Catalytic [2 + 2 + 2] cycloaddition of benzothiophene dioxides with α,ω-diynes for the synthesis of condensed polycyclic compounds

Yu Ki Tahara, Manami Gake, Riku Matsubara, Takanori Shibata

    Research output: Contribution to journalArticle

    10 Citations (Scopus)

    Abstract

    A Rh-catalyzed intermolecular [2 + 2 + 2] cycloaddition of the 2,3-double bond of benzothiophene dioxides with α,ω-diynes gave sulfone-containing cycloadducts in high yields. This is the first example of a catalytic [2 + 2 + 2] cycloaddition that uses the 2,3-double bond of a heterole as an ene moiety. The consecutive reaction of benzodithiophene tetraoxide with 2,3-naphthylene-tethered 1,7-diyne gave an 11-ring condensed polycyclic compound in one pot.

    Original languageEnglish
    Pages (from-to)5980-5983
    Number of pages4
    JournalOrganic Letters
    Volume16
    Issue number22
    DOIs
    Publication statusPublished - 2014 Nov 21

    Fingerprint

    Diynes
    Polycyclic Compounds
    Cycloaddition
    Cycloaddition Reaction
    cycloaddition
    dioxides
    Sulfones
    sulfones
    synthesis
    rings
    benzothiophene

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

    Cite this

    Catalytic [2 + 2 + 2] cycloaddition of benzothiophene dioxides with α,ω-diynes for the synthesis of condensed polycyclic compounds. / Tahara, Yu Ki; Gake, Manami; Matsubara, Riku; Shibata, Takanori.

    In: Organic Letters, Vol. 16, No. 22, 21.11.2014, p. 5980-5983.

    Research output: Contribution to journalArticle

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    AU - Shibata, Takanori

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