Ionic liquid anchored "boomerang" catalysts bearing saturated and unsaturated NHCs: Recyclability in biphasic media for cross-metathesis

Organometallics

Volumn 27, Issue 10, 2008, Pages 2287-2292

  Claviers, Hervé ^a   Nolan, Steven P ^a   Mauduit, Marc ^b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b UNIV RENNES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BEARINGS (STRUCTURAL); CATALYSTS; IONIC LIQUIDS; IONIZATION OF LIQUIDS; OLEFINS; RUTHENIUM; RUTHENIUM COMPOUNDS;

ALKYLIDENE; BIPHASIC; CATALYTIC PERFORMANCES; CROSS METATHESIS (CM); IMIDAZOL; N-HETEROCYCLIC CARBENE (NHC); OLEFIN CROSS-METATHESIS; RECYCLABILITY; X RAY STRUCTURES;

CATALYSIS;

EID: 44649126855     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om8000229     Document Type: Article

References (70)

1. Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Weinheim, Germany, 2003.
2. For reviews, see: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2084.
3. (b) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692.
4. (c) Wilkes, J. S. J. Mol. Catal. A 2004, 214, 11-17.
5. (d) Pârvulescu, V. I.; Hardacre, C. Chem. Rev. 2007, 107, 2615-2665.
6. (a) Walker, A. J.; Bruce, N. C. Chem. Commun. 2004, 2570-2571.
7. (b) van Rantwijk, F.; Sheldon, R. A. Chem. Rev. 2007, 107, 2757-2785.
8. For representative examples, see: (a) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 6388-6390.
9. (b) Sprott, K. T.; Corey, E. J. Org. Lett. 2003, 5, 2465-2467.
10. (c) Ryu, D. H.; Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 4800-4802.
11. (d) Teo, Y.-C; Loh, T.-P. Org. Lett. 2006, 8, 5999-6001.
12. For recent examples, see: (a) Tominaga, K.-I.; Sasaki, Y. Chem. Lett. 2004, 33, 14-15.
13. (b) Illner, P.; Zahl, A.; Puchta, R.; van Eikema Hommes, N.; Wasserscheid, P.; van Eldik, R. J. Organomet. Chem. 2005, 690, 3567-3576.
14. (c) Riisager, A.; Fehrmann, R.; Flicker, S.; van Hal, R.; Haumann, M.; Wasserscheid, P. Angew. Chem., Int. Ed. 2005, 44, 815-819.
15. (d) Yang, Y.; Deng, C.; Yuan, Y. J. Catal. 2005, 232, 108-116.
16. For selected examples, see: (a) Park, S. B.; Alper, H. Org. Lett. 2003, 5, 3209-3212.
17. (b) Zhao, D. B.; Fei, Z. F.; Geldbach, T. J.; Scopelliti, R.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 15876-15882.
18. (c) Xiao, J. C.; Twamley, B.; Shreeve, J. M. Org. Lett. 2004, 6, 3845-3847.
19. (d) Wang, R.; Twamley, B.; Shreeve, J. M. J. Org. Chem. 2006, 71, 426-429.
20. (a) Buijsman, R. C.; van Vuuren, E.; Sterrenburg, J. G. Org. Lett. 2001, 3, 3785-3787.
21. (b) Semeril, D.; Olivier-Bourgbigou, H.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 2002, 146, 147.
22. For reviews of Ru-based catalysts, see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
23. (b) Handbook of Metathesis; Grubbs, R. H.; Ed.;Wiley-VCH:Weinheim, Germany, 2003, Vols. 1-3.
24. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
25. (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633.
26. (e) Beligny, S.; Blechert, S. In N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, Germany, 2006; pp 1-25.
27. (f) Deshmukh, P. H.; Blechert, S. Dalton Trans. 2007, 2479-2491.
28. (g) Despagnet-Ayoub, E.; Ritter, T. In N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Springer-Verlag,: Berlin/Heidelberg, Germany, 2007; pp 193-218.
29. (a) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
30. (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238.
31. (c) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490-4527.
