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

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

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