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Alkylboronic Esters from Copper-Catalyzed Borylation of Primary and Secondary Alkyl Halides and Pseudohalides

Authors

  • Chu-Ting Yang,

    1. Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China)
    2. Department of Chemistry, Tsinghua University, Beijing 100084 (China)
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  • Zhen-Qi Zhang,

    1. Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China)
    2. Department of Chemistry, Tsinghua University, Beijing 100084 (China)
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  • Hazmi Tajuddin,

    1. Department of Chemistry, Durham University, South Road, Durham DH1 3LE (U.K.)
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  • Chen-Cheng Wu,

    1. Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China)
    2. Department of Chemistry, Tsinghua University, Beijing 100084 (China)
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  • Jun Liang,

    1. Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China)
    2. Department of Chemistry, Tsinghua University, Beijing 100084 (China)
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  • Jing-Hui Liu,

    1. Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China)
    2. Department of Chemistry, Tsinghua University, Beijing 100084 (China)
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  • Yao Fu,

    1. Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China)
    2. Department of Chemistry, Tsinghua University, Beijing 100084 (China)
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  • Maria Czyzewska,

    1. Department of Chemistry, Durham University, South Road, Durham DH1 3LE (U.K.)
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  • Dr. Patrick G. Steel,

    Corresponding author
    1. Department of Chemistry, Durham University, South Road, Durham DH1 3LE (U.K.)
    • Department of Chemistry, Durham University, South Road, Durham DH1 3LE (U.K.)
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  • Prof. Dr. Todd B. Marder,

    Corresponding author
    1. Department of Chemistry, Durham University, South Road, Durham DH1 3LE (U.K.)
    • Department of Chemistry, Durham University, South Road, Durham DH1 3LE (U.K.)
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  • Prof. Dr. Lei Liu

    Corresponding author
    1. Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China)
    2. Department of Chemistry, Tsinghua University, Beijing 100084 (China)
    • Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China)
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  • We thank the NSFC (Nos. 20932006 and 20972148), EPSRC, and GlaxoSmithKline (GSK) for financial support of this work (Grant EP/F068158/1) and Drs A. Maxwell and L. Shukla (GSK) for helpful discussions. T.B.M. thanks the EPSRC for an Overseas Research Travel Grant, the RCUK China Office for support of the first UK-China Research Workshop on “Metals in Organic Synthesis: Toward Cleaner, Greener Chemical Processes”, the Royal Society for a Wolfson Research Merit Award, and AllyChem Co. Ltd. for a generous donation of diboron reagents.

Abstract

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Easy access: An unprecedented copper-catalyzed cross-coupling reaction of the title compounds with diboron reagents is described (see scheme; Ts=4-toluenesulfonyl). This reaction can be used to prepare both primary and secondary alkylboronic esters having diverse structures and functional groups. The resulting products would be difficult to access by other means.

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