Redox-active guanidines in proton-coupled electron-transfer reactions

• Verfasst von: Wild, Ute [VerfasserIn]
• Verfasst von: Hübner, Olaf [VerfasserIn]
• Verfasst von: Himmel, Hans-Jörg [VerfasserIn]
• Titel: Redox-active guanidines in proton-coupled electron-transfer reactions
• Titelzusatz: real alternatives to benzoquinones?
• Verf.angabe: Ute Wild, Olaf Hübner, and Hans-Jörg Himmel
• E-Jahr: 2019
• Jahr: 19 September 2019
• Umfang: 5 S.
• Fussnoten: Gesehen am 09.09.2020
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2019
• Band/Heft Quelle: 25(2019), 70, Seite 15988-15992
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201903438
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: guanidine
• Sach-SW: oxidation
• Sach-SW: oxidative coupling
• Sach-SW: proton-coupled electron transfer
• Sach-SW: redox reaction
• K10plus-PPN: 1729174973
• K10plus-PPN:
  Universitätsbibliothek
• Lokale URL UB: Zum Volltext

Abstract

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.