An assembled complex of palladium and non-cross-linked amphiphilic polymer: A highly active and recyclable catalyst for the Suzuki-Miyaura reaction

Organic Letters

Volumn 4, Issue 20, 2002, Pages 3371-3374

  Yamada, Yoichi M A ^a   Takeda, Koji ^a   Takahashi, Hideyo ^a   Ikegami, Shiro ^a  

^a TEIKYO UNIVERSITY   (Japan)

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ARTICLE;

EID: 0000892037     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0264612     Document Type: Article

References (47)

1. For reviews, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
2. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
3. (c) Organometallics in Synthesis: A Manual; Schlosser, M., Ed.; Miley: West Sussex, UK, 2002.
4. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263-303.
5. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
6. (f) Tsuji, J. In Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, UK, 1995.
7. (a) Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, UK, 1998.
8. (b) Tundo, P.; Anastas, P.; Black D. S.; Breen, J.; Collins, T.; Memoli, S.; Miyamoto, J.; Polyakoff, M.; Tumas, W. Pure Appl. Chem. 2000, 72, 1207-1228.
9. For recent reviews of immobilized palladium catalysts, see: (a) de Miguel, Y. R. J. Chem. Soc., Perkin Trans., 1 2000, 4213-4221.
10. (b) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035-1074.
11. (c) Loch, J. A.; Crabtree, R. H. Pure Appl. Chem. 2001, 73, 119-128.
12. (d) Corain, B.; Kralik, M. J. Mol. Catal. A: Chem. 2001, 173, 99-115.
13. (e) Bergbreiter, D. E. Curr. Opin. Drug Discovery Den. 2001, 4, 736-744.
14. For recent developments and improvements for heterogeneous catalysis of the Suzuki-Miyaura reaction, see: (a) Marck, G.; Villiger, A.; Buchecker, R. Tetrahedron Lett. 1994, 35, 3277-3280.
15. (b) Jang, S.-B. Tetrahedron Lett. 1997, 38, 1793-1796.
16. (c) Fenger, I.; Le Drian, C.; Tetrahedron Lett. 1998, 39, 4287-4290.
17. (d) Uozumi, Y.; Danjo, H. Hayashi, T. J. Org. Chem. 1999, 64, 3384-3388.
18. (e) Zhang, T. Y.; Allen M. J. Tetrahedron Lett. 1999, 40, 5813-5816.
19. (f) Li, Y.; Hong, X. M.; Collard, D. M.; El-Sayed, M. A. Org. Lett. 2000, 2, 2385-2388.
20. (g) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820-3827.
21. (h) Mubofu, E. B.; Clark, J. H.; Macquarrie, D. J. Green Chem. 2001, 3, 23-25.
22. (i) Akiyama, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2001, 40, 3469-3471.
23. (j) Cammidge, A. N.; Baines, N. J., Bellingham, R. K. Chem. Commun. 2001, 2588-2589.
24. (k) Barnard, C. F. J.; Griffin, K. G.; Froelich, J.; Ekman, K.; Sundell, M.; Peltonen, R. Chem. Ind. 2001, 82, 563-571.
25. (l) Bedford, R. B.; Cazin, C. S. J.; Hursthouse, M. B.; Light, M. E.; Pike, K. J.; Wimperis, S. J. Organomet. Chem. 2001, 633, 173-181.
26. (m) Buchmeiser, M. R.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39-46.
27. (n) Kosslick, H.; Mönnich, I.; Paetzold, E.; Fuhrmann, H.; Fricke, R.; Müller, D.; Oehme, G. Microporous Mesoporous Mater. 2001, 44-45, 537-545.
28. (o) Gordon, R. S.; Holmes, A. B. Chem. Commun. 2002, 640-641.
29. (p) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721-2722.
30. (a) Yamada, Y. M. A.; Ichinohe, M.; Takahashi, H.; Ikegami, S. Org. Lett. 2001, 3, 1837-1841.
31. (b) Yamada, Y. M. A.; Ichinohe, M.; Takahashi, H.; Ikegami, S. Tetrahedron Lett. 2002, 43, 3431-3434.
32. Bergbreiter and co-workers reported excellent homogeneous palladium catalysts prepared from poly(N-isopropylacrylamidel copolymers as soluble and thermoresponsive polymers: (a) Bergbreiter, D. E. Calal. Today 1998, 42, 389-397.
33. (b) Bergbreiter, D. E.; Liu, Y.-S.; Osburn, P. L. J. Am. Chem. Soc. 1998, 120, 4250-4251.
34. (c) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053-6062.
35. For examples of polymer-protected palladium nanoparticles for hydrogenation, see: (d) Chen, C-W.; Akashi, M. Polym. Adv. Technol. 1999, 10, 127-133.
36. (e) Chen, C-W.; Chen, M.-Q.; Serizawa, T.; Akashi, M. Chem. Commun. 1998, 831-832.
37. The molecular weight of 2 was wide-ranging (ca. 5000-70000), as checked by gel-permeation chromatography relative to polystyrene standards.
38. Mann, F. G.; Purdie, D. J. Chem. Soc. 1935, 1549-1563.
39. 3 and were similar to those of 3 except for the difference in integrated intensity.
40. The reaction was carried out in a reaction vessel equipped with a glass filter under an argon atmosphere.
41. It was confirmed that the filtrate separated from the reaction mixture had no catalytic activity. This result indicated that the catalytic activity observed was due to the heterogeneous component of the system.
42. Catalyst 3 was able to be reused without further treatment.
43. 4, filtered, dried in vacuo, and purified by column chromatography to give the corresponding product 8.
44. Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207-210.
45. (a) For the synthesis of candesartan, see: Kubo, K.; Kohara, Y.; Imamiya, E.; Sugiura, Y.; Inada, Y.; Furukawa, Y.; Nishikawa, K.; Naka, T. J. Med. Chem. 1993, 36, 2182-2195.
46. (b) For the synthesis of losartan, see: Carini, D. J.; Duncia, J. V.; Aldrich, P. E.; Chiu, A. T.; Johnson, A. L.; Pierce, M. E.; Price, W. A.; Santella, J. B., III; Wells, G. J.; Wexler, R. R.; Wong, P. C.; Yoo, S.-E.; Timmermans, P. B. M. W. M. J. Med. Chem. 1991, 34, 2525-2547.
47. (c) For the synthesis of L-158809, see: Mantlo, N. B.; Chakravarty, P. K.; Ondeyka, D. L.; Siegl, P. K. S.; Chang, R. S.; Lotti, V. J.; Faust, K. A.; Chen, T.-B.; Schorn, T. W.; Sweet, C. S.; Emmert, S. E.; Patchett, A. A.; Greenlee, W. J. J. Med. Chem. 1991, 34, 2919-2922.