Highly efficient, recyclable Pd(II) catalysts with bisimidazole ligands for the heck reaction in ionic liquids

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3209-3212

  Park, Soon Bong ^a   Alper, Howard ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; ION; PALLADIUM; SOLVENT;

ARTICLE; CATALYSIS; CATALYST; HECK REACTION; LIQUID;

EID: 0141856320     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol030071d     Document Type: Article

References (38)

1. (a) Negishi, E., Ed.; Handbook of Organopalladium Chemistry for Organic Synthesis; John Wiley & Sons: New York, 2002.
2. (b) Tsuji, J. Palladium Reagents and Catalysts. Innovations in Organic Synthesis; Wiley: Chichester, UK, 1995.
3. For recent reviews, see: (a) Brase, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998. (b) Crips, G. T. Chem. Soc. Rev. 1998, 27, 427. (c) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 1998, 27, 427.
4. For recent reviews, see: (a) Brase, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998. (b) Crips, G. T. Chem. Soc. Rev. 1998, 27, 427. (c) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 1998, 27, 427.
5. For recent reviews, see: (a) Brase, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998. (b) Crips, G. T. Chem. Soc. Rev. 1998, 27, 427. (c) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 1998, 27, 427.
6. (a) Peris, E.; Loch, J. A.; Mata, J.; Crabtree, R. H. Chem. Commun. 2001, 201.
7. (b) Herrmann, W. A.; Elson, M.; Fisher, J.; Kocher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. 1995, 34, 2371.
8. (c) Tulloch, A. A. D.; Danopoulos, A. A.; Tooze, R. P.; Cafferkey, S. M. ; Kleinhenz, S.; Hursthouse, M. B. Chem. Commun. 2000, 1247.
9. (d) Gruber, A. S.; Zim, D.; Ebeling, G.; Osborn, P. L.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531.
10. (e) Reetz, M. T.; Westermann, E. Angew. Chem., Int. Ed. 2000, 39, 165.
11. (a) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035
12. (b) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956.
13. (c) Arya, P.; Panda, G.; Rao. N. V.; Alper, H.; Bourque, S. C.; Manzer, L. E. J. Am. Chem. Soc. 2001, 123, 2399.
14. (d) Antebi, S.; Arya, P.; Manzer, L. E.; Alper, H. J. Org. Chem. 2002, 67, 6623.
15. For reviews, see: (a) Walton, T. Chem. Rev. 1999, 99, 2071. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. (c) Sheldon, R. Chem. Commun. 2001, 2399. (d) Dupont, J.; de Souza, R. F.; Suarez, P. A Z. Chem. Rev. 2002, 102, 3367 and references therein.
16. For reviews, see: (a) Walton, T. Chem. Rev. 1999, 99, 2071. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. (c) Sheldon, R. Chem. Commun. 2001, 2399. (d) Dupont, J.; de Souza, R. F.; Suarez, P. A Z. Chem. Rev. 2002, 102, 3367 and references therein.
17. For reviews, see: (a) Walton, T. Chem. Rev. 1999, 99, 2071. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. (c) Sheldon, R. Chem. Commun. 2001, 2399. (d) Dupont, J.; de Souza, R. F.; Suarez, P. A Z. Chem. Rev. 2002, 102, 3367 and references therein.
18. For reviews, see: (a) Walton, T. Chem. Rev. 1999, 99, 2071. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. (c) Sheldon, R. Chem. Commun. 2001, 2399. (d) Dupont, J.; de Souza, R. F.; Suarez, P. A Z. Chem. Rev. 2002, 102, 3367 and references therein.
19. Kaufmann, D. E.; Nouroozian, M.; Henze, H. Synlett. 1996, 1091.
20. Carmicheal, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997.
21. (a) Xu, L.; Chen, W.; Xiao, J. Organometallics 2000, 19, 1123.
22. (b) Bohm, V. P.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017.
23. (c) Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295.
24. (d) Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031.
25. (e) Vallin, K. S. A.; Emilsson, P.; Larhed, M.; Hallberg, A. J. Org. Chem. 2002, 67, 6243.
26. (a) Gianfranco, B.; Sandro, C.; Giancarlo, F. Synlett. 2002, 439.
27. (b) Consorti, C. S.; Zanini, M. L.; Leal, S.; Ebeling, G.; Dupont, J. Org. Lett. 2003, 5, 2881.
28. (c) Nakoji, M.; Kanayama, T.; Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 3328.
29. Rulke, R. E.; Ernsting, J. M.; Spec, A. L.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K. Inorg. Chem. 1993, 32, 5769.
30. Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319.
31. (a) Kondo, Y.; Inamoto, K.; Sakamoto, T. J. Comb. Chem. 2000, 2, 232.
32. (b) Cairns, N.; Harwood, L. M.; Astles, D. P.; Orr, A. J. Chem. Soc., Perkin Trans. 1994, 3059.
33. (c) Jones, G. H.; Venuti, M. C.; Alvarez, P.; Bruno, J. J. Berks, A. H.; Prince, A. J. Med. Chem. 1987, 30, 295.
34. Xu, L.; Chen, W.; Ross, T.; Xiao, T. Org. Lett. 2001, 3, 295.
35. (a) Nilsson, P.; Larhed, M.; Hallberg, A. J Am. Chem. Soc. 2001, 123, 8217.
36. (b) Itami, K.; Nokami, T.; Ishimura, Y.; Mitsudo, K.; Kamei, T.; Yoshida, J.-I. J. Am. Chem. Soc. 2001, 123, 11577.
37. (c) Tietze, L.F.; Nobel, T.; Spescha, M. J. Am. Chem. Soc. 1998, 120, 8971.
38. 2-I (3.0 equiv) was added to the mixture with stirring for 3 h at 120°C.