Browse > Article
http://dx.doi.org/10.5012/bkcs.2008.29.8.1561

Nanocrystalline Copper Oxide(II)-Catalyzed Alkyne-Azide Cycloadditions  

Song, Young-Jin (Division of Energy Systems Research, Ajou University)
Yoo, Chung-Yul (Division of Energy Systems Research, Ajou University)
Hong, Jong-Tai (Division of Energy Systems Research, Ajou University)
Kim, Seung-Joo (Division of Energy Systems Research, Ajou University)
Son, Seung-Uk (Department of Chemistry, Sungkyunkwan University)
Jang, Hye-Young (Division of Energy Systems Research, Ajou University)
Publication Information
Bulletin of the Korean Chemical Society / v.29, no.8, 2008 , pp. 1561-1564 More about this Journal
Abstract
Although the use of Cu(II) salts as catalysts without reductants is limited in the cycloaddition of acetylenes with azides, the catalytic system employing average 10 nm CuO(II) nanoparticles in the absence of reductants shows good catalytic activity to form 1,4-disubstituted 1,2,3-triazoles even in wet THF as well as water. It is also noticeable that CuO(II) nanoparticle catalysts can be recycled with consistent activity. A range of alkynes and azides were subject to the optimized CuO(II) nanoparticle-catalyzed cycloaddition reaction conditions to afford the desired products in good yields.
Keywords
Click chemistry; Copper oxide nanoparticles; Cycloaddition; Heterogeneous catalysis
Citations & Related Records

