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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 and Viktor V. Zhdankin*

*Department of Chemistry and Biochemistry, University of Minnesota—Duluth, Duluth, Minnesota, 55812, United States, Email:,

A. Yoshimura, K. R. Middleton, A. D. Todora, B. J. Kastern, S. R. Koski, A. V. Maskaev, V. V. Zhdankin, Org. Lett., 2013, 15, 4010-4013.

DOI: 10.1021/ol401815n

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A hypervalent iodine species, which is formed in situ in the presence of oxone as terminal oxidant, catalyzes the oxidation of aldoximes to generate nitrile oxides. A subsequent reaction with alkenes gives the corresponding isoxazolines in good yields, whereas the reaction with alkynes gives the corresponding isoxazoles in moderate yields.

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Key Words

isoxazolines, oxone, hypervalent iodine compounds

ID: J54-Y2013