Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers

Shuhei Sumino, Takahide Fukuyama, Mika Sasano, Ilhyong Ryu, Antoine Jacquet, Frederic Robert, Yannick Landais

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Four-component coupling reactions between xanthogenates, alkenes, CO, and sulfonyl oxime ethers were studied. In the presence of hexabutylditin, working as a propagating radical reagent, the chain reaction proceeds, as expected, taking into account reagents polarities, affording the corresponding functionalized alpha-keto oximes. Although yields are modest, this rare one-pot four-component process is easy to carry out and the resulting compounds, bearing multiple functionalities, have the potential for further elaboration.

    Original languageEnglish
    Pages (from-to)1822-1828
    Number of pages7
    JournalBeilstein Journal of Organic Chemistry
    Volume15
    DOIs
    StatePublished - 31 Jul 2019

    Keywords

    • CO
    • multicomponent reaction
    • radicals
    • sulfonyl oxime ethers
    • xanthogenates
    • MIZOROKI-HECK REACTION
    • CARBON-MONOXIDE
    • ALPHA-SCISSION
    • ALKYL IODIDES
    • CARBONYLATION
    • ISONITRILES
    • PRECURSORS
    • TOOL

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