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

Laksmikanta Adak, Wei Chuen Chan, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

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
Volume6
Issue number2
DOIs
Publication statusPublished - 2011 Feb 1
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Nickel-catalyzed, directing-group-assisted [2+2+2] cycloaddition of imine and alkynes'. Together they form a unique fingerprint.

Cite this