Copper-Catalyzed Aerobic Oxidative C[BOND]H and C[BOND]C Functionalization of 1-[2-(Arylamino)aryl]ethanones Leading to Acridone Derivatives

Authors

  • Jipan Yu,

    1. Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (P.R. China), Fax: (+86) 10-62781695
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  • Dr. Haijun Yang,

    1. Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (P.R. China), Fax: (+86) 10-62781695
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  • Prof. Dr. Yuyang Jiang,

    1. Key Laboratory of Chemical Biology (Guangdong Province), Graduate School of Shenzhen, Tsinghua University, Shenzhen 518057 (P.R. China)
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  • Prof. Dr. Hua Fu 

    Corresponding author
    1. Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (P.R. China), Fax: (+86) 10-62781695
    2. Key Laboratory of Chemical Biology (Guangdong Province), Graduate School of Shenzhen, Tsinghua University, Shenzhen 518057 (P.R. China)
    • Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084 (P.R. China), Fax: (+86) 10-62781695

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Abstract

Efficient copper-catalyzed aerobic oxidative C[BOND]H and C[BOND]C functionalization of 1-[2-(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic C[BOND]H and acetyl C[BOND]C bonds with intramolecular formation of a diarylketone bond. The protocol uses inexpensive Cu(O2CCF3)2 as catalyst, pyridine as additive, and economical and environmentally friendly oxygen as the oxidant, and the corresponding acridones with various functional groups were obtained in moderate to good yields.

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