Nickel-catalyzed, directing-group-assisted [2+2+2] cycloaddition of imine and alkynes

Laksmikanta Adak, Wei Chuen Chan, Naohiko Yoshikai

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28 Citations (Scopus)


An aldimine bearing a 3-methyl-2-pyridyl group undergoes [2+2+2] cycloaddition reaction with two alkyne molecules under nickel catalysis to afford a 1,2-dihydropyridine derivative in moderate to good yield. The reaction is likely to involve oxidative cyclization of the imine and alkyne, insertion of another alkyne, and C-N reductive elimination, followed by a 1,5-sigmatropic hydrogen shift. The pyridyl group is proposed to facilitate the reaction by chelation to the aza-nickelacycle intermediates.

Original languageEnglish
Pages (from-to)359-362
Number of pages4
JournalChemistry - An Asian Journal
Issue number2
Publication statusPublished - 2011 Feb 1


  • alkynes
  • cycloaddition
  • density functional calculations
  • heterocycles
  • nickel


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