One-pot Suzuki/Heck sequence for the synthesis of (E)-stilbenes featuring a recyclable silica-supported palladium catalyst via a multi-component reaction in 1,3-propanediol

Advanced Synthesis and Catalysis

Volumn 352, Issue 11-12, 2010, Pages 1993-2001

  Joucla, Lionel ^a   Cusati, Giuseppe ^a   Pinel, Catherine ^a   Djakovitch, Laurent ^a  

^a UNIVERSITÉ DE LYON   (France)

Author keywords

Cross coupling reactions; Heterogeneous palladium catalysts; Multi component reaction; One pot synthesis; Stilbenes; Suzuki Heck sequence

Indexed keywords

EID: 77956384418     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000028     Document Type: Article

References (42)

1. S. Pröckl, W. Kleist, M. A. Gruber, K. K öhler, Angew. Chem. Int. Ed. 2004, 43, 1881.
2. L. Djakovitch, K. Koehler, J. G. De Vries, in: Nanoparticles and Catalysis. (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2008, pp 303.
3. F.-X. Felpin, T. Ayad, S. Mitra, Eur. J. Org. Chem. 2006, 2006, 2679.
4. F.-X. Felpin, E. Fouquet, ChemSusChem 2008, 1, 718.
5. H. Brunner, N. Le Cousturier de Courcy, J.-P. Genêt, Synlett 2000, 201.
6. M. Gruber, S. Chouzier, K. Koehler, L. Djakovitch, Appl. Catal. A: Gen. 2004, 265, 161.
7. G. Cusati, A. Wedig, L. Djakovitch, Lett. Org. Chem. 2009, 6, 77.
8. M. J. Climent, A. Corma, S. Iborra, M. Mifsud, Adv. Synth. Catal. 2007, 349, 1949.
9. F.-X. Felpin, E. Fouquet, Adv. Synth. Catal. 2008, 350, 863.
10. F.-X. Felpin, J. Coste, C. Zakri, E. Fouquet, Chem. Eur. J. 2009, 15, 7238.
11. O. Ibarguren, C. Zakri, E. Fouquet, F.-X. Felpin, Tetrahedron Lett. 2009, 50, 5071.
12. F.-X. Felpin, O. Ibarguren, L. Nassar-Hardy, E. Fouquet, J. Org. Chem. 2009, 74, 1349.
13. R. H. Taylor, F. X. Felpin, Org. Lett. 2007, 9, 2911.
14. L. Djakovitch, K. Kohler, J. Organomet. Chem. 2000, 606, 101.
15. A. Nejjar, C. Pinel, L. Djakovitch, Adv. Synth. Catal. 2003, 345, 612.
16. L. Djakovitch, M. Wagner, C. G. Hartung, M. Beller, K. Koehler, J. Mol. Catal. A: Chem. 2004, 219, 121.
17. L. Djakovitch, P. Rouge, J. Mol. Catal. A: Chem. 2007, 273, 230.
18. S. Noël, C. Luo, C. Pinel, L. Djakovitch, Adv. Synth. Catal. 2007, 349, 1128.
19. G. Cusati, L. Djakovitch, Tetrahedron Lett. 2008, 49, 2499.
20. N. Batail, A. Bendjeriou, T. Lomberget, R. Barret, V. Dufaud, L. Djakovitch, Adv. Synth. Catal. 2009, 351, 2055.
21. L. Djakovitch, P. Rouge, Catal. Today 2009, 140, 90.
22. S. Chouzier, M. Gruber, L. Djakovitch, J. Mol. Catal. A: Chem. 2004, 212, 43.
23. L. Djakovitch, P. Rollet, Adv. Synth. Catal. 2004, 346, 1782.
24. P. Rollet, W. Kleist, V. Dufaud, L. Djakovitch, J. Mol Catal. A: Chem. 2005, 241, 39.
25. L. Djakovitch, V. Dufaud, R. Zaidi, Adv. Synth. Catal. 2006, 348, 715.
26. L. Joucla, G. Cusati, C. Pinel, L. Djakovitch, Tetrahedron Lett. 2008, 49, 4738.
27. L. Joucla, G. Cusati, C. Pinel, L. Djakovitch, Appl. Catal. A: Gen. 2009, 360, 145.
28. J. A. Baur, D. A. Sinclair, Nat. Rev. Drug. Discov. 2006, 5, 493.
29. R. Singh, H. Kaur, Synthesis 2009, 2009, 2471.
30. A. Gordillo, E. d. Jesus, C. Lopez-Mardomingo, Chem. Commun. 2007, 4056.
31. T. Jeffery, B. Ferber, Tetrahedron Lett. 2003, 44, 193.
32. C. M. Kormos, N. E. Leadbeater, J. Org. Chem. 2008, 73, 3854.
33. L. Djakovitch, K. Koehler, J. Am. Chem. Soc. 2001, 123, 5990.
34. L. Huang, Z. Wang, T. P. Ang, J. Tan, P. K. Wong, Catal. Lett. 2006, 112, 219.
35. I.W. Davies, J. H. Smitrovich, R. Sidler, C. Qu, V. Gresham, C. Bazaral, Tetrahedron 2005, 61, 6425.
36. A. Zulauf, M. Mellah, E. Schulz, Chem. Commun. 2009, 6574.
37. J. C. Vedrine, M. Dufaux, C. Naccache, B. Imelik, J. Chem. Soc. Faraday Trans. 1 1978, 74, 440.
38. K. McEleney, C. M. Crudden, J. H. Horton, J. Phys. Chem. C 2009, 113, 1901.
39. F. Amoroso, S. Colussi, A. Del Zotto, J. Llorca, A. Trovarelli, J. Mol Catal. A: Chem. 2010, 315, 197.
40. L. Djakovitch, K. Koehler, J. Mol Catal. A: Chem. 1999, 142, 275.
41. M. Wagner, K. K öhler, L. Djakovitch, S. Weinkauf, V. Hagen, M. Muhler, Top. Catal. 2000, 13, 319.
42. K. K öhler, M. Wagner, L. Djakovitch, Catal. Today 2001, 66, 105.