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Hypervalent Iodine‐Catalyzed Synthesis of 1,2,4‐Oxadiazoles from Aldoximes and Nitriles
Author(s) -
Yoshimura Akira,
Nguyen Khiem C.,
Klasen Scott C.,
Postnikov Pavel S.,
Yusubov Mekhman S.,
Saito Akio,
Nemykin Victor N.,
Zhdankin Viktor V.
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600247
Subject(s) - chemistry , hypervalent molecule , catalysis , reagent , trifluoromethanesulfonate , iodine , organic chemistry , cycloaddition , aryl , combinatorial chemistry , alkyl
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 1 H NMR spectroscopy, ESI‐mass spectrometry, and by X‐ray diffraction.