Heck and Suzuki coupling reactions in water using poly(2-oxazoline)s functionalized with palladium carbene complexes as soluble, amphiphilic polymer supports

Journal of Organometallic Chemistry

Volumn 690, Issue 21-22, 2005, Pages 4648-4655

  Schönfelder, Daniel ^a   Nuyken, Oskar ^a   Weberskirch, Ralf ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Green chemistry; Heck coupling; Polymer support; Suzuki coupling

Indexed keywords

BLOCK COPOLYMERS; CATALYSIS; CATALYSTS; COMPLEXATION; HYDROPHOBICITY; OLEFINS; REACTION KINETICS; WATER;

GREEN CHEMISTRY; HECK COUPLING; POLYMER SUPPORT; SUZUKI COUPLING;

PALLADIUM COMPOUNDS;

EID: 26444620931     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.07.053     Document Type: Article

References (55)

1. R.A. Sheldon, and H. van Bekkum Fine Chemicals through Heterogeneous Catalysis 2001 Wiley-VCH Weinheim
2. R.F. Heck, and J.P. Nolley Jr. J. Org. Chem. 37 1972 2320
3. R.F. Heck Acc. Chem. Res. 12 1979 146
4. N. Miyaura, and A. Suzuki Chem. Commun. 1979 866
5. N. Miyaura, T. Yanagi, and A. Suzuki Synth. Commun. 11 1982 513
6. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
7. F.Y. Zhao, M. Shirai, Y. Ikushima, and M. Arai J. Mol. Catal. A 180 2002 211
8. M. Gruber, S. Chouzier, K. Koehler, and L. Djakovitch Appl. Catal. A 265 2004 161
9. K. Koehler, R.G. Heidenreich, J.G.E. Krauter, and M. Pietsch Chem. Eur. J. 8 2002 622
10. D.A. Conlon, B. Pipik, S. Ferdinand, C.R. LeBlond, J.R. Sowa, B. Izzo, P. Collins, J.M. Williams, Y.J. Shi, and Y.K. Sun Adv. Synth. Catal. 345 2003 931
11. C.R. LeBlond, A.T. Andrews, Y.K. Sun, and J.R. Sowa Org. Lett. 3 2001 1555
12. C. Baleizao, A. Corma, H. Garcia, and A. Leyva Chem. Commun. 5 2003 606
13. A. Corma, H. Garcia, A. Leyva, and A. Primo Appl. Catal. A 257 2004 77
14. M. Dams, L. Drijkoningen, B. Pauwels, G. vam Tendeloo, D.E. De Vos, and P.A. Jacobs J. Catal. 209 2002 225
15. L. Djakovitch, and K. Koehler J. Am. Chem. Soc. 123 2001 5990
16. M. Wagner, K. Kohler, L. Djakovitch, S. Weinkauf, V. Hagne, and M. Muhler Top. Catal. 13 2000 319
17. B.M. Choudary, K. Jyothi, M. Roy, M.L. Kantam, and B. Sreedhar Adv. Synth. Catal. 346 2004 1471
18. S.S. Prockl, W. Kleist, M.A. Gruber, and K. Kohler Angew. Chem. Int. Ed. 43 2004 1881
19. M.R. Buchmeiser, and K. Wurst J. Am. Chem. Soc 121 1999 11101
20. C.A. Lin, and F.T. Luo Tetrahedron Lett. 44 2003 7565
21. M.M. Dell'Anna, P. Mastrorilli, F. Muscio, C.F. Nobile, and G.P. Suranna Eur. J. Inorg. Chem. 5 2002 1094
22. M.M. Dell'Anna, P. Mastrorilli, F. Muscio, C.F. Nobile, and G.P. Scranna Eur. J. Inorg. Chem. 5 2002 1094
23. A. Datta, K. Ebert, and H. Plenio Organometallics 22 2003 4685
