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Facile synthesis of supported Ru–Triphos catalysts for continuous flow application in selective nitrile reduction

The selective catalytic hydrogenation of nitriles represents an important but challenging transformation for many homogeneous and heterogeneous catalysts. Herein, we report the efficient and modular solid-phase synthesis of immobilized Triphos-type ligands in very high yields, involving only minimal...

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Autores principales: Konrath, Robert, Heutz, Frank J. L., Steinfeldt, Norbert, Rockstroh, Nils, Kamer, Paul C. J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6837175/
https://www.ncbi.nlm.nih.gov/pubmed/31857885
http://dx.doi.org/10.1039/c9sc01415b
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author Konrath, Robert
Heutz, Frank J. L.
Steinfeldt, Norbert
Rockstroh, Nils
Kamer, Paul C. J.
author_facet Konrath, Robert
Heutz, Frank J. L.
Steinfeldt, Norbert
Rockstroh, Nils
Kamer, Paul C. J.
author_sort Konrath, Robert
collection PubMed
description The selective catalytic hydrogenation of nitriles represents an important but challenging transformation for many homogeneous and heterogeneous catalysts. Herein, we report the efficient and modular solid-phase synthesis of immobilized Triphos-type ligands in very high yields, involving only minimal work-up procedures. The corresponding supported ruthenium–Triphos catalysts are tested in the hydrogenation of various nitriles. Under mild conditions and without the requirement of additives, the tunable supported catalyst library provides selective access to both primary amines and secondary imines. Moreover, the first application of a Triphos-type catalyst in a continuous flow process is presented demonstrating high catalyst life-time over at least 195 hours without significant activity loss.
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spelling pubmed-68371752019-12-19 Facile synthesis of supported Ru–Triphos catalysts for continuous flow application in selective nitrile reduction Konrath, Robert Heutz, Frank J. L. Steinfeldt, Norbert Rockstroh, Nils Kamer, Paul C. J. Chem Sci Chemistry The selective catalytic hydrogenation of nitriles represents an important but challenging transformation for many homogeneous and heterogeneous catalysts. Herein, we report the efficient and modular solid-phase synthesis of immobilized Triphos-type ligands in very high yields, involving only minimal work-up procedures. The corresponding supported ruthenium–Triphos catalysts are tested in the hydrogenation of various nitriles. Under mild conditions and without the requirement of additives, the tunable supported catalyst library provides selective access to both primary amines and secondary imines. Moreover, the first application of a Triphos-type catalyst in a continuous flow process is presented demonstrating high catalyst life-time over at least 195 hours without significant activity loss. Royal Society of Chemistry 2019-07-23 /pmc/articles/PMC6837175/ /pubmed/31857885 http://dx.doi.org/10.1039/c9sc01415b Text en This journal is © The Royal Society of Chemistry 2019 http://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
Konrath, Robert
Heutz, Frank J. L.
Steinfeldt, Norbert
Rockstroh, Nils
Kamer, Paul C. J.
Facile synthesis of supported Ru–Triphos catalysts for continuous flow application in selective nitrile reduction
title Facile synthesis of supported Ru–Triphos catalysts for continuous flow application in selective nitrile reduction
title_full Facile synthesis of supported Ru–Triphos catalysts for continuous flow application in selective nitrile reduction
title_fullStr Facile synthesis of supported Ru–Triphos catalysts for continuous flow application in selective nitrile reduction
title_full_unstemmed Facile synthesis of supported Ru–Triphos catalysts for continuous flow application in selective nitrile reduction
title_short Facile synthesis of supported Ru–Triphos catalysts for continuous flow application in selective nitrile reduction
title_sort facile synthesis of supported ru–triphos catalysts for continuous flow application in selective nitrile reduction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6837175/
https://www.ncbi.nlm.nih.gov/pubmed/31857885
http://dx.doi.org/10.1039/c9sc01415b
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