A highly active, heterogeneous catalyst for alkyne metathesis

Angewandte Chemie - International Edition

Volumn 45, Issue 4, 2006, Pages 585-588

  Weissman, Haim ^a   Plunkett, Kyle N ^a   Moore, Jeffrey S ^a  

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

Author keywords

Alkynes; Heterogeneous catalysis; Metathesis; Molybdenum; Silica

Indexed keywords

DIMERIZATION; HYDROCARBONS; MOLYBDENUM; POLYMERIZATION; SILICA; SUBSTRATES;

ALKYNES; CHEMICAL EQUATIONS; METATHESIS; ROOM TEMPERATURE;

CATALYSIS;

EID: 31044440508     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502840     Document Type: Article

References (49)

1. a) W. Zhang, S. Kraft, J. S. Moore, Chem. Commun. 2003, 832;
2. b) W. Zhang, S. Kraft, J. S. Moore, J. Am. Chem. Soc. 2004, 126, 329;
3. c) W. Zhang, J. S. Moore, J. Am. Chem. Soc. 2004, 126, 12 796;
4. d) W. Zhang, J. S. Moore, Macromolecules 2004, 37, 3973;
5. e) J. M. Blackwell, J. S. Figueroa, F. H. Stephens, C. C. Cummins, Organometallics 2003, 22, 3351.
6. a) A. Fürstner, P. W. Davies, Chem Commun. 2005, 2307;
7. b) V. Sashuk, J. Ignatowska, K. Grela, J. Org. Chem. 2004, 69, 7748;
8. c) L. Kloppenburg, D. Jones, U. H. F. Bunz, Macromolecules 1999, 32, 4194;
9. d) L. Kloppenburg, D. Song, U. H. F. Bunz, J. Am. Chem. Soc. 1998, 120, 7973;
10. e) A. Mortreux, J. C. Delgrange, M. Blanchard, B. Lubochinsky, J. Mol. Catal. 1977, 2, 73;
11. f) A. Mortreux, M. Blanchard, Chem. Commun. 1974, 786;
12. g) N. G. Pschirer, W. Fu, R. D. Adams, U. H. F. Bunz, Chem. Commun. 2000, 87;
13. h) A. Fürstner, G. Seidel, J. Organomet. Chem. 2000, 606, 75;
14. i) D. Villemin, P. Cadiot, Tetrahedron Lett. 1982, 23, 5139;
15. j) N. Kaneta, K. Hikichi, S.-i. Asaka, M. Uemura, M. Mori, Chem. Lett. 1995, 1055;
16. k) N. Kaneta, T. Hirai, M. Mori, Chem. Lett. 1995, 627.
17. a) A. Fürstner, L. Turet, Angew. Chem. 2005, 117, 3528;
18. Angew. Chem. Int. Ed. 2005, 44, 3462;
19. b) A. Fürstner, D. De Souza, L. Parra-Rapado, J. T. Jensen, Angew. Chem. 2003, 115, 5516;
20. Angew. Chem. Int. Ed. 2003, 42, 5358;
21. c) A. Fürstner, C. Mathes, Org. Lett. 2001, 3, 221;
22. d) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299;
23. e) A. Fürstner, K. Radkowski, J. Grabowski, C. Wirtz, R. Mynott, J. Org. Chem. 2000, 65, 8758;
24. f) A. Fürstner, K. Grela, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 2000, 122, 11 799;
25. g) A. Fürstner, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 1999, 121, 9453.
26. R. R. Schrock, Polyhedron 1995, 14, 3177.
27. M. D. Liptak, K. C. Gross, P. G. Seybold, S. Feldgus, G. C. Shields, J. Am. Chem. Soc. 2002, 124, 6421.
28. a) S. Grasser, C. Haessner, K. Kohler, F. Lefebvre, J.-M. Basset, Phys. Chem. Chem. Phys. 2003, 5, 1906;
29. b) T. W. Dijkstra, R. Duchateau, R. A. van Santen, A. Meetsma, G. P. A. Yap, J. Am. Chem. Soc. 2002, 124, 9856.
30. a) A. Mortreux, F. Petit, M. Blanchard, J. Mol. Catal. 1980, 8, 97;
31. b) "Metathesis process and catalyst": S. G. Kukes, R. L. Banks, U.S. patent 4,465,890, 1984.
32. "Catalyst Composition to Effect Metathesis of Acetylenes": R. R. Schrock, US patent 4,427,595, 1984.
33. D. Villemin, M. Heroux, V. Blot, Tetrahedron Lett. 2001, 42, 3701.
34. a) C. Coperet, M. Chabanas, R. P. Saint-Arroman, J.-M. Basset, Angew. Chem. 2003, 115, 164;
35. Angew. Chem. Int. Ed. 2003, 42, 156;
36. b) M. Chabanas, A. Baudouin, C. Coperet, J.-M. Basset, W. Lukens, A. Lesage, S. Hediger, L. Emsley, J. Am. Chem. Soc. 2003, 125, 492;
37. c) M. Chabanas, A. Baudouin, C. Coperet, J.-M. Basset, Chem. Eur. J. 2003, 9, 971;
38. d) M. Chabanas, A. Baudouin, C. Coperet, J.-M. Basset, J. Am. Chem. Soc. 2001, 123, 2062;
39. e) E. L. Roux, M. Taoufik, M. Chabanas, D. Alcor, A. Baudouin, C. Coperet, J. Thivolle-Cazat, J.-M. Basset, A. Lesage, S. Hediger, L. Emsley, Organometallics 2005, 24, 4274.
40. 2. A solution of 1 (50.0 mg, 7.51 mM) in toluene (10 mL) was added to silica (350 mg) and vortexed for 1 min. The modified silica was used directly or precipitated by centrifugation, rinsed several times, and lyophilized from benzene.
41. S. J. N. Burgmayer, H. L. Kaufmann, G. Fortunato, P. Hug, B. Fischer, Inorg. Chem. 1999, 38, 2607.
42. [14] in our system, this region is masked by absorptions for silica and aliphatic chains.
43. W. A. Nungent, J. M. Mayer, Metal-Ligand Multiple Bonds, Wiley Interscience, New York, USA, 1988, pp. 123 - 144.
44. R. P. Saint-Arroman, M. Chabanas, A. Baudouin, C. Coperet, J.-M. Basset, A. Lesage, L. Emsley, J. Am. Chem. Soc. 2001, 123, 3820.
45. U. H. F. Bunz, Acc. Chem. Res. 2001, 34, 998.
46. a) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 5005;
47. Angew. Chem. Int. Ed. 2005, 44, 4490;
48. b) A. Fürstner, Angew. Chem. 2000, 112, 3140;
49. Angew. Chem. Int. Ed. 2000, 39, 3012.