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Regio- and Chemoselective C[BOND]H Chlorination/Bromination of Electron-Deficient Arenes by Weak Coordination and Study of Relative Directing-Group Abilities

Authors

  • Xiuyun Sun,

    1. Department of Pharmacology and Pharmaceutical Sciences, School of Medicine and School of Life Sciences, Tsinghua University, Beijing, 100084 (China)
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    • These authors contributed equally to this work.

  • Gang Shan,

    1. Department of Pharmacology and Pharmaceutical Sciences, School of Medicine and School of Life Sciences, Tsinghua University, Beijing, 100084 (China)
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    • These authors contributed equally to this work.

  • Yonghui Sun,

    1. Department of Pharmacology and Pharmaceutical Sciences, School of Medicine and School of Life Sciences, Tsinghua University, Beijing, 100084 (China)
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  • Prof. Dr. Yu Rao

    Corresponding author
    1. Department of Pharmacology and Pharmaceutical Sciences, School of Medicine and School of Life Sciences, Tsinghua University, Beijing, 100084 (China)
    • Department of Pharmacology and Pharmaceutical Sciences, School of Medicine and School of Life Sciences, Tsinghua University, Beijing, 100084 (China)===

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  • This work was supported by the National “973” Grant (grant no 2011CB965300), an NSFC grant (grant no 21142008), and the Tsinghua University Initiative Scientific Research Program.

Abstract

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It's all relative: A practical and efficient PdII-catalyzed regio- and chemoselective chlorination/bromination has been developed for the facile synthesis of a broad range of aromatic chlorides. The reaction demonstrates excellent reactivity, good functional-group tolerance, and high yields. A preliminary study was conducted to evaluate relative directing-group abilities of various functionalities.

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