Hypervalent Iodine‐Catalyzed Synthesis of 1,2,4‐Oxadiazoles from Aldoximes and Nitriles
Тип публикации: Journal Article
Дата публикации: 2016-07-05
scimago Q2
wos Q2
БС1
SJR: 0.542
CiteScore: 5.0
Impact factor: 2.7
ISSN: 21935807, 21935815
Organic Chemistry
Краткое описание
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.
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YOSHIMURA A. et al. Hypervalent Iodine‐Catalyzed Synthesis of 1,2,4‐Oxadiazoles from Aldoximes and Nitriles // Asian Journal of Organic Chemistry. 2016. Vol. 5. No. 9. pp. 1128-1133.
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YOSHIMURA A., Nguyen K. C., Klasen S. C., Postnikov P. S., S. Yusubov M., Saito A., Nemykin V. V., Zhdankin V. V. Hypervalent Iodine‐Catalyzed Synthesis of 1,2,4‐Oxadiazoles from Aldoximes and Nitriles // Asian Journal of Organic Chemistry. 2016. Vol. 5. No. 9. pp. 1128-1133.
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RIS
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TY - JOUR
DO - 10.1002/ajoc.201600247
UR - https://doi.org/10.1002/ajoc.201600247
TI - Hypervalent Iodine‐Catalyzed Synthesis of 1,2,4‐Oxadiazoles from Aldoximes and Nitriles
T2 - Asian Journal of Organic Chemistry
AU - YOSHIMURA, Akira
AU - Nguyen, Khiem C
AU - Klasen, Scott C
AU - Postnikov, Pavel S.
AU - S. Yusubov, Mekhman
AU - Saito, Akio
AU - Nemykin, Victor V.
AU - Zhdankin, Viktor V.
PY - 2016
DA - 2016/07/05
PB - Wiley
SP - 1128-1133
IS - 9
VL - 5
SN - 2193-5807
SN - 2193-5815
ER -
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@article{2016_YOSHIMURA,
author = {Akira YOSHIMURA and Khiem C Nguyen and Scott C Klasen and Pavel S. Postnikov and Mekhman S. Yusubov and Akio Saito and Victor V. Nemykin and Viktor V. Zhdankin},
title = {Hypervalent Iodine‐Catalyzed Synthesis of 1,2,4‐Oxadiazoles from Aldoximes and Nitriles},
journal = {Asian Journal of Organic Chemistry},
year = {2016},
volume = {5},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002/ajoc.201600247},
number = {9},
pages = {1128--1133},
doi = {10.1002/ajoc.201600247}
}
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MLA
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YOSHIMURA, Akira, et al. “Hypervalent Iodine‐Catalyzed Synthesis of 1,2,4‐Oxadiazoles from Aldoximes and Nitriles.” Asian Journal of Organic Chemistry, vol. 5, no. 9, Jul. 2016, pp. 1128-1133. https://doi.org/10.1002/ajoc.201600247.
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