Polymer-supported N-heterocyclic carbene-palladium complex for heterogeneous suzuki cross-coupling reaction

Journal of Organic Chemistry

Volumn 70, Issue 17, 2005, Pages 6714-6720

  Kim, Jong Ho ^a   Kim, Jung Woo ^a   Shokouhimehr, Mohammadreza ^a   Lee, Yoon Sik ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; INFRARED SPECTROSCOPY; MONOMERS; POLYSTYRENES; REACTION KINETICS; SCANNING ELECTRON MICROSCOPY;

CROSS-COUPLING REACTIONS; LIGANDS; N-HETEROCYCLIC CARBENE (NHC); REACTION MIXTURE;

COMPLEXATION;

1 METHYL 3 (4 VINYLBENZYL)IMIDAZOLIUM HEXAFLUOROPHOSPHATE; CARBENE; HETEROCYCLIC AMINE; IMIDAZOLE DERIVATIVE; MONOMER; PALLADIUM COMPLEX; POLYMER; POLYSTYRENE; RESIN; STYRENE; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CONFOCAL LASER MICROSCOPY; INFRARED SPECTROSCOPY; POLYMERIZATION; SCANNING ELECTRON MICROSCOPY; SUZUKI REACTION; SYNTHESIS;

EID: 23644461385     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050721m     Document Type: Article

References (49)

1. (a) Öfele, K. J. Organomet. Chem. 1968, 12, 11.
2. (b) Wanzlick, H. J.; Schönherr, H. J. Angew. Chem. 1968, 80, 154.
3. (c) For a recent review, see: Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
4. (a) Öfele, K.; Herrmann, W. A.; Mihalios, D.; Elison, M.; Herdtweck, E.; Scherer, W. J. Organomet. Chem. 1993, 459, 177.
5. (b) Herrmann, W. A.; Öfele, K.; Elison, M.; Kühn, F. E.; Roesky, P. W. J. Organomet. Chem. 1994, 480, C7.
6. (a) Weskamp, T.; Kohl, F. J.; Hieringer, W.; Gleich, D.; Herrmann, W. A. Angew. Chem., Int. Ed. 1999, 38, 2416.
7. (b) Schwarz, J.; Böhm, V. P. W.; Gardiner, M. G.; Grosche, M.; Herrmann, W. A.; Hieringer, W.; Raudaschl-Sieber, G. Chem.-Eur. J. 2000, 6, 1773.
8. (a) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804.
9. (b) Xu, L.; Chen, W.; Xiao, J. Organometallics 2000, 19, 1123.
10. (c) Andrus, M. B.; Song, C. Org. Lett. 2001, 3, 3761.
11. (d) Peris, E.; Loch, J. A.; Mata, J.; Crabtree, R. H. Chem. Commun. 2001, 210.
12. (e) Yang, C.; Lee, H. M.; Nolan, S. P. Org. Lett. 2001, 3, 1511.
13. (f) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866.
14. (g) Gstöttmayr, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1363.
15. (a) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247.
16. (b) Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Herrmann, W. A. Tetrahedron Lett. 1999, 40, 4787.
17. (c) Hung, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375.
18. (d) Jazzar, R. F. R.; Macgregor, S. A.; Mahon, M. F.; Richards, S. P.; Whittlesey, M. K. J. Am. Chem. Soc. 2002, 124, 4944.
19. (e) Trnka, T. M.; Morgan, J. P.; Sanford, M. S.; Wilhelm, T. E.; Scholl, M.; Choi, T.-L.; Ding, S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 2546.
20. (f) Ung, T.; Hejl, A.; Grubbs, R. H.; Schrodi, Y. Organometallics 2004, 23, 5399.
21. (g) Lebel, H.; Janes, M. K.; Charette, A. B.; Nolan, S. P. J. Am. Chem. Soc. 2004, 126, 5046.
22. (a) Köcher, C.; Herrmann, W. A. J. Organomet. Chem. 1997, 532, 261.
23. (b) Chen, A. C.; Ren, L.; Decken, A.; Crudden, C. M. Organometallics 2000, 19, 3459.
24. (a) Böhm, V. P. W.; Weskamp, T.; Gstöttmayr, C. W. K.; Herrmann, W. A. Angew. Chem., Int. Ed. 2000, 39, 1602.
25. (b) Sato, Y.; Sawaki, R.; Mori, M. Organometallics 2001, 20, 5510.
26. (c) Douthwaite, R. E.; Green, M. L. H.; Silcock, P. J.; Gomes, P. T. Organometallics 2001, 20, 2611.
27. (d) Böhm, V. P. W.; Gstöttmayr, C. W. K.; Weskamp, T.; Herrmann, W. A. Angew. Chem., Int. Ed. 2001, 40, 3387.
28. (e) Dorta, R.; Stevens, E. D.; Hoff, C. D.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 10490.
29. (f) Wang, X.; Liu, S.; Jin, G.-X. Organometallics 2004, 23, 6002.
30. Schwarz, J.; Böhm, V. P. W.; Gardiner, M. G.; Grosche, M.; Herrmann, W. A.; Hieringer, W.; Raudaschl-Sieber, G. Chem.-Eur. J. 2000, 6, 1773.
31. Schürer, S. C.; Gessler, S.; Buschmann, N.; Blechert, S. Angew. Chem., Int. Ed. 2000, 39, 3898.
32. Mayr, M.; Mayr, B.; Buchmeiser, M, R. Angew. Chem., Int. Ed. 2001, 40, 3839.
33. Byun, J. W.; Lee, Y. S. Tetrahedron Lett. 2004, 45, 1837.
34. (a) Cho, J. K.; Park, B. D.; Lee, Y. S. Tetrahedron Lett. 2000, 41, 7481.
35. (b) Cho, J. K.; Kim, D. W.; Namgung, J. Y.; Lee, Y. S. Tetrahedron Lett. 2001, 42, 7443.
36. (c) Cho, J. K.; Park, B. D.; Park, K. B.; Lee, Y. S. Macromol. Chem. Phys. 2002, 203, 2211.
37. (d) Kim, H. Y.; Cho, J. K.; Chung, W. J.; Lee, Y. S. Org. Lett. 2004, 6, 3273.
38. (e) Kim, J. H.; Jun, B. H.; Byun, J. W.; Lee, Y. S. Tetrahedron Lett. 2004, 45, 5827.
39. Herrmann, W. A.; Schwarz, J.; Gardiner, M. G. Organometallics 1999, 18, 4082.
40. Petrak, K.; Degen, I.; Beynon, P. J. Polymer. Science 1982, 20, 783.
41. (a) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997.
42. (b) Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami, S. J. Org. Chem. 2003, 68, 7733.
43. (c) Byun, J. W.; Lee, Y. S. Tetrahedron Lett. 2004, 45, 1837.
44. (a) Li, C. J. Chem. Rev. 1993, 93, 2023.
45. (b) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919.
46. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384.
47. (d) Uozumi, Y.; Kimura, T. Synlett 2002, 12, 2045.
48. The coupling of these substrates was reviewed in Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
49. Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 2, 207.