Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Diversification of Carbazoles by LiCl-mediated Catalytic CuI Reaction

  • Cho, Joong-Hyun (Department of Chemistry, Chungnam National University) ;
  • Ryu, Young-Sil (Department of Chemistry, Chungnam National University) ;
  • Oh, Se-Hwan (Department of Chemistry, Chungnam National University) ;
  • Kwon, Jae-Kwan (Department of Chemistry, Chungnam National University) ;
  • Yum, Eul-Kgun (Department of Chemistry, Chungnam National University)
  • Received : 2011.02.24
  • Accepted : 2011.05.16
  • Published : 2011.07.20
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References

  1. Katritziky, A. R.; Rees, C. W.; Scriven, E. F. V. Comprehensive Heterocyclic Chemistry II 1996, 2, 207-257
  2. Knolker, H.-J. Topics in Current Chemistry 2005, 244, 115
  3. Bubniene, G.; Malinauskas, T.; Daskeviciene, M.; Jankauskas, V.;Getautis, V. Tetrahedron 2010, 66, 3199 https://doi.org/10.1016/j.tet.2010.02.086
  4. Wong, W.-Y.; Ho, C.-L.; Gao, Z.-Q.; Mi, B.-X.; Chen, C.-H.; Cheah,K.-W.; Lin, Z. Angew. Chem. Int. Ed. 2006, 45, 7800. https://doi.org/10.1002/anie.200602906
  5. Zhang, K.; Chen, Z.; Yang, C.; Zhang, X.; Tao, Y.; Duan, L.; Chen, L.; Zhu,L.; Qin, J.; Cao, Y. J. Mater. Chem. 2007, 17, 3451. https://doi.org/10.1039/b705342h
  6. Zhang, X.; Chen, Z.; Yang, C.; Li, Z.; Zhang, K.; Yao, H.; Qin, J.; Chen, J.;Cao, Y. Chem. Phys. Lett. 2006, 422, 386. https://doi.org/10.1016/j.cplett.2006.02.097
  7. Ho, C.-L.; Wang, Q.; Lam, C.-S.; Wong, W.-Y.; Ma, D.; Wang, L.; Gao, Z.-Q.; Chen, C.- H.; Cheah, K.-W.; Lim, Z. Chem. Asian. J. 2009, 4, 89. https://doi.org/10.1002/asia.200800226
  8. Baeupre, S.; Boudreault, P.-L. T.; Leclerc, M. Adv. Mater. 2010, 22, E6-27. https://doi.org/10.1002/adma.200903484
  9. Shen, J.-Y.; Yang, X.-L.; Huang, T.-H.; Lin, J. T.; Ke, T.-H.; Chen, L.-Y.; Wu, C.-C.; Yeh, M.-C. P. Adv. Funct. Mater. 2007, 17, 983. https://doi.org/10.1002/adfm.200600921
  10. Chauhan, S. S.; Yi, H.; Iraqi, A. Mol. Cryst. Liq. Crys. 2008, 497, 129.
  11. Li, J.; Grimsdale, A. C. Chem. Soc. Rev. 2010, 39, 2399 https://doi.org/10.1039/b915995a
  12. Kim, D.; Lee, J. K.; Kang, S. O.; Ko, J. J. Tetrahedron 2007, 63, 1913. https://doi.org/10.1016/j.tet.2006.12.082
  13. Bellina, F.; Calandri, C.; Cauteruccio, S.; Ross, R. Eur. J. Org. Chem. 2007, 2147.
  14. Wong, K.-T.; Ku, S.-Y.; Yen, F.-W. Tetrahedron Lett. 2007, 48, 5051. https://doi.org/10.1016/j.tetlet.2007.05.094
  15. Hosseinzadeh, R.; Tajbakhsh, M.; Alikarami, M.; Mohadjerani, M. J. Heterocyclic Chem. 2008, 45, 1815. https://doi.org/10.1002/jhet.5570450640
