Heck reaction catalyzed by mesoporous SBA-15-supported ionic liquid-Pd(OAc)2

Synlett

Volumn , Issue 1, 2009, Pages 39-42

  Jung, Ji Young ^a   Taher, Abu ^a   Kim, Hyun Jin ^a   Ahn, Wha Seung ^a   Jin, Myung Jong ^a  

^a Inha University   (South Korea)

Author keywords

Heck reaction; Immobilization; Ionic liquid; Palladium; SBA 15

Indexed keywords

EID: 62349109079     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087488     Document Type: Article

References (39)

1. Reviews: (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
2. (b) Amatore, C.; Jutand, A. Acc. Chem. Rev. 2000, 33, 314.
3. (c) Zapf, A. Angew. Chem. Int. Ed. 2003, 42, 5394.
4. (d) Trzeciak, A. M.; Ziółkowski, J. J. Coord. Chem. Rev. 2005, 249, 2308.
5. (a) Tulloch, A. A. D.; Danopoulos, A. A.; Cafferkey, S. M.; Kleinhenz, S.; Hursthouse, M. B.; Tooze, R. P. Chem. Commun. 2000, 1247.
6. (b) McGuinness, D. S.; Cavell, K. J. Organometallics 2000, 19, 741.
7. (c) Reddy, K. R.; Surekha, K.; Lee, G.-H.; Peng, S.-M.; Liu, S.-T. Organometallics 2000, 19, 2637.
8. (d) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290.
9. (e) Lee, H. M.; Zeng, J. Y.; Hu, C.-H.; Lee, M.-T. Inorg. Chem. 2004, 43, 6822.
10. (f) Devasher, R. B.; Moore, L. R.; Shaughnessy, K. H. J. Org. Chem. 2004, 69, 7919.
11. (g) Sliger, M. D.; Broke, G. A.; Shaughnessy, K. H. J. Organomet. Chem. 2005, 690, 1478.
12. (h) Pascu, S. I.; Coleman, K. S.; Cowley, A. R.; Green, M. H.; Rees, N. H. J. Organomet. Chem. 2005, 690, 1645.
13. (i) Smith, R. C.; Bodner, C. R.; Earl, M. J.; Sears, N. C.; Hill, N. E.; Keles, M.; Aydin, Z.; Serindag, O. S. J. Organomet. Chem. 2007, 692, 1951.
14. (j) Scrivanti, A.; Bertoldini, M.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Marini, A.; Crociani, B. J. Mol. Catal. A: Chem. 2005, 235, 12.
15. (k) Taige, M. A.; Zeller, A.; Ahrens, S.; Goutal, S.; Herdtweck, E.; Strassner, T. J. Organomet. Chem. 2007, 692, 1519.
16. (l) Nonnenmacher, M.; Kunz, D.; Rominger, F.; Oeser, T. J. Organomet. Chem. 2007, 692, 2554.
17. (a) Bandini, M.; Luque, R.; Budarin, V.; Macquarrie, D. J. Tetrahedron 2005, 61, 9860.
18. (b) Mingji, D.; Liang, B.; Wang, C.; You, Z.; Xiang, J.; Dong, G.; Chen, J.; Yang, Z. Adv. Synth. Catal. 2004, 346, 1669.
19. (c) Papp, A.; Galbács, G.; Molnár, A. Tetrahedron Lett. 2005, 46, 7725.
20. (d) Polshettiwar, V.; Varma, R. S. Tetrahedron 2008, 64, 4637.
21. (e) Dawood, M. K. Tetrahedron 2007, 63, 9642.
22. (f) Tandukar, S.; Sen, A. J. Mol. Catal. A: Chem. 2007, 268, 112.
23. (a) Wasserscheid, P.; Keim, W. Angew. Chem. Int. Ed. 2000, 39, 3773.
24. (b) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
25. (c) Jain, N.; Kumar, A.; Chauhan, S.; Chauhan, S. M. S. Tetrahedron 2005, 61, 1015.
26. (d) Akiyama, T.; Suzuki, A.; Fuchibe, K. Synlett 2005, 1024.
27. (e) Ranu, B. C.; Banerjee, S.; Jana, R. Tetrahedron 2007, 63, 776.
28. (a) Mehnert, C. P.; Cook, R. A.; Dispenziere, N. C.; Afeworki, M. J. Am. Chem. Soc. 2002, 124, 12932.
29. (b) Breitenlechner, S.; Fleck, M.; Müller, T. E.; Suppan, A. J. Mol. Catal. A: Chem. 2004, 214, 175.
30. (c) Mehnert, C. P. Chem. Eur. J. 2005, 11, 50.
31. (d) Hagiwara, H.; Sugawara, Y.; Isobe, K.; Hoshi, T.; Suzuki, T. Org. Lett. 2004, 6, 2325.
32. (a) Zhao, D.; Huo, Q.; Feng, J.; Chemlka, B. F.; Stucky, G. D. J. Am. Chem. Soc. 1998, 120, 6024.
33. (b) Wight, A. P.; Davis, M. E. Chem. Rev. 2002, 102, 3586.
34. (c) Du, G.; Lim, S.; Pinault, M.; Wang, C.; Fang, F.; Pfefferle, L.; Haller, G. L. J. Catal. 2008, 253, 74.
35. (a) Gadenne, B.; Hesemann, P.; Moreau, J. J. E. Chem. Commun. 2004, 1768.
36. (b) Brenna, S.; Posset, T.; Furrer, J.; Blumel, J. Chem. Eur. J. 2006, 12, 2880.
37. 2, and dried at 90°C under vacuum to yield modified SBA-15 2 (2.48 g). Elemental analysis and weight gain showed that 1.05 mmol of the ionic liquid was anchored on 1.0 g of 2.
38. 2 3 (1.15 g). ICP analysis showed that 0.21 mmol of Pd was immobilized on 1.0 g of 3.
39. 4 and then evaporated under reduced pressure. The residue was purified by column chromatography on silica gel.