Evolution and applications of second-generation ruthenium olefin metathesis catalysts

Aldrichimica Acta

Volumn 40, Issue 2, 2007, Pages 45-52

  Schrodi, Yann ^a   Pederson, Richard L ^a  

^a Materia Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34248327589     PISSN: 00025100     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (136)

1. (a) Chauvin, Y. Angew. Chem., Int. Ed. 2006, 45, 3740.
2. (b) Schrock, R. R. Angew. Chem., Int. Ed. 2006, 45, 3748.
3. (c) Grubbs, R. H. Angew. Chem., Int. Ed. 2006, 45, 3760.
4. (d) Despagnet-Ayoub, E.; Ritter, T. Top. Organomet. Chem. 2007, 21, 193.
5. (e) Grubbs, R. H. Tetrahedron 2004, 60, 7117.
6. (f) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vols. 1-3.
7. (g) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592.
8. (h) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
9. (i) Frenzel, U.; Nuyken, O. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2895.
10. (j) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
11. (k) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
12. (l) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565.
13. (m) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490.
14. Herisson, J.-L.; Chauvin, Y. Makromol. Chem. 1971, 141, 161.
15. (a) Schrock, R. R.; DePue, R. T.; Feldman, J.; Schaverien, C. J.; Dewan, J. C.; Liu, A. H. J. Am. Chem. Soc. 1988, 110, 1423.
16. (b) Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
17. (a) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858.
18. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
19. Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974.
20. (a) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856.
21. (b) Ferguson, M. L.; O'Leary, D. J.; Grubbs, R. H. Org. Synth. 2003, 80, 85.
22. (a) Andrade, R. B.; Plante, O. J.; Melean, L. G.; Seeberger, P. H. Org. Lett. 1999, 1, 1811.
23. (b) Burdett, K. A.; Harris, L. D.; Margl, P.; Maughon, B. R.; Mokhtar-Zadeh, T.; Saucier, P. C.; Wasserman, E. P. Organometallics 2004, 23, 2027.
24. (c) Schrodi, Y. Metathesis of BioRenewable Seed Oils Catalyzed by Grubbs Catalysts. Presented at the 232nd National Meeting of the American Chemical Society, San Francisco, CA, September 10-14, 2006; Paper INOR 551.
25. 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.
26. Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
27. Hoveyda and co-workers discovered a catalyst based on a motif similar to that of Grubbs, where one of the neutral ligands was a trialkylphosphine and the other an ether moiety attached to the alkylidene fragment via a phenylene bridge. The active species involved in catalytic cycles using this catalyst are presumably the same as those present in reactions catalyzed by Grubbs first-generationcatalyst, i.e., 14-electronbis(trialkylphosphine) dichlororuthenium alkylidene and the corresponding ruthenacyclobutane species. For a lead reference, see Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791.
28. Nicola, T.; Brenner, M.; Donsbach, K.; Kreye, P. Org. Process Res. Dev. 2005, 9, 513.
29. Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 1998, 37, 2490.
30. Herrmann, W. A.; Schattenmann, W. C.; Weskamp, T. U.S. Patent 6,635,768, October 10, 2003.
31. See the correction to reference 12 in the Corrigenda section on page 262 of Angew. Chem., Int. Ed., Vol. 38, No. 3 (1999).
32. (a) Weskamp, T.; Kohl, F. J.; Hieringer, W.; Gleich, D.; Herrmann, W. A. Angew. Chem., Int. Ed. 1999, 38, 2416.
33. (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362.
34. (c) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Herrmann, W. A. Tetrahedron Lett. 1999, 40, 4787.
35. (d) Frenzel, U.; Weskamp, T.; Kohl, F. J.; Schattenmann, W. C.; Nuyken, O.; Herrmann, W. A. J. Organomet. Chem. 1999, 586, 263.
36. Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247.
37. (a) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674.
38. (b) Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375.
39. Compare Table 1 of reference 16 to Table 2 of reference 15c.
40. Louie, J.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 247.
41. Schanz, H.-J.; Jafarpour, L.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5187.
42. (a) Jafarpour, L.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5416.
43. (b) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204.
