Hypervalent Iodine-Catalyzed Synthesis of 1,2,4-Oxadiazoles from Aldoximes and Nitriles

Akira Yoshimura, Khiem C. Nguyen, Scott C. Klasen, Pavel S. Postnikov, Mekhman S. Yusubov, Akio Saito, Victor N. Nemykin, Viktor V. Zhdankin

Результат исследований: Материалы для журналаСтатья

15 Цитирования (Scopus)

Аннотация

A convenient procedure for oxidative cycloaddition of aldoximes with nitriles using stoichiometric or catalytic amounts of hypervalent iodine(III) reagent IBA-OTf (2-iodosylbenzoic acid triflate) has been developed. This efficient procedure works well for the preparation of various 1,2,4-oxadiazoles in generally high yields under mild reaction conditions. The actual oxidant in this reaction, IBA-OTf, is prepared from 2-iodosylbenzoic acid (IBA) and trifluoromethanesulfonic acid (TfOH) or it can be generated in situ from 2-iodobenzoic acid and m-chloroperoxybenzoic acid (m-CPBA) in the presence of TfOH. The nature of hydroxy(aryl)iodonium species, generated in situ from 2-iodobenzoic acid, m-CPBA, and TfOH under catalytic reaction conditions, has been confirmed by 1H NMR spectroscopy, ESI-mass spectrometry, and by X-ray diffraction.

Язык оригиналаАнглийский
Страницы (с-по)1128-1133
Число страниц6
ЖурналAsian Journal of Organic Chemistry
Том5
Номер выпуска9
DOI
СостояниеОпубликовано - 1 сен 2016

ASJC Scopus subject areas

  • Organic Chemistry

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