Rapid Continuous Ruthenium-Catalysed Transfer Hydrogenation of Aromatic Nitriles to Primary Amines

A continuous flow method for the selective reduction of aromatic nitriles to the corresponding amine is reported. The method is based on a ruthenium-catalysed transfer-hydrogenation process, requires no additives, and uses isopropanol as both solvent and reducing agent. The process utilizes 1 mol% o...

Descripción completa

Detalles Bibliográficos
Autores principales: Labes, Ricardo, González-Calderón, Davir, Battilocchio, Claudio, Mateos, Carlos, Cumming, Graham R., de Frutos, Oscar, Rincón, Juan A., Ley, Steven V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: © Georg Thieme Verlag 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6193226/
http://dx.doi.org/10.1055/s-0036-1589096
_version_ 1783364041112027136
author Labes, Ricardo
González-Calderón, Davir
Battilocchio, Claudio
Mateos, Carlos
Cumming, Graham R.
de Frutos, Oscar
Rincón, Juan A.
Ley, Steven V.
author_facet Labes, Ricardo
González-Calderón, Davir
Battilocchio, Claudio
Mateos, Carlos
Cumming, Graham R.
de Frutos, Oscar
Rincón, Juan A.
Ley, Steven V.
author_sort Labes, Ricardo
collection PubMed
description A continuous flow method for the selective reduction of aromatic nitriles to the corresponding amine is reported. The method is based on a ruthenium-catalysed transfer-hydrogenation process, requires no additives, and uses isopropanol as both solvent and reducing agent. The process utilizes 1 mol% of the commercially available [Ru( p -cymene)Cl (2) ] (2) , with a residence time of ca. 9 min, and a throughput of 50 mmol/h. The method was successfully applied to a range of aromatic nitriles providing the corresponding primary amines in good yields.
format Online
Article
Text
id pubmed-6193226
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher © Georg Thieme Verlag
record_format MEDLINE/PubMed
spelling pubmed-61932262018-10-30 Rapid Continuous Ruthenium-Catalysed Transfer Hydrogenation of Aromatic Nitriles to Primary Amines Labes, Ricardo González-Calderón, Davir Battilocchio, Claudio Mateos, Carlos Cumming, Graham R. de Frutos, Oscar Rincón, Juan A. Ley, Steven V. Synlett A continuous flow method for the selective reduction of aromatic nitriles to the corresponding amine is reported. The method is based on a ruthenium-catalysed transfer-hydrogenation process, requires no additives, and uses isopropanol as both solvent and reducing agent. The process utilizes 1 mol% of the commercially available [Ru( p -cymene)Cl (2) ] (2) , with a residence time of ca. 9 min, and a throughput of 50 mmol/h. The method was successfully applied to a range of aromatic nitriles providing the corresponding primary amines in good yields. © Georg Thieme Verlag 2017-12-18 2017-08-21 /pmc/articles/PMC6193226/ http://dx.doi.org/10.1055/s-0036-1589096 Text en https://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Labes, Ricardo
González-Calderón, Davir
Battilocchio, Claudio
Mateos, Carlos
Cumming, Graham R.
de Frutos, Oscar
Rincón, Juan A.
Ley, Steven V.
Rapid Continuous Ruthenium-Catalysed Transfer Hydrogenation of Aromatic Nitriles to Primary Amines
title Rapid Continuous Ruthenium-Catalysed Transfer Hydrogenation of Aromatic Nitriles to Primary Amines
title_full Rapid Continuous Ruthenium-Catalysed Transfer Hydrogenation of Aromatic Nitriles to Primary Amines
title_fullStr Rapid Continuous Ruthenium-Catalysed Transfer Hydrogenation of Aromatic Nitriles to Primary Amines
title_full_unstemmed Rapid Continuous Ruthenium-Catalysed Transfer Hydrogenation of Aromatic Nitriles to Primary Amines
title_short Rapid Continuous Ruthenium-Catalysed Transfer Hydrogenation of Aromatic Nitriles to Primary Amines
title_sort rapid continuous ruthenium-catalysed transfer hydrogenation of aromatic nitriles to primary amines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6193226/
http://dx.doi.org/10.1055/s-0036-1589096
work_keys_str_mv AT labesricardo rapidcontinuousrutheniumcatalysedtransferhydrogenationofaromaticnitrilestoprimaryamines
AT gonzalezcalderondavir rapidcontinuousrutheniumcatalysedtransferhydrogenationofaromaticnitrilestoprimaryamines
AT battilocchioclaudio rapidcontinuousrutheniumcatalysedtransferhydrogenationofaromaticnitrilestoprimaryamines
AT mateoscarlos rapidcontinuousrutheniumcatalysedtransferhydrogenationofaromaticnitrilestoprimaryamines
AT cumminggrahamr rapidcontinuousrutheniumcatalysedtransferhydrogenationofaromaticnitrilestoprimaryamines
AT defrutososcar rapidcontinuousrutheniumcatalysedtransferhydrogenationofaromaticnitrilestoprimaryamines
AT rinconjuana rapidcontinuousrutheniumcatalysedtransferhydrogenationofaromaticnitrilestoprimaryamines
AT leystevenv rapidcontinuousrutheniumcatalysedtransferhydrogenationofaromaticnitrilestoprimaryamines

Ejemplares similares