C–C Coupling Enabled by Mn Complexes with Diacyl Peroxides: Alkylation versus Oxygenation

We present another dimension of the reactivity of Mn complexes with peroxides. Contrary to the expected oxidation, Mn­(OAc)2 with diacyl peroxides provides C–H functionalization of imidazole N-oxides by an alkyl fragment via a multistep process. The reaction of peroxide with Mn­(II) is proposed to g...

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Published inJournal of organic chemistry Vol. 90; no. 31; pp. 11074 - 11080
Main Authors Shuingalieva, Diana V., Akulov, Alexey A., Gorlov, Evgenii S., Varaksin, Mikhail V., Charushin, Valery N., Chupakhin, Oleg N., Vil’, Vera A., Terent’ev, Alexander O.
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 08.08.2025
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Summary:We present another dimension of the reactivity of Mn complexes with peroxides. Contrary to the expected oxidation, Mn­(OAc)2 with diacyl peroxides provides C–H functionalization of imidazole N-oxides by an alkyl fragment via a multistep process. The reaction of peroxide with Mn­(II) is proposed to generate the catalytic Mn­(IV)/Mn­(III) species with a noninnocent carboxylate ligand, which is cleaved to afford an alkyl radical and Mn­(III) complex. Further addition of an alkyl radical to the CN bond of imidazole N-oxide and C–H oxidation led to the target product in 23–89% yields.
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content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.5c00912