Carbon dioxide-mediated catalytic rearrangement of propargyl alcohols into α, β-unsaturated ketones

Y Sugawara, W Yamada, S Yoshida…

Index: Sugawara, Yudai; Yamada, Wataru; Yoshida, Shunsuke; Ikeno, Taketo; Yamada, Tohru Journal of the American Chemical Society, 2007 , vol. 129, # 43 p. 12902 - 12903

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Citation Number: 67

Abstract

In the presence of a catalytic amount of a silver salt with DBU under a CO2 atmosphere, various tertiary and secondary propargyl alcohols were efficiently converted into the corresponding α, β-unsaturated carbonyl compounds in high yield. An isotopic experiment using C18O2 revealed that carbon dioxide mediated the rearrangement via an intramolecular nucleophilic attack on the alkyne activated by the silver catalyst.