著者

杉原 多公通 山口 雅彦 西沢 麦夫

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.57, no.3, pp.158-169, 1999-03-01 (Released:2009-11-16)

参考文献数

23

被引用文献数

5 7

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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.