A convenient system for improving the efficiency of first-generation ruthenium olefin metathesis catalysts

Organometallics

Volumn 24, Issue 19, 2005, Pages 4528-4542

  Forman, Grant S ^a   McConnell, Ann E ^a   Tooze, Robert P ^a   Janse Van Rensburg, Werner ^a   Meyer, Wolfgang H ^a   Kirk, Megan M ^a   Dwyer, Catherine L ^a   Serfontein, D Wynand ^a  

^a SASOL TECHNOLOGY PTY LTD   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

BYPRODUCTS; CATALYSTS; DISCRETE FOURIER TRANSFORMS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; PHENOLS; REACTION KINETICS;

CATALYST LOADINGS; METATHESIS CATALYSTS; OLEFINIC SUBSTRATES; REACTION MIXTURES;

RUTHENIUM;

EID: 25444501296     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0503848     Document Type: Article

References (113)

1. For recent reviews on olefin metathesis, see: (a) Schuster, M.; Blechart, S. Angew Chem., Int. Ed. 1997, 109, 2037-2056.
2. (b) Fürstner, A. Top. Catal. 1997, 4, 285-299.
3. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
4. (d) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
5. (e) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75-89.
6. (f) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
7. (g) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
8. (h) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604.
9. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885.
10. (j) Yet, L. Chem. Rev. 2000, 100, 2963-3007.
11. (k) Roy, R.; Das, S. K. J. Chem. Soc., Chem. Commun. 2000, 519-529.
12. (l) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077.
13. (m) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475.
14. (n) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561.
15. (o) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
16. (p) Mol, J. C. J. Mol. Catal. A: Chem. 2004, 273, 39-45.
17. (q) Grubbs, R. H.; Lynn, D. M. In Aqueous-Phase Organometallic Catalysis, 2nd ed.; 2004; 550-566.
18. (r) Astruc, D. New J. Chem. 2005, 29, 42-56.
19. (a) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858-9859.
20. (b) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
21. (c) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
22. (d) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887-3897.
23. (e) Ulman, M.; Grubbs, R. H. J. Org. Chem. 1999, 64, 7202-7207.
24. (f) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71.
25. (a) Weskamp, T.; Schattenmann, W. C.; Speigler, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 1998, 37, 2490-2493.
26. (b) Weskamp, T.; Kohl, F. J.; Hieringer, W.; Gleich, D.; Herrmann, W. A. Angew. Chem., Int. Ed. 1999, 38, 2416-2419.
27. (c) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Herrmann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790.
28. (d) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362-365.
29. (e) Frenzel, U.; Weskamp, T.; Kohl, F. J.; Schattenmann, W. C.; Nuyken, O.; Herrmann, W. A. J. Organomet. Chem. 1999, 586, 263-265.
30. (f) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250.
31. (g) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
32. (h) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
33. (i) Jafarpour, L.; Huang, J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 3760-3763.
34. For selected examples, see: (a) Schuster, M.; Blechert, S. Transition Met. Org. Synth. 1998, 1, 275-284.
35. (b) Nicolaou, K. C.; King, N. Paul; He, Y. Top. Organomet. Chem. 1998, 1, 73-104.
36. (c) Edwards, S. D.; Lewis, T.; Taylor, R. J. K. Tetrahedron Lett. 1999, 40, 4267-4270.
37. (d) Mori, M.; Tonogaki, K.; Nishiguchi, N. J. Org. Chem. 2002, 67, 224-226.
38. (e) Hanessian, S.; Margarita, R.; Hall, A.; Johnstone, S.; Tremblay, M.; Parlanti, L. J. Am. Chem. Soc. 2002, 124, 13342-13343.
39. (f) Matsuya, Y.; Kawaguchi, T.; Nemoto, H. Org. Lett. 2003, 5, 2939-2941.
40. (g) Rosillo, M.; Dominguez, G.; Casarrubios, L.; Amador, U.; Perez-Castells, J. J. Org. Chem. 2004, 69, 2084-2093.
