AuCl-catalyzed [4+2] benzannulation between o-alkynyl(oxo)benzene and benzyne

Asao Naoki, Kenichiro Sato

    Research output: Contribution to journalArticlepeer-review

    77 Citations (Scopus)

    Abstract

    The AuCl-catalyzed benzannulation of o-alkynyl(oxo)benzenes with benzenediazonium 2-carboxylate proceeds under mild conditions and a variety of anthracene derivatives, having a ketone group at the 9-position, are produced in good to high yields. The reaction proceeds most probably through the [4+2] cycloaddition between benzyne and benzopyrylium auric ate complex, which would be generated by the gold-induced electrophilic cyclization of o-alkynyl(oxo)benzenes.

    Original languageEnglish
    Pages (from-to)5361-5363
    Number of pages3
    JournalOrganic letters
    Volume8
    Issue number23
    DOIs
    Publication statusPublished - 2006 Nov 9

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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