Copper oxide nanoparticles catalyzed vinylation of imidazoles with vinyl halides under ligand-free conditions

Tetrahedron Letters

Volumn 51, Issue 24, 2010, Pages 3181-3185

  Prakash Reddy, V ^a   Vijay Kumar, A ^a   Rama Rao, K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER OXIDE; HALIDE; IMIDAZOLE DERIVATIVE; LIGAND; NANOPARTICLE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS; VINYLATION;

EID: 77953120763     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.022     Document Type: Article

References (36)

1. For selected examples, see:. Branowska D. Synthesis (2003) 2096
2. Kurdaziel K., and Glowiak T. J. Coord. Chem. 55 (2002) 327
3. Mano N., Kim Y., Zhang H.H., and Heller A. J. Am. Chem. Soc. 124 (2002) 6480
4. Gist-Brocades, N. V. NL 8005204, 1982
5. Ross W.J., Jamieson W.B., and McCowen M.C. J. Med. Chem. 16 (1973) 347
6. Hamada, Y.; Shinomoto, S.; Yamada, I.; Koike, H. EP 162359, 1985
7. Cockerrill A.F., Rackham D.M., Franklin N.C., and Norman C. J. Chem. Soc., Perkin Trans. 2 (1973) 509
8. Barker S.J., and Storr R.C. J. Chem. Soc., Perkin Trans. 1 (1990) 485
9. Masquestiau A., Beugnies D., Flammang R., Katritzky A.R., Soleiman M., Davis T., and Lam J.N. J. Chem. Soc., Perkin Trans. 2 (1988) 1071
10. Wender P.A., and Cooper C.B. Tetrahedron 42 (1986) 2985
11. Marky M., Schmidt H.J., and Hansen H. Helv. Chim. Acta 62 (1979) 2129
12. Aiscar, B. J. J.; Henkelmann, J.; Preiss, T.; Knochel, P.; Tzalis, D.; Koradin, C. 2000, EP 1055653
13. Tzalis D., Koradin C., and Knochel P. Tetrahedron Lett. 40 (1999) 6193
14. Lam P.Y.S., Vincent G., Clark C.G., Deudon S., and Jadhav P.K. Tetrahedron Lett. 42 (2001) 3415
15. Cooper G., and Irwin W.J. J. Chem. Soc., Perkin Trans. 1 (1976) 545
16. Cooper G., and Irwin W.J. J. Chem. Soc., Perkin Trans. 1 (1975) 798
17. Wang Z.M., Bao W.L., and Jiang R. Chem. Commun. (2005) 2849
18. Shen G., Lv X., Qiu W., and Bao W. Tetrahedron Lett. 49 (2008) 4556
19. Hayat S., Rahman A., Choudhary M.I., Khan K.M., Schumann W., and Bayer E. Tetrahedron 57 (2001) 9951
20. Lebedev A.Y., Izmer V.V., Kazyulkin D.N., Beletskaya I.P., and Voskoboynikov A.Z. Org. Lett. 4 (2002) 623
21. Taillefer M., Ouali A., Renard B., and Spindler J.-F. Chem. Eur. J. 12 (2006) 5301
22. Tzalis D., Henkelmann J., and Heider M. Tetrahedron Lett. 40 (1999) 6193
23. Bao W., Liu Y., and Lv X. Synthesis (2008) 1911
24. Mao J., Hua Q., Guo J., Shi D., and Ji S. Synlett (2008) 2011
25. Mao J., Xie G., Zhan J., Hua Q., and Shi D. Adv. Synth. Catal. 351 (2009) 1268
26. Shen G., Lv X., Qian W., and Bao W. Tetrahedron Lett. 49 (2008) 4556
27. Reddy V.P., Kumar A.V., Swapna K., and Rao K.R. Org. Lett. 11 (2009) 951
28. Reddy V.P., Kumar A.V., Swapna K., and Rao K.R. Org. Lett. 11 (2009) 1697
29. Choudary B.M., Kantam M.L., Ranganath K.V.S., Mahender K., and Sreedhar B. J. Am. Chem. Soc. 126 (2004) 3396
30. Choudary B.M., Ranganath K.V.S., Pal U., Kantam M.L., and Sreedhar B. J. Am. Chem. Soc. 127 (2005) 13167
31. Pacchioni G. Surf. Rev. Lett. 7 (2000) 277
32. Knight W.D., Clemenger K., de Heer W.A., Saunders M., Chou Y., and Cohen M.L. Phys. Rev. Lett. 52 (1984) 2141
33. Kaldor A., Cox D., and Zakin M.R. Adv. Chem. Phys. 70 (1988) 211
34. The reaction taking place in the presence of DMSO and its absence in water may be explained by the formation of dimsyl ion (Ref. Hunter, D. H.; Cram, D. J. J. Am. Chem. Soc. 1966, 88, 5765.).
35. 13C NMR spectroscopic analysis.Recycling of the catalyst: After the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (2.0 mL) was added, and CuO was removed by centrifugation. After each cycle, the catalyst was recovered by simple centrifugation, washed with deionized water and ethylacetate, and then dried in vacuo. The recovered nano CuO was used directly in the next cycle.
36. 3, TMS): δ = 143.9, 140.8, 138.0, 131.6, 129.5, 126.0, 123.7, 122.9, 120.5, 120.3, 120.1, 110.2, 21.7; mass (ESI): m/z 235 [M+1].