Ruthenium Allenylidenes and Indenylidenes as Catalysts in Alkene Metathesis

Metal Vinylidenes and Allenylidenes in Catalysis: From Reactivity to Applications in Synthesis

Volumn , Issue , 2008, Pages 251-277

  Malacea, Raluca ^a   Dixneuf, Pierre H ^a,b  

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

^b INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

Author keywords

Alkene metathesis ruthenium catalysts; Allenylidenes; Cross metathesis; Indenylidenes; Polymerization; Propargylic initiators; Ring closing metathesis; ROMP; Vinylcarbenes

Indexed keywords

EID: 84890970080     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527622870.ch8     Document Type: Chapter

References (78)

1. Grubbs, R.H. (2003) Handbook of metathesis, Wiley VCH, Weinheim.
2. Hérisson, J.L. and Chauvin, Y. (1971) Makromolekulare Chemie, 141, 161.
3. Chauvin, Y. (1973) Comptes Rendus de LAcademie des Sciences, Paris, 276, 169.
4. Chauvin, Y., Commereuc, D. and Cruypelinck, D. (1976) Makromolekulare Chemie, 177, 2637.
5. Schröck, R.R., Murdzek, J.S., Bazan, G.C., Robbins, J., Di Mare, M. and O'Regan, M. (1990) Journal of the American Chemical Society, 112, 3875
6. Schröck, R.R. (2004) Journal of Molecular Catalysis A-Chemical, 213, 21.
7. Nguyen, S.T., Johnson, L.K., Grubbs, R.H. and Ziller, J.W. (1992) Journal of the American Chemical Society, 114, 3974.
8. Landon, S.J., Shulman, P.M. and Geoffroy, G.L. (1985) Journal of the American Chemical Society, 107, 6739.
9. Schwab, P., Grubbs, R.H. and Ziller, J.W. (1996) Journal of the American Chemical Society, 118, 100.
10. Semeril, D., Bruneau, C. and Dixneuf, P.H. (2001) Helvetica Chimica Acta, 84, 3335.
11. Semeril, D., Bruneau, C. and Dixneuf, P.H. (2002) Advanced Synthesis and Catalysis, 344, 585.
12. Katayama, H. and Ozawa, F. (1998) Chemistry Letters, 67.
13. Louie, J. and Grubbs, R.H. (2001) Angewandte Chemie International Edition, 40, 247.
14. Bruneau, C. and Dixneuf, P.H. (2006) Angewandte Chemie-International Edition, 45, 2176.
15. Katayama, H. and Ozawa, F. (2004) Coordination Chemistry Reviews, 248. 1703.
16. Dragutan, V. and Dragutan, I. (2004) Platinum Metal Reviews, 48, 148.
17. Fürstner, A., Picquet, M., Bruneau, C. and Dixneuf, P.H. (1998) Chemical Communications, 1315.
18. Selegue, J.P. (1982) Organometallics, 1, 217.
19. Rigaut, S., Monnier, F., Mousset, F., Touchard, D. and Dixneuf, P.H. (2002) Organometallics, 21, 2654.
20. Baya, M., Buil, M.L., Esteruelas, M.A., López, A.M., Onate, E. and Rodriguez J.R. (2002) Organometallics, 21, 1841.
21. Bustelo, E., Jimenez-Tenorio, M., Mereiter, K., Puerta, M.C. and Valerga, P. (2002) Organometallics, 21, 1903.
22. Cadierno, V., Conejero, S., Gamasa, M.P., Gimeno, J., Falvello, L.R. and Llusar, R.M. (2002) Organometallics, 21, 3716.
23. Trost, B.M. and Flygare, J.A. (1992) Journal of the American Chemical Society, 114, 5476.
