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Organic Chemistry International
Volume 2012 (2012), Article ID 515092, 7 pages
http://dx.doi.org/10.1155/2012/515092
Research Article

Room Temperature N-Arylation of 1,2,4-Triazoles under Ligand-Free Condition

1Department of Applied Chemistry, Priyadarshini College of Engineering and Technology, Hingna, Maharashtra, Nagpur 440019, India
2Department of Chemistry, Government Institute of Science, Civil Lines, Maharashtra, Nagpur 440001, India

Received 13 June 2012; Accepted 14 August 2012

Academic Editor: Robert Batey

Copyright © 2012 Nikhil V. Suramwar et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. Y. Kuwabara, H. Ogawa, H. Inada, N. Noma, and Y. Shirota, “Thermally stable multilayered organic electroluminescent devices using novel starburst molecules, 4,4′,4-tri(N-carbazolyl)triphenylamine (TCTA) and 4,4′,4-tris(3-methylphenylphenyl-amino)triphenylamine (m-MTDATA), as hole-transport materials,” Advanced Materials, vol. 6, no. 9, pp. 677–679, 1994. View at Scopus
  2. N. X. Hu, S. Xie, Z. Popovic, B. Ong, A. M. Hor, and S. Wang, “5,11-dihydro-5,11-di-1-naphthylindolo[3,2-b]carbazole: atropisomerism in a novel hole-transport molecule for organic light-emitting diodes,” Journal of the American Chemical Society, vol. 121, no. 21, pp. 5097–5098, 1999. View at Publisher · View at Google Scholar · View at Scopus
  3. S. Maiorana, C. Baldoli, P. Del Buttero, M. Di Ciolo, and A. Papagni, “Aromatic nucleophilic substitution on haloarene chromium tricarbonyl complexes: mild N-arylation on indoles,” Synthesis, no. 5, pp. 735–738, 1998. View at Scopus
  4. A. Kiyomori, J. F. Marcoux, and S. L. Buchwald, “An efficient copper-catalyzed coupling of aryl halides with imidazoles,” Tetrahedron Letters, vol. 40, no. 14, pp. 2657–2660, 1999. View at Publisher · View at Google Scholar · View at Scopus
  5. W. J. Smith and J. S. Sawyer, “A novel and selective method for the N-arylation of indoles mediated by KF/Al2O3,” Tetrahedron Letters, vol. 37, no. 3, pp. 299–302, 1996. View at Publisher · View at Google Scholar · View at Scopus
  6. I. P. Beletskaya, D. V. Davydov, and M. Moreno-Mañas, “Pd- and Cu-catalyzed selective arylation of benzotriazole,” Tetrahedron Letters, vol. 39, no. 31, pp. 5617–5620, 1998. View at Publisher · View at Google Scholar · View at Scopus
  7. G. Mann, J. F. Hartwig, M. S. Driver, and C. F. Rivas, “Palladium-catalyzed C−N(sp2) bond formation: N-Arylation of aromatic and unsaturated nitrogen and the reductive elimination chemistry of palladium azolyl and methyleneamido complexes,” Journal of the American Chemical Society, vol. 120, pp. 827–828, 1998. View at Publisher · View at Google Scholar
  8. K. Prabakaran, P. Manivel, and F. Nawaz Khan, “An effective BINAP and microwave accelerated palladium-catalyzed amination of 1-chloroisoquinolines in the synthesis of new 1,3-disubstituted isoquinolines,” Tetrahedron Letters, vol. 51, no. 33, pp. 4340–4343, 2010. View at Publisher · View at Google Scholar · View at Scopus
  9. A. Klapars, J. C. Antilla, X. Huang, and S. L. Buchwald, “A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles,” Journal of the American Chemical Society, vol. 123, no. 31, pp. 7727–7729, 2001. View at Publisher · View at Google Scholar · View at Scopus