Times Cited By Web Of Science : 11  (Related Records In Web of Science)
Times Cited By SCOPUS : 12
연도 인용수 순위
1 Ye, M.-C.; Zhou, J.; Huang, Z.-Z.; Tang, Y. Chem. Commun. 2003, 2554
2 Kantam, M. L.; Jaya, V. S.; Sreedhar, B.; Rao, M. N.; Choudary, B. M. J. Mol. Catalysis A: Chemical 2006, 256, 273
3 Chassaing, S.; Kumarraja, M.; Sido, A. S. S.; Pale, P.; Sommer, J. Org. Lett. 2007, 9, 883   DOI   ScienceOn
4 Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; Van der Eycken, E. Org. Lett. 2004, 6, 4223   DOI   ScienceOn
5 Beckmann, H. S. G.; Wittmann, V. Org. Lett. 2007, 9, 1   DOI   ScienceOn
6 Choudary, B. M.; Mulukutla, R. S.; Klabunde, K. J. J. Am. Chem. Soc. 2003, 125, 2020   DOI   ScienceOn
7 Koryabkina, N. A.; Phatak, A. A.; Ruettinger, W. F.; Farrauto, R. J.; Ribeiro, F. H. J. Catal. 2003, 217, 233
8 Kulkarni, A. A.; Maki, K. Org. Synth. 2006, 83, 200   DOI
9 Haruta, M. CATTECH 2002, 6, 102   DOI   ScienceOn
10 Gladysz, J. A. Pure Appl. Chem. 2001, 73, 1319   DOI   ScienceOn
11 Gladysz, J. A. Chem. Rev. 2002, 102, 3215   DOI   ScienceOn
12 Bell, A. T. Science 2003, 299, 1688   DOI   ScienceOn
13 Müller, P.; Imogaï, H. Tetrahedron: Asymmetry 1998, 9, 4419   DOI   ScienceOn
14 Hooper, N.; Beeching, L. J.; Dyke, J. M.; Morris, A.; Ogden, J. S.; Dias, A. A.; Costa, M. L.; Barros, M. T.; Cabral, M. H.; Moutinho, A. M. C. J. Phys. Chem. A 2002, 106, 9968   DOI   ScienceOn
15 Park, S. B.; Alper, H. Chem. Commun. 2005, 1315
16 Reddy, K. R.; Rajgopal, K.; Kantam, M. L. Synlett 2006, 957
17 Guerreiro, E. D.; Gorriz, O. F.; Rivarola, J. B.; Arrua, L. A. Appl. Catal. A 1997, 165, 259   DOI   ScienceOn
18 JCPDS-International Centre for Diffraction Data PCPDFWIN, V. 2.4; 2003
19 L'abbé, G. Chem. Rev. 1969, 69, 345   DOI
20 Kantam, M. L.; Laha, S.; Yadav, J.; Likhar, P. R.; Sreedhar, B.; Choudary, B. M. Adv. Synth. Catal. 2007, 349, 1797   DOI   ScienceOn
21 Rout, L.; Jammi, S.; Punniyamurthy, T. Org. Lett. 2007, 9, 3397   DOI   ScienceOn
22 Zhu, J.; Li, D.; Chen, H.; Yang, X.; Lu, L.; Wang, X. Materials Lett. 2004, 58, 3324   DOI   ScienceOn
23 Kolb, H. C.; Sharpless, K. B. Drug Discov. Today 2003, 8, 1128   DOI   ScienceOn
24 Meldal, M.; Christensen, C.; Tornoe, C. W. J. Org. Chem. 2002, 67, 3057   DOI   ScienceOn
25 Yan, Z.-Y.; Zhao, Y.-B.; Fan, M.-J.; Liu, W.-M.; Liang, Y.-M. Tetrahedron 2005, 61, 9331   DOI   ScienceOn
26 Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004   DOI   ScienceOn
27 Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51
28 Sharpless, K. B.; Fokin, V. V.; Green, L. G.; Rostovtsev, V. V. Angew. Chem. Int. Ed. 2002, 41, 2596   DOI   ScienceOn
29 Link, A. J.; Vink, M. K. S.; Tirrell, D. A. J. Am. Chem. Soc. 2004, 126, 10598   DOI   ScienceOn
30 Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853   DOI   ScienceOn
31 Pérez-Balderas, F.; Ortega-Munoz, M.; Morales-Sanfrutos, J.; Hernández-Mateo, F.; Calvo-Flores, F. G.; Calvo-Asín, J. A.; Isac- García, J.; Santoyo-Gonzalez, F. Org. Lett. 2003, 5, 1951   DOI   ScienceOn
32 Lee, L. V.; Mitchell, M. L.; Huang, S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 2003, 125, 9588   DOI   ScienceOn
33 Buckle, D. R.; Rockell, C. J. M. J. Chem. Soc. Perkin Trans. I 1982, 627
34 Alvarez, R.; Velazquez, S.; San-Felix, A.; Aquaro, S.; De Clereq, E.; Perno, C.-F.; Karlsson, A.; Balzarini, J.; Carmarasa, M. J. J. Med. Chem. 1994, 37, 4185   DOI   ScienceOn
35 Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2004, 126, 210
36 Lewis, W. G.; Magallon, F. G.; Fokin, V. V.; Finn, M. G. J. Am. Chem. Soc. 2004, 126, 9152   DOI   ScienceOn
37 Lutz, J.-F.; Börner, H. G.; Weichenhan, K. Macromol. Rapid Commun. 2005, 26, 514   DOI   ScienceOn
38 Gerard, B.; Ryan, J.; Beeler, A. B.; Porco Jr., J. A. Tetrahederon 2006, 62, 6405   DOI   ScienceOn
39 Díez-González, S.; Correa, A.; Cavallo, L.; Nolan, S. P. Chem. Eur. J. 2006, 7558
40 Orgueira, H. A.; Fokas, D.; Isome, Y.; Chan, P. C.-M.; Baldino, C. M. Tetrahedron Lett. 2005, 46, 2911   DOI   ScienceOn
41 Molteni, G.; Bianchi, C. L.; Marinoni, G.; Santo, N.; Ponti, A. New J. Chem. 2006, 30, 1137   DOI   ScienceOn
42 Lipshutz, B. H.; Taft, B. R. Angew. Chem. Int. Ed. 2006, 45, 8235   DOI   ScienceOn
43 Girard, C.; Önen, E.; Aufort, M.; Beauvière, S.; Samson, E.; Herscovici, J. Org. Lett. 2006, 8, 1689   DOI   ScienceOn
44 Pachón, L. D.; van Maarseveen, J. H.; Rothenberg, G. Adv. Synth. Catal. 2005, 347, 811   DOI   ScienceOn
45 Sarvari, M. H.; Sharghi, H. J. Org. Chem. 2004, 69, 6953   DOI   ScienceOn
46 Choudary, B. M.; Kantam, M. L.; Ranganath, K. V. S.; Mahender, K.; Sreedhar, B. J. Am. Chem. Soc. 2004, 126, 3396   DOI   ScienceOn
47 Schlögl, R.; Hamid, S. B. A. Angew. Chem. Int. Ed. 2004, 43, 1628   DOI   ScienceOn
48 Martinez-Arias, A.; Hungria, A. B.; Fernandez-Garcia, M.; Conesa, J. C.; Munuera, G. J. Phys. Chem. B 2004, 108, 17983   DOI   ScienceOn
49 Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192   DOI   ScienceOn
50 Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686   DOI   ScienceOn
51 Bennici, S.; Auroux, A.; Guimon, C.; Gervasini, A. Chem. Mater. 2006, 18, 3641   DOI   ScienceOn
52 Gervasini, A.; Carniti, P.; Bennici, S.; Messi, C. Chem. Mater. 2007, 19, 1319   DOI   ScienceOn
53 Rout, L.; Sen, T. K.; Punniyamurthy, T. Angew. Chem. Int. Ed. 2007, 46, 1   DOI   ScienceOn
54 Carniti, P.; Gervasini, A.; Modica, V. H.; Ravsio, N. Appl. Catal. B 2000, 28, 175   DOI   ScienceOn
55 Choudary, B. M.; Ranganath, K. V. S.; Pal, U.; Kantam, M. L.; Sreehar, B. J. Am. Chem. Soc. 2005, 127, 13167   DOI   ScienceOn
56 Choudary, B. M.; Mahendar, K.; Kantam, M. L.; Ranganath, K. V. S.; Athar, T. Adv. Synth. Catal. 2006, 348, 1977   DOI   ScienceOn
57 Nolte, C.; Mayer, P.; Straub, B. F. Angew. Chem. Int. Ed. 2007, 46, 2101   DOI   ScienceOn