AuCl-catalyzed reaction of ortho-alkynyl(oxo)benzene with benzenediazonium 2-carboxylate as a synthetic method towards anthracene, triptycene, and phthalazine derivatives

Kenichiro Sato, Menggenbateer, Toshihiko Kubota, Naoki Asao

    Research output: Contribution to journalArticle

    15 Citations (Scopus)

    Abstract

    The AuCl-catalyzed benzannulation of ortho-alkynylphenyl ketones with benzenediazonium 2-carboxylate proceeded efficiently at 40 °C in (CH2Cl)2 and a variety of anthracene derivatives, having a ketone group at 9-position, were produced in good to high yields. On the other hand, the reaction of ortho-alkynylbenzaldehydes with benzenediazonium 2-carboxylate afforded triptycyl ketones. The reactions most probably proceed through the formation of a zwitterionic intermediate by the gold-induced electrophilic cyclization of ortho-alkynyl(oxo)benzenes, followed by the cycloaddition of benzyne. In contrast, when the above reaction was carried out at rt in 1,4-dioxane, phthalazine derivative was produced without the generation of benzyne.

    Original languageEnglish
    Pages (from-to)787-796
    Number of pages10
    JournalTetrahedron
    Volume64
    Issue number5
    DOIs
    Publication statusPublished - 2008 Jan 28

    Keywords

    • Anthracene
    • Benzannulation
    • Benzyne
    • Gold catalyst

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

    Fingerprint Dive into the research topics of 'AuCl-catalyzed reaction of ortho-alkynyl(oxo)benzene with benzenediazonium 2-carboxylate as a synthetic method towards anthracene, triptycene, and phthalazine derivatives'. Together they form a unique fingerprint.

  • Cite this