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Oxidation of organic molecules with a redox-Active guanidine catalyst

Herein, we report the first examples of the use of redox-active guanidines as catalysts in the green oxidation of organic molecules with dioxygen. In one half-reaction, the oxidized form of the redox-active guanidine is converted into the reduced, protonated state, thereby enabling dehydrogenative o...

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Hauptverfasser: Wild, Ute (VerfasserIn) , Schön, Florian (VerfasserIn) , Himmel, Hans-Jörg (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 18 October 2017
In: Angewandte Chemie. International edition
Year: 2017, Jahrgang: 56, Heft: 51, Pages: 16410-16413
ISSN:1521-3773
DOI:10.1002/anie.201709809
Online-Zugang:Verlag, Volltext: http://dx.doi.org/10.1002/anie.201709809
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201709809
Volltext
Verfasserangaben:Ute Wild, Florian Schön, Hans-Jörg Himmel

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520 |a Herein, we report the first examples of the use of redox-active guanidines as catalysts in the green oxidation of organic molecules with dioxygen. In one half-reaction, the oxidized form of the redox-active guanidine is converted into the reduced, protonated state, thereby enabling dehydrogenative oxidation of the substrate (3,5-di-tert-butylcatechol→ortho-benzoquinone, benzoin→benzil, and 2,4-di-tert-butylphenol→biphenol). In the other half-reaction, efficient re-oxidation of the guanidine to the oxidized state is achieved with dioxygen in the presence of a copper catalyst. These results pave the way for the broader use of redox-active guanidines as oxidation catalysts. 
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