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Issue 32, 2019
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Electrochemical C–H oxygenation and alcohol dehydrogenation involving Fe-oxo species using water as the oxygen source

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Abstract

High-valent iron-oxo complexes are key intermediates in C–H functionalization reactions. Herein, we report the generation of a (TAML)Fe-oxo species (TAML = tetraamido macrocyclic ligand) via electrochemical proton-coupled oxidation of the corresponding (TAML)FeIII–OH2 complex. Cyclic voltammetry (CV) and spectroelectrochemical studies are used to elucidate the relevant (TAML)Fe redox processes and determine the predominant (TAML)Fe species present in solution during bulk electrolysis. Evidence for iron(IV) and iron(V) species is presented, and these species are used in the electrochemical oxygenation of benzylic C–H bonds and dehydrogenation of alcohols to ketones.

Graphical abstract: Electrochemical C–H oxygenation and alcohol dehydrogenation involving Fe-oxo species using water as the oxygen source

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Publication details

The article was received on 29 May 2019, accepted on 25 Jun 2019 and first published on 27 Jun 2019


Article type: Edge Article
DOI: 10.1039/C9SC02609F
Chem. Sci., 2019,10, 7542-7548
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Electrochemical C–H oxygenation and alcohol dehydrogenation involving Fe-oxo species using water as the oxygen source

    A. Das, J. E. Nutting and S. S. Stahl, Chem. Sci., 2019, 10, 7542
    DOI: 10.1039/C9SC02609F

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