Copper-catalyzed domino intra- And intermodular C-S cross-coupling reactions: Synthesis of 2-(Arylthio)arylcyanamides

Organic Letters

Volumn 12, Issue 1, 2010, Pages 84-87

  Ramana, Tamminana ^a   Saha, Prasenjit ^a   Das, Manas ^a   Punniyamurthy, Tharmalingam ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 73949090950     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9024088     Document Type: Article

References (48)

1. For some recent reviews, see: (a) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337-2364.
2. (b) Hartwig, J. F. Synlett 2006, 1283-1294.
3. (c) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
4. (d) Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651-2710.
5. (e) Evano, G.; Blanchard, N.; Toymi, M. Chem. Rev. 2008, 108, 3054-3131.
6. (f) Kondo, T.; mitsudo, T.-A. Chem. Rev. 2000, 100, 3205-3220.
7. (g) Choi, T. A.; Czerwonka, R.; Forke, R.; Jaeger, A.; Knoell, J.; Krahl, M. P.; Krause, T.; Reddy, K. R.; Franzblau, S. G.; Knoelker, H.-J. Med. Chem. Res. 2008, 17, 374-385.
8. (h) Correa, A.; García Mancheño, O.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108-1117.
9. (i) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954-6971.
10. (j) Würtz, S.; Glorius, F. Acc. Chem. Res. 2008, 41, 1523-1533.
11. For some studies on C-S coupling reactions, see: (a) Zheng, N.; McWilliams, J. C; Fleitz, F. J.; Armstrong, J. D.; Volante, R. P. J. Org. Chem. 1998, 63, 9606-9607.
12. (b) Fernandez-Rodriguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180-2181.
13. (c) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513-1516.
14. (d) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677-8681.
15. (e) Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863-4386
16. (f) Sperotto, E.; van Klink, G. P. M.; de Vries, J. G.; van Koten, G. J. Org. Chem. 2008, 73, 5625-5628.
17. (g) Rout, L.; Saha, P.; Jammi, S.; Punniyamurthy, T. Eur. J. Org. Chem. 2008, 4, 640-643.
18. (h) Rout, L.; Sen, T. K.; Punniyamurthy, T. Angew. Chem., Int. Ed. 2007, 46, 5583-6558
19. (i) Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880-2883.
20. (j) Buchwald, S. L.; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 5586-5587.
21. For some studies on cyanamide synthesis, see: (a) Kaupp, G.; Schmeyers, J.; Boy, J. Chem.-Eur. J. 1998, 4, 2467-2474.
22. (b) Sato, R.; Itoh, K.; Itoh, K.; Nishina, H.; Goto, T.; Saito, M. Chem. Lett. 1984, 1913-1916.
23. (c) Bakunov, S. A.; Rukavishnikov, A. V.; Tkachev, A. V. Synthesis 2000, 1148-1159.
24. (d) Chen, C.-Y.; Wong, F. F.; Huang, J. J.; Lin, S.-K.; Yeh, M.-Y. Tetrahedron Lett. 2008, 49, 6505-6507.
25. (e) Chaudhuri, K. H.; Mahajan, U. S.; Bhalerao, D. S.; Akamanchi, K. G. Synlett 2007, 2815-2818.
26. For structure and reactivity of cyanamides, see: (a) Sandler, S. R.; Karo, W. Organic Functional Group Preparations; Academic: New York, 1972; Vol.3, pp 286-287.
27. (b) Miyasaka, H.; Clerac, R.; Campos-Fernandez, C. S.; Dunbar, K. R. Inorg. Chem. 2001, 40, 1663-1671.
28. (c) Hollebone, B. R.; Nyholm, R. S. J. Chem. Soc. A 1971, 332-337.
29. (d) Pombeiro, A. J. L. Inorg. Chim. Acta 1992, 198, 179-186.
30. (e) Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 1780-1782.
31. (f) Brand, H.; Mayer, P.; Schulz, A.; Soller, T.; Villinger, A. Chem. Asian J. 2008, 3, 1050-1058.
32. (g) Renodon-Corniere, A.; Dijols, S.; Perollier, C.; Lefevre-Groboillot, D.; Boucher, J.-L.; Attias, R.; Sari, M.-A.; Stuehr, D.; Mansuy, D. J. Med. Chem. 2002, 45, 944-954.
33. (h) Hughes, T. V.; Hammond, S. D.; Cava, M. P. J. Org. Chem. 1998, 63, 401-402.
34. McCall, J. M.; TenBrink, R. E.; Ursprung, J. J. J. Org. Chem. 1975, 40, 3304-3306.
35. (a) Hu, L. Y.; Guyo, J.; Magar, S. S.; Fischer, J. B.; Burke-Howie, K. J.; Durant, G. J. J. Med. Chem. 1997, 40, 4281-4289.
36. (b) Robinson, J. R.; Brown, W. H. Can. J. Chem. 1951, 29, 1069-1074.
37. (a) Gilman, G.; Goodman, L. S.; Rail, T. W.; Murad, F. Goodman and Gilman's The Pharmacological Basis of Therapeutics, 7th ed.; Pergamon Press: New York, 1990; p 89.
38. (b) Saneyoshi, M.; Tokuzen, R.; Maeda, M.; Fukuoka, F. Chem. Pharm. Bull. 1968, 16, 505-508.
39. (c) Nickon, A.; Fieser, L. F. J. Am. Chem. Soc. 1952, 74, 5566-5570.
40. (d) Jia, Q.; Cai, T.; Huang, M.; Li, H.; Xian, M.; Poulos, T. L.; Wang, P. G. J. Med. Chem. 2003, 46, 2271-2274.
41. (e) Kumar, L.; Kaushik, M. P.; Mazumdar, A. Eur. J. Org. Chem. 2008, 1910-1916.
42. (a) Donetti, A.; Omodei-Sale, A.; Mantegani, A. Tetrahedron Lett. 1969, 39, 3327-3328.
43. (b) Pala, G.; Mantegani, A.; Zugna, E. Tetrahedron 1970, 26, 1275-1279.
44. (c) Currie, A. C.; Newbold, G. T.; Spring, F. S. J. Chem. Soc. 1961, 4693-4700.
45. (a) Ding, Q.; He, X.; Wu, J. J. Comb. Chem. 2009, 11, 587-591.
46. (b) Wang, J.; Peng, F.; Jiang, J.; Lu, Z.; Wang, L.; Bai, J.; Pan, Y. Tetrahedron Lett. 2008, 49, 467-470.
47. 2) = 1.005.
48. For the reduction of copper(II) salts to copper(I) species using thiourea, see: Bowmaker, G. A.; Hanna, J. V.; Pakawatchai, C.; Skelton, B. W.; Thanyasirikul, Y.; White, A. H. Inorg. Chem. 2009, 48, 350-368.