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

Shiguang Pan, Takayuki Wakaki, Naoto Ryu, Takanori Shibata

    研究成果: Article

    45 引用 (Scopus)

    抄録

    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.

    元の言語English
    ページ(範囲)1257-1260
    ページ数4
    ジャーナルChemistry - An Asian Journal
    9
    発行部数5
    DOI
    出版物ステータスPublished - 2014

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    Alkenylation
    Alkenes
    Air
    Oxidative Coupling
    Cats
    Nitrogen
    Atoms
    Catalysts
    indoline

    ASJC Scopus subject areas

    • Chemistry(all)

    これを引用

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

    :: Chemistry - An Asian Journal, 巻 9, 番号 5, 2014, p. 1257-1260.

    研究成果: Article

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    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.",
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    AU - Shibata, Takanori

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    KW - C-H activation

    KW - indoline

    KW - iridium

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