Copper oxide nanoparticles catalyzed synthesis of aryl sulfides via cascade reaction of aryl halides with thiourea

Tetrahedron Letters

Volumn 52, Issue 21, 2011, Pages 2679-2682

  Reddy, K Harsha Vardhan ^a   Reddy, V Prakash ^a   Shankar, J ^a   Madhav, B ^a   Anil Kumar, B S P ^a   Nageswar, Y V D ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aryl halides; Aryl sulfides; Copper oxide; Cross coupling; Thiourea

Indexed keywords

AROMATIC COMPOUND; ARYL HALOGENIDE; ARYL SULFIDE; COPPER OXIDE; HALIDE; METAL NANOPARTICLE; SULFIDE; THIOL DERIVATIVE; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CONTROLLED STUDY; CROSS COUPLING REACTION; REACTION OPTIMIZATION; SYNTHESIS;

EID: 79955465782     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.070     Document Type: Article

References (53)

1. M.-L. Alcaraz, S. Atkinson, P. Cornwall, A.C. Foster, D.M. Gill, L.A. Humphries, P.S. Keegan, R. Kemp, E. Merifield, R.A. Nixon, A.J. Noble, D. Obeirne, Z.M. Patel, J. Perkins, P. Rowan, P. Sadler, J.T. Singleton, J. Tornos, A.J. Watts, and I.A. Woodland Org. Process Res. Dev. 9 2005 555
2. G. Liu, J.T. Link, Z. Pei, E.B. Reilly, S. Leitza, B. Nguyen, K.C. Marsh, G.F. Okasinski, T.W. von Geldern, M. Ormes, K. Fowler, and M. Gallatin J. Med. Chem. 43 2000 4025
3. Y. Wang, S. Chackalamannil, W. Chang, W. Greenlee, V. Ruperto, R.A. Duffy, R. Mcquade, and J.E. Lachowicz Bioorg. Med. Chem. Lett. 11 2001 891
4. B. Bonnet, D. Soullez, S. Girault, L. Maes, V. Landry, E. Davioud-Charvet, and C. Sergheraert Bioorg. Med. Chem. 8 2000 95
5. C.P. Baird, and C.M. Rayner J. Chem. Soc., Perkin Trans. 1 1998 1973
6. D.J. Procter J. Chem. Soc., Perkin Trans. 1 2001 335
7. J. Lindley Tetrahedron 40 1984 1433
8. T. Yamamoto, and Y. Sekine Can. J. Chem. 62 1984 1544
9. R.J.S. Hickman, B.J. Christie, R.W. Guy, and T.J. White Aust. J. Chem. 38 1985 899
10. A.V. Bierbeek, and M. Gingras Tetrahedron Lett. 39 1998 6283
11. M. Murata, and S.L. Buchwald Tetrahedron 60 2004 7397
12. C. Mispelaere-Canivet, J.-F. Spindler, S. Perrio, and P. Beslin Tetrahedron 61 2005 5253
13. T. Itoh, and T. Mase Org. Lett. 6 2004 4587
14. M.A. Fernandez-Rodriguez, Q. Shen, and J.F. Hartwig J. Am. Chem. Soc. 128 2006 218
15. J.-Y. Lee, and P.H. Lee J. Org. Chem. 73 2008 7413
16. N. Taniguchi J. Org. Chem. 69 2004 6904
17. S. Jammi, P. Barua, L. Rout, P. Saha, and T. Punniyamurthy Tetrahedron Lett. 49 2008 1484
18. G. Takagi Chem. Lett. 15 1986 1379 1380
19. F.Y. Kwong, and S.L. Buchwald Org. Lett. 4 2002 3517
20. Y.-J. Chen, and H.-H. Chen Org. Lett. 8 2006 5609
