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Issue 57, 2019
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Aromatic hydroxylation of anthracene derivatives by a chromium(iii)-superoxo complex via proton-coupled electron transfer

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Abstract

The chemistry of metal-superoxo intermediates started being unveiled in oxidation reactions by enzymes and their synthetic model compounds. However, aromatic hydroxylation reactions by the metal-superoxo species are yet to be demonstrated. In this study, we report for the first time that the hydroxylation of aromatic compounds such as anthracene and its derivatives by a mononuclear nonheme Cr(III)-superoxo complex, [(Cl)(TMC)CrIII(O2)]+ (1), occurs in the presence of triflic acid (HOTf) via the rate-determining proton-coupled electron transfer (PCET) from anthracene to 1, followed by a fast further oxidation to give anthraquinone. The rate constants of electron transfer from anthracene derivatives to 1 in the presence of HOTf are well analyzed in light of the Marcus theory of electron transfer.

Graphical abstract: Aromatic hydroxylation of anthracene derivatives by a chromium(iii)-superoxo complex via proton-coupled electron transfer

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Publication details

The article was received on 26 Apr 2019, accepted on 20 Jun 2019 and first published on 24 Jun 2019


Article type: Communication
DOI: 10.1039/C9CC03245B
Chem. Commun., 2019,55, 8286-8289

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    Aromatic hydroxylation of anthracene derivatives by a chromium(III)-superoxo complex via proton-coupled electron transfer

    T. Devi, Y. Lee, W. Nam and S. Fukuzumi, Chem. Commun., 2019, 55, 8286
    DOI: 10.1039/C9CC03245B

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