An active and recyclable polystyrene-supported N-heterocyclic carbene-palladium catalyst for the Suzuki reaction of arylbromides with arylboronic acids under mild conditions

Synlett

Volumn , Issue 15, 2005, Pages 2305-2308

  Kang, Tairan ^a,b   Feng, Qiang ^a   Luo, Meiming ^a  

^a Sichuan University   (China)

^b CHINA WEST NORMAL UNIVERSITY   (China)

Author keywords

N heterocyclic carbene palladium complex; Polymer supported catalyst; Recyclable catalyst; Suzuki reaction

Indexed keywords

ARYLBORONIC ACID; ARYLBROMIDE; BISIMIDAZOLIUM SALT; BORONIC ACID DERIVATIVE; BROMINE DERIVATIVE; CARBENE PALLADIUM COMPLEX; CARBENOID; CHLOROMETHYLPOLYSTERENE; IMIDAZOLE DERIVATIVE; IMIDAZOLIUM SALT; PALLADIUM COMPLEX; POLYSTYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; RECYCLING; ROOM TEMPERATURE; SUZUKI REACTION;

EID: 25444509812     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872669     Document Type: Article

References (32)

1. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
2. (a) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew. Chem. Int. Ed. 2002, 41, 4120.
3. (b) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290.
4. (c) Littke, A. F.; Dai, C; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
5. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553.
6. (e) Weng, Z.; Teo, S.; Koh, L. L.; Hor, T. S. A. Organometallics 2004, 23, 3603.
7. (f) Li, J. H.; Liu, W. J. Org. Lett. 2004, 6, 2809.
8. (g) Chen, C. L.; Liu, Y. H.; Peng, S. M.; Liu, S. T. Organometallics 2005, 24, 1075.
9. (a) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820.
10. (b) Cammidge, A. N.; Baines, N. J.; Bellingham, R. K. Chem. Commun. 2001, 2588.
11. (c) Gordon, R. S.; Holmes, A. B. Chem. Commun. 2002, 640.
12. (d) Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami, S. J. Org. Chem. 2003, 68, 7733.
13. (e) Phan, N. T. S.; Brown, D. H.; Styring, P. Tetrahedron Lett. 2004, 45, 7915.
14. (a) Zhang, C.; Trudell, M. L. Tetrahedron Lett. 2000, 41, 595.
15. (b) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866.
16. (c) Vargas, V. C.; Rubio, R. J.; Hollis, T. K.; Salcido, M. E. Org. Lett. 2003, 5, 4847.
17. (d) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194.
18. (a) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew. Chem. Int. Ed. 2002, 41, 4120.
19. (b) Feuerstein, M.; Berthiol, F.; Doucet, H.; Santelli, M. Synlett 2002, 1807.
20. (c) Mori, K.; Yamaguchi, K.; Hara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2002, 124, 11572.
21. (d) Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162.
22. (e) Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343.
23. (f) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
24. 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.
25. (a) Zhao, Y.; Zhou, Y.; Ma, D.; Liu, J.; Zhang, T. Y.; Zhang, H. Org. Biomol. Chem. 2003, 1, 1643.
26. (b) Byun, J. W.; Lee, Y. S. Tetrahedron Lett. 2004, 45, 1837.
27. (c) Kim, J. H.; Jun, B. H.; Byun, J. W.; Lee, Y. S. Tetrahedron Lett. 2004, 45, 5827.
28. 2+: 111.0741; found: 111.0729.
29. 2O (6 × 10 mL), and then dried under vacuum. The loading of the imidazolium groups was determined by means of the nitrogen content obtained from elemental analysis (N, 1.4%, 0.5 mmol imidazolium/g).
30. 2O (10 × 10 mL), MeOH (10 × 10 mL), and dried under reduced pressure to give 3. ICP-AES: 100 μmol Pd/g.
31. Procedure for Measuring the Swelling Properties of the Polystyrene-Supported Bisimidazolium Salt 2 and the Catalyst 3. The swelling volumes of polymeric supports in various solvents were measured in a fritted column (ID 0.8 cm, length 20 cm). The polymeric support (1.0 g) was swollen in a solvent at r.t. for 2 h, and then washed with a 10-fold volume of each solvent. After filtration, the volume of the polymeric support was measured.
32. 4 and evaporated under reduced pressure. The biphenyl product (91 mg, yield 99%) was isolated by column chromatography (eluent: n-hexane).