Issue 10, 2021

Modulating alkene reactivity from oxygenation to halogenation via electrochemical O2 activation by Mn porphyrin

Abstract

Oxidation of organic substrates is achieved in nature under mild conditions thanks to metalloenzymes but remains a challenge for chemists. Herein we show by UV-Vis spectroelectrochemistry that when MnIIITPPCl is electrochemically reduced to MnII in CH2Cl2 under O2, a MnIIO2˙ species is generated. Benzoic anhydride reacts with the latter triggering a catalytic current in cyclic voltammetry. Electrolysis on the catalytic wave in the presence of cyclooctene leads to its oxygenation or halogenation depending on the axial ligand present as reported here for the first time.

Graphical abstract: Modulating alkene reactivity from oxygenation to halogenation via electrochemical O2 activation by Mn porphyrin

Supplementary files

Article information

Article type
Communication
Submitted
17 nov. 2020
Accepted
24 déc. 2020
First published
26 déc. 2020

Chem. Commun., 2021,57, 1198-1201

Modulating alkene reactivity from oxygenation to halogenation via electrochemical O2 activation by Mn porphyrin

N. Kostopoulos, F. Banse, C. Fave and E. Anxolabéhère-Mallart, Chem. Commun., 2021, 57, 1198 DOI: 10.1039/D0CC07531K

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