32. (d) Donohoe, T. J.; Orr, A. J.; Bingham, M. Angew. Chem., Int. Ed. 2006, 45, 2664-2670.
33. (e) Villar, H.; Frings, M.; Bolm, C. Chem. Soc. Rev. 2007, 36, 55-66.
34. (f) Compain, P. Adv. Synth. Catal. 2007, 349, 1829-1846.
35. (g) Holub, N.; Blechert, S. Chem. Asian J. 2007, 2, 1064-1082.
36. Clavier, H.; Grela, K.; Kirschning, A.; Mauduit, M.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 6786-6801.
37. (a) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799.
38. (b) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
39. (c) Gessler, S.; Randl, S.; Blechert, S. Tetrahedron Lett. 2000, 41, 9973-9976.
40. (a) Gulajski, L.; Michrowska, A.; Bujok, R.; Grela, K. J. Mol. Catal. A 2006, 254, 118-123.
41. (b) Michrowska, A.; Gulajski, L.; Kaczmarska, Z.; Mennecke, K.; Kirschning, A.; Grela, K. Green Chem. 2006, 8, 685-688.
42. (a) Rix, D.; Clavier, H.; Coutard, Y.; Gulajski, L.; Grela, K.; Mauduit, M. J. Organomet. Chem. 2006, 691, 5397-5406.
43. (b) Rix, D.; Caijo, F.; Laurent, I.; Gulajski, L.; Grela, K.; Mauduit, M. Chem. Commun. 2007, 3771, 3773.
44. (a) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248-9249.
45. (b) Clavier, H.; Audic, N.; Mauduit, M.; Guillemin, J.-C. Chem. Commun. 2004, 2282, 2283.
46. (c) Clavier, H.; Audic, N.; Mauduit, M.; Guillemin, J.-C. J. Organomet. Chem. 2005, 690, 3585-3599.
47. (a) Yao, Q.; Zhang, Y. Angew. Chem., Int. Ed. 2003, 42, 3395-3398.
48. (b) Yao, Q.; Sheets, M. J. Organomet. Chem. 2005, 690, 3577-3584.
49. (a) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
50. (a) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
51. (b) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250.
52. Ritter, T.; Hejl, A.; Wenzel, A. G.; Funk, T. W.; Grubbs, R. H. Organometallics 2006, 25, 5740-5745.
53. (a) Hillier, A. C.; Sommer, W. J.; Yong, B. S.; Petersen, J. L.; Cavallo, L.; Nolan, S. P. Organometallics 2003, 22, 4322-4326.
54. (b) Díez-González, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874-883.
55. For further details, see the Experimental Section.
56. Clavier, H.; Nolan, S. P. Chem. Eur. J. 2007, 13, 8029-8036.
57. Complex 12 is now commercially available from Strem and Umicore.
58. For reports with X-ray structures of NHC-containing "boomerang" type catalysts, see::(a) Van Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954-4955.
59. (b) Krause, J. O.; Nuyken, O.; Wurst, K.; Buchmeiser, M. R. Chem. Eur. J. 2004, 10, 111-184.
60. (c) Yang, L.; Mayr, M.; Wurst, K.; Buchmeiser, M. R. Chem. Eur. J. 2004, 10, 5761-5770.
61. (d) Despagnet-Ayoub, E.; Grubbs, R. H. Organometallics 2005, 24, 338-340.
62. (e) Weigl, K.; Köhler, K.; Dechert, S.; Meyer, F. Organometallics 2005, 24, 4049-4056.
63. (f) Fürstner, A.; Davies, P. W.; Lehmann, C. W. Organometallics 2005, 24, 4065-4071.
64. (g) Vehlow, K.; Maechling, S.; Blechert, S. Organometallics 2006, 25, 25-28.
65. Thurier, C.; Fischmeister, C.; Bruneau, C.; Olivier-Bourbigou, H.; Dixneuf, P. H. J. Mol. Catal. A 2007, 268, 127-133.
66. (a) Surette, J. K. D.; Green, L.; Singer, R. D. Chem. Commun. 1996, 2753, 2754.
67. (b) Holbrey, J. D.; Reichert, M. W.; Nieuwenhuyzen, M.; Sheppard, O.; Hardacre, C.; Rogers, R. D. Chem. Commun. 2003, 476, 477.
68. Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Chem. Commun. 1998, 1765, 1766.
69. Kabalka, G. W.; Gooch, E. E. J. Org. Chem. 1980, 45, 3578-3580.
70. Busqué, F.; de March, P.; Figueredo, M.; Font, J. Tetrahedron 1995, 51, 1503-1508.