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

Research output: Contribution to journalArticle

12 Citations (Scopus)

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 languageEnglish
Pages (from-to)2340-2344
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume358
Issue number14
DOIs
Publication statusPublished - 1 Jan 2016

Fingerprint

Maleimides
Oximes
Cycloaddition
Cyclization
Isoxazoles
Acids
Oxidants
Iodine
Nuclear magnetic resonance spectroscopy
Mass spectrometry

Keywords

  • cyclization
  • heterocycles
  • iodine
  • iodonium species
  • oxidation
  • pyrrolo-isoxazoles

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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.

In: Advanced Synthesis and Catalysis, Vol. 358, No. 14, 01.01.2016, p. 2340-2344.

Research output: Contribution to journalArticle

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