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Iron(II)‐Catalyzed Aerobic Biomimetic Oxidation of Amines using a Hybrid Hydroquinone/Cobalt Catalyst as Electron Transfer Mediator
Herein we report the first Fe(II)‐catalyzed aerobic biomimetic oxidation of amines. This oxidation reaction involves several electron transfer steps and is inspired by biological oxidation in the respiratory chain. The electron transfer from the amine to molecular oxygen is aided by two coupled cata...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252094/ https://www.ncbi.nlm.nih.gov/pubmed/33725364 http://dx.doi.org/10.1002/anie.202102681 |
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author | Guðmundsson, Arnar Manna, Srimanta Bäckvall, Jan‐E. |
author_facet | Guðmundsson, Arnar Manna, Srimanta Bäckvall, Jan‐E. |
author_sort | Guðmundsson, Arnar |
collection | PubMed |
description | Herein we report the first Fe(II)‐catalyzed aerobic biomimetic oxidation of amines. This oxidation reaction involves several electron transfer steps and is inspired by biological oxidation in the respiratory chain. The electron transfer from the amine to molecular oxygen is aided by two coupled catalytic redox systems, which lower the energy barrier and improve the selectivity of the oxidation reaction. An iron hydrogen transfer complex was utilized as the substrate‐selective dehydrogenation catalyst along with a bifunctional hydroquinone/cobalt Schiff base complex as a hybrid electron transfer mediator. Various primary and secondary amines were oxidized in air to their corresponding aldimines or ketimines in good to excellent yield. |
format | Online Article Text |
id | pubmed-8252094 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-82520942021-07-07 Iron(II)‐Catalyzed Aerobic Biomimetic Oxidation of Amines using a Hybrid Hydroquinone/Cobalt Catalyst as Electron Transfer Mediator Guðmundsson, Arnar Manna, Srimanta Bäckvall, Jan‐E. Angew Chem Int Ed Engl Communications Herein we report the first Fe(II)‐catalyzed aerobic biomimetic oxidation of amines. This oxidation reaction involves several electron transfer steps and is inspired by biological oxidation in the respiratory chain. The electron transfer from the amine to molecular oxygen is aided by two coupled catalytic redox systems, which lower the energy barrier and improve the selectivity of the oxidation reaction. An iron hydrogen transfer complex was utilized as the substrate‐selective dehydrogenation catalyst along with a bifunctional hydroquinone/cobalt Schiff base complex as a hybrid electron transfer mediator. Various primary and secondary amines were oxidized in air to their corresponding aldimines or ketimines in good to excellent yield. John Wiley and Sons Inc. 2021-05-04 2021-05-17 /pmc/articles/PMC8252094/ /pubmed/33725364 http://dx.doi.org/10.1002/anie.202102681 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://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 Guðmundsson, Arnar Manna, Srimanta Bäckvall, Jan‐E. Iron(II)‐Catalyzed Aerobic Biomimetic Oxidation of Amines using a Hybrid Hydroquinone/Cobalt Catalyst as Electron Transfer Mediator |
title | Iron(II)‐Catalyzed Aerobic Biomimetic Oxidation of Amines using a Hybrid Hydroquinone/Cobalt Catalyst as Electron Transfer Mediator |
title_full | Iron(II)‐Catalyzed Aerobic Biomimetic Oxidation of Amines using a Hybrid Hydroquinone/Cobalt Catalyst as Electron Transfer Mediator |
title_fullStr | Iron(II)‐Catalyzed Aerobic Biomimetic Oxidation of Amines using a Hybrid Hydroquinone/Cobalt Catalyst as Electron Transfer Mediator |
title_full_unstemmed | Iron(II)‐Catalyzed Aerobic Biomimetic Oxidation of Amines using a Hybrid Hydroquinone/Cobalt Catalyst as Electron Transfer Mediator |
title_short | Iron(II)‐Catalyzed Aerobic Biomimetic Oxidation of Amines using a Hybrid Hydroquinone/Cobalt Catalyst as Electron Transfer Mediator |
title_sort | iron(ii)‐catalyzed aerobic biomimetic oxidation of amines using a hybrid hydroquinone/cobalt catalyst as electron transfer mediator |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252094/ https://www.ncbi.nlm.nih.gov/pubmed/33725364 http://dx.doi.org/10.1002/anie.202102681 |
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