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 language | English |
|---|---|
| Pages (from-to) | 1128-1133 |
| Number of pages | 6 |
| Journal | Asian Journal of Organic Chemistry |
| Volume | 5 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 1 Sep 2016 |
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Keywords
- 1,2,4-oxadiazoles
- cyclization
- heterocycles
- iodine
- oxidation
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Hypervalent Iodine-Catalyzed Synthesis of 1,2,4-Oxadiazoles from Aldoximes and Nitriles. / Yoshimura, Akira; Nguyen, Khiem C.; Klasen, Scott C.; Postnikov, Pavel S.; Yusubov, Mekhman S.; Saito, Akio; Nemykin, Victor N.; Zhdankin, Viktor V.
In: Asian Journal of Organic Chemistry, Vol. 5, No. 9, 01.09.2016, p. 1128-1133.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Hypervalent Iodine-Catalyzed Synthesis of 1,2,4-Oxadiazoles from Aldoximes and Nitriles
AU - Yoshimura, Akira
AU - Nguyen, Khiem C.
AU - Klasen, Scott C.
AU - Postnikov, Pavel S.
AU - Yusubov, Mekhman S.
AU - Saito, Akio
AU - Nemykin, Victor N.
AU - Zhdankin, Viktor V.
PY - 2016/9/1
Y1 - 2016/9/1
N2 - 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.
AB - 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.
KW - 1,2,4-oxadiazoles
KW - cyclization
KW - heterocycles
KW - iodine
KW - oxidation
UR - http://www.scopus.com/inward/record.url?scp=84987934329&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84987934329&partnerID=8YFLogxK
U2 - 10.1002/ajoc.201600247
DO - 10.1002/ajoc.201600247
M3 - Article
AN - SCOPUS:84987934329
VL - 5
SP - 1128
EP - 1133
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
SN - 2193-5807
IS - 9
ER -