An imidazolium-based phosphinite ionic liquid (IL-OPPh2) as a reusable reaction medium and PdII ligand in Heck reactions of aryl halides with styrene and n-butyl acrylate

European Journal of Organic Chemistry

Volumn , Issue 13, 2007, Pages 2197-2201

  Iranpoor, Nasser ^a   Firouzabadi, Habib ^a   Azadi, Roya ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Aryl halide; Heck reaction; Ionic liquid; Palladium

Indexed keywords

EID: 34250632844     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601021     Document Type: Article

References (37)

1. a) I. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009;
2. b) M. T. Reetz, in Transition Metal Catalyzed Reactions (Eds.: S. G. Davies, S.-I. Murahashi); Blackwell Science: Oxford, 1999;
3. c) G. T. Grisp, Chem. Soc. Rev. 1998, 27, 427;
4. d) J. T. Link, L. E. Overman, in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998;
5. e) J. T. Link, L. E. Overman, Chemtech 1998, 28, 19;
6. f) S. Brase, A. Meijere, In Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. P. Diederich, J. Stang), Wiley-VCH, New York, 1998;
7. g) H. A. Dieck, R. F. Heck, J. Org. Chem. 1975, 40, 1083;
8. h) H. A. Dieck, R. F. Heck, J. Am. Chem. Soc. 1974, 96, 1133.
9. A. F. Littke, G. C. Fu, J. Org. Chem. 1999, 64, 10.
10. G. P. F. Van Strijdonck, M. D. K. Boele, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, Eur. J. Inorg. Chem. 1999, 1073.
11. Y. Bendavid, M. Portnoy, M. Gozin, D. Milstein, Organometallics 1992, 11, 1995.
12. M. Portnoy, Y. Bendavid, D. Milstein, Organometallics 1993, 12, 4734.
13. a) B. L. Shaw, S. D. Perera, Chem. Commun. 1998, 1863;
14. b) L. E. Overman, D. J. Poon, Angew. Chem. Int. Ed Engl. 1997, 36, 518;
15. c) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2;
16. d) W. Cabri, I. Candiani, A. Bedeschi, J. Org. Chem. 1992, 57, 3558.
17. A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 6989.
18. K. Selvakumar, A. Zapf, M. Beller, Org. Lett. 2002, 4, 3031.
19. J. Ch. Xiao, B. Twamley, J. M. Shreeve, Org. Lett. 2004, 6, 3845.
20. L. Xu, W. Chen, J. Xiao, Organometallics 2000, 19, 1123.
21. Q. Yao, E. P. Kinney, Z. Yang, J. Org Chem. 2003, 68, 7528 and earlier references therein.
22. K. S. A. Vallin, P. Emilsson, M. Larhed, A. Hallberg, J. Org. Chem. 2002, 67, 6243.
23. B. Karimi, D. Enders, Org. Lett. 2006, 8, 1237.
24. a) Y. Uozumi, T. Watanabe, J. Org. Chem. 1999, 64, 6921-6923;
25. b) L. Wang, Y. Zhang, Ch. Xie, Y. Wang, Synlett 2005, 12, 1861-1864.
26. V. Calo, A. Nacci, A. Monopoli, Eur. J. Org. Chem. 2006, 17, 3791-3802.
27. C. C. Cassol, A. P. Umpierre, G. Machado, S. I. Wolke, J. Dupont, J. Am. Chem. Soc. 2005, 127, 3298-3299.
28. a) Ch. Yang, H. M. Lee, S. P. Nolan, Org. Lett. 2001, 3, 1511-1514;
29. b) J. Huang, S. Nolan, J. Am. Chem. Soc. 1999, 121, 9889-9890;
30. c) H. M. Lee, S. P. Nolan, Org. Lett. 2000, 2, 2053-2055.
31. V. P. W. Böhm, W. A. Herrmann, Chem. Eur. J. 2000, 6, 1017.
32. H. M. Lee, S. P. Nolan, Org. Lett. 2000, 2, 2053.
33. N. Iranpoor, H. Firouzabadi, R. Azadi, Tetrahedron Lett. 2006, 47, 5531-5534.
34. H. Hagiwara, Y. Sugawara, K. Isobe, T. Hoshi, T. Suzuki, Org. Lett. 2004, 6, 2325-2328.
35. R. Barik, Ch. V. Kumar, P. K. Das, M. V. J. George, J. Org. Chem. 1985, 50, 4309.
36. Ö. Aksin, H. Türkmen, L. Artok, B. Çetinkaya, C. Ni, O. Büyükgüngörd, E. Ozkal, J. Organomet. Chem. 2006, 691, 3027-3036.
37. B. Gaugain, J. Barbet, N. Capelle, B. P. Roques, J. B. Le Pecq, Biochemistry 1978, 17, 5078-5088.