Pd(II) acts simultaneously as a Lewis acid and as a transition-metal catalyst: Synthesis of cyclic alkenyl ethers from acetylenic aldehydes

Naoki Asao, Tsutomu Nogami, Kumiko Takahashi, Yoshinori Yamamoto

    Research output: Contribution to journalArticlepeer-review

    284 Citations (Scopus)

    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.

    Original languageEnglish
    Pages (from-to)764-765
    Number of pages2
    JournalJournal of the American Chemical Society
    Volume124
    Issue number5
    DOIs
    Publication statusPublished - 2002 Feb 6

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)
    • Biochemistry
    • Colloid and Surface Chemistry

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