Oxidative Cycloaddition of Aldoximes with Maleimides using Catalytic Hydroxy(aryl)iodonium Species

Akira Yoshimura; Khiem C. Nguyen; Gregory T. Rohde; Akio Saito; Mekhman S. Yusubov; Viktor V. Zhdankin

doi:10.1002/adsc.201600331

Oxidative Cycloaddition of Aldoximes with Maleimides using Catalytic Hydroxy(aryl)iodonium Species

Akira Yoshimura, Khiem C. Nguyen, Gregory T. Rohde, Akio Saito, Mekhman S. Yusubov, Viktor V. Zhdankin

Chemistry & Biochemistry

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

30 Scopus citations

Abstract

A mild catalytic procedure for the efficient oxidative cyclization of aldoximes with maleimides mediated by hypervalent iodine(III) active species has been developed. This catalytic cyclization affords the corresponding pyrrolo-isoxazole products in generally good yields. The catalytic cycle involves active hydroxy(aryl)iodonium species generated in situ from 2-iodobenzoic acid as precatalyst and m-chloroperoxybenzoic acid (m-CPBA) as terminal oxidant in the presence of trifluoromethanesulfonic acid. The presence of active hydroxy(aryl)iodonium species in this reaction has been confirmed by ESI-mass spectrometry and¹H NMR spectroscopy. (Figure presented.) .

Original language	English (US)
Pages (from-to)	2340-2344
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	358
Issue number	14
DOIs	https://doi.org/10.1002/adsc.201600331
State	Published - Jul 14 2016

Bibliographical note

Funding Information:
This work was supported by research grants from the National Science Foundation (CHE-1262479), Russian Science Foundation (RSF-16-13-10081), and by the Asahi Glass Foundation.

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

Keywords

cyclization
heterocycles
iodine
iodonium species
oxidation
pyrrolo-isoxazoles

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10.1002/adsc.201600331

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title = "Oxidative Cycloaddition of Aldoximes with Maleimides using Catalytic Hydroxy(aryl)iodonium Species",

abstract = "A mild catalytic procedure for the efficient oxidative cyclization of aldoximes with maleimides mediated by hypervalent iodine(III) active species has been developed. This catalytic cyclization affords the corresponding pyrrolo-isoxazole products in generally good yields. The catalytic cycle involves active hydroxy(aryl)iodonium species generated in situ from 2-iodobenzoic acid as precatalyst and m-chloroperoxybenzoic acid (m-CPBA) as terminal oxidant in the presence of trifluoromethanesulfonic acid. The presence of active hydroxy(aryl)iodonium species in this reaction has been confirmed by ESI-mass spectrometry and1H NMR spectroscopy. (Figure presented.) .",

keywords = "cyclization, heterocycles, iodine, iodonium species, oxidation, pyrrolo-isoxazoles",

author = "Akira Yoshimura and Nguyen, {Khiem C.} and Rohde, {Gregory T.} and Akio Saito and Yusubov, {Mekhman S.} and Zhdankin, {Viktor V.}",

note = "Funding Information: This work was supported by research grants from the National Science Foundation (CHE-1262479), 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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doi = "10.1002/adsc.201600331",

language = "English (US)",

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T1 - Oxidative Cycloaddition of Aldoximes with Maleimides using Catalytic Hydroxy(aryl)iodonium Species

AU - Yoshimura, Akira

AU - Nguyen, Khiem C.

AU - Rohde, Gregory T.

AU - Saito, Akio

AU - Yusubov, Mekhman S.

AU - Zhdankin, Viktor V.

N1 - Funding Information: This work was supported by research grants from the National Science Foundation (CHE-1262479), Russian Science Foundation (RSF-16-13-10081), and by the Asahi Glass Foundation. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2016/7/14

Y1 - 2016/7/14

N2 - A mild catalytic procedure for the efficient oxidative cyclization of aldoximes with maleimides mediated by hypervalent iodine(III) active species has been developed. This catalytic cyclization affords the corresponding pyrrolo-isoxazole products in generally good yields. The catalytic cycle involves active hydroxy(aryl)iodonium species generated in situ from 2-iodobenzoic acid as precatalyst and m-chloroperoxybenzoic acid (m-CPBA) as terminal oxidant in the presence of trifluoromethanesulfonic acid. The presence of active hydroxy(aryl)iodonium species in this reaction has been confirmed by ESI-mass spectrometry and1H NMR spectroscopy. (Figure presented.) .

AB - A mild catalytic procedure for the efficient oxidative cyclization of aldoximes with maleimides mediated by hypervalent iodine(III) active species has been developed. This catalytic cyclization affords the corresponding pyrrolo-isoxazole products in generally good yields. The catalytic cycle involves active hydroxy(aryl)iodonium species generated in situ from 2-iodobenzoic acid as precatalyst and m-chloroperoxybenzoic acid (m-CPBA) as terminal oxidant in the presence of trifluoromethanesulfonic acid. The presence of active hydroxy(aryl)iodonium species in this reaction has been confirmed by ESI-mass spectrometry and1H NMR spectroscopy. (Figure presented.) .

KW - cyclization

KW - heterocycles

KW - iodine

KW - iodonium species

KW - oxidation

KW - pyrrolo-isoxazoles

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DO - 10.1002/adsc.201600331

M3 - Article

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SN - 1615-4150

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JF - Advanced Synthesis and Catalysis

IS - 14

ER -

Oxidative Cycloaddition of Aldoximes with Maleimides using Catalytic Hydroxy(aryl)iodonium Species

Abstract

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Keywords

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