41. Forman, G. S.; McConnell, A. E.; Hanton, M. J.; Slawin, A. M. Z.; Tooze, R. P.; Janse van Rensburg, W.; Meyer, W. H.; Dwyer, C.; Kirk, M. M.; Serfontein, D. W. Organometallics 2004, 23, 4824-4827.
42. (a) Huang, J.; Stevens, E. D.; Nolan, S. P.; Peterson, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
43. (b) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250.
44. (c) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207.
45. (d) Wagner, J.; Martin Cabrejas, L. M.; Grossmith, C. E.; Papageorgiou, C.; Senia, F.; Wagner, D.; France, J.; Nolan, S. P. J. Org. Chem. 2000, 65, 9255-9260.
46. (e) Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Org. Lett. 2001, 13, 2045-2048.
47. (f) Lehman, S. E., Jr.; Schwendeman, J. E.; O'Donnell, P. M.; Wagener, K. B. Inorg. Chim. Acta 2003, 345, 190-198.
48. Janse van Rensburg, W.; Steynberg, P. J.; Meyer, W. H.; Kirk, M. M.; Forman, G. S. J. Am. Chem. Soc. 2004, 126, 14332-14333.
49. Dry, M. E. In Encyclopedia of Catalysis; Horváth, I. T., Ed.; Wiley-Interscience: New York, 2003; Vol. 3, p 347.
50. A similar enrichment of trans-tetradecene is observed for the cyclohexylphoban catalyst 5 relative to 1: unpublished results.
51. Nubel P. O.; Hunt, C. L. J. Mol. Catal. A: Chem. 1999, 145, 323-327.
52. Mihailović, M. L; Ćeković, Z. In The Chemistry of the Hydroxyl Group; Patai, S., Ed.: Wiley-Interscience: New York, 1971; Vol. 1, p 506.
53. Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543-6554.
54. Sanford, M. S.; Love, J. A.; Grubbs, R. H. Organometallics 2001, 20, 5314-5318.
55. Grubbs and co-workers used a DANTE pulse sequence and a CIFIT program to extract exchange rate constants, and reported the data per coordinated phosphine (see ref 12). Using this methodology, an exchange value of 0.381 at 50°C using 3 equiv of phosphine was obtained.
56. Because the NMR pulse sequences used by Grubbs and ourselves for measuring phosphine exchange rates were not the same (see ref 13), a direct comparison between the two sets of results is not possible.
57. (obs) exchange rate value was multiplied by 2 because of a symmetrical transition state as described by Green and co-workers: Green, M. L. H.; Wong, L.-L.; Sella, A. Organometallics 1992, 11, 2660-2668.
58. The nature of the decomposition species observed in these reactions is the subject of further investigation.
59. Kunkely, H.; Vogler, A. Inorg. Chim. Acta 2001, 325, 179-181.
60. Hansen, S. M.; Rominger, F.; Eisenträger, F.; Metz, M.; Hofmann, P. Chem. -Eur. J. 1999, 5, 557-566.
61. Wright, R. E.; Vogler, A. J. Organomet. Chem. 1978, 160, 197-205.
62. Amir-Ebrahimi, V.; Hamilton, J. G.; Nelson, J.; Rooney, J. J.; Thompson, J. M.; Beaumont, A. J.; Rooney, A. D.; Harding, C. J. J. Chem Soc., Chem. Commun. 1991, 1621-1622.
63. Turk and Ford have reported the oxidation of 2,6-di-tert-butylphenol catalyzed by CoPcTs is pH and temperature dependent: Turk, H.; Ford, W. T. J. Org. Chem. 1988, 53, 461-462.
64. Grubbs, R. H. Tetrahedron 2004, 126, 7117-7140.
65. (a) Adlhart, C.; Chen, P. J. Am. Chem. Soc. 2004, 126, 3496-3510.
66. (b) Suresh, C. H.; Koga, N. Organometallics 2004, 23, 76-80.
67. (c) Burdett, K. A.; Harris, L. D.; Margl, P.; Maughon, B. R.; Mokhtar-Zadeh, T.; Saucier, P. C.; Wasserman, E. P. Organometallics 2004, 23, 2027-2047.
68. (d) Fomine, S.; Martinez Vargas, S.; Tlenkopatchev, M. A. Organometallics 2003, 22, 93-99.
69. (e) Cavallo, L. J. Am. Chem. Soc. 2002, 124, 8965-8973.
70. (f) Vyboishcikov, S. F.; Bühl, M.; Thiel, W. Chem. Eur. J. 2002, 8, 3962-3975.
71. Parr, R. G.; Yang, W. J. Am. Chem. Soc. 1984, 106, 4049-4050.
72. Yandulov, D. V.; Caulton, K. G.; Belkova, N. V.; Shubina, E. S.; Epstein, L. M.; Khoroshun, D. V.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 12553-12563.
73. (a) Aullon, G.; Bellamy, D.; Brammer, L.; Bruton, E. A.; Orpen, A. G. Chem. Commun. 1998, 653-654.
