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

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)1128-1133
Number of pages6
JournalAsian Journal of Organic Chemistry
Volume5
Issue number9
DOIs
StatePublished - Sep 1 2016

Bibliographical note

Funding Information:
This work was supported by research grants from the National Science Foundation (CHE-1262479 and MRI-1420373), Russian Science Foundation (RSF-16-13-10081), and by the Asahi Glass Foundation.

Keywords

  • 1,2,4-oxadiazoles
  • cyclization
  • heterocycles
  • iodine
  • oxidation

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