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Nickel-Catalyzed Sonogashira Reactions of Non-activated Secondary Alkyl Bromides and Iodides

Authors

  • Jun Yi,

    1. Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (China)
    2. State Key Laboratory for Oxo Synthesis and Selective Oxidation Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, 730000 Lanzhou (China)
    3. Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China)
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  • Xi Lu,

    1. Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China)
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  • Yan-Yan Sun,

    1. Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China)
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  • Bin Xiao,

    1. Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (China)
    2. State Key Laboratory for Oxo Synthesis and Selective Oxidation Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, 730000 Lanzhou (China)
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  • Prof. Lei Liu

    Corresponding author
    1. Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (China)
    2. State Key Laboratory for Oxo Synthesis and Selective Oxidation Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, 730000 Lanzhou (China)
    3. Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China)
    • Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (China)

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  • This study was supported by the “863” Program of the Ministry of Science and Technology (2012AA02A700), the National Basic Research Program of China (973 program, No. 2013CB932800), and the NSFC (Nos. 21221062 and 21225207).

Abstract

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A nicked reaction: The title reaction of terminal alkynes with non-activated secondary alkyl iodides and bromides was accomplished for the first time. This reaction provides a new and practical approach for the synthesis of substituted alkynes (see scheme; cod=cyclo-1,5-octadiene).

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