  16. Xi, Z.; Liu, F.; Zhou, Y.; Chen, W. Tetrahedron 2008, 64, 4254. https://doi.org/10.1016/j.tet.2008.02.082
  17. Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689. https://doi.org/10.1021/ja00017a059
  18. Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652. https://doi.org/10.1021/jo9803277
  19. Hong, K. B.; Lee, C. W.; Yum, E. K. Tetrahderon Lett. 2004, 45, 693. https://doi.org/10.1016/j.tetlet.2003.11.075
  20. Park, S. S.; Choi, J.-K.; Yum, E. K.; Ha, D.-C. Tetrahedron Lett. 1998, 39, 627. https://doi.org/10.1016/S0040-4039(97)10662-1
  21. Chi, S. M.; Choi, J.-K.; Yum, E. K.; Chi, D. Y. Tetrahedron Lett. 2000, 41, 919. https://doi.org/10.1016/S0040-4039(99)02190-5
  22. Lee, M. S.; Yum, E. K. Bull. Korean Chem. Soc. 2002, 23, 535. https://doi.org/10.5012/bkcs.2002.23.4.535
  23. Kang, S. S.; Yum, E. K.; Sung, N. D. Heterocycles 2003, 60, 2727. https://doi.org/10.3987/COM-03-9895
  24. Hong, C. S.; Seo, J. Y.; Yum, E. K.; Sung, N.-D. Heterocycles 2004, 63, 631. https://doi.org/10.3987/COM-03-9965
  25. Hong, C. S.; Seo, J. Y.; Yum, E. K. Tetrahedron Lett. 2007, 48, 4831. https://doi.org/10.1016/j.tetlet.2007.05.062
  26. Kang, S. K.; Park, S. S.; Kim, S. S.; Choi, J.-K.; Yum, E. K. Tetrahedron Lett. 1999, 40, 4379. https://doi.org/10.1016/S0040-4039(99)00753-4
  27. Yum, E. K.; Kang, S. K.; Kim, S. S.; Choi, J.-K.; Cheon, H. G. Bioorg. Med. Chem. Lett. 1999, 9, 1819. https://doi.org/10.1016/S0960-894X(99)00291-7
  28. Lee, W. J.; Gee, M. B.; Yum, E. K. Heterocycles 2003, 60, 1821. https://doi.org/10.3987/COM-03-9798
  29. Freeman, A. W.; Urovoy, M.; Criswell, M. E. J. Org. Chem. 2005, 70, 5014. https://doi.org/10.1021/jo0503299
  30. Dierschke, F.; Grimsdale, A. C.; Mullen, K. Synthesis 2003, 2470.
  31. Barton, N.; Fabre-Franch, I.; Bourrat, D.; Chanbezen, F.; Sadki, S. J. Phys. Chem. 2009, 113, 14087.
  32. Li, J.; Mark, J. J. Chem. Mater. 2008, 20, 4873. https://doi.org/10.1021/cm703689j
  33. Low, P. J.; Paterson, M. J.; Yufit, D. S.; Howward, J. A. K.; Cherryman, J. C.; Tackley, D. R.; Brrok, R.; Brown, B. J. Mater. Chem. 2005, 15, 2304. https://doi.org/10.1039/b417962e
  34. Ma, B.; Lauterwasser, F.; Deng, L.; Zonte, S.; Kim, B. J.; Frechet, J. M. J. Chem. Mater. 2007, 19, 4827. https://doi.org/10.1021/cm0715500
  35. Kitawaki, T.; Hayashi, Y.; Ueno, A.; Chida, N. Tetrahedron 2006, 62, 6792. https://doi.org/10.1016/j.tet.2006.04.087
  36. Kwon, J. K.; Cho, J. H.; Ryu, Y.-S.; Oh, S. H.; Yum, E. K. Tetrahedron 2011, 67, 4820. https://doi.org/10.1016/j.tet.2011.05.022

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