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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...

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Autores principales: Bäumler, Christoph, Bauer, Christof, Kempe, Rhett
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
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.
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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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