Imidazolium and imidazolinium salts as carbene precursors or solvent for ruthenium-catalysed diene and enyne metathesis

Advanced Synthesis and Catalysis

Volumn 344, Issue 6-7, 2002, Pages 585-595

  Sémeril, David ^a   Bruneau, Christian ^a   Dixneuf, Pierre H ^a  

^a UMR 6509 Organometalliques et Catalyse Chimie et Electrochimie Moleculaires   (France)

Author keywords

Cycloisomerisation; Enyne metathesis; Homogeneous catalysis; Ionic solvents; N heterocyclic carbene (NHC) ligands; Ring closing metathesis; Ruthenium

Indexed keywords

EID: 0000234343     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/1615-4169(200208)344:6/7<585::AID-ADSC585>3.0.CO;2-0     Document Type: Review

References (75)

1. V. P. W. Böhm, C. W. K. Gstöttmayr, T. Weskamp, W. A. Herrmann, J. Organomet. Chem. 2000, 595, 186-190;
2. C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805;
3. D. S. McGuinness, K. J. Cavell, Organometallics 2000, 19, 741-748.
4. C. Yang, H. M. Lee, S. P. Nolan, Org. Lett. 2001, 3, 1511-1514.
5. H. Kücükbay, B. Çetinkaya, S. Guesmi, P. H. Dixneuf, Organometallics 1996, 15, 2434-2439;
6. B. Çetinkaya, I. Özdemir, C. Bruneau, P. H. Dixneuf, J. Mol. Catal. A: Chem. 1997, 118, L1-L4.
7. B. Çetinkaya, I. Özdemir, P. H. Dixneuf, J. Organomet. Chem. 1997, 534, 153-158.
8. H. M. Lee, D. C. Smith, Jr., Z. He, E. D. Stevens, C. Yi, S. P. Nolan, Organometallics 2001, 20, 794-797;
9. H. M. Lee, T. Jiang, E. D. Stevens, S. P. Nolan, Organometallics 2001, 20, 1255-1258.
10. C. Yang, S. P. Nolan, J. Org. Chem. 2002, 67, 591-593.
11. Alkene Metathesis in Organic Synthesis, (Ed.: A. Fürstner), Springer, Berlin, 1998;
12. M. Schuster, S. Blechert, Angew. Chem. Int. Ed. 1997, 36, 2036-2056;
13. S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388;
14. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29;
15. S. Blechert, Pure Appl. Chem. 1999, 71, 1393-1399;
16. K. J. Ivin, J. C. Mol, Olefin Metathesis Polymerization, Academic Press, New York, 1997.
17. T. Weskamp, W. C. Schattenmann, M. Spiegler, W. A. Herrmann, Angew. Chem. Int. Ed. 1998, 37, 2490-2493;
18. T. Weskamp, F. J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. Int. Ed. 1999, 38, 2416-2419;
19. T. Weskamp, F. J. Kohl, W. A. Herrmann, J. Organomet. Chem. 1999, 582, 362-365;
20. L. Ackermann, A. Fürstner, T. Weskamp, F. J. Kohl, W. A. Herrmann, Tetrahedron Lett. 1999, 40, 4787-4790;
21. M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247-2250;
22. J. Huang, H. J. Schang, E. D. Stevens, S. P. Nolan, Organometallics 1999, 18, 5375-5380.
23. A. K. Chatterjee, J. P. Morgan, M. Scholl, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 3783-3784;
24. D. L. Wright, J. P. Schulte, M. A. Page, Org. Lett. 2000, 2, 1847-1850.
25. M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953-956.
26. R. Stragies, U. Voigtmann, S. Blêchert, Tetrahedron Lett. 2000, 41, 5465-5468;
27. J. A. Smulik, S. T. Diver, Org. Lett. 2000, 2, 2271-2274;
28. A. K. Chatterjee, R. H. Grubbs, Org. Lett. 1999, 1, 1751-1753.
29. J. Louie, R. H. Grubbs, Angew. Chem. Int. Ed. 2001, 40, 247-249.
30. H. Katayama, H. Urushima, F. Ozawa, J. Organomet. Chem. 2000, 606, 16-25;
31. H. Katayama, F. Ozawa, Organometallics 1998, 17, 5190-5196.
32. L. Ackermann, C. Bruneau, P. H. Dixneuf, Synlett 2001, 397-399.
33. L. Delaude, A. Demonceau, A. F. Noels, Chem. Commun. 2001, 986-987.
34. D. Sémeril, M. Cléran, C. Bruneau, P. H. Dixneuf, Adv. Synth. Catal. 2001, 343, 184-187;
35. D. Sémeril, M. Cléran, A. Jimerez Perez, C. Bruneau, P. H. Dixneuf, J. Mol. Catal. A: Chem. in press.
36. D. Sémeril, C. Bruneau, P. H. Dixneuf, Helv. Chim. Acta 2001, 84, 3335-3341.
37. D. Sémeril, H. Olivier-Bourbigou, C. Bruneau, P. H. Dixneuf, Chem. Commun. 2002, 146-147.
38. 3 in the molar ratio 1:2:4 were dissolved in toluene (8 mL) and stirred under nitrogen at 80 °C for 0.5 h. The enyne in toluene (2 mL) was added and the resulting suspension was stirred at 80 °C. The solvent was evaporated and the crude product was purified by flash chromatography.
