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.
Язык оригиналаАнглийский
Страницы (с-по)463-473
Число страниц11
ЖурналJournal of Organic Chemistry
Номер выпуска1
СостояниеОпубликовано - 5 янв. 2024

    Предметные области ASJC Scopus

  • Organic Chemistry

    Предметные области WoS

  • Химия, Органическая

ID: 51612703