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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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Detalles Bibliográficos
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
Descripción
Sumario: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.