Palladium-catalyzed homocoupling and cross-coupling reactions of aryl halides in poly(ethylene glycol)

Journal of Organic Chemistry

Volumn 71, Issue 3, 2006, Pages 1284-1287

  Wang, Liang ^a   Zhang, Yuhong ^a   Liu, Leifang ^a   Wang, Yanguang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; HALOGEN COMPOUNDS; HYDROXYLATION; POLYETHYLENE GLYCOLS; SYNTHESIS (CHEMICAL);

CATALYST SYSTEM; CROSS-COUPLING REACTIONS; HYDRODEHALOGENATION; UNSYMMETRICAL BIARYLS;

AROMATIC COMPOUNDS;

HALIDE; HYDROXYL GROUP; MACROGOL; PALLADIUM;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; DEHALOGENATION; DIMERIZATION; REDUCTION; SOLUBILITY; STEREOSPECIFICITY;

CATALYSIS; CROSS-LINKING REAGENTS; HYDROCARBONS, HALOGENATED; IODOBENZENES; MOLECULAR STRUCTURE; PALLADIUM; POLYETHYLENE GLYCOLS;

EID: 32144445209     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052300a     Document Type: Article

References (55)

1. (a) Nicolaou, K. C.; Boddy, C. N. C.; Brase, S.; Winssinger, N. Angew. Chem., Int. Ed. 1999, 38, 2096.
2. (b) Pu, L. Chem. Rev. 1998, 98, 2405.
3. (c) Tsuji, J. In Palladium Reagents and Catalyst; John Wiley and Sons: New York, 1995.
4. (a) Wallow, T. I.; Norak, B. M. J. Org. Chem. 1994, 59, 5034.
5. (b) Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153.
6. (c) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
7. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
8. (b) Xiao, J.-C.; Shreeve, J. M. J. Org. Chem. 2005, 70, 3072.
9. (c) Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249.
10. (d) Miao, W.; Chan, T. H.; Org. Lett. 2003, 5, 5003.
11. (e) Revell, J. D.; Ganesan, A. Org. Lett. 2002, 4, 3071.
12. (a) Hudkins, R. L.; Diebold, J. L.; Marsh, F. D. J. Org. Chem. 1995, 60, 6218.
13. (b) Barchin, B. M.; Valenciano, J.; Cuadro, A. M.; Builla-Alvarez, J.; Vaquera, J. J. Org. Lett. 1999, 1, 545.
14. (c) Schubert, U. S.; Eschbaumer, C. Org. Lett. 1999, 1, 1027.
15. (d) Baxter, P. N. W. J. Org. Chem. 2000, 65, 1257.
16. (e) Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233.
17. (a) Jutand, A.; Mosleh, A. Synlett. 1993, 568.
18. (b) Jutand, A.; Mosleh, A. J. Org. Chem. 1997, 62, 261.
19. (c) Hossain, K. M.; Shibata, T.; Takagi, K. Synlett 2000, 1137.
20. (a) Widdowson, D. A.; Zhang, Y.-Z. Tetrahedron 1986, 42, 2111.
21. (b) Fechtenkoetter, A.; Saalwaechter, K.; Harbison, M. A.; Muellen, K.; Spiess, H. W. Angew. Chem., Int. Ed. 1999, 38, 3039.
22. (c) Bumagin, N. A.; Luzikova, E. V. J. Organomet. Chem. 1997, 532, 271.
23. (d) Huang, J.; Nolan, S. P. J. Am. Chem. Soc. 1999, 121, 9889.
24. (e) Spivey, A. C.; Fekner, T.; Spey, S. E. J. Org. Chem. 2000, 65, 3154.
25. (a) Yamaguchi, S.; Ohno, S.; Tamao, K. Synlett 1997, 1199.
26. (b) Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471.
27. (c) Gouda, K.-I.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232.
28. (d) Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2, 2053.
29. (e) Frid, M.; Pérez, D.; Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9469.
30. (a) Ullman, F. Chem. Ber. 1903, 36, 2389.
31. (b) Fanta, P. E. Chem. Rev. 1945, 36, 139.
32. (c) Fanta, P. E. Chem. Rev. 1964, 64, 613.
33. (a) Hennings, D. D.; Iwama, T.; Rawel, V. H. Org. Lett. 1999, 1, 1205.
34. (b) Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Wiener, H.; Sasson, Y. J. Chem. Soc., Perkin Trans. 2 1999, 2481.
35. (c) Mukhopadhyay, S.; Rothenberg, G.; Qafisheh, N.; Sasson, Y. Tetrahedron Lett. 2001, 42, 6117.
36. (d) Mukhopadhyay, S.; Rothenberg, G.; Wiener, H.; Sasson, Y. Tetrahedron 1999, 55, 14763.
37. (e) Kuroboshi, M.; Waki, Y.; Tanaka, H. J. Org. Chem. 2003, 68, 3938.
38. (f) Hassan, J.; Penalva, V.; Lavenot, L.; Gozzi, C.; Lemaire, M. Tetrahedron 1998, 54, 13793.
39. (g) Penalva, V.; Hassan, J.; Lavenot, L. Gozzi, C.; Lemaire, M. Tetrahedron Lett. 1998, 39, 2559.
40. (h) Venkatraman, S.; Li, C.-J. Org. Lett. 1999, 1, 1133.
41. (i) Shezad, N.; Clifford, A. A.; Rayner, C. M. Green Chem. 2002, 4, 64.
42. (j) Li, J.-H.; Xie, Y. -X.; Yin, D. -L. J. Org. Chem. 2003, 68, 9867.
43. (k) Venkatraman, S.; Li, C.-J. Tetrahedron Lett. 2000, 41, 4831.
44. (l) Soon, B. P.; Howard, A. Tetrahedron Lett. 2004, 45, 5515.
45. (m) Huo, S. Org. Lett. 2003, 5, 423.
46. Hassan, J.; Hathroubi, C.; Gozzi, C.; Lemaire, M. Tetrahedron 2001, 57, 7845.
47. (a) Liu, L.; Zhang, Y.; Wang, Y. J. Org. Chem. 2005, 70, 6122.
48. (b) Chandrasekhar, S.; Narsihmulu, Ch.; Sultana, S. S.; Reddy, N. R. Org. Lett. 2002, 4, 4399.
49. (c) Luo, C.; Zhang, Y.; Wang, Y. J. Mol. Catal. A: Chem. 2005, 229, 7.
50. (a) Ji, C.; Scott, K. S.; Jonathan, G. H.; Robin, D. R. Green Chem. 2005, 7, 64.
51. (b) Akiya, N.; Savage, P. E. Chem. Rev. 2002, 102, 2725.
52. (c) Lindstrom, U. M. Chem. Rev. 2002, 102, 2751.
53. Li, J.-H.; Liu, W. -J.; Xie, Y. -X. J. Org. Chem. 2005, 70, 5409.
54. (a) Mukhopadhyay, S.; Joshi, A. V.; Peleg, L.; Sasson, Y. Org. Process Res. Dev. 2003, 7, 44.
55. (b) Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Sasson, Y. Org. Lett. 2000, 2, 211.