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Iodine-Catalyzed Radical C–H Amination of Nonaromatic Imidazole Oxides: Access to Cyclic α-Aminonitrones Full article

Journal Journal of Organic Chemistry
ISSN: 0022-3263
Output data Year: 2024, Volume: 89, Number: 1, Pages: 463-473 Pages count : 11 DOI: 10.1021/acs.joc.3c02230
Authors Akulov Alexey A. 1 , Varaksin Mikhail V. 1,2 , Nelyubina Anna A. 1 , Tsmokaluk Anton N. 1 , Mazhukin Dmitrii G. 3 , Tikhonov Alexsei Y. 3 , Charushin Valery N. 1,2 , Chupakhin Oleg N. 1,2
Affiliations
1 Ural Federal University, 19 Mira Street, Ekaterinburg 620002, Russian Federation
2 I.Ya. Postovsky Institute of Organic Synthesis, 22 S. Kovaleskoy Street, Ekaterinburg 620991, Russian Federation
3 N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Akademika Lavrentieva Avenue, Novosibirsk 630090, Russian Federation

Abstract: Abstract A straightforward cross-dehydrogenative coupling approach to incorporate alicyclic amino residues into the structure of model cyclic aldonitrones, 2H-imidazole oxides, is reported. The elaborated C(sp2)–H functionalization is achieved by employing cyclic amines in the presence of the I2–tert-butyl hydroperoxide (TBHP) reagent system. As a result, a series of 19 novel heterocyclic derivatives were obtained in yields of up to 97%. A mechanistic study involving electron paramagnetic resonance spectroscopic experiments allowed the radical nature of the reaction to be confirmed. In particular, the envisioned mechanistic rationale comprises N-iodination of a cyclic amine, followed by N–I bond homolysis of the resulting intermediate and subsequent amination of the nitrone moiety via the newly generated nitrogen-centered radical.
Cite: Akulov A.A. , Varaksin M.V. , Nelyubina A.A. , Tsmokaluk A.N. , Mazhukin D.G. , Tikhonov A.Y. , Charushin V.N. , Chupakhin O.N.
Iodine-Catalyzed Radical C–H Amination of Nonaromatic Imidazole Oxides: Access to Cyclic α-Aminonitrones
Journal of Organic Chemistry. 2024. V.89. N1. P.463-473. DOI: 10.1021/acs.joc.3c02230 WOS Scopus OpenAlex
Dates:
Submitted: Sep 30, 2023
Accepted: Dec 4, 2023
Published online: Dec 13, 2023
Published print: Jan 5, 2024
Identifiers:
Web of science: WOS:001137566300001
Scopus: 2-s2.0-85180954306
OpenAlex: W4389702629
Citing:
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OpenAlex 5
Scopus 4
Web of science 7
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