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Redox-active guanidines in proton-coupled electron-transfer reactions: real alternatives to benzoquinones?

Guanidino-functionalized aromatics (GFAs) are readily available, stable organic redox-active compounds. In this work we apply one particular GFA compound, 1,2,4,5-tetrakis(tetramethylguanidino)benzene, in its oxidized form in a variety of oxidation/oxidative coupling reactions to demonstrate the sco...

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Bibliographic Details
Main Authors: Wild, Ute (Author) , Hübner, Olaf (Author) , Himmel, Hans-Jörg (Author)
Format: Article (Journal)
Language:English
Published: 19 September 2019
In: Chemistry - a European journal
Year: 2019, Volume: 25, Issue: 70, Pages: 15988-15992
ISSN:1521-3765
DOI:10.1002/chem.201903438
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201903438
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201903438
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Author Notes:Ute Wild, Olaf Hübner, and Hans-Jörg Himmel
Description
Summary:Guanidino-functionalized aromatics (GFAs) are readily available, stable organic redox-active compounds. In this work we apply one particular GFA compound, 1,2,4,5-tetrakis(tetramethylguanidino)benzene, in its oxidized form in a variety of oxidation/oxidative coupling reactions to demonstrate the scope of its proton-coupled electron transfer (PCET) reactivity. Addition of an excess of acid boosts its oxidation power, enabling the oxidative coupling of substrates with redox potentials of at least +0.77 V vs. Fc+/Fc. The green recyclability by catalytic re-oxidation with dioxygen is also shown. Finally, a direct comparison indicates that GFAs are real alternatives to toxic halo- or cyano-substituted benzoquinones.
Item Description:Gesehen am 09.09.2020
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201903438

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