Radical bromoallylation of alkynes leading to 1-bromo-1,4-dienes

Takashi Kippo, Kanako Hamaoka, Mitsuhiro Ueda, Takahide Fukuyama, Ilhyong Ryu*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    6 Scopus citations

    Abstract

    The full scope (30 examples) of the radical bromoallylation of alkynes using allyl bromides was studied. In this reaction, bromine radical adds to alkynes to form vinyl radicals, which then undergo an SH2′ reaction with allyl bromides to produce good yields of 1-bromo-1,4-dienes with the liberation of a bromine radical, which creates a radical chain. The sp2-carbon–bromine bond of the product dienes was further functionalized via cross-coupling and carbonylation reactions.

    Original languageEnglish
    Pages (from-to)7866-7874
    Number of pages9
    JournalTetrahedron
    Volume72
    Issue number48
    DOIs
    StatePublished - 1 Jan 2016

    Keywords

    • Alkynes
    • Allyl bromides
    • Bromoallylation
    • Dienes
    • Radical reaction

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