Ru complexes bearing bidentate carbenes: From innocent curiosity to uniquely effective catalysts for olefin metathesis

Organic and Biomolecular Chemistry

Volumn 2, Issue 1, 2004, Pages 8-23

  Hoveyda, Amir H ^a   Gillingham, Dennis G ^a   Van Veldhuizen, Joshua J ^a   Kataoka, Osamu ^a   Garber, Steven B ^a   Kingsbury, Jason S ^a   Harrity, Joseph P A ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; MOLECULAR STRUCTURE; OLEFINS; SOLVENTS; SYNTHESIS (CHEMICAL);

BIDENTATE CARBENES; ENANTIOSELECTIVE METATHESIS; OLEFIN METATHESIS;

RUTHENIUM COMPOUNDS;

EID: 1642462100     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b311496c     Document Type: Article

References (100)

1. For reviews on catalytic olefin metathesis, see: (a) R. H. Grubbs, S. J. Miller and G. C. Fu, Acc. Chem. Res., 1995, 28, 446-452
2. (b) H-G. Schmalz, Angew. Chem., Int. Ed. Engl., 1995, 34, 1833-1836
3. (c) M. Schuster and S. Blechert, Angew. Chem., Int. Ed. Engl., 1997, 36, 2036-2056
4. (d) Alkene Metathesis in Organic Synthesis, ed. A. Furstner, Springer, Berlin, 1998
5. (e) S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371-388
6. (f) R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413-4450
7. (g) A. J. Phillips and A. D. Abell, Aldrichimica Acta, 1999, 32, 75-90
8. (h) A. Furstner, Angew. Chem., Int. Ed., 2000, 39, 3012-3043
9. (i) T. M. Trnka and R. H. Grubbs, Acc. Chem. Res., 2001, 34, 18-29
10. (j) R. R. Schrock and A. H. Hoveyda, Angew. Chem., Int. Ed., 2003, 42, 4592-4633.
11. J. P. A. Harrity, M. S. Visser, J. D. Gleason and A. H. Hoveyda, J. Am. Chem. Soc., 1997, 119, 1488-1489.
12. J. P. A. Harrity, D. S. La, D. R. Cefalo, M. S. Visser and A. H. Hoveyda, J. Am. Chem. Soc., 1998, 120, 2343-2351.
13. (a) P. Schwab, M. B. France, J. W. Ziller and R. H. Grubbs, Angew. Chem., Int. Ed. Engl., 1995, 34, 2039-2041
14. (b) P. Schwab, R. H. Grubbs and J. W. Ziller, J. Am. Chem. Soc., 1996, 118, 100-110.
15. (a) R. R. Schrock, J. S. Murdzek, G. C. Bazan, J. Robbins, M. DiMare and M. O'Regan, J. Am. Chem. Soc., 1990, 112, 3875-3886
16. (b) G. C. Bazan, R. R. Schrock, H.-N. Cho and V. C. Gibson, Macromolecules, 1991, 24, 4495-4502.
17. C. W. Johannes, M. S. Visser, G. S. Weatherhead and A. H. Hoveyda, J. Am. Chem. Soc., 1998, 120, 8340-8347.
18. The first example of a catalytically active mono-phosphine Ru complex was reported by Snapper and coworkers: J. A. Tallarico, P. J. Bonitatebus and M. L. Snapper, J. Am. Chem. Soc., 1997, 119, 7157-7158.
19. J. S. Kingsbury, J. P. A. Harrity and A. H. Hoveyda, J. Am. Chem. Soc., 1999, 121, 791-799.
20. E. L. Dias and R. H. Grubbs, Organometallics, 1998, 17, 2758-2767.
21. For application of the release/return mechanism to the design of a supported Ru catalyst. see: M. Ahmed, A. G. M. Barrett, D. C. Braddock, S. M. Cramp and P. A. Procopiou, Tetrahedron Lett., 1999, 40, 8657-8662.
22. E. L. Dias, S. T. Nguyen and R. H. Grubbs, J. Am. Chem. Soc., 1997, 119, 3887-3897.
23. S. B. Garber, J. S. Kingsbury, B. L. Gray and A. H. Hoveyda, J. Am. Chem. Soc., 2000, 122, 8168-8179.
24. (a) M. Scholl, S. Ding, C. W. Lee and R. H. Grubbs, Org. Lett., 1999, 1, 953-956
25. (b) A. K. Chatterjee and R. H. Grubbs, Org. Lett., 1999, 1, 1751-1753.
