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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...

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Autores principales: Guðmundsson, Arnar, Manna, Srimanta, Bäckvall, Jan‐E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
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.
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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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