Nickel-catalyzed Cycloaddition of Aromatic (<i>O</i>-Benzyl)ketoximes with Alkynes to Produce Isoquinoline and Isoquinoline <i>N</i>-Oxide Derivatives

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  • Yuji Yoshida
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University
  • Takuya Kurahashi
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University
  • Seijiro Matsubara
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University

Abstract

<jats:title>Abstract</jats:title> <jats:p>A nickel-catalyzed cycloaddition of aromatic (O-benzyl)ketoximes with alkynes to afford 3,4-disubstituted isoquinoline derivatives has been developed. The reaction involves oxidative addition of N–O bond of O-benzylketoxime to Ni(0) and subsequent intermolecular C–H bond activation via elimination of benzyl alcohol. It was also found that ketoximes participate in the nickel-catalyzed reaction with alkynes to furnish isoquinoline N-oxide derivatives.</jats:p>

Journal

  • Chemistry Letters

    Chemistry Letters 40 (10), 1140-1142, 2011-09-23

    Oxford University Press (OUP)

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