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首页> 外文期刊>Chemistry: A European journal >A General Nickel-Catalyzed Method for C-H Bond Alkynylation of Heteroarenes Through Chelation Assistance
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A General Nickel-Catalyzed Method for C-H Bond Alkynylation of Heteroarenes Through Chelation Assistance

机译：通过螯合助力辅助的一般镍催化方法C-H键炔醇烷基化

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摘要

A general nickel-catalyzed method for the alkynylation of heteroarenes through monodentate chelation assistance is described. Many heterocycles, including indoles, pyrroles, imidazoles, and pyrazole, efficiently coupled with (triisopropylsilyl) alkynyl bromide, and synthetically important functional groups, such as halides, ether, nitrile, and nitro, are tolerated. Synthetic applicability of this Ni-catalyzed method is demonstrated by the removal of the triisopropylsilyl group and further functionalization to triazolyl, benzofuranyl, and alkynyl arene derivatives. Preliminary mechanistic investigations of the alkynylation of indole suggest that the reaction proceeds through kinetically relevant C-H activation and follows a two-electron redox pathway. A catalytically relevant Ni species, namely, [(Phen)_3Ni]NiBr_4 (PheN= 1,10-phenanthroline), was isolated and structurally characterized.
机译：描述了一种通过单齿螯合辅助来烷基化杂烯化烷基化的一般镍催化方法。 许多杂环，包括与（三异丙基甲硅烷基）炔基溴和合成的卤化物，乙醚，腈和硝基等合成重要的官能团（如卤化物，乙醚，腈和硝基）的吲哚，胃溶解，咪唑和吡唑。 通过除去三丙基甲硅烷基和三唑基，苯并呋喃基和炔基芳烃衍生物，证明了该Ni催化方法的合成适用性。 吲哚醇丙基化的初步机械研究表明，反应通过动力学上相关的C-H激活进行，并遵循双电子氧化还原途径。 分离和结构表征催化相关的Ni物种，即[（phen）_3Ni] nibr_4（phen = 1,10-菲咯啉）。

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  • 来源
    《Chemistry: A European journal》 |2017年第12期|共8页
  • 作者

    Shrikant M. Khake; Vineeta Soni; Rajesh G. Gonnade; Benudhar Punji;

  • 作者单位

    Organometallic Synthesis and Catalysis Group Chemical Engineering Division CSIR-National Chemical Laboratory (CSIR-NCL) Dr. Homi Bhabha Road Pune 411 008 Maharastra (India);

    Organometallic Synthesis and Catalysis Group Chemical Engineering Division CSIR-National Chemical Laboratory (CSIR-NCL) Dr. Homi Bhabha Road Pune 411 008 Maharastra (India);

    Centre for Material Characterization CSIR-National Chemical Laboratory (CSIR-NCL) Dr. Homi Bhabha Road Pune 411 008 Maharastra (India);

    Organometallic Synthesis and Catalysis Group Chemical Engineering Division CSIR-National Chemical Laboratory (CSIR-NCL) Dr. Homi Bhabha Road Pune 411 008 Maharastra (India);

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 应用化学;
  • 关键词

    alkynylation; C-H activation; homogeneous catalysis; nickel; nitrogen heterocycles;

    机译：alkynylation;C-H激活;均匀催化;镍;氮杂环;

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