Nickel-catalyzed [2+2+2] cycloaddition of two alkynes and an imine

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  • Sensuke Ogoshi
    Department of Applied Chemistry, Osaka University Suita, Osaka 565-0871, Japan
  • Haruo Ikeda
    Department of Applied Chemistry, Osaka University Suita, Osaka 565-0871, Japan
  • Hideo Kurosawa
    Department of Applied Chemistry, Osaka University Suita, Osaka 565-0871, Japan

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<jats:title>Abstract</jats:title><jats:p>The reaction of<jats:italic>N</jats:italic>-benzenesulfonylbenzaldimine with Ni(cod)<jats:sub>2</jats:sub>and PCy<jats:sub>3</jats:sub>gave the corresponding η<jats:sup>2</jats:sup>-iminenickel complex quantitatively. Diphenylacetylene reacted with the η<jats:sup>2</jats:sup>-iminenickel complex to generate five-membered aza-nickelacycle. Insertion of second alkynes into the five-membered aza-nickelacycle led to the formation of the corresponding seven-membered aza-nickelacycles. Heating the solution of the seven-membered aza-nickelacycles induced the reductive elimination to give 1,2-dihydropyridine. In the presence of 10 mol % of Ni(cod)<jats:sub>2</jats:sub>and PMe<jats:italic><jats:sup>t</jats:sup></jats:italic>Bu<jats:sub>2</jats:sub>at 100 °C, the intermolecular [2+2+2] cycloaddition of<jats:italic>N</jats:italic>-benzenesulfonylbenzaldimine and 2-butyne occurred to give the expected 1,2-dihydropyridine in 87 % yield. In the presence of PCy<jats:sub>3</jats:sub>, the reaction also proceeded catalytically, however, PMe<jats:italic><jats:sup>t</jats:sup></jats:italic>Bu<jats:sub>2</jats:sub>gave better results. Less bulky or less basic phosphine, P<jats:italic><jats:sup>n</jats:sup></jats:italic>Bu<jats:sub>3</jats:sub>or P(<jats:italic>o</jats:italic>-tol)<jats:sub>3</jats:sub>, was not efficient for the reaction. Although Ni(0)-NHC complex was a good catalyst for [2+2+2] cycloaddition of two alkynes and a ketone or an aldehyde, this reaction did not proceed in the presence of an NHC ligand, 1,3-bis-(2,4,6-trimethylphenyl)imidazol-2-ylidene.</jats:p>

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