A Study on N-Arylation of Indole Using Copper Nitrate or Copper Carbonate as a Catalyst

Copper Nitrate와 Copper Carbonate를 촉매로 이용한 Indole의 N-Arylation 연구

  • Lee, Jun Young (Department of Chemical System Engineering, Keimyung University) ;
  • Yang, Min Ho (Department of Chemical System Engineering, Keimyung University) ;
  • Paik, Seung Uk (Department of Chemical System Engineering, Keimyung University)
  • 이준영 (계명대학교 공과대학 화학시스템공학과) ;
  • 양민호 (계명대학교 공과대학 화학시스템공학과) ;
  • 백승욱 (계명대학교 공과대학 화학시스템공학과)
  • Received : 2008.08.25
  • Accepted : 2008.09.27
  • Published : 2008.12.10

Abstract

N-Arylation of indole with aryl iodides has been achieved by employing copper nitrate or copper cabonate as a catalyst, which might be more practical and economical over any other copper- or palladium-based catalysts for industrial applications. N,N'-dimethylethylenediamine was found to be the most effective with copper nitrate catalyst systems, while ethylenediamine was the most active with copper carbonate.

Keywords

arylation;copper nitrate;copper cabonate;indole

Acknowledgement

Supported by : 계명대학교

References

  1. F. He, B. M. Foxman, and B. B. Snider, J. Am. Chem. Soc., 120, 6417 (1998) https://doi.org/10.1021/ja9809408
  2. A. Klapars, J. C. Antilla, X. Huang, and S. L. Buchward, J. Am. Chem. Soc., 123, 7727 (2001). https://doi.org/10.1021/ja016226z
  3. J. C. Antilla and S. L. Buchwald, Org. Lett., 3, 2077 (2001) https://doi.org/10.1021/ol0160396
  4. P. Lopez-Alvarado, C. Avandano, and J. C. Menendez, J. Org. Chem., 61, 5865 (1996) https://doi.org/10.1021/jo960566z
  5. M. Sainsbury, Tetrahedron, 36, 3327 (1980) https://doi.org/10.1016/0040-4020(80)80185-2
  6. S.V. Ley, and A. W. Thomas, Angew. Chem. Int. Ed., 42, 5400 (2003) https://doi.org/10.1002/anie.200300594
  7. F. Ullmann, Ber. Dtsch. Chem. Ges. 36, 2382 (1903). https://doi.org/10.1002/cber.190303602174
  8. G. R. Martinez, K. A. M. Walker, D. R. Herschfield, J. J. Bruno, D. S. Yang, and P. J. Moloney, J. Med. Chem., 35, 620 (1992) https://doi.org/10.1021/jm00082a002
  9. J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, and M. Lemaire, Chem. Rev., 102, 1359 (2002) https://doi.org/10.1021/cr000664r
  10. S. K. Kang, D. H. Kim, and J. N. Park, Synlett, 3, 427 (2002)
  11. T. Manifar, S. Rohani, T. P. Bender, H. B. Goodbrand, R. Gaynor, and M. Saban, Ind. Eng. Chem. Res., 44, 789 (2005). https://doi.org/10.1021/ie0493513
  12. R. J. Sorenson, Org. Chem., 65, 7747 (2000) https://doi.org/10.1021/jo000614m
  13. H. M. Lee and S. P. Nolan, Org. Lett., 2, 2053 (2000) https://doi.org/10.1021/ol005956t
  14. G. I. Elliott and J. P. Konopelski, Org. Lett. 2, 3055 (2000) https://doi.org/10.1021/ol006271w
  15. M. Wolter, A. Klapars, and S. L. Buchwald, Org. Lett., 3, 3803 (2001) https://doi.org/10.1021/ol0168216