Efficient Stille cross-coupling reaction using aryl chlorides or bromides in water

Journal of Organic Chemistry

Volumn 68, Issue 19, 2003, Pages 7551-7554

  Wolf, Christian ^a   Lerebours, Rachel ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; PALLADIUM; RECYCLING;

ORGANIC COSOLVENTS;

ORGANIC COMPOUNDS;

BROMIDE; CHLORIDE; FUNCTIONAL GROUP; KETONE; NITRILE; ORGANIC SOLVENT; PALLADIUM; PALLADIUM COMPLEX; PHOSPHORUS ACID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYST; CHEMICAL REACTION; MOLECULAR STABILITY; RECYCLING; SOLUBILITY; STILLE REACTION;

EID: 0141454832     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0347056     Document Type: Article

References (73)

1. For a recent review see: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
2. (a) Riermeier, T. H.; Zapf, A.; Beller, M. Top. Catal. 1997, 4, 301-309.
3. (b) Shirakawa, E.; Yamasaki, K.; Hiyama, T. Synthesis 1998, 1544-1549.
4. (c) Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10-11.
5. (d) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
6. (e) Shiota, T.; Yamamori, T. J. Org. Chem. 1999, 64, 453-457.
7. (f) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411-2412.
8. (g) Zhang, C. M.; Huang, J. K.; Trudell, M. L.; Nolan, M. L. J. Org. Chem. 1999, 64, 3804-3805.
9. (h) Mowery, M. E.; DeShong, P. Org. Lett. 1999, 1, 2137-2140.
10. (i) Bei, X.; Turner, H. W.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 3855-3858.
11. (j) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797-6803.
12. (k) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550-9561.
13. (l) Huang, J.; Nolan, S. P. J. Am. Chem. Soc. 1999, 121, 9889-9890.
14. (m) Bohm, V. P. W.; Herrmann, W. A. Chem.-Eur. J. 2000, 6, 1017-1025.
15. (n) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. I.; Dupont, J. Org. Lett. 2000, 1287-1290.
16. (o) Morales-Morales, D.; Redon, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619-1620.
17. (p) Bohm, V. P. W.; Weskamp, T.; Gstottmayr, C. W. K.; Herrmann, W. A. Angew. Chem., Int. Ed. 2000, 39, 1602-1604.
18. (q) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
19. (r) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028.
20. (s) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153-4155.
21. (t) Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677-2678.
22. (u) Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719-2724.
23. (v) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000.
24. (w) Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449-7476.
25. (x) Yin, J. J.; Rainka, M. P.; Zhang, X. X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162-1163.
26. (y) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. J. Chem Soc., Chem. Commun. 2002, 2608-2609.
27. (z) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. J. Chem Soc., Chem. Commun. 2002, 2610-2611.
28. (a) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170-7173.
29. (b) Uozomi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384-3388.
30. (c) Gelpke, A. E. S.; Veerman, J. J. N.; Goedheijt, M. S.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Hiemstra, H. Tetrahedron 1999, 55, 6657-6670.
31. (d) Paetzold, E.; Oehme, G. J. Mol. Catal. A: Chem. 2000, 152, 69-76.
32. (e) LeBlond, C. R.; Andrews, A. T.; Sun, Y.; Sowa, J. R. Org. Lett. 2001, 3, 1555-1557.
33. (f) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757-2759.
34. (g) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 2001, 42, 6523-6526.
35. (h) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett 2000, 856-858.
36. (i) Botella, L.; Najera, C. Angew. Chem. 2002, 41, 179-181.
