A Highly Fluorous Room-Temperature Ionic Liquid Exhibiting Fluorous Biphasic Behavior and Its Use in Catalyst Recycling

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3851-3854

  Van Den Broeke, Joep ^a   Winter, Ferry ^a   Deelman, Berth Jan ^a,b   Van Koten, Gerard ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b ARKEMA   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0041572003     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026700l     Document Type: Article

References (39)

1. Recent reviews and references therein: (a) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789. (b) Sheldon, R. Chem. Commun. 2001, 2399-2407. (c) Welton, T. Chem. Rev. 1999, 99, 2071-2083. (d) Olivier, H. J. Mol. Catal. A 1999, 146, 285-289.
2. Recent reviews and references therein: (a) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789. (b) Sheldon, R. Chem. Commun. 2001, 2399-2407. (c) Welton, T. Chem. Rev. 1999, 99, 2071-2083. (d) Olivier, H. J. Mol. Catal. A 1999, 146, 285-289.
3. Recent reviews and references therein: (a) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789. (b) Sheldon, R. Chem. Commun. 2001, 2399-2407. (c) Welton, T. Chem. Rev. 1999, 99, 2071-2083. (d) Olivier, H. J. Mol. Catal. A 1999, 146, 285-289.
4. Recent reviews and references therein: (a) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789. (b) Sheldon, R. Chem. Commun. 2001, 2399-2407. (c) Welton, T. Chem. Rev. 1999, 99, 2071-2083. (d) Olivier, H. J. Mol. Catal. A 1999, 146, 285-289.
5. Wilkes, J. S.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1992, 965-967.
6. (a) Chauvin, Y.; Mussmann, L., Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700.
7. (b) Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; de Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217-1219.
8. (c) Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997-1000.
9. (d) Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247-1248.
10. (e) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838.
11. (f) Carmichael, A. J.; Haddleton, D. M.; Bon, S. A. F.; Seddon, K. R. Chem. Commun. 2000, 1237-1238.
12. (a) Bonhôte, P.; Dias, A.-P.; Papageorgiou, N.; Kalyanasundaram, K.; Grätzel, M. Inorg. Chem. 1996, 35, 1168-1178.
13. (b) Koel, M. Proc. Estonian Acad. Sci. Chem. 2000, 3, 145-155.
14. (a) Einloft, S.; Dietrich, F. K.; de Souza, R. F.; DuPont, J. Polyhedron 1996, 15, 3257-3259.
15. (b) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Chem. Commun. 1999, 25-26.
16. (a) van den Broeke, J.; Lutz, M.; Kooijman, H.; Spek, A. L.; Deelman, B.-J.; van Koten, G. Organometallics 2001, 20, 2114-2117.
17. (b) de Wolf, E.; Spek, A. L.; Kuipers, B. W. M.; Philipse, A. P.; Meeldijk, J. D.; Bomans, P. H. H.; Frederik, P. M.; Deelman, B.-J.; van Koten, G. Tetrahedron 2002, 58, 3911-3922..
18. Lucas, P.; El Mehdi, N.; Ho, H. A.; Belanger, D.; Breau, L. Synthesis 2000, 9, 1253-1258.
19. Hagiwara, R.; Ito, Y. J. Fluorine Chem. 2000, 105, 221-227.
20. Deye, J. F.; Berger, T. A. Anal. Chem. 1990, 62, 615-622.
21. Brasse, C. C.; Englert, U.; Salzer, A. Organometallics 2000, 19, 3818-3823.
22. Waffenschmidt, H. Ph.D. Thesis, Rheinisch-Westfalische Technische Hochschule Aachen, Aachen, Germany, 2000.
23. (a) Carmichael, A. J.; Seddon, K. R. J. Phys. Org. Chem. 2000, 13, 591-595.
24. (b) Fletcher, K. A.; Storey, I. A.; Hendricks, A. E.; Pandey, S.; Pandey, S. Green Chem. 2001, 3, 210-215.
25. Cammarata, L.; Kazarian, S. G.; Salter, P. A.; Welton, T. Phys. Chem. Chem. Phys. 2001, 3, 5192-5200.
26. Hildebrand, J. H.; Cochran, D. R. F. J. Am. Chem. Soc. 1949, 71, 22-25.
27. de Wolf, E.; Speets, E. A.; Deelman, B.-J.; van Koten, G. Organometallics 2001, 20, 3686-3690. The authors used 1-hexene as an olefinic substrate.
28. (a) Richter, B.; de Wolf, E.; Deelman, B.-J.; van Koten, G. PCT Int. Appl. WO 0018444, 2000.
29. (b) Richter, B.; Spek, A. L.; van Koten, G.; Deelman, B.-J. J. Am. Chem. Soc. 2000, 122, 3945-3951.
30. The formation of disilanes is catalyzed by Wikinson's complex but can be suppressed by using an excess of olefin: (a) Brown-Wensley, K. A. Organometallics 1987, 6, 1590-1591. (b) Chang, L. S.; Corey, J. Y. Organometallics 1989, 8, 1885-1893.
31. The formation of disilanes is catalyzed by Wikinson's complex but can be suppressed by using an excess of olefin: (a) Brown-Wensley, K. A. Organometallics 1987, 6, 1590-1591. (b) Chang, L. S.; Corey, J. Y. Organometallics 1989, 8, 1885-1893.
32. (a) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1965, 87, 16-21.
33. (b) Chalk, A. J. J. Organomet. Chem. 1970, 21, 207-213.
34. The drop in activity after the first recycle is well above average.
35. Yoshida, J.-I.; Itami, K.; Mitsudo, K.; Suga, S. Tetrahedron Lett. 1999, 40, 3403-3406.
36. ICP-AAS analysis showed the presence of 147 mass ppm of boron in the product layer, which corresponds with a leaching of 4 wt % of ionic liquid per cycle.
37. The ratio of Rh and P observed was 1:1.5 but is known to be 1:2 in the spent catalyst (ref 15). This can be explained by phosphine oxidation, resulting in the formation of rhodium particles and phosphine oxides. The latter will have a higher affinity for the fluorous phase, resulting in a relatively higher leaching of the metal.
38. Substrate quality also proved to be important for the observed activity. Freshly distilled 1-octene resulted in increased conversions relative to aged material. Formation of epoxides, which is known to decrease the activity of Wilkinson's catalyst in hydrogenation, is a likely cause for this lower activity.
39. Marcus, Y. in The Properties of Solvents; Fogg, P. G. T., Ed.; Wiley & Sons: Chicester, UK, 1998.