Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Rapid Microwave-Assisted Copper-Catalyzed Nitration of Aromatic Halides with Nitrite Salts

  • Paik, Seung-Uk (Department of Chemical System Engineering, Keimyung University) ;
  • Jung, Myoung-Geun (Department of Chemical System Engineering, Keimyung University)
  • Received : 2011.10.26
  • Accepted : 2011.11.24
  • Published : 2012.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Schofield, K. Aromatic Nitration; University Press: Cambridge, 1980
  2. Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration: Methods and Mechanism; VCH: New York, 1989.
  3. Fener, H.; Nielson, A. T. Nitro Compounds, Recent Advances in Synthesis and Chemistry; VCH Publisher: New York, 1990.
  4. Vogel, A. A. Text Book of Practical Organic Chemistry; Longman, London, 1978.
  5. Gigante, B.; Prazeres, A. O.; Marcero-Curto, M. J. J. Org. Chem.1995, 60, 3445. https://doi.org/10.1021/jo00116a034
  6. Dove, M. F. A.; Manz, N.; Montgomery, J.; Pattenden, G.; Wood, S. A. J. Chem Soc., Perkin Trans. I 1998, 1589.
  7. Gu, S. X.; Jing, H. W.; Wu, J. G.; Liang, Y. M. Synth. Commun. 1997, 27, 2793. https://doi.org/10.1080/00397919708004154
  8. Mellor, J. M.; Mittoo, S.; Parkes, R.; Millor, R. W. Tetrahedron 2000, 56, 8019. https://doi.org/10.1016/S0040-4020(00)00720-1
  9. Samajdar, S.; Becker, F. F.; Banik, B. K. Tetrahedron Lett. 2000, 41, 8017. https://doi.org/10.1016/S0040-4039(00)01397-6
  10. Zolfigol, M. A.; Ghaemi, E.; Madrakian, E. Molecules 2001, 6, 614. https://doi.org/10.3390/60700614
  11. Rajagopal, R.; Srinivasan, K. V. Synth. Commun. 2003, 33, 961. https://doi.org/10.1081/SCC-120016360
  12. Iranpoor, N.; Firouzabadi, H.; Heydari, R.; Shiri, M. Synth. Commun. 2005, 35, 263. https://doi.org/10.1081/SCC-200048450
  13. Haghnazari, N.; Karami, C.; Ghodrati, K.; Malrki, F. Int. Nano Lett. 2011, 1, 30.
  14. Nowrouzi, N.; Jonaghani, M. Z. Tetrahedron Lett. 2011, 52, 5081. https://doi.org/10.1016/j.tetlet.2011.07.097
  15. Zolfigol, M. A.; Ghaemi, E.; Madrakian, E. Synlett. 2003, 191.
  16. Akhalaghinia, B.; Pourali, A. Turk. J. Chem. 2010, 34, 753.
  17. Zarchi, M. A. K.; Rahmani, F. J. Appl. Polym. Sci. 2011, 121, 582. https://doi.org/10.1002/app.33679
  18. Laali, K.; Gettwert, V. J. J. Org, Chem. 2001, 66, 35. https://doi.org/10.1021/jo000523p
  19. Kwon, P. S.; Kim, J. K.; Kwom, T. W.; Kim, Y. H.; Chung, S. K. Bull. Korean Chem. Soc. 1997, 18, 1118.
  20. Shackeford, S. A.; Anderson, M. B.; Christie, L. C.; Goetzen, T.; Guzman, M. C.; Hananel, M. A.; Korneich, W. D.; Li, H.; Pathak, V. P.; Rabinovich,A. K.; Rajapakse, R. J.; Truesdale, L. K.; Tsank, S. M.; Vazir, H. N. J. Org. Chem. 2003, 68, 267 https://doi.org/10.1021/jo026202q
  21. Deleersnyder, K.; Schaltin, S.; Fransaer, J.; Binnemans, K.; Parac-Vogt, T. N. Tetrahedron Lett. 2009, 50, 4582. https://doi.org/10.1016/j.tetlet.2009.05.093
  22. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. https://doi.org/10.1021/ol0273396
  23. Okano, K.; Tokuyama, H.; Fukuyama, Org. Lett. 2003, 5, 4987. https://doi.org/10.1021/ol035942y
  24. Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, p 133.
  25. Saito, S.; Koizumi, Y. Tetrahedron Lett. 2005, 46, 4715. https://doi.org/10.1016/j.tetlet.2005.05.033
  26. Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 12898. https://doi.org/10.1021/ja905768k

Cited by

  1. Copper-catalyzed rapid C–H nitration of 8-aminoquinolines by using sodium nitrite as the nitro source under mild conditions vol.6, pp.92, 2016, https://doi.org/10.1039/C6RA19583K
  2. Transition‐Metal‐Free Hypervalent Iodine(III) Reagent‐Promoted Site‐Selective Solid‐Phase Synthesis of Mononitroarylamines vol.3, pp.45, 2012, https://doi.org/10.1002/slct.201801783
  3. Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents vol.142, pp.1, 2012, https://doi.org/10.1021/jacs.9b11282
  4. Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer vol.11, pp.None, 2012, https://doi.org/10.1021/acscatal.1c02272
  5. Recent Advances in Microwave-Assisted Copper-Catalyzed Cross-Coupling Reactions vol.11, pp.1, 2021, https://doi.org/10.3390/catal11010046
  6. Selective Copper-Catalyzed Azidation and Amination of Aryl Halides with Sodium Azide vol.32, pp.2, 2012, https://doi.org/10.14478/ace.2021.1012