Ruthenium-indenylidene olefin metathesis catalyst with enhanced thermal stability

Chemistry - A European Journal

Volumn 16, Issue 40, 2010, Pages 12255-12261

  Kabro, Anzhelika ^a   Roisnel, Thierry ^a   Fischmeister, Cédric ^a   Bruneau, Christian ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

indenylidene; latent catalysts; metathesis; olefins; ruthenium

Indexed keywords

COMPLEX 1; CYCLOHEXYL; DICYCLOPENTADIENE; HALF LIVES; HIGH ACTIVITY; HIGH THERMAL STABILITY; INDENYLIDENE; LATENT CATALYSTS; METATHESIS; NMR SPECTROSCOPY; OLEFIN METATHESIS; RING OPENING METATHESIS POLYMERIZATION; RING-CLOSING METATHESIS REACTIONS; ROOM TEMPERATURE; RUTHENIUM COMPLEXES; THERMAL ACTIVATION; THERMAL STABILITY; THERMALLY STABLE;

BEARINGS (STRUCTURAL); CATALYSTS; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; RING OPENING POLYMERIZATION; RUTHENIUM; THERMODYNAMIC STABILITY; TOLUENE; X RAY CRYSTALLOGRAPHY;

RUTHENIUM COMPOUNDS;

EID: 78249237873     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001659     Document Type: Article

References (120)

