Pd(II) acts simultaneously as a Lewis acid and as a transition-metal catalyst: synthesis of cyclic alkenyl ethers from acetylenic aldehydes |
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Authors: | Asao Naoki Nogami Tsutomu Takahashi Kumiko Yamamoto Yoshinori |
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Affiliation: | Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. |
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Abstract: | The reaction of carbon-tethered acetylenic aldehydes with alcohols in the presence of a catalytic amount of Pd(OAc)2 in 1,4-dioxane at room temperature gave the 5- or 6-membered acetal products in high yields. The 13C NMR studies suggested that a Pd(II) catalyst exhibited dual roles in the present reaction; the attack of ROH to aldehyde is catalyzed by Lewis acidic Pd(OAc)2, and the nucleophilic oxygen of the resulting hemiacetal reacts with alkyne complexed by Pd(II), giving the alkenyl ethers. |
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