74. (b) Davies, P. J.; Veldman, N.; Grove, D. M.; Spek, A. L.; Lutz, B. T. G.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1959-1961.
75. Amir-Ebrahimi, V.; Corry, D. A.; Hamilton, J. G.; Thompson, J. M.; Rooney, J. J. Macromolecules 2000, 33, 717-724.
76. A similar argument applies upon changing the Cl ligands in 1 with trifluoro aoetyl fragmenta, see: Wu, Z.; Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1985, 117, 5503-5511.
77. (a) Hirshfeld, F. L. Theor. Chim. Acta B 1977, 44, 129.
78. (b) Delley, B. Chem. Phys. Lett. 1986, 110, 329.
79. Buchowicz, W.; Mol, J. C. J. Mol. Catal. A 1999, 148, 97-103.
80. (a) Al Samak, B.; Amir-Ebrahimi, V.; Corry, D. A.; Hamilton, J. G.; Rigby, S.; Rooney, J. J. Thompson, J. M. J. Mol. Cat A: Chem. 2000, 160, 13-21.
81. Slugovc, C.; Demel, S.; Stelzer. F. J. Chem Soc., Chem. Commun. 2002, 2572-2573.
82. (a) Sanford, M. S.; Henling, L. M.; Grubbs, R. H. Organometallics 1998, 17, 5384-5389.
83. (b) Lynn, D. M.; Mohr, B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 1627-1628.
84. (c) Huang, J.; Schanz, H. J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375-5380.
85. Rivard, M.; Blechert, S. Eur. J. Org. Chem. 2003, 2225-2228.
86. Bourgeois, D.; Pancrazi, A.; Nolan, S. P.; Prunet, J. J. Organomet. Chem. 2002, 643-644, 247-252.
87. Gordon, A. J.; Ford, R. A. The Chemists Companion; John Wiley and Sons: New York, 1972; p 2.
88. Scharlin, P. Acta Chem. Scan. 1986, A40, 207-209.
89. For selected examples, see: (a) Cole-Hamilton, D. J.; Young, R. J.; Wilkinson, G. J. Chem Soc., Dalton Trans. 1976, 1995-2001.
90. (b) Braga, D.; Sabatino, P.; Di Bugno, C.; Leoni, P.; Pasquali, M. J. Organomet. Chem. 1987, 334, C46-C48.
91. (c) Heppert, J. A.; Boyle, T. J.; Takusagawa, F. Organometallics 1989, 8, 461-467.
92. (d) Atwood, D. A.; Cowley, A. H.; Schluter, R. D.; Bond, M. R.; Carrano, C. J. Inorg. Chem. 1995, 34, 2186-2189.
93. (e) Hirano, M.; Kurata, N.; Marumo, T.; Komiya, S. Organometallics 1998, 17, 501-503.
94. (f) Brandts, J. A. M.; Boersma, J.; Spek, A. L.; Van Koten, G. Eur. J. Inorg. Chem. 1999, 10, 1727-1733.
95. Fogg and co-workers have recently reported the synthesis of new alkylidene complexes in which aryloxide groups function as pseudohalide groups: Conrad, J.; Amoroso, D.; Czechura, P.: Yap, G. P. A.; Fogg, D. Organometallics 2003, 22, 3634-3636.
96. (a) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799.
97. (b) Barber, S. B.; Kingsbury, J. S.; Gray, B. L. Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
98. (c) Hoveyda, A. H.; Gillingham, D. G.; van Veldhuizen, J. J.; Kataoka, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 1-16.
99. (a) Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 794-796.
100. (b) Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 2403-2405.
101. (c) Dunne, A. M.; Mix, S.; Blechert, S. Tetrahedron Lett. 2003, 44, 2733-2736.
102. (d) Grela, K.; Kim, M. Eur. J. Org. Chem. 2003, 963-966.
103. (e) Grela, K.; Harutyunyan, S.; Michrowska, A. Angew. Chem., Int. Ed. 2002, 41, 4038-4040.
104. (f) Michrowska, A.; Bujo, R.; Harutyunyan, S.; Sashuk, V.; Dolgonos, G.; Grela, K. J. Am. Chem. Soc. 2004, 126, 9318-9325.
105. A report detailing the full scope and generality of phenol addition to CM reactions catalyzed by 2 will be published shortly.
106. Forman, G. S.; Tooze, R. P. (Sasol Technology UK), World Patent, WO 2004056728, 2004.
107. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4th ed; Butterworth Heinemann: Oxford, 2002.
108. (a) Delley, B. J. Chem. Phys. 1990, 92, 508-517.
109. (b) Delley, B. J. Phys. Chem. 1996, 100, 6107-6110.
110. (c) Delley, B. J. Chem. Phys. 2000, 113, 7756-7764.
111. Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13244-13249.
112. Delley, B. In Density Functional Theory: A Tool for Chemistry; Seminario, J. M., Politzer, P., Eds.; Elsevier: Amsterdam, The Netherlands, 1995.
113. Andzelm, J.; King-Smith, R. D.; Fitzgerald, G. Chem. Phys. Lett. 2001, 335, 321.