- About this Journal ·
- Abstracting and Indexing ·
- Aims and Scope ·
- Article Processing Charges ·
- Author Guidelines ·
- Bibliographic Information ·
- Citations to this Journal ·
- Contact Information ·
- Editorial Board ·
- Editorial Workflow ·
- Free eTOC Alerts ·
- Publication Ethics ·
- Recently Accepted Articles ·
- Reviewers Acknowledgment ·
- Submit a Manuscript ·
- Subscription Information ·
- Table of Contents
Organic Chemistry International
Volume 2012 (2012), Article ID 515092, 7 pages
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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- M. Kim and S. Chang, “Rhodium(NHC)-catalyzed amination of aryl bromides,” Organic Letters, vol. 12, pp. 1640–1643, 2010.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- A. Correa and C. Bolm, “Ligand-Free copper-catalyzed N-arylation of nitrogen nucleophiles,” Advanced Synthesis & Catalysis, vol. 349, pp. 2673–2676, 2007.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- B. Raveau, C. Michel, M. Herview, and D. Groult, Superconducting Copper Oxide, Springer, Berlin, Germany, 1991.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.