24. P.T. Anastas, and J.C. Warner Green Chemistry: Theory and Practice 1998 Oxford University Press Oxford
25. P. Tundo, P. Anastas, D.S. Black, J. Breen, T. Collins, S. Memoli, J. Miyamoto, M. Polyakoff, and W. Tumas Pure Appl. Chem. 72 2000 1207
26. B. Cornils, and W.A. Herrmann Aqueous Phase Organometallic Catalysis - Concept and Application 1998 Wiley-VCH Weinheim
27. F. Sieber, P. Wentworth, and K.D. Janda J. Combinat. Chem. 1 1999 540
28. P. Wentworth, and K.D. Janda Chem. Commun. 19 1999 1917
29. T. Malmström, and C. Andersson Chem. Commun. 10 1996 1135
30. D.E. Bergbreiter, B.L. Case, Y.S. Liu, and J.W. Caraway Macromolecules 31 1998 6053
31. P.L. Osburn, and D.E. Bergbreiter Prog. Polym. Sci. 26 2001 2015
32. For a recent review see: Y. Uozumi Top. Curr. Chem. 242 2004 77 and references therein
33. Y.M.A. Yamada, H. Takahashi, and S. Ikegami Tetrahedron Lett. 44 2003 2379
34. Y.M.A. Yamada, K. Takeda, H. Takahashi, and S. Ikegami Tetrahedron 60 2004 4097
35. C.W.K. Gstottmayr, V.P.W. Bohm, E. Herdtweck, M. Grosche, and W.A. Herrmann Angew. Chem. Int. Ed. 41 2002 1363
36. H.M. Lee, C.Y. Lu, C.Y. Chen, W.L. Chen, H.C. Lin, P.L. Chiu, and P.Y. Chen Tetrahedron 60 2004 5807
37. A.R. Kovacevic, B.M. Zeglis, J.W. Faller, and R.H. Crabtree Organometallics 23 2004 2461
38. M.T. Zarka, M. Bortenschlager, K. Wurst, O. Nuyken, and R. Weberskirch Organometallics 23 2004 4817
39. N. Hadej, E.A.B. Kantchey, C.J. O'Brien, and M.G. Organ Org. Lett. 10 2005 1991
40. M. Shi, and H.X. Qian Tetrahedron 61 2005 4949
41. J.O. Krause, M.T. Zarka, U. Anders, R. Weberskirch, O. Nuyken, and M.R. Buchmeiser Angew. Chem. Int. Ed. 42 2003 5965
42. T. Kotre, O. Nuyken, and R. Weberskirch Macromol. Rapid. Commun. 23 2002 871
43. M.T. Zarka, O. Nuyken, and R. Weberskirch Chem. Eur J. 9 2003 3228
44. D. Schönfelder, O. Nuyken, and R. Weberskirch Macromolecules 38 2005 254
45. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009
46. J. Li, L.M. Zheng, I. King, T.W. Doyle, and S.H. Chen Curr. Med. Chem. 8 2001 121
47. A.D. Schlüter, and G. Wegner Acta Polym. 44 1993 59
48. T. Jeffery Tetrahedron Lett. 35 1994 3051
49. H. Zhao, M.-Z. Cai, C.-Y. Peng, and C.-S. Song J. Chem. Res. (S) 2002 28
50. Y. Uozumi, and T. Kimura Synlett 12 2002 2045
51. W.A. Herrmann, M. Elison, J. Fischer, C. Köcher, and G.R.J. Artus Angew. Chem., Int. Ed. Engl. 34 1995 2371
52. Y. Uozumi, H. Danjo, and T. Hayashi J. Org. Chem. 64 1999 3384
53. Y. Uozumi, and Y. Nakai Org. Lett. 4 2002 2997
54. J.-W. Byun, and Y.-S. Lee Tetrahedron Lett. 45 2004 1837
55. C.W. Gstöttmayr, V.P.W. Böhm, E. Herdtweck, M. Grosche, and W.A. Herrmann Angew. Chem. Int. Ed. 41 2002 1363