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

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

Журнал

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Вых. Данные

Год: 2025, Том: 90, Номер: 31, Страницы: 11074–11080 Страниц : DOI: 10.1021/acs.joc.5c00912

Авторы

Shuingalieva Diana V. ¹ , Akulov Alexey A. ² , Gorlov Evgenii S. ¹ , Varaksin Mikhail V. ^3,2 , Charushin Valery N. ^3,2 , Chupakhin Oleg N. ^3,2 , Vil’ Vera A. ¹ , Terent’ev Alexander O. ¹

Организации

1	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow 119991, Russian Federation
2	Ural Federal University, 19 Mira Strasse, 620062 Ekaterinburg, Russian Federation
3	Postovsky Institute of Organic Synthesis, UB RAS, 22 S. Kovalevskaya Strasse, 620108 Ekaterinburg, Russian Federation

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.

Shuingalieva D.V. , Akulov A.A. , Gorlov E.S. , Varaksin M.V. , Charushin V.N. , Chupakhin O.N. , Vil’ V.A. , Terent’ev A.O.
C–C Coupling Enabled by Mn Complexes with Diacyl Peroxides: Alkylation versus Oxygenation
Journal of Organic Chemistry. 2025. V.90. N31. P.11074–11080. DOI: 10.1021/acs.joc.5c00912 WOS OpenAlex

Web of science:	WOS:001537082700001
OpenAlex:	W4412654022

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