  10. J. D. Hicks, A. M. Hyde, A. M. Cuezva, and S. L. Buchwald, “Pd-catalyzed N-arylation of secondary acyclic amides: Catalyst development, scope, and computational study,” Journal of the American Chemical Society, vol. 131, no. 46, pp. 16720–16734, 2009. View at Publisher · View at Google Scholar · View at Scopus
  11. M. Kim and S. Chang, “Rhodium(NHC)-catalyzed amination of aryl bromides,” Organic Letters, vol. 12, pp. 1640–1643, 2010. View at Publisher · View at Google Scholar
  12. R. Omar-Amrani, A. Thomas, E. Brenner, R. Schneider, and Y. Fort, “Efficient nickel-mediated intramolecular amination of aryl chlorides,” Organic Letters, vol. 5, no. 13, pp. 2311–2314, 2003. View at Publisher · View at Google Scholar · View at Scopus
  13. P. F. Larsson, A. Correa, M. Carril, P. O. Norrby, and C. Bolm, “Copper-catalyzed cross-couplings with part-per-million catalyst loadings,” Angewandte Chemie, vol. 48, no. 31, pp. 5691–5693, 2009. View at Publisher · View at Google Scholar · View at Scopus
  14. A. Shafir and S. L. Buchwald, “Highly selective room-temperature copper-catalyzed C–Ncoupling reactions,” Journal of the American Chemical Society, vol. 128, pp. 8742–8743, 2006. View at Publisher · View at Google Scholar
  15. J. C. Antilla, J. M. Baskin, T. E. Barder, and S. L. Buchwald, “Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles,” Journal of Organic Chemistry, vol. 69, no. 17, pp. 5578–5587, 2004. View at Publisher · View at Google Scholar · View at Scopus
  16. H. B. Goodbrand and N. X. Hu, “Ligand-accelerated catalysis of the Ullmann condensation: application to hole conducting triarylamines,” The Journal of Organic Chemistry, vol. 64, pp. 670–674, 1999. View at Publisher · View at Google Scholar
  17. R. Gujadhur, D. Venkataraman, and J. T. Kintigh, “Formation of aryl-nitrogen bonds using a soluble copper(I) catalyst,” Tetrahedron Letters, vol. 42, no. 29, pp. 4791–4793, 2001. View at Publisher · View at Google Scholar · View at Scopus
  18. D. W. Ma, Q. Cai, and H. Zhang, “Mild method for Ullmann coupling reaction of amines and aryl halides,” Organic Letters, vol. 5, pp. 2453–2455, 2003. View at Publisher · View at Google Scholar
  19. H. Kaddouri, V. Vicente, A. Ouali, F. Ouazzani, and M. Taillefer, “Copper-catalyzed arylation of nucleophiles by using butadienylphosphines as ligands: mechanistic insight,” Angewandte Chemie, vol. 48, no. 2, pp. 333–336, 2009. View at Publisher · View at Google Scholar · View at Scopus
  20. E. Haldón, E. Alvarez, M. Carmen Nicasio, and P. J. Pérez, “Dinuclear copper(I) complexes as precatalysts in Ulimann and Goldberg coupling reactions,” Organometallics, vol. 28, no. 13, pp. 3815–3821, 2009. View at Publisher · View at Google Scholar · View at Scopus
  21. K. Okano, H. Tokuyama, and T. Fukuyama, “Synthesis of secondary arylamines through copper-mediated intermolecular aryl amination,” Organic Letters, vol. 5, no. 26, pp. 4987–4990, 2003. View at Publisher · View at Google Scholar · View at Scopus
  22. A. Correa and C. Bolm, “Ligand-Free copper-catalyzed N-arylation of nitrogen nucleophiles,” Advanced Synthesis & Catalysis, vol. 349, pp. 2673–2676, 2007. View at Publisher · View at Google Scholar
  23. M. Taillefer, N. Xia, and A. Ouali, “Efficient iron/copper co-catalyzed arylation of nitrogen nucleophiles,” Angewandte Chemie, vol. 46, no. 6, pp. 934–936, 2007. View at Publisher · View at Google Scholar · View at Scopus