1. Y. Chauvin, Angew. Chem. 2006, 118, 3824 - 3831
2. Angew. Chem. Int. Ed. 2006, 45, 3740 - 3747
3. R. R. Schrock, Angew. Chem. 2006, 118, 3832 - 3844
4. Angew. Chem. Int. Ed. 2006, 45, 3748 - 3759
5. R. H. Grubbs, Angew. Chem. 2006, 118, 3845 - 3850
6. Angew. Chem. Int. Ed. 2006, 45, 3760 - 3765
7. R. H. Grubbs., Handbook of Metathesis, Vols. 1-3, Wiley-VCH, Weinheim, 2003
8. S. J. Connon, S. Blechert, in Ruthenium Catalysts and Fine Chemistry, Vol. 11 (Eds.:, P. H. Dixneuf, C. Bruneau,), Springer, Heidelberg, 2004, 93
9. A. Fürstner, Angew. Chem. 2000, 112, 3140 - 3172
10. Angew. Chem. Int. Ed. 2000, 39, 3012 - 3043
11. A. H. Hoveyda, A. R. Zhugralin, Nature 2007, 450, 243 - 251
12. P. H. Deshmukh, S. Blechert, Dalton Trans. 2007, 2479 - 2491.
13. T. J. Donohoe, L. P. Fishlock, P. A. Procopiou, Chem. Eur. J. 2008, 14, 5716 - 5726
14. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564 - 4601
15. Angew. Chem. Int. Ed. 2005, 44, 4490 - 4527
16. W. A. L. van Otterlo, C. B. de Koning, Chem. Rev. 2009, 109, 3743 - 3782
17. A. Gradillas, J. Perez-Castells, Angew. Chem. 2006, 118, 6232 - 6247
18. Angew. Chem. Int. Ed. 2006, 45, 6086 - 6101.
19. M. R. Buchmeiser, Chem. Rev. 2000, 100, 1565 - 1604
20. J. E. Schwendeman, A. C. Church, K. B. Wagener, Adv. Synth. Catal. 2002, 344, 597 - 613.
21. S. T. Nguyen, L. K. Johnson, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1992, 114, 3974 - 3975.
22. For Ru-based catalysts, see G. C. Vougioukalakis, R. H. Grubbs, Chem. Rev. 2010, 110, 1746 - 1787
23. C. E. Diesendruck, E. Tzur, N. G. Lemcoff, Eur. J. Inorg. Chem. 2009, 4185 - 4203
24. C. Samojłowicz, M. Bieniek, K. Grela, Chem. Rev. 2009, 109, 3708 - 3742. For molybdenum- and tungsten-based catalysts, see
25. R. R. Schrock, A. H. Hoveyda, Angew. Chem. 2003, 115, 4740 - 4782
26. Angew. Chem. Int. Ed. 2003, 42, 4592 - 4633
27. R. R. Schrock, J. Mol. Catal. A 2004, 213, 21 - 30.
28. C. Bruneau, C. Fischmeister, X. Miao, R. Malacea, P. H. Dixneuf, Eur. J. Lipid Sci. Technol. 2010, 112, 3 - 9
29. C. Thurier, C. Fischmeister, C. Bruneau, H. Olivier-Bourbigou, P. H. Dixneuf, ChemSusChem 2008, 1, 118 - 122
30. R. Malacea, C. Fischmeister, C. Bruneau, J.-L. Dubois, J.-L. Couturier, P. H. Dixneuf, Green Chem. 2009, 11, 152 - 155
31. V. Le Ravalec, C. Fischmeister, C. Bruneau, Adv. Synth. Catal. 2009, 351, 1115 - 1122
32. X. Miao, C. Fischmeister, C. Bruneau, P. H. Dixneuf, ChemSusChem 2009, 2, 542 - 545
33. M. A. R. Meier, J. O. Metzger, U. S. Schubert, Chem. Soc. Rev. 2007, 36, 1788 - 1802
34. A. Rybak, P. A. Fokou, M. A. R. Meier, Eur. J. Lipid Sci. Technol. 2008, 110, 797 - 804
35. B. M. Marvey, Int. J. Mol. Sci. 2008, 9, 1393 - 1406
36. J. C. Mol, Green Chem. 2002, 4, 5 - 13.
37. A. H. Hoveyda, S. J. Malcolmson, S. J. Meek, A. R. Zhugralin, Angew. Chem. 2010, 122, 38 - 49
38. Angew. Chem. Int. Ed. 2010, 49, 34 - 44
39. T. J. Seiders, D. W. Ward, R. H. Grubbs, Org. Lett. 2001, 3, 3225 - 3228.
40. P. Schwab, M. B. France, J. W. Ziller, R. H. Grubbs, Angew. Chem. 1995, 107, 2179 - 2181
41. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039 - 2041.
42. T. Weskamp, W. C. Schattenmann, M. Spiegler, W. A. Herrmann, Angew. Chem. 1998, 110, 2631 - 2633
43. Angew. Chem. Int. Ed. 1998, 37, 2490 - 2493
44. J. Huang, E. D. Stevens, S. P. Nolan, L. J. Petersen, J. Am. Chem. Soc. 1999, 121, 2674 - 2678
45. M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247 - 2250
