Direct Cross-Couplings of Propargylic Diols

Nicholas J. Green, Anthony C. Willis, Michael S. Sherburn*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    27 Citations (Scopus)

    Abstract

    [Pd(PPh3)4] catalyzes a Suzuki–Miyaura-like twofold cross-coupling sequence between underivatized propargylic diols and either aryl or alkenyl boronic acids to furnish highly substituted 1,3-dienes. Thus, 2,3-diaryl-1,3-butadienes and their dialkenic congeners ([4]dendralenes) are delivered in a (pseudo)halogen-free, single-step synthesis which supersedes existing methods. Allenols are also readily formed. Treatment of these single- and twofold cross-coupled products with acid leads to remarkably short syntheses of highly-substituted benzofulvenes and aryl indenes, respectively.

    Original languageEnglish
    Pages (from-to)9244-9248
    Number of pages5
    JournalAngewandte Chemie - International Edition
    Volume55
    Issue number32
    DOIs
    Publication statusPublished - Aug 2016

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