  24. Z. J. Liu, J. P. Vors, E. R. F. Gesing, and C. Bolm, “Microwave-assisted solvent- and ligand-free copper-catalysed cross-coupling between halopyridines and nitrogen nucleophiles,” Green Chemistry, vol. 13, no. 1, pp. 42–45, 2011. View at Publisher · View at Google Scholar · View at Scopus
  25. B. M. Choudary, C. Sridhar, M. L. Kantam, G. T. Venkanna, and B. Sreedhar, “Design and evolution of copper apatite catalysts for N-arylation of heterocycles with chloro- and fluoroarenes,” Journal of the American Chemical Society, vol. 127, no. 28, pp. 9948–9949, 2005. View at Publisher · View at Google Scholar · View at Scopus
  26. L. Rout, T. K. Sen, and T. Punniyamurthy, “Efficient CuO-nanoparticle-catalyzed C-S cross-coupling of thiols with iodobenzene,” Angewandte Chemie, vol. 46, no. 29, pp. 5583–5586, 2007. View at Publisher · View at Google Scholar · View at Scopus
  27. L. Rout, S. Jammi, and T. Punniyamurthy, “Novel CuO nanoparticle catalyzed C–N cross coupling of amines with Lodobenzene,” Organic Letters, vol. 9, no. 17, pp. 3397–3399, 2007. View at Publisher · View at Google Scholar · View at Scopus
  28. M. Kidwai, S. Bhardwaj, and R. Poddar, “C-arylation reactions catalyzed by CuO-nanoparticles under ligand free conditions,” Beilstein Journal of Organic Chemistry, vol. 6, article no. 35, 2010. View at Publisher · View at Google Scholar · View at Scopus
  29. P. Larsson and A. Andersson, “Complete oxidation of CO, ethanol, and ethyl acetate over copper oxide supported on titania and ceria modified titania,” Journal of Catalysis, vol. 179, pp. 72–89, 1998. View at Publisher · View at Google Scholar
  30. B. Raveau, C. Michel, M. Herview, and D. Groult, Superconducting Copper Oxide, Springer, Berlin, Germany, 1991.
  31. Y. Liu, Q. Fu, and M. F. Stephanopoulos, “Preferential oxidation of CO in H2 over CuO-CeO2 catalysts,” Catalysis Today, vol. 93-95, pp. 241–246, 2004. View at Publisher · View at Google Scholar · View at Scopus
  32. A. A. Martinez, A. B. Hungria, M. Fernandez-Garcia, J. C. Conesa, and J. C. Munuera, “Interfacial Redox processes under CO/O2 in a Nanoceria-supported copper oxide catalyst,” The Journal of Physical Chemistry B, vol. 108, pp. 17983–17991, 2004. View at Publisher · View at Google Scholar
  33. M. L. Kantam, S. Laha, J. Yadav, P. R. Likhar, B. Sreedhar, and B. M. Choudary, “Asymmetric hydrosilylation of prochiral ketones catalyzed by nanocrystalline copper(II) oxide,” Advanced Synthesis and Catalysis, vol. 349, no. 10, pp. 1797–1802, 2007. View at Publisher · View at Google Scholar · View at Scopus
  34. M. L. Kantam, T. Ramani, L. Chakrapani, and K. V. Kumar, “Direct asymmetric aldol reactions catalyzed by nanocrystalline copper(II) oxide,” Tetrahedron Letters, vol. 49, no. 9, pp. 1498–1501, 2008. View at Publisher · View at Google Scholar · View at Scopus
  35. N. V. Suramwar, S. R. Thakare, N. N. Karade, and N. T. Khaty, “Green synthesis of predominant (1 1 1) facet CuO nanoparticles: Heterogeneous and recyclable catalyst for N-arylation of indoles,” Journal of Molecular Catalysis A, vol. 359, pp. 28–34, 2012. View at Publisher · View at Google Scholar
  36. D. Wang, F. Zhang, D. Kuang, J. Yu, and J. Li, “A highly efficient Cu-catalyst system for N-arylation of azoles in water,” Green Chemistry, vol. 14, no. 5, pp. 1268–1271, 2012. View at Publisher · View at Google Scholar · View at Scopus