26. (a) T. Weskamp, W. C. Schattenmann, M. Spiegler and W. A. Hermann, Angew. Chem., Int. Ed., 1998, 37, 2490-2493
27. (b) T. Weskamp, F. J. Kohl, W. Hieringer, D. Gleich and W. A. Hermmann, Angew. Chem. Int. Ed., 1999, 38, 2416-2419
28. (c) M. Scholl, T. M. Trnka, J. P. Morgan and R. H. Grubbs, Tetrahedron Lett., 1999, 40, 2247-2250
29. (d) J. Huang, E. D. Stevens, S. P. Nolan and J. L. Petersen, J. Am. Chem. Soc., 1999, 121, 2647-2678
30. (e) L. Ackermann, A. Furstner, T. Weskamp, F. J. Kohl and W. A. Hermann, Tetrahedron Lett., 1999, 40, 4787-4790
31. (f) A. Furstner, O. R. Thiel, L. Ackermann, H-J. Schanz and S. P. Nolan, J. Org. Chem., 2000, 65, 2204-2207.
32. For reviews of nucleophilic carbenes, see: (a) M. Regitz, Angew. Chem., Int. Ed., 1996, 35, 725-728
33. (b) W. A. Herrmann and C. Kocher, Angew. Chem., Int. Ed., 1997, 36, 2162-2187
34. (c) A. J. Arduengo and R. Krafczyk, Chem. Z., 1998, 32, 6-14
35. (d) A. J. Arduengo, Acc. Chem. Res., 1999, 32, 913-921.
36. For a report on the accelerating effect of an α-hydroxyl group on Ru-catalyzed RCM reactions, see: T. R. Hoye and H. Zhao, Org. Lett., 1999, 1, 1123-1125.
37. For examples where 2 and 17 are reported to exhibit similar levels of efficiency (involving cross metathesis reactions), see: (a) A. J. Geissert, L. Snyder, J. Markham and S. T. Diver, Org. Lett., 2003, 5, 1793-1796
38. (b) O. M. Demchuk, K. M. Pietrusiewicz, A. Michrowska and K. Grela, Org. Lett., 2003, 5, 3217-3220.
39. (a) S. BouzBouz and J. Cossy, Org. Lett., 2001, 3, 1451-1454
40. (b) J. Cossy, S. BouzBouz and A. H. Hoveyda, J. Organomet. Chem., 2001, 624, 327-332.
41. M. S. Sanford, J. A. Love and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 6543-6554.
42. (a) S. Imhof, S Randl and S. Blechert, Chem. Commun., 2001, 1692-1693
43. (b) S. Randl, S. Gessler, H. Wakamatsu and S. Blechert, Synlett, 2001, 430-432
44. (c) S. Randl, S. J. Connon and S. Blechert, Chem. Commun., 2001, 1796-1797
45. (d) S. Gessler, S. Randl and S. Blechert, Tetrahedron Lett., 2000, 41, 9973-9976.
46. H. Mizutani, S. J. Degrado and A. H. Hoveyda, J. Am. Chem. Soc., 2001, 123, 779-780.
47. S. BouzBouz, E. De Lemos and J. Cossy, Adv. Synth. Catal., 2002, 344, 627-630.
48. F. Royer, C. Vilain, L. Ekraim and L. Grimaud, Org. Lett., 2003, 5, 2007-2009.
49. (a) T. Naota, H. Takaya and S-I. Murahashi, Chem. Rev., 1998, 98, 2599-2660
50. (b) B. M. Trost, F. D. Toste and A. B. Pinkerton, Chem. Rev., 2001, 101, 2067-2096.
51. For other Ru-catalyzed tandem protocols, where one of the transformations is an olefin metathesis, see: (a) C. W. Bielawski, J. Louie and R. H. Grubbs, J. Am. Chem. Soc., 2000, 122, 12872-12873
52. (b) A. E. Sutton, B. A. Seigal, D. F. Finnegan and M. L. Snapper, J. Am. Chem. Soc., 2002, 124, 13390-13391
53. (c) C. Cadot, P. Dalko and J. Cossy, Tetrahedron Lett., 2002, 43, 1839-1841
54. (d) M. Arisawa, Y. Terada, M. Nakagawa and A. Nishida, Angew. Chem., Int. Ed., 2002, 41, 4732-4734.
55. (a) J. Cossy, F. C. Bargiggia and S. BouzBouz, Tetrahedron Lett., 2002, 43, 6715-6717
56. (b) J. Cossy, F. Bargiggia and S. BouzBouz, Org. Lett., 2003, 5, 459-462.
57. (a) S. BouzBouz and J. Cossy, Org. Lett., 2001, 3, 1451-1454
58. (b) J. Cossy, S. BouzBouz, F. Pradaux, C. Willis and V. Bellosta, Synlett, 2002, 1595-1606.
