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Efficient Copper-Catalyzed Ullmann Reaction of Aryl Bromides with Imidazoles in Water Promoted by a pH-Responsive Ligand

Authors

  • Rui Lv,

    1. State Key Laboratory of Structural Chemistry, Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Science, Fuzhou, Fujian, 350002 (China), Fax: (+86) 591-83714946
    2. University of Chinese Academy of Sciences, Beijing 100049 (China)
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  • Yangxin Wang,

    1. State Key Laboratory of Structural Chemistry, Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Science, Fuzhou, Fujian, 350002 (China), Fax: (+86) 591-83714946
    2. University of Chinese Academy of Sciences, Beijing 100049 (China)
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  • Dr. Chunshan Zhou,

    1. State Key Laboratory of Structural Chemistry, Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Science, Fuzhou, Fujian, 350002 (China), Fax: (+86) 591-83714946
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  • Dr. Liuyi Li,

    1. State Key Laboratory of Structural Chemistry, Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Science, Fuzhou, Fujian, 350002 (China), Fax: (+86) 591-83714946
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  • Prof. Ruihu Wang

    Corresponding author
    1. State Key Laboratory of Structural Chemistry, Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Science, Fuzhou, Fujian, 350002 (China), Fax: (+86) 591-83714946
    • State Key Laboratory of Structural Chemistry, Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Science, Fuzhou, Fujian, 350002 (China), Fax: (+86) 591-83714946
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Abstract

A series of 1,10-phenanthroline derivatives were used as supporting ligands for copper-catalyzed Ullmann reaction in neat water. The catalytic system based on 4,7-dihydroxy-1,10-phenanthroline has demonstrated the promising catalytic performances for aryl bromides. The catalytic system was applicable to a wide scope of substrates, high catalytic activity and selectivity were observed for the reactions of electron-deficient, electron-rich, and heterocyclic aryl bromides with imidazoles containing different steric hindrance. The superior promoting effect of 4,7-dihydroxy-1,10-phenanthroline is attributed to its water solubility under the basic conditions.

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