4.3 Article

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

Journal

CHEMISTRY LETTERS
Volume 40, Issue 10, Pages 1140-1142

Publisher

CHEMICAL SOC JAPAN
DOI: 10.1246/cl.2011.1140

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology, Japan
  2. Asahi Glass Foundation
  3. Kansai Research Foundation
  4. Toyota Physical and Chemical Research Institute
  5. Grants-in-Aid for Scientific Research [21106001] Funding Source: KAKEN

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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.

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