44. (c) Fürstner, A.; Guth, O.; Düffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. - Eur. J. 2001, 7, 4811.
45. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
46. For a systematic comparison of catalyst activity in various metathesis reactions, see Ritter, T.; Hejl, A.; Wenzel, A. G.; Funk, T. W.; Grubbs, R. H. Organometallics 2006, 25, 5740.
47. The only transformations where IMes catalysts outperform SIMes catalysts seem to be ring-closing metatheses to form five-membered-ring, tetrasubstituted olefins. See references 16, 17b, 21a, 21b, 23, and 31. See also Section 5.4.
48. (a) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749.
49. (b) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543.
50. Certain ROMPs of strained cyclic olefinic monomers are highly exothermic. Depending on the monomer, the catalyst, and the conditions, some ROMPs can start and reach a 200°C exotherm within seconds.
51. Pederson, R. L.; Fellows, I. M.; Ung, T. A.; Ishihara, H.; Hajela, S. P. Adv. Synth. Catal. 2002, 344, 728.
52. Sanford, M. S.; Love, J. A.; Grubbs, R. H. Organometallics 2001, 20, 5314.
53. Love, J. A.; Sanford, M. S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 10103.
54. See Section 6 for more details on reaction temperature ranges when using these olefin metathesis catalysts.
55. Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. - Eur. J. 2001, 7, 3236.
56. Dinger, M. B.; Mol, J. C. Adv. Synth. Catal. 2002, 344, 671.
57. Lee, C. W.; Grubbs, R. H. J. Org. Chem. 2001, 66, 7155.
58. (a) Van de Weghe, P.; Bisseret, P.; Blanchard, N.; Eustache, J. J. Organomet. Chem. 2006, 691, 5078.
59. (b) Whitehead, A.; Moore, J. D.; Hanson, P. R. Tetrahedron Lett. 2003, 44, 4275.
60. (c) Chao, W.; Weinreb, S. M. Org. Lett. 2003, 5, 2505.
61. (a) Garbaccio, R. M.; Danishefsky, S. J. Org. Lett. 2000, 2, 3127.
62. (b) Garbaccio, R. M.; Stachel, S. J.; Baeschlin, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903.
63. (c) Fürstner, A.; Müller, C. Chem. Commun. 2005, 5583.
64. Vernall, A. J.; Abell, A. D. Aldrichimica Acta 2003, 36, 93.
65. (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
66. (b) Choi, T.-L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 1277.
67. (c) Choi, T.-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417.
68. Chatterjee, A. K.; Choi, T.-L.; Grubbs, R. H. Synlett 2001, 1034.
69. (a) Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751.
70. (b) Chatterjee, A. K.; Sanders, D. P.; Grubbs, R. H. Org. Lett. 2002, 4, 1939.
71. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
72. Choi, T.-L.; Rutenberg, I. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 3839.
73. For a lead reference, see Smulik, J. A.; Diver, S. T. Org. Lett. 2000, 2, 2271.
74. Shimizu, K.; Takimoto, M.; Sato, Y.; Mori, M. J. Organomet. Chem. 2006, 691, 5466.
75. Harned, A. M.; Zhang, M.; Vedantham, P.; Mukherjee, S.; Herpel, R. H.; Flynn, D. L.; Hanson, P. R. Aldrichimica Acta 2005, 38, 3.
76. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
77. These types of compound are often referred to as second-generation Hoveyda-Grubbs catalysts.
78. (a) Randl, S.; Gessler, S.; Wakamatsu, H.; Blechert, S. Synlett 2001, 430.
79. (b) Imhof, S.; Randl, S.; Blechert, S. Chem. Commun. 2001, 1692.
80. (c) Hoveyda, A. H.; Gillingham, D. G.; van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8.
81. (a) Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 794.
82. (b) Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 2403.
83. (a) Grela, K.; Harutyunyan, S.; Michrowska, A. Angew. Chem., Int. Ed. 2002, 41, 4038.
84. (b) Michrowska, A.; Bujok, R.; Harutyunyan, S.; Sashuk, V.; Dolgonos, G.; Grela, K. J. Am. Chem. Soc. 2004, 126, 9318.
85. (c) Bieniek, M.; Bujok, R.; Cabaj, M.; Lugan, N.; Lavigne, G.; Arlt, D.; Grela, K. J. Am. Chem. Soc. 2006, 128, 13652.
86. Ung, T.; Hejl, A.; Grubbs, R. H.; Schrodi, Y. Organometallics 2004, 23, 5399.
87. For additional examples of latent catalyst design, see: (a) Gulajski, L.; Michrowska, A.; Bujok, R.; Grela, K. J. Mol. Catal. A: Chem. 2006, 254, 118.
88. (b) Fürstner, A.; Thiel, O. R.; Lehmann, C. W. Organometallics 2002, 21, 331.
89. (c) Slugovc, C.; Perner, B.; Stelzer, F.; Mereiter, K. Organometallics 2004, 23, 3622.
90. (d) Slugovc, C.; Burtscher, D.; Stelzer, F.; Mereiter, K. Organometallics 2005, 24, 2255.
91. (e) Barbasiewicz, M.; Szadkowska, A.; Bujok, R.; Grela, K. Organometallics 2006, 25, 3599.
