Synthetic applications with use of a silica-supported alkyne metathesis catalyst

Journal of Organic Chemistry

Volumn 73, Issue 11, 2008, Pages 4256-4258

  Hyeon, Mo Cho ^a   Weissman, Haim ^a   Moore, Jeffrey S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CATALYSIS; CHEMICAL REACTIONS; COMPUTER NETWORKS; MOLYBDENUM; SILICA; SILICATE MINERALS; SILICON COMPOUNDS;

ALKYNE METATHESIS; AMERICAN CHEMICAL SOCIETY (ACS); APPLIED (CO); CHEMICAL EQUATIONS; CYCLOOLIGOMERIZATION; FUMED SILICA (FS); NEAR ROOM TEMPERATURE; SYNTHETIC APPLICATIONS;

HIGH TEMPERATURE APPLICATIONS;

ALKYNE; MOLYBDENUM; SILICON DIOXIDE;

ARTICLE; CATALYST; CYCLIZATION; OLIGOMERIZATION; QUANTUM YIELD; REACTION ANALYSIS; RING CLOSING METATHESIS; ROOM TEMPERATURE; SYNTHESIS;

EID: 44949096482     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8003919     Document Type: Article

References (37)

1. Weissman, H.; Plunkett, K. N.; Moore, J. S. Angew. Chem., Int. Ed. 2006, 45, 585.
2. For alkyne metathesis with a heterogeneous system see: (a) Chabanas, M.; Baudouin, A.; Copéret, C.; Basset, J.-M. J. Am. Chem. Soc. 2001, 123, 2062.
3. (b) Mortreux, A.; Delgrange, J. C.; Blanchard, M.; Lubochinsky, B. J. Mol. Catal. 1977, 2, 73.
4. (c) Mortreux, A.; Petit, F.; Blanchard, M. J. Mol. Catal. 1980, 8, 97.
5. For alkene metathesis with a heterogeneous system see: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195.
6. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657.
7. (c) Yao, Q. Angew. Chem., Int. Ed. 2000, 39, 3896.
8. (d) Jafarpour, L.; Nolan, S. P. Org. Lett. 2000, 2, 4075.
9. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2001, 40, 4251.
10. (f) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37.
11. (g) Copéret, C.; Chabanas, M.; Saint-Arroman, R. P.; Basset, J.-M. Angew. Chem., Int. Ed. 2003, 42, 156.
12. (h) Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 4510.
13. (a) Fürstner, A.; Radkowski, K. Chem. Commun. 2002, 2182.
14. (b) Lacombe, F.; Radkowski, K.; Seidel, G.; Fürstner, A. Tetrahedron 2004, 60, 7315.
15. (c) Fürstner, A.; Seidel, G. Angew. Chem., Int. Ed. 1998, 37, 1734.
16. (d) Fürstner, A.; Mathes, C.; Lehmann, C. W. Chem. Eur. J. 2001, 7, 5299.
17. (e) Fürstner, A.; Davies, P. W. Chem. Commun. 2005, 2307.
18. (f) Bunz, U. H. F.; Kloppenburg, L. Angew. Chem., Int. Ed. 1999, 38, 478.
19. Fürstner, A.; Guth, O.; Rumbo, A.; Seidel, G. J. Am. Chem. Soc. 1999, 121, 11108.
20. Grela, K.; Ignatowska, J. Org. Lett. 2002, 4, 3747.
21. (a) Fürstner, A.; Mathes, C.; Lehmann, C. W. J. Am. Chem. Soc. 1999, 121, 9453.
22. (b) Sashuk, V.; Ignatowska, J.; Grela, K. J. Org. Chem. 2004, 69, 7748.
23. Brizius and Bunz obtained a mixture of 4d-M in 79% yield and 4d-D in 2% yield, see: Brizius, G.; Bunz, U. H. F. Org. Lett. 2002, 4, 2829.
24. (a) Klyatskaya, S.; Dingenouts, N.; Rosenauer, C.; Müller, B.; Höger, S. J. Am. Chem. Soc. 2006, 128, 3150.
25. (b) Ziegler, A.; Mamdouh, W.; Ver Heyen, A.; Surin, M.; Uji-i, H.; Abdel-Mottaleb, M. M. S.; De Schryver, F. C.; De Feyter, S.; Lazzaroni, R.; Höger, S. Chem. Mater. 2005, 17, 5670.
26. (c) Höger, S. Chem. Eur. J. 2004, 10, 1320.
27. (d) Zhao, D.; Moore, J. S. Chem. Commun. 2003, 807.
28. (e) Yamaguchi, Y.; Yoshida, Z. Chem. Eur. J. 2003, 9, 5430.
29. (f) Grave, C.; Schluter, A. D. Eur. J. Org. Chem. 2002, 3075.
30. (g) Höger, S. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 2685.
31. (h) Prautzsch, V.; Ibach, S.; Vogtle, F. J. Inclusion Phenom. Macrocycl. Chem. 1999, 33, 427.
32. (i) Seo, S. H.; Jones, T. V.; Seyler, H.; Peters, J. O.; Kim, T. H.; Chang, J. Y.; Tew, G. N. J. Am. Chem. Soc. 2006, 128, 9264.
33. (j) Eickmeier, C.; Junga, H.; Matzger, A. J.; Scherhag, F.; Shim, M.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. 1997, 36, 2103.
34. (k) Ferrara, J. D.; Tessier-Youngs, C.; Youngs, W. J. J. Am. Chem. Soc. 1985, 107, 6719.
35. (l) Ferrara, J. D.; Djebli, A.; Tessier-Youngs, C.; Youngs, W. J. J. Am. Chem. Soc. 1988, 110, 647.
36. Zhang, W.; Moore, J. S. J. Am. Chem. Soc. 2004, 126, 12796.
37. Zhang, W.; Brombosz, S. M.; Mendoza, J. L.; Moore, J. S. J. Org. Chem. 2005, 70, 10198.