37. (j) Alonso, D. A.; Najera, C.; Pacheco, M. A. J. Org. Chem. 2002, 67, 5588-5594.
38. (k) Bedford, R. B.; Blake, M. E.; Butts, C. P.; Holder, D. Chem. Commun. 2003, 466-467.
39. (l) Leadbeater, N. E.; Marco, M. J. Org. Chem. 2003, 68, 888-892.
40. Wuellner, G.; Jaensch, H.; Kannenberg, S.; Schubert, F.; Boche, G. Chem. Commun. 1998, 1509-1510.
41. (a) Amatore, C.; Blart, E.; Genet, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829-39.
42. (b) Hessler, A.; Stelzer, O.; Dibowski, H.; Worm, K.; Schmidtchen, F. P. J. Org. Chem. 1997, 62, 2362-2369.
43. (c) Lopez-Deber, M. P.; Castedo, L.; Granja, J. R. Org. Lett. 2001, 3, 2823-2826.
44. (a) Roshchin A. I.; Bumagin, N. A.; Beletskaya, I. P. Tetrahedron Lett. 1995, 36, 125-128.
45. (b) Rai, R.; Aubrecht, K. B.; Collum, D. B. Tetrahedron Lett. 1995, 36, 3111-3114
46. (c) Kang, S.-K.; Baik, T.-G.; Song, S.-Y. Synlett 1999, 3, 327-329.
47. Genet, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717.
48. (a) Genet, P. J.; Savignac, M. J. Organomet. Chem. 1999, 576 (1-2), 305-317.
49. (b) Takami, K.; Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K. Org. Lett. 2001, 3, 1997-1999.
50. (c) Murata, M.; Shimazaki, R.; Watanabe, S.; Masuda, Y. Synthesis 2001, 2231-2233.
51. (a) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513-1516.
52. (b) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677-8681.
53. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643-3650.
54. Attempts to increase yields of the optimized POPd-catalyzed coupling reaction using equimolar additives of TBAF or TBAB were not successful.
55. 2NMe.
56. (a) De, D.; Byers, L. D.; Krogstad, D. J. J. Hetercycl. Chem. 1997, 34, 315-320.
57. (b) O'Neill, P. M.; Willock, D. J.; Hawley, S. R.; Bray, P. G.; Storr, R. C.; Ward, S. A.; Park, B. K. J. Med. Chem. 1997, 40, 437-448.
58. (c) O'Neill, P. M.; Bray, P. G.; Hawley, S. R.; Ward, S. A.; Park, B. K. Pharmacol. Ther. 1998, 77, 29-58.
59. (d) De, D.; Krogstad, F. M.; Byers, L. D.; Krogstad, D. J. J. Med. Chem. 1998, 41, 4918-4926.
60. (e) Raynes, K. J.; Stocks, P. A.; O'Neill, P. M.; Park, B. K.; Ward, S. A. J. Med. Chem. 1999, 42, 2747-2751.
61. We found that esters and aldehydes are not stable under the coupling reaction conditions reported herein. Employing methyl 4-chlorobenzoate in the Stille coupling resulted in extensive hydrolysis, and 4-phenylbenzoic acid was obtained in 60% yield. The cross-coupling of 4-bromobenzaldehyde and phenyltrimethyltin gave 45% 4-phenyl-benzyl alcohol and 45% 4-phenylbenzoic acid, which is probably a result of Cannizzaro disproportionation.
62. Ridley, R. G. Nature 2002, 415, 686-693.
63. (a) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. Synthesis 1987, 693-696.
64. (b) Godard, A.; Fourquez, J. M.; Tamoin, R.; Marsais, F.; Queguiner, G. Synlett 1994, 235-236.
65. (c) Ciufolini, M. A.; Mitchell, J. W.; Roschangar, F. Tetrahedron Lett. 1996, 37, 8281-8284.
66. (d) Shiota, T.; Yamamori, T. J. Org. Chem. 1999, 64, 453-457.
67. (e) Legros, J.-Y.; Primault, G.; Fiaud, J.-C. Tetrahedron 2001, 57, 2507-2514.
68. Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B J. Am. Chem. Soc. 2002, 124, 14127-14136.
69. Karikomi, M.; Tsukada, H.; Toda, T. Heterocycles 2001, 55, 1249-1252.
70. Rao, M. L. N.; Shimada, S.; Yamazaki, O.; Tanaka, M. J. Organomet. Chem. 2002, 659, 117-120.
71. Riguet, E.; Alami, M.; Cahiez, G. J. Organomet. Chem. 2001, 624, 376-379.
72. Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343-6348.
73. Padwa, A.; Akiba, M.; Cohen, L. A.; MacDonald, J. G. J. Org. Chem. 1983, 48, 695-703.