Lewis acid catalyzed stereoselective carbosilylation. Intramolecular trans-vinylsilylation and trans-arylsilylation of unactivated alkynes

Naoki Asao, T. Shimada, T. Shimada, Y. Yamamoto

    Research output: Contribution to journalArticlepeer-review

    50 Citations (Scopus)

    Abstract

    Intramolecular trans-vinylsilylation using silicon-tethered alkynylvinylsilanes 3b-c was catalyzed dramatically by Lewis acids such as EtAlCl2 to give the corresponding six-membered silacycles 4b-c in high yields. The reaction proceeded via an exo-mode cyclization. In addition to the vinylsilylation, the intramolecular trans-arylsilylations using carbon-tethered alkynylarylsilanes 8a-b were also catalyzed by Lewis acids such as HfCl4 to give six- and seven-membered cyclic (E)-vinylsilanes 9a-b, respectively. The cyclization of silicon-tethered substrates 13a-d afforded five- and six-membered silacycle products 14a-d in low to high yields. All arylsilylation reactions proceeded via an exo-mode fashion exclusively.

    Original languageEnglish
    Pages (from-to)10899-10902
    Number of pages4
    JournalJournal of the American Chemical Society
    Volume123
    Issue number44
    DOIs
    Publication statusPublished - 2001 Nov 7

    ASJC Scopus subject areas

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

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