24. Nishibayashi, Y., Wakiji, I. and Hidai, M. (2000) Journal of the American Chemical Society, 122, 11019.
25. Nishibayashi, Y., Inada, Y., Hidai, M. and Uemura, S. (2003) Journal of the American Chemical Society, 125, 6060.
26. Nishibayashi, Y., Inada, Y., Hidai, M. and Uemura, S. (2002) Journal of the American Chemical Society, 124, 7900.
27. Nishibayashi, Y., Inada, Y., Hidai, M. and Uemura, S. (2003) Journal of the American Chemical Society, 125, 6060.
28. Nishibayashi, Y., Milton, M.D., Inada, Y., Yoshikawa, M., Wakiji, I., Hidai, M. and Uemura, S. (2005) Chemistry-A European Journal, 11, 1453.
29. Inada, Y., Nishibayashi, Y. and Uemura, S. (2005) Angewandte Chemie-International Edition, 44, 7715.
30. Nishibayashi, Y., Milton, M.D., Inada, Y., Yoshikawa, M. and Uemura, S. (2006) European Journal of Organic Chemistry, 881.
31. Bustelo, E. and Dixneuf, P.H. (2005) Advanced Synthesis and Catalysis, 347, 393.
32. Fischmeister, C., Toupet, L. and Dixneuf, P.H. (2005) New Journal of Chemistry, 29, 765.
33. Bustelo, E. and Dixneuf, P.H. (2007) Advanced Synthesis and Catalysis, 349, 933.
34. Maddock, S.M. and Finn, M.G. (2001) Angewandte Chemie-International Edition, 40, 2138.
35. Saoud, M., Romerosa, A., Manas Carpio, S., Gonsalvi, L. and Peruzzini, M. (2003) European Journal of Inorganic Chemistry, 1614.
36. Yeh, K.-L., Liu, B., Lo, C.-Y., Huang, H.-L. and Liu, R.-S. (2002) Journal of the American Chemical Society, 124, 6510.
37. Opstal, T. and Verpoort, F. (2003) Polymer Bulletin, 50, 17.
38. Picquet, M., Touchard, D., Bruneau, C. and Dixneuf, P.H. (1999) New Journal of Chemistry, 23, 141.
39. Fürstner, A., Liebl, M., Lehmann, C.W., Picquet, M., Kunz, R., Bruneau, C., Touchard, D. and Dixneuf, P.H. (2000) Chemistry-A European Journal, 6, 1847.
40. Castarlenas, R. and Dixneuf, P.H. (2003) Angewandte Chemie-International Edition, 42, 4524.
41. Castarlenas, R., Vovard, C., Fischmeister, C. and Dixneuf, P.H. (2006) Journal of the American Chemical Society, 128, 4079.
42. Schwab, P., Grubbs, R.H. and Ziller, J.W. (1996) Journal of the American Chemical Society, 118, 100.
43. Osipov, S.N., Artyushin, O.I., Kolomiets, A.F., Bruneau, C., Picquet, M. and Dixneuf, P.H. (2001) European Journal of Inorganic Chemistry, 3891.
44. Picquet, M., Bruneau, C. and Dixneuf, P.H. (1998) Chemical Communications, 2249.
45. Sémeril, D., Le Notre, J., Bruneau, C., Dixneuf, P.H., Kolomiets, A.F. and Osipov, S. (2001) New Journal of Chemistry, 25, 16.
46. Castarlenas, R., Semeril, D., Noels, A.F., Demonceau, A. and Dixneuf, P.H. (2002) Journal of Organometallic Chemistry, 663,235.
47. Alaoui Abdallaoui, I., Semeril, D. and Dixneuf, P.H. (2002) Journal of Molecular Catalysis A: Chemical, 182-183, 577.
48. Jafarpour, L., Huang, J., Stevens, E.D. and Nolan, S.P. (1999) Organometallics, 18, 3760.
49. Schanz, H.-J., Jafarpour, L., Stevens, E.D. and Nolan, S.P. (1999) Organometallics, 18, 5187.
50. Fürstner, A., Grabowski, J. and Lehmann, C.W. (1999) Journal of Organic Chemistry, 64, 8275.
