Ruthenium-catalyzed olefin metathesis in ionic liquids

Organic Letters

Volumn 3, Issue 23, 2001, Pages 3785-3787

  Buijsman, Rogier C ^a   Van Vuuren, Elizabeth ^a   Sterrenburg, Jan Gerard ^a  

^a NV ORGANON   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0043205316     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016769d     Document Type: Article

References (46)

1. For recent reviews on olefin metathesis, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
2. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
3. (c) Wright, D. L. Curr. Org. Chem. 1999, 3, 211.
4. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
5. Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9858.
6. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
7. Maynard, H. D.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 4137.
8. (a) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657.
9. (b) Schürer, S. C.; Gessler, S.; Buschmann, N.; Blechen, S. Angew. Chem., Int. Ed. 2000, 39, 3898.
10. (c) Yao, Q. Angew. Chem., Int. Ed. 2000, 39, 3896.
11. Paquette, L. A., Schloss, J. D.; Efremov, I.; Fabris, F.; Gallou, F.; Méndez-Andino, J.; Yang, J. Org. Lett. 2000, 2, 1259.
12. Ahn, Y. M.; Yang, K.-L. Georg, G. I. Org. Lett. 2001, 3, 411.
13. For recent reviews on ionic liquids, see: Welton, T. Chem. Rev. 1999, 99, 2071. Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. Seddon, K. R. J. Chem. Technol. Biotechnol. 1997, 68, 351.
14. For recent reviews on ionic liquids, see: Welton, T. Chem. Rev. 1999, 99, 2071. Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. Seddon, K. R. J. Chem. Technol. Biotechnol. 1997, 68, 351.
15. For recent reviews on ionic liquids, see: Welton, T. Chem. Rev. 1999, 99, 2071. Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. Seddon, K. R. J. Chem. Technol. Biotechnol. 1997, 68, 351.
16. For some examples of organic reactions in ionic liquids, see the following. Alkylation: Earle, M.; McCormac, P. B.; Seddon, K. R. Chem. Commun 1998, 2245. Beckmann rearrangement: Peng, J.; Deng, Y. Tetrahedron Lett. 2001, 42, 403. Diels-Alder reaction: Fisher, T.; Sethi, A.; Welton, T.; Woolf, J. Tetrahedron Lett. 1999, 40, 793. Earle, M. J.; McCormac, P. B.; Seddon, K. R. Green Chem. 1999, 23. Friedel-Crafts reactions: Adams, C. J.; Earle, M. J.; Roberts, G.; Seddon, K. R Chem. Commun 1998, 2097. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Reduction of aldehydes: Kabalka, G.; Malladi, R. R. Chem. Commun. 2000, 2191. Wittig reaction: Le Boulaire, V.; Gree, R. Chem. Commun. 2000, 2195.
17. For some examples of organic reactions in ionic liquids, see the following. Alkylation: Earle, M.; McCormac, P. B.; Seddon, K. R. Chem. Commun 1998, 2245. Beckmann rearrangement: Peng, J.; Deng, Y. Tetrahedron Lett. 2001, 42, 403. Diels-Alder reaction: Fisher, T.; Sethi, A.; Welton, T.; Woolf, J. Tetrahedron Lett. 1999, 40, 793. Earle, M. J.; McCormac, P. B.; Seddon, K. R. Green Chem. 1999, 23. Friedel-Crafts reactions: Adams, C. J.; Earle, M. J.; Roberts, G.; Seddon, K. R Chem. Commun 1998, 2097. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Reduction of aldehydes: Kabalka, G.; Malladi, R. R. Chem. Commun. 2000, 2191. Wittig reaction: Le Boulaire, V.; Gree, R. Chem. Commun. 2000, 2195.
18. For some examples of organic reactions in ionic liquids, see the following. Alkylation: Earle, M.; McCormac, P. B.; Seddon, K. R. Chem. Commun 1998, 2245. Beckmann rearrangement: Peng, J.; Deng, Y. Tetrahedron Lett. 2001, 42, 403. Diels-Alder reaction: Fisher, T.; Sethi, A.; Welton, T.; Woolf, J. Tetrahedron Lett. 1999, 40, 793. Earle, M. J.; McCormac, P. B.; Seddon, K. R. Green Chem. 1999, 23. Friedel-Crafts reactions: Adams, C. J.; Earle, M. J.; Roberts, G.; Seddon, K. R Chem. Commun 1998, 2097. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Reduction of aldehydes: Kabalka, G.; Malladi, R. R. Chem. Commun. 2000, 2191. Wittig reaction: Le Boulaire, V.; Gree, R. Chem. Commun. 2000, 2195.
