Cobalt-catalyzed aryl-sulfur bond formation

Organic Letters

Volumn 8, Issue 24, 2006, Pages 5613-5616

  Wong, Ying Chieh ^a   Jayanth, Thiruvellore Thatai ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33846010734     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062344l     Document Type: Article

References (48)

1. (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; Vol. 1, pp 1051-1106.
2. (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
3. (c) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
4. (d) Kondo, T.; Mitsudo, T.-a. Chem. Rev. 2000, 100, 3205.
5. (e) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
6. (a) Liu, G.; Link, J. T.; Pei, Z.; Reilly, E. B.; Leitza, S.; Nguyen, B.; Marsh, K. C.; Okasinski, G. F.; von Geldern, T. W.; Ormes, M.; Fowler, K.; Gallatin, M. J. Med. Chem. 2000, 43, 4025.
7. (b) Wang, Y.; Chackalamannil, S.; Chang, W.; Greenlee, W.; Ruperto, V.; Duffy, R. A.; McQuade, R.; Lachowicz, J. E. Bioorg. Med. Chem. Lett. 2001, 11, 891.
8. (c) Bonnet, B.; Soullez, D.; Girault, S.; Maes, L.; Landry, V.; Davioud-Charvet, E.; Sergheraert, C. Bioorg. Med. Chem. 2000, 8, 95.
9. (d) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J., III. J. Org. Chem. 1998, 63, 6338.
10. (e) Baird, C. P.; Rayner, C. M. J. Chem. Soc., Perkin Trans. 1 1998, 1973.
11. (f) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 2001, 335.
12. (g) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019.
13. (h) Alcaraz, M.-L.; Atkinson, S.; Cornwall, P.; Foster, A. C.; Gill, D. M.; Humphries, L. A.; Keegan, P. S.; Kemp, R.; Merifield, E.; Nixon, R. A.; Noble, A. J.; O'Beirne, D.; Patel, Z. M.; Perkins, J.; Rowan, P.; Sadler, P.; Singleton, J. T.; Tornos, J.; Watts, A. J.; Woodland, I. A. Org. Process Res. Dev. 2005, 9, 555.
14. For Cu-catalyzed coupling of aryl halides and thiols, see: (a) Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803.
15. (b) Kwong, F. Y; Buchwald, S. L. Org. Lett. 2002, 4, 3517.
16. (c) Wu, Y.-J.; He, H. Synlett 2003, 1789.
17. (d) Bates, C. G.; Saejueng, P.; Doherty, M. Q.; Venkataraman, D. Org. Lett. 2004, 6, 5005.
18. (e) Deng, W.; Zou, Y.; Wang, Y.-F.; Liu, L.; Guo, Q.-X. Synlett 2004, 1254.
19. For other Cu-catalyzed syntheses of thioethers, see: (f) Palomo, C.; Oiarbide, M.; López, R.; Gómez-Bengoa, E.; Tetrahedron Lett. 2000, 41, 1283.
20. (g) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309.
21. (h) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019.
22. For Pd-catalyzed reactions, see: (i) Mispelaere-Canivet, C.; Spindler, J.-F.; Perrio, S.; Beslin, P. Tetrahedron 2005, 61, 5253.
23. (j) Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587.
24. (k) Fernández Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180.
25. (l) Murata, M.; Buchwald, S. L. Tetrahedron 2004, 60, 7397.
26. (m) Schopfer, U.; Schlapbach, A. Tetrahedron 2001, 57, 3069.
27. (n) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513.
28. For Ni-catalyzed reactions, see: (o) Cristau, H. J.; Chabaud, B.; Chêne, A.; Christol, H. Synthesis 1981, 892.
29. (p) Millois, C.; Diaz, P. Org. Lett. 2000, 2, 1705.
30. (q) Percec, V.; Bae, J. Y.; Hill, D. H. J. Org. Chem. 1995, 60, 6895.
31. (r) Takagi, K. Chem. Lett. 1987, 2221.
32. (a) Lindley, J. Tetrahedron 1984, 40, 1433.
33. (b) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
34. (a) Yorimitsu, H.; Oshima, K. Pure Appl. Chem. 2006, 78, 441.
35. (b) Ohmiya, H.; Wakabayashi, K.; Yorimitsu, H.; Oshima, K. Tetrahedron 2006, 62, 2207.
36. (c) Shinokubo, H.; Oshima, K. Eur. J. Org. Chem. 2004, 10, 2081.
37. (d) Korn, T. J.; Schade, M. A.; Wirth, S.; Knochel, P. Org. Lett. 2006, 8, 725.
38. (e) Amatore, M.; Gosmini, C.; Perichon, J. J. Org. Chem. 2006, 71, 6130.
39. (f) Kazmierski, I.; Gosmini, C.; Paris, J.-M.; Perichon, J. Synlett 2006, 6, 881.
40. (a) Korn, T. J.; Cahiez, G.; Knochel, P. Synlett 2003, 12, 1892.
41. (a) Chang, H.-T.; Jeganmohan, M.; Cheng, C.-H. Chem. Commun. 2005, 39, 4955.
42. (b) Chang, K.-J.; Rayabarapu, D. K.; Cheng, C.-H. J. Org. Chem. 2004, 69, 4781.
43. (c) Chang, K.-J.; Rayabarapu, D. K.; Cheng, C.-H. Org. Lett. 2003, 5, 3963.
44. (a) Shukla, P.; Hsu, Y. -C.; Cheng, C. -H. J. Org. Chem. 2006, 71, 655.
45. See also: (b) Wang, C.-C.; Lin, P.-S.; Cheng, C.-H. J. Am. Chem. Soc. 2002, 124, 9696.
46. (c) Wang, C.-C.; Lin, P.-S.; Cheng, C.-H. Tetrahedron Lett. 2004, 45, 6203.
47. The reactivity of aryl bromides and aryl iodides with electron-donating substituents was not found to be remarkable with this catalyst system under reaction conditions similar to those reported earlier in our labortories. See ref 6b.
48. However, recently there has been improvement in the Cu-catalyzed synthesis of thioethers. The catalyst loading has been decreased up to 5 mol % at reaction temperatures of 80 °C. See ref 3b.