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The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst
The reductive amination of ketones and aldehydes by ammonia is a highly attractive method for the synthesis of primary amines. The use of catalysts, especially reusable catalysts, based on earth‐abundant metals is similarly appealing. Here, the iron‐catalyzed synthesis of primary amines through redu...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7317915/ https://www.ncbi.nlm.nih.gov/pubmed/32314866 http://dx.doi.org/10.1002/cssc.202000856 |
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author | Bäumler, Christoph Bauer, Christof Kempe, Rhett |
author_facet | Bäumler, Christoph Bauer, Christof Kempe, Rhett |
author_sort | Bäumler, Christoph |
collection | PubMed |
description | The reductive amination of ketones and aldehydes by ammonia is a highly attractive method for the synthesis of primary amines. The use of catalysts, especially reusable catalysts, based on earth‐abundant metals is similarly appealing. Here, the iron‐catalyzed synthesis of primary amines through reductive amination was realized. A broad scope and a very good tolerance of functional groups were observed. Ketones, including purely aliphatic ones, aryl–alkyl, dialkyl, and heterocyclic, as well as aldehydes could be converted smoothly into their corresponding primary amines. In addition, the amination of pharmaceuticals, bioactive compounds, and natural products was demonstrated. Many functional groups, such as hydroxy, methoxy, dioxol, sulfonyl, and boronate ester substituents, were tolerated. The catalyst is easy to handle, selective, and reusable and ammonia dissolved in water could be employed as the nitrogen source. The key is the use of a specific Fe complex for the catalyst synthesis and an N‐doped SiC material as catalyst support. |
format | Online Article Text |
id | pubmed-7317915 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-73179152020-06-29 The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst Bäumler, Christoph Bauer, Christof Kempe, Rhett ChemSusChem Communications The reductive amination of ketones and aldehydes by ammonia is a highly attractive method for the synthesis of primary amines. The use of catalysts, especially reusable catalysts, based on earth‐abundant metals is similarly appealing. Here, the iron‐catalyzed synthesis of primary amines through reductive amination was realized. A broad scope and a very good tolerance of functional groups were observed. Ketones, including purely aliphatic ones, aryl–alkyl, dialkyl, and heterocyclic, as well as aldehydes could be converted smoothly into their corresponding primary amines. In addition, the amination of pharmaceuticals, bioactive compounds, and natural products was demonstrated. Many functional groups, such as hydroxy, methoxy, dioxol, sulfonyl, and boronate ester substituents, were tolerated. The catalyst is easy to handle, selective, and reusable and ammonia dissolved in water could be employed as the nitrogen source. The key is the use of a specific Fe complex for the catalyst synthesis and an N‐doped SiC material as catalyst support. John Wiley and Sons Inc. 2020-05-26 2020-06-19 /pmc/articles/PMC7317915/ /pubmed/32314866 http://dx.doi.org/10.1002/cssc.202000856 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Bäumler, Christoph Bauer, Christof Kempe, Rhett The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst |
title | The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst |
title_full | The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst |
title_fullStr | The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst |
title_full_unstemmed | The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst |
title_short | The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst |
title_sort | synthesis of primary amines through reductive amination employing an iron catalyst |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7317915/ https://www.ncbi.nlm.nih.gov/pubmed/32314866 http://dx.doi.org/10.1002/cssc.202000856 |
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