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

  1. Jipan Yu1,
  2. Dr. Haijun Yang1,
  3. Prof. Dr. Yuyang Jiang2,
  4. Prof. Dr. Hua Fu 1,2,*

Article first published online: 10 FEB 2013

DOI: 10.1002/chem.201204169

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 19, Issue 13, pages 4271–4277, March 25, 2013

Additional Information

How to Cite

Yu, J., Yang, H., Jiang, Y. and Fu , H. (2013), Copper-Catalyzed Aerobic Oxidative C[BOND]H and C[BOND]C Functionalization of 1-[2-(Arylamino)aryl]ethanones Leading to Acridone Derivatives. Chem. Eur. J., 19: 4271–4277. doi: 10.1002/chem.201204169

Author Information

  1. 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. 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

Publication History

  1. Issue published online: 15 MAR 2013
  2. Article first published online: 10 FEB 2013
  3. Manuscript Revised: 20 DEC 2012
  4. Manuscript Received: 22 NOV 2012

Funded by

  • National Natural Science Foundation of China. Grant Numbers: 21172128, 21105054
  • Ministry of Science and Technology of China. Grant Number: 2012CB722605
  • Doctoral Program of Higher Education. Grant Number: 20090002110058

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Keywords:

  • C[BOND]C activation;
  • C[BOND]H activation;
  • cyclization;
  • nitrogen heterocycles;
  • synthetic methods

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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