Evaluation of the synthetic scope and the reaction pathways of proton-coupled electron transfer with redox-active guanidines in C−H activation processes

• Verfasst von: Wild, Ute [VerfasserIn]
• Verfasst von: Walter, Petra [VerfasserIn]
• Verfasst von: Hübner, Olaf [VerfasserIn]
• Verfasst von: Kaifer, Elisabeth [VerfasserIn]
• Verfasst von: Himmel, Hans-Jörg [VerfasserIn]
• Titel: Evaluation of the synthetic scope and the reaction pathways of proton-coupled electron transfer with redox-active guanidines in C−H activation processes
• Verf.angabe: Ute Wild, Petra Walter, Olaf Hübner, Elisabeth Kaifer, and Hans-Jörg Himmel
• Jahr: 2020
• Umfang: 10 S.
• Fussnoten: First published: 07 September 2020 ; Gesehen am 25.10.2021
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2020
• Band/Heft Quelle: 26(2020), 69, Seite 16504-16513
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.202003424
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: electron transfer
• Sach-SW: oxidation
• Sach-SW: C−H activation
• Sach-SW: oxidative coupling
• Sach-SW: redox chemistry
• K10plus-PPN: 1775162540
• K10plus-PPN:
  Universitätsbibliothek
• Lokale URL UB: Zum Volltext

Abstract

Proton-coupled electron transfer (PCET) is currently intensively studied because of its importance in synthetic chemistry and biology. In recent years it was shown that redox-active guanidines are capable PCET reagents for the selective oxidation of organic molecules. In this work, the scope of their PCET reactivity regarding reactions that involve C−H activation is explored and kinetic studies carried out to disclose the reaction mechanisms. Organic molecules with potential up to 1.2 V vs. ferrocenium/ferrocene are efficiently oxidized. Reactions are initiated by electron transfer, followed by slow proton transfer from an electron-transfer equilibrium.