51. Fürstner, A. and Thiel, O.R. (2000) Journal of Organic Chemistry, 65. 1738.
52. The activity of the catalyst was not due to the expected allenylidene [46,47] but to its rearranged indenylidene complex [43,44].
53. Harlow, K.J., Hill, A.F. and Wilton-Ely, J.D.E.T. (1999) Journal of the Chemical Society-Dalton Transactions, 285.
54. Fürstner, A., Hill, A.F., Liebl, M. and Wilton-Ely, J.D.E.T. (1999) Chemical Communications, 601.
55. Touchard, D., Haquette, P., Daridor, A., Toupet, L. and Dixneuf, P.H. (1994) Journal of the American Chemical Society, 116, 11157.
56. Jung, S., Brandt, C.D. and Werner, H. (2001) New Journal of Chemistry, 25, 1101.
57. Le Gendre, P., Picquet, M., Richard, P. and Moise, C. (2002) Journal of Organometallic Chemistry, 643-644, 231.
58. Cetinkaya, B., Demir, S., Özdemir, I., Toupet, L., Seémeril, D., Bruneau, C. and Dixneuf, P.H. (2003) Chemistry-A European Journal, 9, 2323.
59. Bassetti, M., Centola, F., Semeril, D., Bruneau, C. and Dixneuf, P.H. (2003) Organometallics, 22, 4459.
60. Wilhelm, T.E., Belderrain, T.R., Brown, S.N. and Grubbs, R.H. (1997) Organometallics, 16, 3867.
61. Castarlenas, R., Eckert, M. and Dixneuf, P.H. (2005) Angewandte Chemie International Edition, 44, 2576.
62. Ipaktschi, J., Mohsseni-Ala, J., Dulmer, A., Loschen, C. and Frenkin, G. (2005) Organometallics, 24, 977.
63. Ipaktschi, J., Rooshenas, P. and Dülmer, A. (2005) Organometallics, 24, 6239.
64. Fürstner, A., Davies, P.W. and Lehmann, C.W. (2005) Organometallics, 24, 4065.
65. Jafarpour, L., Schanz, H.-J., Stevens, E.D. and Nolan, S.P. (1999) Organometallics, 18, 5416.
66. Fürstner, A., Thiel, O.R., Ackermann, L., Schanz, H.-J. and Nolan, S.P. (2000) Journal of Organic Chemistry, 65, 2204.
67. Nolan, S.P. and Huang, J. (2000) EP1115491A1.
68. Fürstner, A., Guth, O., Duffels, A., Seidel, G., Liebl, M., Gabor, B. and Mynott, R. (2001) Chemistry-A European Journal, 7, 481.
69. Clavier, H., Petersen, J.L. and Nolan, S.P. (2006) Journal of Organometallic Chemistry, 691, 5444.
70. Forman, G.S., Bellabarba, R.M., Tooze, R.P., Slawin, A.M.Z., Karch, R. and Winde, R. (2006) Journal of Organometallic Chemistry, 691, 5513.
71. Opstal, T. and Verpoort, F. (2003) Angewandte Chemie-International Edition, 42, 2876.
72. Opstal, T. and Verpoort, F. (2003) New Journal of Chemistry, 25,257.
73. Opstal, T. and Verpoort, F. (2002) Synlett, 6, 935.
74. Drozdzak, R., Allaert, B., Ledoux, N., Dragutan, I., Dragutan, V. and Verpoort, F. (2005) Advanced Synthesis and Catalysis, 347, 1721.
75. Fiirstner, A., Grabowski, J., Lehmann, C.W., Kataoka, T. and Nagai, K. (2001) Chem Bio Chem, 2, 60.
76. Fiirstner, A. and Schlede, M. (2002) Advanced Synthetic Catalysis, 344, 657.
77. Furstner, A., Radkowski, K., Wirtz, C., Goddard, R., Lehmann, C.W. and Mynott, R. (2002) Journal of the American Chemical Society, 124, 7061.
78. Guerin, F (2005). EP172091A1.