Ir(III)-catalyzed C7-position-selective oxidative C -H alkenylation of indolines with alkenes in air

Shiguang Pan, Takayuki Wakaki, Naoto Ryu, Takanori Shibata

    Research output: Contribution to journalArticle

    45 Citations (Scopus)

    Abstract

    An efficient method for C7-position-selective alkenylation of N-substituted indolines with alkenes is reported. Various 7-alkenylindolines were obtained in moderate to excellent yields in air in the presence of catalytic amounts of [CpIrCl2]2, AgOTf, and Cu(OAc)2. The protocol relies on the use of a carbonyl or carbamoyl group on the nitrogen atom of indoline as a directing group and is potentially applicable to the synthesis of 7-alkenylindoles and 7-alkylindoles. Lettin the cat outta the bag: An efficient IrIII-catalyzed oxidative coupling of N-substituted indolines with various alkenes at the C7-position in air assisted by a carbonyl or carbamoyl group as a directing group is reported. The catalyst was prepared from [CpIrCl2]2 and AgOTf. A variety of 7-alkenylindolines were obtained in moderated to high yields. The reaction is potentially applicable to the synthesis of 7-alkylindoles and 7-alkenylindoles.

    Original languageEnglish
    Pages (from-to)1257-1260
    Number of pages4
    JournalChemistry - An Asian Journal
    Volume9
    Issue number5
    DOIs
    Publication statusPublished - 2014

    Fingerprint

    Alkenylation
    Alkenes
    Air
    Oxidative Coupling
    Cats
    Nitrogen
    Atoms
    Catalysts
    indoline

    Keywords

    • alkenes
    • alkenylation
    • C-H activation
    • indoline
    • iridium

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Ir(III)-catalyzed C7-position-selective oxidative C -H alkenylation of indolines with alkenes in air. / Pan, Shiguang; Wakaki, Takayuki; Ryu, Naoto; Shibata, Takanori.

    In: Chemistry - An Asian Journal, Vol. 9, No. 5, 2014, p. 1257-1260.

    Research output: Contribution to journalArticle

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