92. (f) Hejl, A.; Day, M. W.; Grubbs, R. H. Organometallics 2006, 25, 6149.
93. Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 4035.
94. Choi, T.-L.; Grubbs, R. H. Angew. Chem., Int. Ed. 2003, 42, 1743.
95. For another example of an active ruthenium catalyst bearing a pyridine ligand, see Conrad, J. C.; Amoroso, D.; Czechura, P.; Yap, G. P. A.; Fogg, D. E. Organometallics 2003, 22, 3634.
96. Romero, P. E.; Piers, W. E.; McDonald, R. Angew. Chem., Int. Ed. 2004, 43, 6161.
97. Romero, P. E.; Piers, W. E. J. Am. Chem. Soc. 2005, 127, 5032.
98. Dinger, M. B.; Nieczypor, P.; Mol, J. C. Organometallics 2003, 22, 5291.
99. Vehlow, K.; Maechling, S.; Blechert, S. Organometallics 2006, 25, 25.
100. The more active metathesis catalysts give olefinic mixtures with higher percentages of the thermodynamic E alkenes (i.e., higher E/Z ratios). For a discussion on the E/Z selectivity of metathesis catalysts, see references 1d and 23.
101. Highly active and highly enantioselective chiral molybdenum catalysts have been developed by Schrock and Hoveyda. For lead references and reviews, see: (a) Totland, K. M.; Boyd, T. J.; Lavoie, G. G.; Davis, W. M.; Schrock, R. R. Macromolecules 1996, 29, 6114.
102. (b) Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 4041.
103. (c) Zhu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251.
104. (d) Hoveyda, A. H.; Schrock, R. R. Chem. - Eur. J. 2001, 7, 945. See also reference 1g.
105. Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225.
106. Van Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954.
107. (a) Van Veldhuizen, J. J.; Gillingham, D. G.; Garber, S. B.; Kataoka, O.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 12502.
108. (b) Gillingham, D. G.; Kataoka, O.; Garber, S. B.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 12288.
109. Funk, T. W.; Berlin, J. M.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 1840.
110. Kingsbury, J. S.; Hoveyda, A. H. In Polymeric Materials in Organic Synthesis and Catalysis; Buchmeiser, M. R., Ed.; Wiley-VCH: Weinheim, 2003; Chapter 11.
111. (a) Yao, Q. Angew. Chem., Int. Ed. 2000, 39, 3896.
112. (b) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37.
113. (c) Randl, S.; Buschmann, N.; Connon, S. J.; Blechert, S. Synlett 2001, 1547.
114. (d) 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.
115. (e) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671.
116. (f) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 3835.
117. (g) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002, 12, 1873.
118. (h) Yao, Q.; Zhang, Y. J. Am. Chem. Soc. 2004, 126, 74.
119. (i) Yao, Q.; Motta, A. R. Tetrahedron Lett. 2004, 45, 2447.
120. (a) Schürer, S. C.; Gessler, S.; Buschmann, N.; Blechert, S. Angew. Chem., Int. Ed. 2000, 39, 3898.
121. (b) Prühs, S.; Lehmann, C. W.; Fürstner, A. Organometallics 2004, 23, 280.
122. (a) Mayr, M.; Buchmeiser, M. R.; Wurst, K. Adv. Synth. Catal. 2002, 344, 712.
123. (b) Krause, J. O.; Lubbad, S.; Nuyken, O.; Buchmeiser, M. R. Adv. Synth. Catal. 2003, 345, 996.
124. (c) Yang, L.; Mayr, M.; Wurst, K.; Buchmeiser, M. R. Chem.-Eur. J. 2004, 10, 5761.
125. (d) Halbach, T. S.; Mix, S.; Fischer, D.; Maechling, S.; Krause, J. O.; Sievers, C.; Blechert, S.; Nuyken, O.; Buchmeiser, M. R. J. Org. Chem. 2005, 70, 4687.
126. (a) Gallivan, J. P.; Jordan, J. P.; Grubbs, R. H. Tetrahedron Lett. 2005, 46, 2577.
127. (b) Hong, S. H.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 3508.
128. Correa da Costa, R.; Gladysz, J. A. Chem. Commun. 2006, 2619.
129. Ritter, T.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 11768.
130. Grubbs, R. H. Organic Synthesis Using The Olefin Metathesis Reactions. Presented at the 231st National Meeting of the American Chemical Society, Atlanta, GA, March 26-30, 2006; Paper ORGN 179.
131. Berlin, J. M.; Campbell, K.; Ritter, T.; Funk, T. W.; Chlenov, A.; Grubbs, R. H. Org. Lett. 2007, 9, ASAP.
132. Pletnev, A. A.; Ung, T.; Schrodi, Y. Materia, Inc., Pasadena, CA. Unpublished results, 2006.
133. Stewart, I. C.; Ung, T.; Pletnev, A. A.; Berlin, J. M.; Grubbs, R. H.; Schrodi, Y. Org. Lett. 2007, 9, in press. (Patent pending.)
134. (a) Maynard, H. D.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 4137.
135. (b) Ferguson, M. L.; O'Leary, D. J.; Grubbs, R. H. Org. Synth. 2003, 80, 85.
136. (c) U.S. Patent 6,376,690, April 23, 2002. (d) U.S. Patent 6,215,019, April 19, 2001.