A general, efficient, and inexpensive catalyst system for the coupling of aryl iodides and thiols

Organic Letters

Volumn 4, Issue 20, 2002, Pages 3517-3520

  Kwong, Fuk Yee ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; IODIDE; THIOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ECONOMICS; ORGANIC CHEMISTRY; SYNTHESIS;

CATALYSIS; CHEMISTRY, ORGANIC; COPPER; IODIDES; MOLECULAR STRUCTURE; SULFHYDRYL COMPOUNDS;

EID: 0037015435     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0266673     Document Type: Article

References (60)

1. For reviews, see: (a) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, p 133.
2. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576 (1-2), 125.
3. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
4. (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
5. (e) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2014.
6. (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
7. (b) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
8. (c) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
9. (d) Wolter, M.; Nordmann, G.; Job, G.; Buchwald, S. L. Org. Lett. 2002, 4, 973.
10. (e) Wolter, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803.
11. (f) Kiyomori, A.; Marcoux, J.-F.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657.
12. (g) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am Chem. Soc. 1997, 119, 10539.
13. (h) Antilla, J. C.; Buchwald, S. L. Org. Lett. 2001, 3, 2077.
14. (a) Gujadhur, R.; Venkataraman, D.; Kintigh, J. T. Tetrahedron Lett. 2001, 42, 4791.
15. (b) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4135.
16. (c) Kang, S.-K.; Kim, D.-H.; Park, J.-N. Synlett 2002, 427.
17. (d) Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. J. Am. Chem. Soc. 2000, 122, 5043.
18. (e) Goodbrand, H. B.; Hu, N.-X. J. Org. Chem. 1999, 64, 670.
19. (f) Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623.
20. (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.
21. (b) Beard, R. L.; Colon, D. F.; Song, T. K.; Davies, P. J. A.; Kochhar, D. M.; Chandraratna, R. A. S. J. Med. Chem. 1996, 39, 3556.
22. (c) Nagai, Y.; Irie, A.; Nakamura, H.; Hino, K.; Uno, H.; Nishimura, H. J. Med. Chem. 1982, 25, 1065.
23. (d) 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.
24. (e) Bonnet, B.; Soullez, D.; Girault, S.; Maes, L.; Landry, V.; Davioud-Charvet, E.; Sergheraert, C. Bioorg. Med. Chem. 2000, 8, 95.
25. (f) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J., III. J. Org. Chem. 1998, 63, 6338.
26. Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205.
27. 2O reagent in a 1:4 pyridine/quinoline solvent at 160°C: Pinchart, A.; Dallaire, C.; Gingras, M. Tetrahedron Lett. 1998, 39, 543.
28. (b) Using 5 mol % Cu in refluxing NMP: Sindelár, K.; Hrubantová, M.; Svátek, E.; Matousová, O.; Metysová, J.; Valchár, M.; Protiva, M. Collect. Czech. Chem. Commun. 1989, 54, 2240.
29. (c) Use of a stoichiometric amount of CuI to prepare S-arylated cysteine derivatives at 100°C in ∼30% yield: Hickman, R. J. S.; Christie, B. J.; Guy, R. W.; White, T. J. Aust. J. Chem. 1985, 38, 899.
30. (a) Kalinin, A. V.; Bower, J. F.; Riebel, P.; Snieckus, V. J. Org. Chem. 1999, 64, 2986.
31. (b) Baxter, A. J. G.; Teague, S. J. Tetrahedron 1993, 49, 9089.
32. (c) Rábai, J.; Kapovits, I.; Tanács, B.; Tamás, J. Synthesis 1990, 847.
33. (d) Kulkarni, N. N.; Kulkarni, V. S.; Lele, S. R.; Hosangadi, B. D. Tetrahedron 1988, 44, 5145.
34. (e) Dhareshwar, G. P.; Chhaya, P. N.; Hosangadi, B. D. Indian J. Chem. Sect. B. 1980, 831.
35. (f) Rajsner, M.; Svátek, E.; Metysová, J.; Protiva, M. Collect. Czech. Chem. Commun. 1975, 40, 1604.
36. (g) Rajsner, M.; Metysová, J.; Svátek, E.; Miksík, F.; Protiva, M. Collect. Czech. Chem. Commun. 1975, 40, 719.
37. (h) Machek, V. G.; Haas, H. J. Prakt. Chem. 1942, 41.
38. (i) Steinkopf, von W.; Schmitt, H. F.; Fiedler, H. Liebigs Ann. Chem. 1937, 527, 237.
39. (j) Roberts, K. C.; Smiles, S. J. Chem. Soc. 1929, 863.
40. (a) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-i.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385.
41. (b) Kosugi, M.; Ogata, T.; Terada, M.; Sano, H.; Migita, T. Bull. Chem. Soc. Jpn. 1985, 58, 3657.
42. (a) Zheng, N.; McWilliams, J. C.; Fleitz, F. J.; Armstrong, J. D., III; Volante, R. P. J. Org. Chem. 1998, 63, 9606.
43. (b) McWilliams, J. C.; Fleitz, F. J.; Zheng, N.; Armstrong, J. D., III. Org. Synth. 2002, 79, 43.
44. (a) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513.
45. (b) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677.
46. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643.
47. Schopfer, U.; Schlapbach, A. Tetrahedron 2001, 57, 3069.
48. (a) Harr, M. S.; Presley, A. L.; Thorarensen, A. Synlett 1999, 1579.
49. (b) Ishiyama, T.; Mori, M.; Suzuki, A.; Miyaura, N. J. Organomet. Chem. 1996, 525, 225.
50. (c) Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1995, 36, 4133.
51. Ullmann couplings: (a) Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382. For a review, see:
52. (b) Lindley, J. Tetrahedron 1984, 40, 1433.
53. (c) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
54. 2 and arylboronic acids as S-arylating agents, see: Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019.
55. Palomo, C.; Oiarbide, M.; López, R.; Gómez-Bengoa, E. Tetrahedron Lett. 2000, 41, 1283.
56. 2-Et base ($ 260 for 5 mL from Aldrich) was used.
57. 4 may be used as the base, where needed, for functionalized substrates. No examples, however, were provided: Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803-2806.
58. 2O all worked well. We are currently examining the latter as an industrially interesting precatalyst.
59. 3N 68 (64).
60. Control experiments revealed that (a) anhydrous 2-propanol (packed under argon from Aldrich in a Sure-Seal bottle) gave the same conversion and yield of the reaction and (b) the oxidative coupling product, diaryl disulfide (ArS-SAr), was the major product if the reaction was performed in air.