmed-66446362019-08-27 Platinum-Based Heterogeneous Catalysts for Nitrile Synthesis via Aerobic Oxidative Coupling of Alcohols and Ammonia Preger, Yuliya Root, Thatcher W. Stahl, Shannon S. ACS Omega [Image: see text] Transition-metal-catalyzed aerobic oxidative coupling of alcohols and ammonia represents an attractive atom-economical synthetic route to prepare nitriles. Heterogeneous platinum catalysts have been widely used for aerobic alcohol oxidation to aldehydes and carboxylic acids but have not been applied to nitrile synthesis. In this work, we show that carbon-supported Pt catalysts are effective for this transformation. Unpromoted Pt is competent with benzylic substrates bearing either electron-donating or electron-withdrawing substituents. Use of both K(2)CO(3) and Bi additives accelerates the rate of alcohol oxidation and affords high yields with challenging heterocyclic alcohols. American Chemical Society 2018-06-05 /pmc/articles/PMC6644636/ /pubmed/31458796 http://dx.doi.org/10.1021/acsomega.8b00911 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Preger, Yuliya
Root, Thatcher W.
Stahl, Shannon S.
Platinum-Based Heterogeneous Catalysts for Nitrile Synthesis via Aerobic Oxidative Coupling of Alcohols and Ammonia
title Platinum-Based Heterogeneous Catalysts for Nitrile Synthesis via Aerobic Oxidative Coupling of Alcohols and Ammonia
title_full Platinum-Based Heterogeneous Catalysts for Nitrile Synthesis via Aerobic Oxidative Coupling of Alcohols and Ammonia
title_fullStr Platinum-Based Heterogeneous Catalysts for Nitrile Synthesis via Aerobic Oxidative Coupling of Alcohols and Ammonia
title_full_unstemmed Platinum-Based Heterogeneous Catalysts for Nitrile Synthesis via Aerobic Oxidative Coupling of Alcohols and Ammonia
title_short Platinum-Based Heterogeneous Catalysts for Nitrile Synthesis via Aerobic Oxidative Coupling of Alcohols and Ammonia
title_sort platinum-based heterogeneous catalysts for nitrile synthesis via aerobic oxidative coupling of alcohols and ammonia
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644636/
https://www.ncbi.nlm.nih.gov/pubmed/31458796
http://dx.doi.org/10.1021/acsomega.8b00911
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