Preparation of a Nafion-Teflon bimembrane-supported palladium catalyst and its use in the Heck reaction

Tetrahedron Letters

Volumn 46, Issue 36, 2005, Pages 6159-6162

  Li, Yangzhou ^a   Li, Zhiming ^a   Li, Feng ^a   Wang, Quanrui ^a   Tao, Fenggang ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

Heck reaction; Nafion film; Palladium catalyst; Sonogashira couplings

Indexed keywords

ALKENE; IODINE DERIVATIVE; NAFION; PALLADIUM; PHENYLACETYLENE; POLITEF; POLYETHER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; HECK REACTION; MEMBRANE; MOLECULAR STABILITY; SONOGASHIRA REACTION;

EID: 23244432927     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.091     Document Type: Article

References (32)

1. For a selected review, see: W.A. Herrmann, and B. Cornils Angew. Chem., Int. Ed. 36 1997 1049 1067
2. S. Bräse, and A. de Meijere F. Diederich P.J. Stang Metal-Catalyzed Cross-Coupling Reactions 1998 Wiley-VCH Weinheim, Germany 99 166
3. For recent examples, see: M. Miyashita, M. Sasaki, I. Hattori, M. Sakai, and K. Tanino Science 305 2004 495 499
4. M. Yoshida, K. Sugimoto, and M. Hara Org. Lett. 10 2004 1979 1982
5. D. Yang, Y.C. Chen, and N.Y. Zhu Org. Lett. 6 2004 1577 1580
6. A. Perosa, P. Tundo, M. Selva, S. Zinovyev, and A. Testa Org. Biomol. Chem. 2 2004 2249 2252
7. J.P. Liu, Y.H. Zhao, Y.Y. Zhou, L. Li, T.Y. Zhang, and H.B. Zhang Org. Biomol. Chem. 1 2003 3227 3231
8. For recent examples, see: B.B. Zeng, and S.B. King Synthesis 2002 2335 2337
9. A. Hosokawa, and K. Yoshida Synthesis 2003 1321 1323
10. F. Berthiol, H. Doucet, and M. Santelli Tetrahedron Lett. 45 2004 5633 5636
11. For selected reviews, see: B.C.G. Soderberg Coord. Chem. Rev. 224 2002 79 145
12. B.M. Bhanage, and M. Arai Cat. Rev. Sci. Eng. 43 2001 315 344
13. Y.R. de Miguel J. Chem. Soc., Perkin Trans. 1 2000 4213 4221
14. M.S. Anson, A.R. Mirza, L. Tonks, and J.M.J. Williams Tetrahedron Lett. 40 1999 7147 7150
15. J. Schwarz, V.P.W. Böhm, M.G. Gardiner, M. Grosche, W.A. Herrmann, W. Hieringer, and G. Raudaschl-Sieber Chem. Eur. J. 6 2000 1773 1780
16. D.P. Catsoulacos, B.R. Steele, G.A. Heropoulos, M. Micha-Screttas, and A.G. Livingston Tetrahedron Lett. 44 2003 4575 4578
17. Y. Uozumi, and T. Kimura Synlett 2002 2045 2048
18. E. Gonthier, and R. Breinbauer Synlett 2003 1049 1051
19. Y.M.A. Yamada, K. Takeda, H. Takahashi, and S. Ikegami Tetrahedron 60 2004 4097 4105
20. D.E. Bergbreiter, and S. Furyk Green Chem. 6 2004 280 285
21. J.J.E. Hardy, S. Hubert, D.J. Macquarrie, and A.J. Wilson Green Chem. 6 2004 53 56
22. For examples of silica-supported palladium catalyst in the Heck reactions, see: H. Hagiwara, Y. Sugawara, K. Isobe, T. Hoshi, and T. Suzuki Org. Lett. 6 2004 2325 2328
23. J.H. Clark, D.J. Macquarrie, and E.B. Mubofu Green Chem. 2 2000 53 55
24. S.C. Stinson Chem. Eng. News 60 1982 2 27
25. A.J. Seen J. Mol. Catal. A: Chem. 177 2001 105 122
26. A.J. Seen, K.J. Carvell, A.M. Hodges, and A.W.H. Mau J. Mol. Catal. 94 1994 163 171
27. A.J. Seen, A.T. Townsend, J.C. Bellis, and K.J. Carvell J. Mol. Catal. A: Chem. 149 1999 233 242
28. H. Dibowski, and F.P. Schmidtchen Tetrahedron 51 1995 2325 2330
29. 3): -15.4 ppm.
30. 3. The vial was heated under selected microwave conditions (∼250 W output) for two times, each for 10 min. After irradiation, the polymer was taken out by filtration, washed successively with degassed water, acetone and ether, and dried in vacuo at 50°C to give the supported ligand 3, which was characterized by IR analysis. The loading value was determined to be 0.314 mmol/g by nitrogen elemental analysis.
31. 2 (5 mg, 0.022 mmol) was added in one portion to the resulted suspension at ambient temperature, and the mixture was stirred at room temperature for an additional 2 h. The polymer was taken out from the mixture by filtration, washed successively with dichloromethane, ethanol and acetone to ensure exclusive removal of the unbound metal. Drying at 50°C in vacuum afforded the supported catalyst 4 as a yellowish solid. The palladium content was determined to be 0.665 wt % by Graphite Furnace Atomic Absorption (GFAA) analysis.
32. 3): 21.19, 61.38, 121.70, 125.34, 126.10, 127.01, 130.57, 139.55, 171.26 ppm.