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

doi:10.1002/ajoc.201600247

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

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

34 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 language	English (US)
Pages (from-to)	1128-1133
Number of pages	6
Journal	Asian Journal of Organic Chemistry
Volume	5
Issue number	9
DOIs	https://doi.org/10.1002/ajoc.201600247
State	Published - 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.

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

1,2,4-oxadiazoles
cyclization
heterocycles
iodine
oxidation

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title = "Hypervalent Iodine-Catalyzed Synthesis of 1,2,4-Oxadiazoles from Aldoximes and Nitriles",

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.",

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author = "Akira Yoshimura and Nguyen, {Khiem C.} and Klasen, {Scott C.} and Postnikov, {Pavel S.} and Yusubov, {Mekhman S.} and Akio Saito and Nemykin, {Victor N.} and Zhdankin, {Viktor V.}",

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. Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Postnikov, Pavel S.

AU - Yusubov, Mekhman S.

AU - Saito, Akio

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor V.

N1 - 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. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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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.

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KW - heterocycles

KW - iodine

KW - oxidation

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Hypervalent Iodine-Catalyzed Synthesis of 1,2,4-Oxadiazoles from Aldoximes and Nitriles

Abstract

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Keywords

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