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V. V. Zhdankin (2014)
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A Convenient Method of Generation of Nitrile Oxides by Iodosylbenzene and Its Reaction.Nippon Kagaku Kaishi
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.
Asian Journal of Organic Chemistry – Wiley
Published: Sep 1, 2016
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