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 journalArticlepeer-review

18 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 languageEnglish (US)
Pages (from-to)2340-2344
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume358
Issue number14
DOIs
StatePublished - 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.

Keywords

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

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