21. N. Taniguchi J. Org. Chem. 72 2007 1241
22. E. Sperotto, G.P.M.V. Klink, J.G. De Vries, and G.V. Koten J.Org. Chem. 73 2008 5625
23. L. Rout, P. Saha, S. Jammi, and T. Punniyamurthy Eur. J. Org. Chem. 2008 640
24. M.T. Herrero, R. SanMartin, and E. Dominguez Tetrahedron 65 2009 1500
25. D.J.C. Prasad, A.B. Naidu, and G. Sekar Tetrahedron Lett. 50 2009 1411
26. H. Wang, L. Jiang, T. Chen, and Y. Li Eur. J. Org. Chem. 12 2010 2324
27. J. She, Z. Jiang, and Y. Wang Tetrahedron Lett. 50 2009 593
28. B. Basu, B. Mandal, S. Das, and S. Kundu Tetrahedron Lett. 50 2009 5523
29. Y. Feng, H. Wang, F. Sun, Y. Li, X. Fu, and K. Jin Tetrahedron 65 2009 9737
30. N.R. Jogdand, B.B. Shingate, and M.S. Shingare Tetrahedron Lett. 50 2009 6092
31. Y.-S. Feng, Y.-Y. Li, L. Tang, W. Wu, and H.-J. Xu Tetrahedron Lett. 51 2010 2489
32. C.G. Bates, R.K. Gujadhur, and D. Venkataraman Org. Lett. 4 2002 2803
33. C. Savarin, J. Srogl, and L.S. Liebeskind Org. Lett. 4 2002 4309
34. B.C. Ranu, A. Saha, and R. Jana Adv. Synth. Catal. 349 2007 2690
35. C.-K. Chen, Y.-W. Chen, C.-H. Lin, H.-P. Lin, and C.-F. Lee Chem. Commun. 46 2010 282
36. L. Rout, T.K. Sen, and T. Punniyamurthy Angew. Chem., Int. Ed. 46 2007 5583
37. A. Correa, M. Carril, and C. Bolm Angew. Chem., Int. Ed. 47 2008 2880
38. V.P. Reddy, K. Swapna, A.V. Kumar, and K.R. Rao J. Org. Chem. 74 2009 3189
39. V.P. Reddy, A.V. Kumar, K. Swapna, and K.R. Rao Org. Lett. 11 2009 1697
40. S.N. Murthy, B. Madhav, V.P. Reddy, and Y.V.D. Nageswar Eur. J. Org. Chem. 2009 5902
41. Y.-C. Wong, T.T. Jayanth, and C.-H. Cheng Org. Lett. 8 2006 5613
42. Ke, F.; Qu, Y.; Jiang, Z.; Li, Z.; Wu, D.; Zhou, X. doi: 10.1021/ol102784c.
43. G. Pacchioni Surf. Rev. Lett. 7 2000 277
44. W.D. Knight, K. Clemenger, W.A. de Heer, W.A.M. Saunders, Y. Chou, and M.L. Cohen Phys. Rev. Lett. 52 1984 2141
45. A. Kaldor, D. Cox, and M.R. Zakin Adv. Chem. Phys. 70 1988 211
46. V.P. Reddy, K. Swapna, A.V. Kumar, and K.R. Rao J. Org. Chem. 74 2009 3189
47. K. Swapna, A.V. Kumar, V.P. Reddy, and K.R. Rao.J. Org. Chem. 74 2009 7514
48. V.P. Reddy, A.V. Kumar, K. Swapna, and K.R. Rao Org. Lett. 11 2009 951
49. V.P. Reddy, A.V. Kumar, K. Swapna, and K.R. Rao Synlett 2009 2783
50. V.P. Reddy, A.V. Kumar, and K.R. Rao Chem. Lett. 39 2010 212
51. V.P. Reddy, A.V. Kumar, and K.R. Rao Tetrahedron Lett. 51 2010 3181
52. K. Swapna, S.N. Murthy, and Y.V.D. Nageswar Eur. J. Org. Chem. 6 2010 678
53. 4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; found: C, 50.45; H, 3.13; N, 29.41; S, 16.81.