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Copper-catalyzed intramolecular C–N coupling reaction of aryl halide with amide

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Abstract

An efficient and concise method for the ligand-free copper-catalyzed intramolecular C–N bond coupling was developed, which afforded various (NH)-phenanthridinones in good to excellent yields with tolerance of various substrates.

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References

  1. Z. Jin, Nat. Prod. Rep. 28, 1126 (2011)

    Article  CAS  Google Scholar 

  2. S. Ghosal, P.H. Rao, D.K. Jaiswal, Y. Kumar, A.W. Frahm, Phytochemistry 20, 2003 (1981)

    Article  CAS  Google Scholar 

  3. J.M. Llabrés, F. Viladomat, J. Bastida, C. Codina, M. Rubiralta, Phytochemistry 25, 2637 (1986)

    Article  Google Scholar 

  4. S. Ghosal, K.S. Saini, A.W. Frahm, Phytochemistry 22, 2305 (1983)

    Article  CAS  Google Scholar 

  5. J. Hu, W.-D. Zhang, Y.-H. Shen, C. Zhang, L. Xu, R.-H. Liu, B. Wang, X.-K. Xu, Biochem. Syst. Ecol. 35, 114 (2007)

    Article  CAS  Google Scholar 

  6. S. Patil, S. Kamath, T. Sanchez, N. Neamati, R.F. Schinazi, J.K. Buolamwini, Bioorg. Med. Chem. 15, 1212 (2007)

    Article  CAS  Google Scholar 

  7. D. Bellocchi, A. Macchiarulo, G. Costantino, R. Pellicciari, Bioorg. Med. Chem. 13, 1151 (2005)

    Article  CAS  Google Scholar 

  8. T. Watanabe, Y. Ohashi, R. Yoshino, N. Komano, M. Eguchi, S. Maruyama, T. Ishikawa, Org. Biomol. Chem. 1, 3024 (2003)

    Article  CAS  Google Scholar 

  9. P. Lv, K. Huang, L. Xie, X. Xu, Org. Biomol. Chem. 9, 3133 (2011)

    Article  CAS  Google Scholar 

  10. B.S. Bhakuni, A. Kumar, S.J. Balkrishna, J.A. Sheikh, S. Konar, S. Kumar, Org. Lett. 14, 2838 (2012)

    Article  CAS  Google Scholar 

  11. E. Dubost, R. Magnelli, T. Cailly, R. Legay, F. Fabis, S. Rault, Tetrahedron 66, 5008 (2010)

    Article  CAS  Google Scholar 

  12. M.-J. Wu, C.-F. Lin, W.-D. Lu, J. Org. Chem. 67, 5907 (2002)

    Article  CAS  Google Scholar 

  13. M.D. Ganton, M.A. Kerr, Org. Lett. 7, 4777 (2005)

    Article  CAS  Google Scholar 

  14. C. Lu, A.V. Dubrovskiy, R.C. Larock, J. Org. Chem. 77, 8648 (2012)

    Article  CAS  Google Scholar 

  15. G. Zhang, X. Zhao, Y. Yan, C. Ding, Eur. J. Org. Chem. 2012, 669 (2012)

  16. C.S. Yeung, X. Zhao, N. Borduas, V.M. Dong, Chem. Sci. 1, 331 (2010)

    Article  CAS  Google Scholar 

  17. G.-W. Wang, T.-T. Yuan, D.-D. Li, Angew. Chem. Int. Ed. 50, 1380 (2011)

    Article  CAS  Google Scholar 

  18. J. Karthikeyan, C.-H. Cheng, Angew. Chem. Int. Ed. 50, 9880 (2011)

    Article  CAS  Google Scholar 

  19. V. Rajeshkumar, T.-H. Lee, S.-C. Chuang, Org. Lett. 15, 1468 (2013)

    Article  CAS  Google Scholar 

  20. Y.-F. Chen, Y.-S. Wu, Y.-H. Jhan, J.-C. Hsieh, Org. Chem. Front. 1, 253 (2014)

    Article  CAS  Google Scholar 

  21. J.-C. Hsieh, Y.-C. Chen, A.-Y. Cheng, H.-C. Tseng, Org. Lett. 14, 1282 (2012)

    Article  CAS  Google Scholar 

  22. J.-C. Wan, J.-M. Huang, Y.-H. Jhan, J.-C. Hsieh, Org. Lett. 15, 2742 (2013)

    Article  CAS  Google Scholar 

  23. Y.-F. Chen, J.-C. Hsieh, Org. Lett. 16, 4642 (2014)

    Article  CAS  Google Scholar 

  24. J.-C. Hsieh, A.-Y. Cheng, J.-H. Fu, T.-W. Kang, Org. Biomol. Chem. 10, 6404 (2012)

    Article  CAS  Google Scholar 

  25. Y.-H. Jhan, T.-W. Kang, J.-C. Hsieh, Tetrahedron Lett. 54, 1155 (2013)

    Article  CAS  Google Scholar 

  26. S. Tanimori, U. Inaba, Y. Kato, H. Ura, H. Kashiwagi, T. Nishimura, M. Kirihata, Res. Chem. Intermed. 40, 2157 (2014)

    Article  CAS  Google Scholar 

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Acknowledgment

We thank the Ministry of Science and Technology of Republic of China (MOST 103-2113-M-032-009-MY2) for financial support of this research.

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Correspondence to Jen-Chieh Hsieh.

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Chen, WL., Jhang, YY. & Hsieh, JC. Copper-catalyzed intramolecular C–N coupling reaction of aryl halide with amide. Res Chem Intermed 43, 3517–3526 (2017). https://doi.org/10.1007/s11164-016-2438-6

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  • DOI: https://doi.org/10.1007/s11164-016-2438-6

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