46. T. Weskamp, F. J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. 1999, 111, 2573 - 2576
47. Angew. Chem. Int. Ed. 1999, 38, 2416 - 2419
48. M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953 - 956.
49. J. P. A. Harrity, D. S. La, D. R. Cefalo, M. S. Visser, A. H. Hoveyda, J. Am. Chem. Soc. 1998, 120, 2343 - 2351
50. J. S. Kingsbury, J. P. A. Harrity, P. J. Bonitatebus, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 791 - 799
51. S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168 - 8179
52. S. Gessler, S. Randl, S. Blechert, Tetrahedron Lett. 2000, 41, 9973 - 9976
53. H. Wakamatsu, S. Blechert, Angew. Chem. 2002, 114, 2509 - 2511
54. Angew. Chem. Int. Ed. 2002, 41, 2403 - 2405
55. K. Grela, S. Harutyunyan, A. Michrowska, Angew. Chem. 2002, 114, 4210 - 4212
56. Angew. Chem. Int. Ed. 2002, 41, 4038 - 4040
57. A. H. Hoveyda, D. G. Gillingham, J. J. Van Veldhuizen, O. Kataoka, S. B. Garber, J. S. Kingsbury, J. P. A. Harrity, Org. Biomol. Chem. 2004, 2, 8 - 23.
58. V. Dragutan, I. Dragutan, Platinum Met. Rev. 2004, 48, 148 - 153
59. T. Opstal, F. Verpoort, J. Mol. Catal. A 2003, 200, 49 - 61
60. H. Katayama, H. Urushima, F. Ozawa, J. Organomet. Chem. 2000, 606, 16 - 25
61. J. Louie, R. H. Grubbs, Angew. Chem. 2001, 113, 253 - 255
62. Angew. Chem. Int. Ed. 2001, 40, 247 - 249.
63. A. Fürstner, M. Picquet, C. Bruneau, P. H. Dixneuf, Chem. Commun. 1998, 1315 - 1316
64. 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
65. R. Castarlenas, C. Fischmeister, C. Bruneau, P. H. Dixneuf, J. Mol. Catal. A 2004, 213, 31 - 37
66. N. Ledoux, R. Drozdzak, B. Allaert, A. Linden, P. Van Der Voort, F. Verpoort, Dalton Trans. 2007, 5201 - 5210.
67. R. Castarlenas, P. H. Dixneuf, Angew. Chem. 2003, 115, 4662 - 4665
68. Angew. Chem. Int. Ed. 2003, 42, 4524 - 4527
69. R. Castarlenas, C. Vovard, C. Fischmeister, P. H. Dixneuf, J. Am. Chem. Soc. 2006, 128, 4079 - 4089
70. T. Opstal, F. Verpoort, Angew. Chem. 2003, 115, 2982 - 2985
71. Angew. Chem. Int. Ed. 2003, 42, 2876 - 2879. For recent reviews, see
72. V. Dragutan, I. Dragutan, F. Verpoort, Platinum Met. Rev. 2005, 49, 33 - 40
73. F. Boeda, H. Clavier, S. P. Nolan, Chem. Commun. 2008, 2726 - 2740.
74. A. Fürstner, O. Guth, A. Düffels, G. Seidel, M. Liebl, B. Gabor, R. Mynott, Chem. Eur. J. 2001, 7, 4811 - 4820.
75. L. Jafarpour, H.-J. Schanz, E. D. Stevens, S. P. Nolan, Organometallics 1999, 18, 5416 - 5419.
76. K. Puentener, M. Scalone, PCT Int. Appl., WO 2006111491, 2006.
77. H. Clavier, C. A. Urbina-Blanco, S. P. Nolan, Organometallics 2009, 28, 2848 - 2854
78. S. Monsaert, E. De Canck, R. Drozdzak, P. Van Der Voort, F. Verpoort, J. C. Martins, P. M. S. Hendrickx, Eur. J. Org. Chem. 2009, 655 - 665
79. H. Clavier, F. Caijo, E. Borré, D. Rix, F. Boeda, S. P. Nolan, M. Mauduit, Eur. J. Org. Chem. 2009, 4254 - 4265.
80. H. Clavier, J. L. Petersen, S. P. Nolan, J. Organomet. Chem. 2006, 691, 5444 - 5477.
81. A. M. Lozano Vila, S. Monsaert, R. Drozdzak, S. Wolowiec, F. Verpoort, Adv. Synth. Catal. 2009, 351, 2689 - 2701.
82. S. Monsaert, A. M. Lozano Vila, R. Drozdzak, P. Van Der Voort, F. Verpoort, Chem. Soc. Rev. 2009, 38, 3360 - 3372
83. S. Monsaert, N. Ledoux, R. Drozdzak, F. Verpoort, J. Polym. Sci. Polym. Chem. Ed. 2010, 48, 302 - 310
84. C. E. Diesendruck, Y. Vidavsky, A. Ben-Asuly, N. G. Lemcoff, J. Polym. Sci. Polym. Chem. Ed. 2009, 47, 4209 - 4213