19. For some examples of organic reactions in ionic liquids, see the following. Alkylation: Earle, M.; McCormac, P. B.; Seddon, K. R. Chem. Commun 1998, 2245. Beckmann rearrangement: Peng, J.; Deng, Y. Tetrahedron Lett. 2001, 42, 403. Diels-Alder reaction: Fisher, T.; Sethi, A.; Welton, T.; Woolf, J. Tetrahedron Lett. 1999, 40, 793. Earle, M. J.; McCormac, P. B.; Seddon, K. R. Green Chem. 1999, 23. Friedel-Crafts reactions: Adams, C. J.; Earle, M. J.; Roberts, G.; Seddon, K. R Chem. Commun 1998, 2097. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Reduction of aldehydes: Kabalka, G.; Malladi, R. R. Chem. Commun. 2000, 2191. Wittig reaction: Le Boulaire, V.; Gree, R. Chem. Commun. 2000, 2195.
20. For some examples of organic reactions in ionic liquids, see the following. Alkylation: Earle, M.; McCormac, P. B.; Seddon, K. R. Chem. Commun 1998, 2245. Beckmann rearrangement: Peng, J.; Deng, Y. Tetrahedron Lett. 2001, 42, 403. Diels-Alder reaction: Fisher, T.; Sethi, A.; Welton, T.; Woolf, J. Tetrahedron Lett. 1999, 40, 793. Earle, M. J.; McCormac, P. B.; Seddon, K. R. Green Chem. 1999, 23. Friedel-Crafts reactions: Adams, C. J.; Earle, M. J.; Roberts, G.; Seddon, K. R Chem. Commun 1998, 2097. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Reduction of aldehydes: Kabalka, G.; Malladi, R. R. Chem. Commun. 2000, 2191. Wittig reaction: Le Boulaire, V.; Gree, R. Chem. Commun. 2000, 2195.
21. For some examples of organic reactions in ionic liquids, see the following. Alkylation: Earle, M.; McCormac, P. B.; Seddon, K. R. Chem. Commun 1998, 2245. Beckmann rearrangement: Peng, J.; Deng, Y. Tetrahedron Lett. 2001, 42, 403. Diels-Alder reaction: Fisher, T.; Sethi, A.; Welton, T.; Woolf, J. Tetrahedron Lett. 1999, 40, 793. Earle, M. J.; McCormac, P. B.; Seddon, K. R. Green Chem. 1999, 23. Friedel-Crafts reactions: Adams, C. J.; Earle, M. J.; Roberts, G.; Seddon, K. R Chem. Commun 1998, 2097. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Reduction of aldehydes: Kabalka, G.; Malladi, R. R. Chem. Commun. 2000, 2191. Wittig reaction: Le Boulaire, V.; Gree, R. Chem. Commun. 2000, 2195.
22. For some examples of organic reactions in ionic liquids, see the following. Alkylation: Earle, M.; McCormac, P. B.; Seddon, K. R. Chem. Commun 1998, 2245. Beckmann rearrangement: Peng, J.; Deng, Y. Tetrahedron Lett. 2001, 42, 403. Diels-Alder reaction: Fisher, T.; Sethi, A.; Welton, T.; Woolf, J. Tetrahedron Lett. 1999, 40, 793. Earle, M. J.; McCormac, P. B.; Seddon, K. R. Green Chem. 1999, 23. Friedel-Crafts reactions: Adams, C. J.; Earle, M. J.; Roberts, G.; Seddon, K. R Chem. Commun 1998, 2097. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Reduction of aldehydes: Kabalka, G.; Malladi, R. R. Chem. Commun. 2000, 2191. Wittig reaction: Le Boulaire, V.; Gree, R. Chem. Commun. 2000, 2195.
23. For some examples of organic reactions in ionic liquids, see the following. Alkylation: Earle, M.; McCormac, P. B.; Seddon, K. R. Chem. Commun 1998, 2245. Beckmann rearrangement: Peng, J.; Deng, Y. Tetrahedron Lett. 2001, 42, 403. Diels-Alder reaction: Fisher, T.; Sethi, A.; Welton, T.; Woolf, J. Tetrahedron Lett. 1999, 40, 793. Earle, M. J.; McCormac, P. B.; Seddon, K. R. Green Chem. 1999, 23. Friedel-Crafts reactions: Adams, C. J.; Earle, M. J.; Roberts, G.; Seddon, K. R Chem. Commun 1998, 2097. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Reduction of aldehydes: Kabalka, G.; Malladi, R. R. Chem. Commun. 2000, 2191. Wittig reaction: Le Boulaire, V.; Gree, R. Chem. Commun. 2000, 2195.
24. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977.
25. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
26. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
27. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
28. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
29. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
30. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
31. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
32. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
33. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
34. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
35. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
36. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
37. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
38. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
39. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
40. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
41. For some examples of transition-metal catalyzed reactions in ionic liquids, see the following. (Asymmetric) epoxidation: Owens, G. S.; Abu-Omar, M. M. Chem. Commun. 2000, 1165. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837. Asymmetric hydrogenation: Brown, R. A.; Polett, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. J. Am. Chem. Soc. 2001, 123, 1254. Asymmetric ring opening of epoxides: Song, C. E.; Rim Oh, C.; Roh, E. J.; Choo, D. J. Chem. Commun. 2000, 1743. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Coupling of aryl halides: Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2000, 41, 10319. Suzuki cross-coupling: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Heck arylation of vinyl ethers: Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Heck reaction: Kaufmann, D. E.; Nouzoorian, M.; Henze, H. Synlett 1996, 7, 1091. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 977. Hydrogenation/hydroformylation: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K. W.; Stelzer, O. Chem. Commun. 2001, 451. Negishi cross-coupling: Sirieix, J.; Ossberger, M.; Betzemeier, B.; Knochel, P. Synlett 2000, 11, 1613. Pd-catalyzed allylation reaction: Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun. 1999, 1247. Stille coupling: Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233. Trost-Tsuji reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
42. Ru-catalyzed RCM in ionic liquids has been described in a recent patent application. Gurtler, C.; Jautelat, M. EP 1035093 A2, 2000. First example of an olefin metathesis (Ni-catalyzed) in ionic liquids has been described by Chauvin, Y.; Olivier-Bourbigou, H. CHEMTECH 1995, 9, 26.
43. Ru-catalyzed RCM in ionic liquids has been described in a recent patent application. Gurtler, C.; Jautelat, M. EP 1035093 A2, 2000. First example of an olefin metathesis (Ni-catalyzed) in ionic liquids has been described by Chauvin, Y.; Olivier-Bourbigou, H. CHEMTECH 1995, 9, 26.
44. Dyatkin, A. B. Tetrahedron Lett. 1997, 38, 2065.
45. All ICP-AES (inductively coupled plasma - atomic emission spectrometer) samples were prepared first by accurately weighing the samples (∼4 mg) and then adding 10 mL of 0.12 M hydrochloric acid in glacial acetic acid. To correct for matrix effects, a Pt standard was added to the sample (100 μL, 1 mg Pt/mL, Baker Instra analyzed, AAS standard). Samples were analyzed on a Perkin-Elmer Optima 3000 ICP-AE spectrometer. Intensities of spectral lines at 240.272 and 349.894 nm were measured in all samples and standards. The Ru level in the samples was determined by comparing the intensity of the spectral line with a ruthenium standard curve. Each sample was measured three times, and the average Ru contaminant level of these measurements has been reported.
46. + 299.