Browse > Article
http://dx.doi.org/10.5012/bkcs.2011.32.12.4167

Microwave Assisted, Solvent- and Ligand-Free Copper Catalyzed N-Arylation of Phenylurea with Aryl Halides  

Gavade, Sandip (Organic Research Laboratory, S.C.S. College)
Shingare, Murlidhar (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Mane, Dhananjay (Organic Research Laboratory, S.C.S. College)
Publication Information
Abstract
An inexpensive and efficient catalyst system has been developed for the N-arylation of phenylurea including a variety of aryl halides. This simple protocol uses $Cu_2O$ as the catalyst, microwave assisted, solvent- and ligand-free, $K_3PO_4{\cdot}H_2O$ as the base.
Keywords
Microwave assisted; Ligand free; Solvent free; Phenylurea;
Citations & Related Records

Times Cited By Web Of Science : 1  (Related Records In Web of Science)
Times Cited By SCOPUS : 1
연도 인용수 순위
  • Reference
1 Davis, T. L.; Blanchard, K. C. J. Am. Chem. Soc. 1929, 51, 1790.   DOI
2 Skowronska-Serafin, B. and Urbanski, T. Tetrahedron 1960, 10, 12.   DOI   ScienceOn
3 Dondori, A.; Barbaro, G.; Battaglia, A. J. Org. Chem. 1977, 42, 3372.   DOI
4 Etter, M. C.; Urbanczyk-Lipkowska, Z.; Zia-Ebrahimi, M. et al. J. Am. Chem. Soc. 1990, 112, 8415.   DOI
5 Briody, T. A.; Hegarty, A. F.; Scott, F. L. Tetrahedron 1977, 33, 1469.   DOI   ScienceOn
6 Minatchy, S.; Mathew, N. Indian J. Chem. 1998, 37B, 1066.
7 Artamkina, G. A.; Sergeev, A. G.; Beletskaya, I. P. Tetrahedron Lett. 2001, 42, 4381.   DOI   ScienceOn
8 Sergeev, A. G.; Artamkina, G. A.; Beletskaya, I. P. Tetrahedron Lett. 2003, 44, 4719.   DOI   ScienceOn
9 Abad, A.; Agullo, C.; Cunat, A. C.; Vilanova, C. Synthesis 2005, 6, 915.
10 McLaughlin, M.; Palucki, M.; Davies, I. W. Org. Lett. 2006, 8, 3311.   DOI   ScienceOn
11 Willis, M. C.; Snell, R. H.; Fletcher, A. J.; Woodward, R. L. Org. Lett. 2006, 8, 5089.   DOI   ScienceOn
12 Dunn, P. J.; Wells, A. S.; Williams, M. T. Green Chemistry in the Pharmaceutical Industry; Wiley-VCH: Weinheim, 2010.
13 Tanaka, K. Solvent-free Organic Synthesis; 2nd ed., Wiley-VCH: Weinheim, 2009.
14 Sheldon, R. A.; Arends, I.; Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, 2007.
15 Doble, M.; Kumar, A. Green Chemistry and Engineering; Elsevier: New York, 2007.
16 Doxsee, K.; Hutchison, J. Green Organic Chemistry: Strategies, Tools, and Laboratory Experiments; Brooks/Cole: Belmont, CA, 2004.
17 Sun, L. P.; Dai, W. M. Angew. Chem., Int. Ed. 2006, 45, 7255.   DOI   ScienceOn
18 Shore, G.; Morin, S.; Organ, M. G. Angew. Chem., Int. Ed. 2006, 45, 2761.   DOI   ScienceOn
19 Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2006, 45, 1589.   DOI   ScienceOn
20 Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.   DOI   ScienceOn
21 Huang, H.; Liu, H.; Chen, K. X.; Jiang, H. L. J. Comb. Chem. 2007, 9, 197.   DOI   ScienceOn
22 Gavade, S. N.; Balaskar, R. S.; Mane, M. S.; Shingare, M. S.; Mane D. V. Chinese Chemical Letters 2011, 22, 292.   DOI   ScienceOn
23 Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.   DOI   ScienceOn
24 Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144.   DOI   ScienceOn
25 Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.   DOI   ScienceOn
26 Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525.   DOI
27 He, F.; Foxman, B. M.; Snider, B. B. J. Am. Chem. Soc. 1998, 120, 6417.   DOI   ScienceOn
28 Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.   DOI   ScienceOn
29 Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35.   DOI   ScienceOn
30 Shakespeare, W. C. Tetrahedron Lett. 1999, 40, 2035.   DOI   ScienceOn
31 Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101.   DOI   ScienceOn
32 Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043.   DOI   ScienceOn
33 Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539.   DOI   ScienceOn
34 Browning, R. G.; Mahmud, H.; Badarinarayana, V.; Lovely, C. J. Tetrahedron Lett. 2001, 42, 7155.   DOI   ScienceOn
35 Artamkina, G. A.; Sergeev, A. G.; Beletskaya, I. P. Zh. Org. Khim. Russian Journal of Organic Chemistry 2002, 38, 563.
36 Nandakumar, M. V. Tetrahedron Lett. 2004, 45, 1989   DOI   ScienceOn
37 Hartwig, J. F.; Shekhar, S.; Shen, Q.; Barrios-Landeros, F. In Chemistry of Anilines; Rapporport, Z., Ed.; Wiley-Interscience: New York 2007, 1, 455.
38 Jiang, L.; Buchwald, S. L. In Metal- Catalyzed Cross-Coupling Reactions; 2nd ed.; De Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
39 Looker, A. R.; Littler, B. J.; Blythe, T. A.; Snoonian, J. R.; Ansell, G. K.; Jones, A. D.; Nyce, P.; Chen, M.; Neubert, B. J. Org. Process Res. Dev. 2008, 12(4), 666.   DOI   ScienceOn
40 Gallou, I. Org. Prep. Proced. Int. 2007, 4, 355.
41 Dai, Y.; Hartandi, K.; Ji, Z.; Ahmed, A. A.; Albert, D. H.; Bauch, J. L.; Bouska, J. J.; Bousquet, P. F.; Cunha, G. A.; Glaser, K. B.; Harris, C. M.; Hickman, D.; Guo, J.; Li, J.; Marcotte, P. A.; Marsh, K. C.; Moskey, M. D.; Martin, R. L.; Olson, A. M.; Osterling, D. J.; Pease, L. J.; Soni, N. B.; Stewart, K. D.; Stoll, V. S.; Tapang, P.; Reuter, D. R.; Davidsen, S. K.; Michaelides, M. R. J. Med. Chem. 2007, 50(7), 1584.   DOI   ScienceOn
42 Vyshnyakova, T. P.; Golubeva, I. A.; Glebova, E. V. Russ. Chem. Rev. (Engl. Transl.) 1985, 54, 249.   DOI   ScienceOn
43 Melnikov, N. N.; Novozhilov, K. V.; Belan, S. P. Pesticides and Plant Growth Regulators; Khimia: Moscow 1995 (pp 27-486, in Russian)
44 Movsumzadze, E. M.; Valitov, R. B.; Bazunova, G. G.; Aminova, G. K. Growth Stimulators and a Harvest; Reactiv: Ufa, 2000 (pp 52-99, in Russian).
45 Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley- Interscience: New York, 2002; Vol. 2, pp 1051-1097.
46 Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.   DOI   ScienceOn
47 Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.   DOI   ScienceOn