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Evaluation of the Synthetic Scope and the Reaction Pathways of Proton‐Coupled Electron Transfer with Redox‐Active Guanidines in C−H Activation Processes
Author(s) -
Wild Ute,
Walter Petra,
Hübner Olaf,
Kaifer Elisabeth,
Himmel HansJörg
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003424
Subject(s) - proton coupled electron transfer , electron transfer , redox , chemistry , reagent , reactivity (psychology) , proton , ferrocene , molecule , photochemistry , kinetics , combinatorial chemistry , electrochemistry , organic chemistry , electrode , medicine , physics , alternative medicine , pathology , quantum mechanics
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.