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

Исследовательская школа химических и биомедицинских технологий

Результат исследований: Материалы для журнала › Статья

Аннотация

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.) .

Язык оригинала	Английский
Страницы (с-по)	2340-2344
Число страниц	5
Журнал	Advanced Synthesis and Catalysis
Том	358
Номер выпуска	14
DOI	https://doi.org/10.1002/adsc.201600331
Состояние	Опубликовано - 1 янв 2016

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Доступ к документу

10.1002/adsc.201600331

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Цитировать

Yoshimura, A., Nguyen, K. C., Rohde, G. T., Saito, A., Yusubov, M. S., & Zhdankin, V. V. (2016). Oxidative Cycloaddition of Aldoximes with Maleimides using Catalytic Hydroxy(aryl)iodonium Species. Advanced Synthesis and Catalysis, 358(14), 2340-2344. https://doi.org/10.1002/adsc.201600331

Oxidative Cycloaddition of Aldoximes with Maleimides using Catalytic Hydroxy(aryl)iodonium Species. / Yoshimura, Akira; Nguyen, Khiem C.; Rohde, Gregory T.; Saito, Akio; Yusubov, Mekhman S.; Zhdankin, Viktor V.

В: Advanced Synthesis and Catalysis, Том 358, № 14, 01.01.2016, стр. 2340-2344.

Результат исследований: Материалы для журнала › Статья

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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.}",

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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.

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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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