Transition-Metal-Catalyst-Free Cross-Coupling Reaction of Secondary Propargylic Acetates with Alkenyl- and Arylboronic Acids

Mitsuhiro Ueda*, Daiki Nakakoji, Takahiro Morisaki, Ilhyong Ryu

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    5 Scopus citations

    Abstract

    A cross-coupling reaction between secondary propargylic acetates and alkenylboronic acids proceeded to give 1,4-enynes in good yields without addition of transition metal catalyst and base. This simple protocol was also applicable to arylboronic acids, which gave 3-arylated alkynes in good yields. The observed induction period suggested that the reaction of propargylic acetates and organoboronic acids was affected by the in-situ generated AcOH as a catalyst, which was confirmed by a separate experiment.

    Original languageEnglish
    Pages (from-to)7040-7045
    Number of pages6
    JournalEuropean Journal of Organic Chemistry
    Volume2017
    Issue number47
    DOIs
    StatePublished - 22 Dec 2017

    Keywords

    • Alkenylboronic acids
    • Arylboronic acids
    • Catalyst-free reactions
    • Cross-coupling
    • Propargylic acetates

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