85. A. Ben-Asuly, A. Aharoni, C. E. Diesendruck, Y. Vidavsky, I. Goldberg, B. N. Straub, N. G. Lemcoff, Organometallics 2009, 28, 4652 - 4655
86. T. Kost, M. Sigalov, I. Goldberg, A. Ben-Asuly, N. G. Lemcoff, J. Organomet. Chem. 2008, 693, 2200 - 2203
87. A. Ben-Asuly, E. Tzur, C. E. Diesendruck, M. Sigalov, I. Goldberg, N. G. Lemcoff, Organometallics 2008, 27, 811 - 813
88. A. Szadkowska, X. Gstrein, D. Burtscher, K. Jarzembska, K. Wozniak, C. Slugovc, K. Grela, Organometallics 2010, 29, 117 - 124
89. M. Barbasiewicz, A. Szadkowska, R. Bujok, K. Grela, Organometallics 2006, 25, 3599 - 3604
90. C. Slugovc, D. Burtscher, F. Stelzer, K. Mereiter, Organometallics 2005, 24, 2255 - 2258
91. A. Hejl, M. W. Day, R. H. Grubbs, Organometallics 2006, 25, 6149 - 6154
92. T. Ung, A. Hejl, R. H. Grubbs, Y. Schrodi, Organometallics 2004, 23, 5399 - 5401
93. T. C. Mauldin, M. R. Kessler, J. Therm. Anal. Calorim. 2009, 96, 705 - 713
94. N. Ledoux, B. Allaert, D. Schaubroeck, S. Monsaert, R. Drozdzak, P. Van Der Voort, F. Verpoort, J. Organomet. Chem. 2006, 691, 5482 - 5486
95. P. A. van der Schaaf, A. Kolly, H.-J. Kirner, F. Rime, A. Muhlebach, A. Hafner, J. Organomet. Chem. 2000, 606, 65
96. H. Kunkely, A. Vogler, Inorg. Chim. Acta 2001, 325, 179
97. J. Louie, R. H. Grubbs, Organometallics 2002, 21, 2153
98. B. De Clercq, F. Verpoort, Tetrahedron Lett. 2002, 43, 9101.
99. For a mechanistic study on indenylidene synthesis, see E. A. Shaffer, C.-L. Chen, A. M. Beatty, E. J. Valente, H.-J. Schanz, J. Organomet. Chem. 2007, 692, 5221 - 5233
100. M. Bassetti, F. Centola, D. Sémeril, C. Bruneau, P. H. Dixneuf, Organometallics 2003, 22, 4459 - 4466.
101. T. Akita, N. Koga, Polyhedron 2005, 24, 2321 - 2325.
102. 2] gave a signal at δ=28.7 ppm (see ref. [14]).
103. Structural data of complex 4b could not be found.
104. M. Ulman, R. H. Grubbs, J. Org. Chem. 1999, 64, 7202 - 7207.
105. T. Ritter, A. Hejl, A. G. Wenzel, T. W. Funk, R. H. Grubbs, Organometallics 2006, 25, 5740 - 5745.
106. Weakening the Ru-O bond by steric or electronic effects resulted in faster initiation reactions, see ref [10e] and [10f].
107. C. Lo, C. Fischmeister, C. Bruneau, P. H. Dixneuf, Adv. Synth. Catal. 2007, 349, 546 - 550
108. I. C. Stewart, T. Ung, A. A. Pletnev, J. M. BerlinR. H. Grubbs, Y. Schrodi, Org. Lett. 2007, 9, 1589 - 1592
109. H. Clavier, S. Nolan, Chem. Eur. J. 2007, 13, 8029 - 8036
110. C. Samłojowicz, M. Bieniek, A. Zarecki, R. Kadyrov, K. Grela, Chem. Commun. 2008, 6282 - 6284
111. D. Rost, M. Porta, S. Gessler, S. Blechert, Tetrahedron Lett. 2008, 49, 5968 - 5971
112. T. Vorfalt, S. Leuthußer, H. Plenio, Angew. Chem. 2009, 121, 5293 - 5296
113. Angew. Chem. Int. Ed. 2009, 48, 5191 - 5193
114. V. Sashuk, L. H. Peeck, H. Plenio, Chem. Eur. J. 2010, 16, 3983 - 3993.
115. M. Mori, N. Sakakibora, A. Kinoshita, J. Org. Chem. 1998, 63, 6082 - 6083.
116. DMC was recently shown to be a greener solvent for olefin-metathesis transformations
117. X. Miao, C. Fischmeister, C. Bruneau, P. H. Dixneuf, ChemSusChem 2008, 1, 813 - 816
118. A. Keraani, T. Renouard, C. Fischmeister, C. Bruneau, M. Rabiller-Baudry, ChemSusChem 2008, 1, 927 - 933.
119. Complex 10 was fully soluble in DCPD and did not require preliminary dissolution in a solvent like dichloromethane.
120. CCDC-791241 (9) and CCDC-791240 (10) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.