Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes

Akira Yoshimura, Kyle R. Middleton, Anthony D. Todora, Brent J. Kastern, Steven R. Koski, Andrey V. Maskaev, Viktor V. Zhdankin

Research output: Contribution to journalArticle

89 Citations (Scopus)

Abstract

Hypervalent iodine catalyzed oxidation of aldoximes using oxone as a terminal oxidant generates nitrile oxides, which react with alkenes and alkynes to give the corresponding isoxazolines and isoxazoles in moderate to good yields. This reaction involves active hypervalent iodine species formed in situ from catalytic iodoarene and oxone in the presence of hexafluoroisopropanol in aqueous methanol solution.

Original languageEnglish
Pages (from-to)4010-4013
Number of pages4
JournalOrganic Letters
Volume15
Issue number15
DOIs
Publication statusPublished - 2 Aug 2013
Externally publishedYes

Fingerprint

Nitriles
Oximes
Alkynes
Cycloaddition
nitriles
Cycloaddition Reaction
cycloaddition
Alkenes
alkynes
Iodine
Oxides
alkenes
iodine
Isoxazoles
oxides
Oxidants
Methanol
methyl alcohol
Oxidation
oxidation

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes. / Yoshimura, Akira; Middleton, Kyle R.; Todora, Anthony D.; Kastern, Brent J.; Koski, Steven R.; Maskaev, Andrey V.; Zhdankin, Viktor V.

In: Organic Letters, Vol. 15, No. 15, 02.08.2013, p. 4010-4013.

Research output: Contribution to journalArticle

Yoshimura, Akira ; Middleton, Kyle R. ; Todora, Anthony D. ; Kastern, Brent J. ; Koski, Steven R. ; Maskaev, Andrey V. ; Zhdankin, Viktor V. / Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes. In: Organic Letters. 2013 ; Vol. 15, No. 15. pp. 4010-4013.
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