Activation of alkyne-dicobalt hexacarbonyl complexes by the Lewis bases - A new trend in the Pauson-Khand reaction

Takumichi Sugihara, Masahiko Yamaguchi, Mugio Nishizawa

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Cyclic cotrimerization of an alkyne, an alkene, and carbon monoxide mediated by dicobalt octacarbonyl, which is well known as the Pauson-Khand reaction, was promoted by the addition of certain Lewis bases. Primary amines with secondary alkyl groups, such as cyclohexylamine, promoted the stoichiometric Pauson-Khand reaction to give the desired cyclopentenones in good yields. The same reaction can be conveniently carried out in 1,4-dioxane-aqueous NH4OH biphasic system. Some reactive cobalt complexes might be produced as the coproduct in the reaction mixture and decomposed the substrate and/or the product in some cases. To overcome this disadvantage, alkyl methyl sulfides were introduced as the promoter. The catalytic Pauson-Khand reaction was also promoted by the addition of a tiny amount of DME or water. A novel decomplexation method of alkyne-dicobalt hexacarbonyl complexes by using ethylenediamine and a hydrocarbamoylation reaction were also presented.

Original languageEnglish
Pages (from-to)158-169
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume57
Issue number3
DOIs
Publication statusPublished - 1999 Jan 1

Keywords

  • Alkyne-dicobalt hexacarbonyl complex
  • Amine
  • Catalytic cyclization
  • Decomplexation
  • Hydrocarbamoylation
  • Pauson-Khand reaction
  • Sulfide
  • Water

ASJC Scopus subject areas

  • Organic Chemistry

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