AuCl3-catalyzed benzannulation: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes

Naoki Asao, Kumiko Takahashi, Sunyoung Lee, Taisuke Kasahara, Yoshinori Yamamoto

    Research output: Contribution to journalArticlepeer-review

    405 Citations (Scopus)

    Abstract

    (Chemical Equation Presented) The reaction of o-alkynylbenzaldehydes 1 and alkynes 2 in the presence of a catalytic amount of AuCl3 in (CH2Cl)2 at 80 °C gave naphthyl ketone products in high yields. The AuCl3-catalyzed formal [4 + 2] benzannulation proceeds most probably through the coordination of the triple bond of 1 to AuCl3, the formation of benzo[c]pyrylium auric ate complex via the nucleophilic addition of the carbonyl oxygen atom, the Diels-Alder addition of alkynes 2 to the auric ate complex, and subsequent bond rearrangement. Similarly, the AuCl3-catalyzed reactions of o-alkynylacetophenone and o-alkynylbenzophenone with phenylacetylene afforded the corresponding naphthyl ketone products in good yields.

    Original languageEnglish
    Pages (from-to)12650-12651
    Number of pages2
    JournalJournal of the American Chemical Society
    Volume124
    Issue number43
    DOIs
    Publication statusPublished - 2002 Oct 30

    ASJC Scopus subject areas

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

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