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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| Hauptverfasser: | , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
19 September 2019
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| In: |
Chemistry - a European journal
Year: 2019, Jahrgang: 25, Heft: 70, Pages: 15988-15992 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201903438 |
| Online-Zugang: | 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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| Verfasserangaben: | Ute Wild, Olaf Hübner, and Hans-Jörg Himmel |
| Zusammenfassung: | 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. |
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| Beschreibung: | Gesehen am 09.09.2020 |
| Beschreibung: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201903438 |