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

Tarali Devi, Yong Min Lee, Wonwoo Nam, Shunichi Fukuzumi

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

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.

Original languageEnglish
Pages (from-to)8286-8289
Number of pages4
JournalChemical Communications
Volume55
Issue number57
DOIs
StatePublished - 2019

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