Chemo- And regioselective intramolecular hydrosilylative carbocyclization of allenynes

Takanori Shibata, Sho Kadowaki, Kentaro Takagi

    Research output: Contribution to journalArticle

    22 Citations (Scopus)

    Abstract

    Rhodium complex catalyzed hydrosilylative carbocyclization of various allenynes and trialkoxysilanes proceeded smoothly under an atmosphere of carbon monoxide to give hydrosilylated cyclic products. The intramolecular coupling of allene and alkyne is chemo-and regioselective: silylrhodation to an internal olefinic moiety of the allene proceeded exclusively, and subsequent carbometalation to the alkyne provided cyclic 1,4-dienes. The use of alkoxysilane and the substituents on the allene terminus play pivotal roles in the selectivity.

    Original languageEnglish
    Pages (from-to)4116-4120
    Number of pages5
    JournalOrganometallics
    Volume23
    Issue number17
    DOIs
    Publication statusPublished - 2004 Aug 16

    Fingerprint

    alkynes
    Alkynes
    dienes
    rhodium
    carbon monoxide
    Rhodium
    selectivity
    Carbon Monoxide
    atmospheres
    products
    propadiene

    ASJC Scopus subject areas

    • Inorganic Chemistry
    • Organic Chemistry

    Cite this

    Chemo- And regioselective intramolecular hydrosilylative carbocyclization of allenynes. / Shibata, Takanori; Kadowaki, Sho; Takagi, Kentaro.

    In: Organometallics, Vol. 23, No. 17, 16.08.2004, p. 4116-4120.

    Research output: Contribution to journalArticle

    Shibata, Takanori ; Kadowaki, Sho ; Takagi, Kentaro. / Chemo- And regioselective intramolecular hydrosilylative carbocyclization of allenynes. In: Organometallics. 2004 ; Vol. 23, No. 17. pp. 4116-4120.
    @article{1bd2e28445634b89aa98a1c82006c004,
    title = "Chemo- And regioselective intramolecular hydrosilylative carbocyclization of allenynes",
    abstract = "Rhodium complex catalyzed hydrosilylative carbocyclization of various allenynes and trialkoxysilanes proceeded smoothly under an atmosphere of carbon monoxide to give hydrosilylated cyclic products. The intramolecular coupling of allene and alkyne is chemo-and regioselective: silylrhodation to an internal olefinic moiety of the allene proceeded exclusively, and subsequent carbometalation to the alkyne provided cyclic 1,4-dienes. The use of alkoxysilane and the substituents on the allene terminus play pivotal roles in the selectivity.",
    author = "Takanori Shibata and Sho Kadowaki and Kentaro Takagi",
    year = "2004",
    month = "8",
    day = "16",
    doi = "10.1021/om049677b",
    language = "English",
    volume = "23",
    pages = "4116--4120",
    journal = "Organometallics",
    issn = "0276-7333",
    publisher = "American Chemical Society",
    number = "17",

    }

    TY - JOUR

    T1 - Chemo- And regioselective intramolecular hydrosilylative carbocyclization of allenynes

    AU - Shibata, Takanori

    AU - Kadowaki, Sho

    AU - Takagi, Kentaro

    PY - 2004/8/16

    Y1 - 2004/8/16

    N2 - Rhodium complex catalyzed hydrosilylative carbocyclization of various allenynes and trialkoxysilanes proceeded smoothly under an atmosphere of carbon monoxide to give hydrosilylated cyclic products. The intramolecular coupling of allene and alkyne is chemo-and regioselective: silylrhodation to an internal olefinic moiety of the allene proceeded exclusively, and subsequent carbometalation to the alkyne provided cyclic 1,4-dienes. The use of alkoxysilane and the substituents on the allene terminus play pivotal roles in the selectivity.

    AB - Rhodium complex catalyzed hydrosilylative carbocyclization of various allenynes and trialkoxysilanes proceeded smoothly under an atmosphere of carbon monoxide to give hydrosilylated cyclic products. The intramolecular coupling of allene and alkyne is chemo-and regioselective: silylrhodation to an internal olefinic moiety of the allene proceeded exclusively, and subsequent carbometalation to the alkyne provided cyclic 1,4-dienes. The use of alkoxysilane and the substituents on the allene terminus play pivotal roles in the selectivity.

    UR - http://www.scopus.com/inward/record.url?scp=4344602770&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=4344602770&partnerID=8YFLogxK

    U2 - 10.1021/om049677b

    DO - 10.1021/om049677b

    M3 - Article

    AN - SCOPUS:4344602770

    VL - 23

    SP - 4116

    EP - 4120

    JO - Organometallics

    JF - Organometallics

    SN - 0276-7333

    IS - 17

    ER -