A novel approach for ligand promoted palladium (II)-catalyzed suzuki coupling of aryl iodides and bromides with arylboronic acid in aqueous media

Letters in Organic Chemistry

Volumn 4, Issue 7, 2007, Pages 486-490

  Pawar, Shivaji S ^a   Shingare, Murlidhar S ^b   Thore, Shivaji N ^a  

^a Vinyakrao Patil Mahavidyala Vaijapur ^*  (India)

^b DR BABASAHEB AMBEDKAR MARATHWADA UNIVERSITY   (India)

Author keywords

Aqueous media; Aryl iodides and bromides; Boronic acid; PdCl2 P(Ph)3 2catalyzed; Reuse of catalyst; Suzuki coupling reaction

Indexed keywords

EID: 36749046230     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017807782006371     Document Type: Article

References (52)

1. (a) Miyaura, N.; Suzuki, A. Chem. Rev., 1995, 95, 2457;
2. (b) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev., 2002, 102, 1359;
3. (c) Miyaura, N. Top. Curr. Chem., 2002, 219, 11.
4. (a) Nicolaou, K. C.; Boddy, C. N. C.; Brase, S.; Winssinger, N. Angew. Chem. Int. Ed., 1999, 38, 2096;
5. (b) Baudoin, O.; Cesario, M.; Guenard, D.; Gueritte, F. J. Org. Chem., 2002, 67, 1199;
6. (c) Pu, L. Chem. Rev., 1998, 98, 2405;
7. (d) Tsuji, J. In Palladium Reagents and Catalysts; John Wiley and Sons: NewYork, 1995.
8. (a) Shaughnessy, K. H.; Booth, R. S. Org. Lett., 2001, 3, 2757;
9. (b) Dupuis, C.; Adiey, K.; Charrault, L.; Michelet, V.; Savignac, M.; Genet, J.-P. Tetrahedron Lett., 2001, 42, 6523;
10. (c) Uozumi, Y.; Nakai, Y. Org. Lett., 2002, 4, 2997,
11. (d) Zou, G.; Wang, Z.; Zhu, J.; Tang, J.; He, M. Y. J. Mol. Catal. A Chem., 2003, 206, 193;
12. (e) Arcadi, A.; Cerichelli, G.; Chiarini, M.; Correa, M.; Zorzan, D. Eur. J. Org. Chem., 2003, 20, 4080;
13. (f) Moore, L. R.; Shaughnessy, K. H. Org. Lett., 2004, 6, 225;
14. (g) Leadbeater, N. E. Chem. Commun., 2005, 2881.
15. (a) Li, C.-J.; Chan, T. H. Organic Reactions in Aqueous Media; Wiley: New York, 1997;
16. (b) Grieco, P. A., Ed.; Organic Synthesis in Water; Kluwer Academic Publishers: Dordrecht, 1997.
17. (a) Leadbeater, N. E.; Marco, M. Org. Lett., 2002, 4, 2973;
18. (b) Leadbeater, N. E.; Marco, M. J. Org. Chem., 2003, 68, 5660;
19. (c) Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem., 1997, 62, 7170;
20. (d) Bedford, R. B.; Blake, M. E.; Butts, C. P.; Holder, D. Chem. Commun., 2003, 466;
21. (e) Blettner, C. G.; Koenig, W. A.; Stenzel, W.; Schotten, T. J. Org. Chem., 1999, 64, 3885.
22. Campi, E. M.; Jackson, W. R.; Marcuccio, S. M.; Naeslund, C. G. M. Chem. Commun., 1994, 2395.
23. Bumagin, N. A.; Bykov, V. V.; Beletskaya, I. P. Bull. Acad Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1989, 38, 2206.
24. (a) Miyaura, N.; Ishiyarna, T.; Sasaki, H.; Ishikawa, M.; Satoh, M.; Suzuki, A. J. Am. Chem. Soc., 1989, 111, 314;
25. (b) Bryson, T. A.; Gibson, J. M.; Stewart, J. J.; Voegtle, H.; Tiwari, A.; Dawson, J. H.; Marley, W.; Harmon, B. Green Chem., 2003, 5, 177.
26. Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun., 1981, 11, 513.
27. Imrie, C.; Loubser, C.; Engelbrecht, P.; McCleland, C. W. J. Chem. Soc. Perkin 1, 1999, 2513.
28. Taylor, P. N.; O'Connell, M. J.; McNeill, L. A.; Hall, M. J.; Aplin, R. T.; Anderson, H. L. Angew. Chem. Int. Ed., 2000, 39, 3456.
29. Stanier, C. A.; O'Connell, M. J.; Anderson, H. L.; Clegg, W. Chem. Commun., 2001, 493.
30. Western, E. C.; Daft, J. R.; Johnson, E. M., II Gannett, P. M.; Shaughnessy, K. H. J. Org. Chem., 2003, 68, 6767.
31. Occhiato, E. G.; Trabocchi, A.; Guarna, A. Org. Lett., 2000, 2, 1241.
32. Gong, Y.; Pauls, H. W. Synlett, 2000, 829.
33. Havelkova, M.; Dvorak, D.; Hocek, M. Synthesis, 2001, 1704.
34. Occhiato, E. G.; Trabocchi, A.; Guama, A. J. Org. Chem., 2001, 66, 2459.
35. (a) Hesse, S.; Kirsch, G. Tetrahedron Lett., 2002, 43, 1213.
36. (b) Zhu, Q.; Wu, J.; Fathi, R.; Yang, Z. Org. Lett., 2002, 4, 3333.
37. Morin Deveau, A.; Macdonald, T. L. Tetrahedron Lett., 2004, 45, 803.
38. (a) Li, C. J. Chem. Rev., 2005, 105, 3095;
39. (b) Venkatraman, S.; Li, C. J. Org. Lett., 1999, 1, 1133;
40. (c) Venkatraman, S.; Huang, T. S.; Li, C. J. Adv. Syn. Catal., 2002, 344, 399.
41. (a) Botella, L.; Najera, C. Angew. Chem. Int. Ed., 2002, 41, 179;
42. (b) Baleizao, C.; Corma, A.; Garcia, H.; Leyva, A. J. Org. Chem., 2004, 69, 439.
43. Colacot, T. J.; Gore, E. S.; Kuber, A. Organometallics, 2002, 21, 3301.
44. (a) Leadbeater, N. E.; Marco, M. J. Org. Chem., 2003, 68, 888;
45. (b) Bai, L.; Wang, J.-X; Zhang, Y. Green Chem., 2003, 5, 615.
46. (a) Molander, G. A.; Fumagalli, T. J. Org. Chem., 2006, 71, 5743;
47. (b) Molander, G. A.; Felix, L. A. J. Org. Chem., 2005, 70, 3950;
48. (c) Wong, M. S.; Zhang, X. L. Tetrahedrqn Lett., 2001, 42, 4087.
49. (a) Leadbeater, N. E.; Marco, M. Org. Lett., 2002, 4, 2973;
50. (b) Uozumi, Y.; Nakai, Y. Org. Lett., 2002, 4, 2997.
51. (a) Baleizao, C.; Corma, A.; Garcia, H.; Leyva, A. Chem. Commun., 2003, 606;
52. (b) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem., 2002, 67, 2721.