Iminophosphine palladium complexes in catalytic stille coupling reactions: From monomers to dendrimers

Organometallics

Volumn 21, Issue 22, 2002, Pages 4680-4687

  Koprowski, Marek ^a   Sebastián, Rosa Maria ^b   Maraval, Valérie ^b   Zablocka, Maria ^a   Cadierno, Victorio ^b   Donnadieu, Bruno ^b   Igau, Alain ^b   Caminade, Anne Marie ^b   Majoral, Jean Pierre ^b  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; DENDRIMERS; MONOMERS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

COUPLING REACTIONS;

PALLADIUM COMPOUNDS;

EID: 0013398153     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om011076m     Document Type: Article

References (31)

1. Kwong, F. Y.; Chan, K. S. Organometallics 2001, 20, 2570, and references therein.
2. Reddy, K. R.; Surekka, K.; Lee, G. H.; Peng, S. M.; Liu, S. T. Organometallics 2000, 19, 2637.
3. Shirakawa, E.; Yoshida, H.; Takaya, H. Tetrahedron Lett. 1997, 21, 3759; 1997, 29, 5177.
4. Shirakawa, E.; Yoshida, H.; Takaya, H. Tetrahedron Lett. 1997, 21, 3759; 1997, 29, 5177.
5. Pelagatti, P.; Bacci, A.; Carcelli, M.; Costa, M.; Fochi, A.; Ghidini, P.; Leporati, E.; Masi, M.; Pelizzi, C.; Pellizi G. J. Organomet. Chem. 1999, 583, 94.
6. Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 27, 3567.
7. Shirakawa, E.; Yoshida, H., Kurahashi, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 2975.
8. Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
9. Saitoh, A.; Misawa, M.; Morimoto, T. Synlett. 1999, 4, 483.
10. Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221.
11. Reddy, K. R.; Surekka, K.; Lee, G. H.; Peng, S. M.; Liu S. T. Organometallics 2000, 19, 2637.
12. Cadierno, V.; Zablocka, M.; Donnadieu, B.; Igau, A.; Majorai, J. P.; Skowronska, A. J. Am. Chem. Soc. 1999, 121, 11086.
13. (a) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. 2001, 40, 1828.
14. (b) Astruc, D.; Chardac, F. Chem. Rev. 2001, 101, 2991.
15. Caminade, A. M.; Maraval, V.; Laurent R.; Majorai, J. P. Curr. Org. Chem. 2002, 6, 739.
16. Maraval, V.; Laurent, R.; Caminade A. M.; Majorai J. P. Organometallics 2000, 19, 4025.
17. Eggeling, E. B.; Hovestad, N. J.; Jastrzebski, J. T. B. H.; Vogt, D.; van Koten, G. J. Org. Chem. 2000, 65, 8857.
18. Hovestad, N. J.; Eggeling, E. B.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. 1999, 38, 1665.
19. de Groot, D.; Emmerink, P. G.; Coucke, C.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Inorg. Chem. Commun. 2000, 3, 711.
20. de Groot, D.; de Waal, B. F. M.; Reek, J. N. H.; Schenning, A. P. H. J.; Kamer, P. C. J.; Meyer, E. W.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2001, 123, 8453.
21. Mizugaki, T.; Ooe, M.; Ebitani, K.; Kaneda, K. J. Mol. Catal. A 1999, 145, 329.
22. Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526.
23. Wehman, P.; van Donge, H. M. A.; Hagos, A.; Kamer P. C. J.; van Leeuwen, P. W. N. M. J. Organomet. Chem. 1997, 535, 183.
24. Launay, N.; Caminade, A. M.; Lahana, R.; Majorai, J. P. Angew. Chem., Int. Ed. Engl. 1994, 33, 1589.
25. All the amount of dendritic catalyst was precipitated during the recycling procedure. No detectable traces of the catalyst were found in the solution. However it was always difficult during the workup (filtration) not to lose a small amount of catalyst, as we were working with a very small quantity of it. We do believe that this fact explains why we observed the slight decrease of activity of the dendritic catalyst 18 when reused. Obviously several other options (membrane reactors, etc.) can be envisaged.
26. (a) Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. SIR92-A program for crystal structure solution. J. Appl. Crystallogr. 1993, 26, 343.
27. (b) Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. SIR97. J. Appl. Crystallogr. 1999, 32, 115.
28. Sheldrick, G. M. SHELX97 [Includes SHELXS97, SHELXL97, CIFTAB/-Programs for Crystal Structure Analysis; 1998 (Release 97-2).
29. Farrugia, L. WinGX-1.64.03 Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single-Crystal X-Ray Diffraction Data. J. Appl. Crystallogr. 1999, 32, 837.
30. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol IV.
31. Farrugia, L. J. ORTEP32 for Windows. J. Appl. Crystallogr. 1997, 30, 565.