Domino allylation and cyclization of ortho-alkynylbenzaldehydes with allyltrimethylsilane catalyzed by Pd(II)-Cu(II) bimetallic systems

Naoki Asao, Siew Chan Ching, Kumiko Takahashi, Yoshinori Yamamoto

    Research output: Contribution to journalArticle

    84 Citations (Scopus)

    Abstract

    The reaction of ortho-alkynylated benzaldehydes 1 with allyltrimethylsilane under the Pd(OAc)2-CuCl2 catalyst system gave the isochromene derivatives 2 together with the chlorinated products 3. When the reaction was conducted in the presence of half equiv of H2O, the formation of 3 was suppressed and 2 was obtained in good to high yields. When the reaction of 1a was carried out with trimethylsilylcyanide instead of allylsilane, the cyano group-substituted isochromene 9 was obtained in 94% yield.

    Original languageEnglish
    Pages (from-to)11322-11326
    Number of pages5
    JournalTetrahedron
    Volume61
    Issue number48
    DOIs
    Publication statusPublished - 2005 Nov 28

    Keywords

    • Allyltrimethylsilane
    • Bimetallic catalyst
    • Copper
    • Cyclization
    • Domino reaction
    • Isochromene skeleton
    • Palladium
    • ortho-Alkynylbenzaldehyde

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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