Evaluation of the synthetic scope and the reaction pathways of proton-coupled electron transfer with redox-active guanidines in C−H activation processes
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 thei...
Saved in:
| Main Authors: | , , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
2020
|
| In: |
Chemistry - a European journal
Year: 2020, Volume: 26, Issue: 69, Pages: 16504-16513 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202003424 |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202003424 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202003424 
|
| Author Notes: | Ute Wild, Petra Walter, Olaf Hübner, Elisabeth Kaifer, and Hans-Jörg Himmel |
| Summary: | 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. |
|---|---|
| Item Description: | First published: 07 September 2020 Gesehen am 25.10.2021 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202003424 |