39. M. Picquet, C. Bruneau, P. H. Dixneuf, Chem. Commun. 1998, 2249-2250.
40. L. Jafarpour, J. Huang, E. D. Stevens, S. P. Nolan, Organometallics 1999, 18, 3760-3763.
41. L. Perrin, E. Clot, O. Eisenstein, J. Loch, R. H. Crabtree, Inorg. Chem. 2001, 40, 5806-5811.
42. C. W. Bielanski, R. H. Grubbs, Angew. Chem. Int. Ed. 2000, 39, 2903-2906.
43. 3 in the molar ratio 1:2:4}, 1 mmol of enyne and 5 mL of degassed toluene were introduced. The reaction mixture was then heated until full conversion. The solvent was removed in vacuum and the crude product was purified by flash chromatography.
44. Q. Yao, Org. Lett. 2001, 3, 2069-2072.
45. S. C. Schürer, S. Blechert, Tetrahedron Lett. 1999, 40, 1877-1880;
46. S. Kotha, N. Sreenivasachary, E. Brahmachary, Tetrahedron Lett. 1998, 39, 2805-2808;
47. D. Sémeril, J. Le Nôtre, C. Bruneau, P. H. Dixneuf, A. F. Kolomiets, S. N. Osipov, New J. Chem. 2001, 25, 16-18.
48. 3 in the molar ratio 1:2:4}, 0.5 mmol of enyne and 2.5 mL of degassed toluene were introduced. The reaction mixture was then heated at 80 °C until complete conversion as observed by GC-MS and then 0.16 mL (1 mmol) of diethyl acetylenedicarboxylate (DEAD) was added to the crude reaction mixture, which was heated at 110 °C. The solvent was removed in vacuum and the crude product was purified by flash chromatography.
49. S. Kotha, N. Screenivasachary, Chem. Commun. 2000, 503-504.
50. K. Tamao, N. Ishida, T. Tanaka, M. Kumada, Organometallics 1983, 2, 1694-1696;
51. T. Fujiwara, K. Yanai, K. Shimane, M. Takamori, T. Takeda, Eur. J. Org. Chem. 2001, 155-161.
52. R. Stragies, S. Blechert, Tetrahedron 1999, 55, 8179-8188.
53. B. M. Trost, Acc. Chem. Res. 1990, 23, 34-42.
54. Y. Yamamoto, N. Ohkoshi, M. Kameda, K. Itoh, J. Org. Chem. 1999, 64, 2178-2179;
55. Y. Yamamoto, Y. Nakagai, N. Ohkoshi, K. Itoh, J. Am. Chem. Soc. 2001, 123, 6372-6380.
56. C. Bruneau, P. H. Dixneuf, Acc. Chem. Rev. 1999, 32, 311-323;
57. C. Grünwald, O. Gevert, J. Wolf, P. Bonzález-Herrero, H. Werner, Organometallics 1996, 15, 1960-1962.
58. Y. Miyaki, T. Onishi, S. Ogoshi, H. Kurosawa, J. Organomet. Chem. 2000, 616, 135-139.
59. -2 mmol, 10 mol %)], 0.5 mmol of diene and 2.5 mL of degassed toluene were introduced. The Schlenk tube was then purged 3 times with acetylene and charged with 1 atmosphere of acetylene. The reaction mixture was then heated at 80 °C until full conversion. The solvent was removed in vacuum and the crude product was purified by flash chromatography.
60. R. Sheldon, Chem. Commun. 2001, 2399-2407;
61. P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 2000, 39, 3772-3789;
62. T. Welton, Chem. Rev. 1999, 99, 2071-2084;
63. Y. Chauvin, Chemtech. 1995, 9, 26-30;
64. H. Olivier-Bourbigou, L. Magna, J. Mol. Catal. A: Chemical 2002, 3484, 1-19.
65. D. Bourissou, O. Guerret, F. P. Gabba, G. Bertrand, Chem. Rev. 2000, 100, 39-91;
66. L. Jafarpour, S. P. Nolan, J. Organomet. Chem. 2001, 617-618, 17-27;
67. D. J. Cardin, B. Çetinkaya, M. F. Lappert, Chem. Rev. 1972, 72, 545-574;
68. B. Çetinkaya, P. Dixneuf, M. F. Lappert, J. Chem. Soc. Dalton Trans. 1974, 1827-1833.
69. A. Fürstner, M. Liebl, C. W. Lehmann, M. Picquet, R. Kunz, C. Bruneau, D. Touchard, P. H. Dixneuf, Chem. Eur. J. 2000, 6, 1847-1857.
70. M. Picquet, D. Touchard, C. Bruneau, P. H. Dixneuf, New J. Chem. 1999, 23, 141-143.
71. D. Sémeril, Thesis, Université de Rennes 1, 2001.
72. Bayer AG, EP 1035093A2, 2000.
73. R. C. Buijsman, E. van Vuuren, J. G. Sterrenburg, Org. Lett. 2001, 3, 3785-3787;
74. K. G. Mayo, E. H. Nearhoof, J. J. Kiddle, Org. Lett. 2002, in press.
75. 6] (1 mL) was added and the solution was stirred at room temperature for 10 min before addition of 0.5 mmol of diene. The reaction mixture was then heated at 80 °C until full conversion and the product was extracted with 3 × 5 mL of toluene.