59. K. E. Murphy and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 4690-4691.
60. For recent key reports and reviews regarding catalytic CM reactions, see: (a) H. E. Blackwell, D. J. O'Leary, A. K. Chatterjee, R. A. Washenfelder, D. A. Bussmann and R. H. Grubbs, J. Am. Chem. Soc., 2000, 122, 58-71
61. (b) A. K. Chatterjee, T-L. Choi, D. P. Sanders and R. H. Grubbs, J. Am. Chem. Soc., 2003, 125, 11360-11370
62. S. J. Cannon and S. Blechert, Angew. Chem., Int. Ed., 2003, 42, 1900-1923.
63. T. Lazarova, J. S. Chen, B. Hamann, J. M. Kang, D. Homuth-Trombino, F. Han, E. Hoffmann, C. McClure, J. Eckstein and Y. S. Or, J. Med. Chem., 2003, 46, 674-676.
64. P. Wipf, S. R. Rector and H. Takahashi, J. Am. Chem. Soc., 2002, 124, 14848-14849.
65. R. R. Cesati, J. de Armas and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, in press.
66. K. J. Hale, M. M. Domostoj, D. A. Tocher, E. Irving and F. Scheinmann, Org. Lett., 2003, 5, 2927-2930.
67. B. Nosse, R. B. Chhor, W. B. Jeong, C. Bohm and O. Reiser, Org. Lett., 2003, 5, 941-944.
68. For a more recent non-phosphine Ru-based metathesis catalyst and discussion of related mechanistic issues, see: J. A. Love, J. P. Morgan, T. M. Trnka and R. H. Grubbs, Angew. Chem., Int. Ed., 2002, 41, 4035-4037.
69. T. M. Trnka, M. W. Day and R. H. Grubbs, Angew. Chem., Int. Ed., 2001, 40, 3441-3444.
70. For a comprehensive review of supported catalysts for olefin metathesis, see: J. S. Kingsbury, A. H. Hoveyda, in Polymeric Materials in Organic Synthesis and Catalysis, ed. M. R. Buchmeiser, Wiley-VCH, Weinheim, 2003, pp. 467-502.
71. Q. Yao, Angew. Chem., Int. Ed., 2000, 39, 3896-3898.
72. J. Dowden and J. Savovic, Chem. Commun., 2001, 37-38.
73. Q. Yao and Y. Zhang, Angew. Chem., Int. Ed., 2003, 42, 3395-3398.
74. Sol-Gel Science: The Physics and Chemistry of Sol-Gel Processing, C. J. Brinkler and G. W. Scherer, Academic Press, San Diego, CA, 1990.
75. J. S. Kingsbury, S. B. Garber, J. M. Giftos, B. L. Gray, M. M. Okamoto, R. A. Farrer, J. T. Fourkas and A. H. Hoveyda, Angew. Chem., Int. Ed., 2001, 40, 4251-4256.
76. S. Randl, N. Buschmann, S. J. Connon and S. Blechert, Synlett, 2001, 1547-1550.
77. K. Grela, M. Tryznowski and M. Bieniek, Tetrahedron Lett., 2002, 43, 9055-9059.
78. S. J. Connon, A. M. Dunne and S. Blechert, Angew. Chem., Int. Ed., 2002, 41, 3835-3838.
79. For reviews of Mo-catalyzed enantioselective olefin metathesis, see: (a) A. H. Hoveyda and R. R. Schrock, Chem. Eur. J., 2001, 7, 945-950
80. (b) R. R. Schrock and A. H. Hoveyda, Angew. Chem., Int. Ed., 2003, 42, 4592-4633.
81. J. J. VanVeldhuizen, S. B. Garber, J. S. Kingsbury and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 4954-4955.
82. For an alternative chiral Ru-based metathesis catalyst, see: T. J. Seiders, D. W. Ward and R. H. Grubbs, Org. Lett., 2001, 3, 3225-3228.
83. For a review of complexes chiral at the metal, see: H. Brunner, Angew. Chem., Int. Ed., 1999, 38, 1194-1208.
84. For an example regarding the utility of achiral non-phosphine complex 2 in ROM/CM, see: B. H. White and M. L. Snapper, J. Am. Chem. Soc., 2003, 125, in press.
85. (a) D. S. La, J. G. Ford, E. S. Sattely, J. P. Bonitatebus, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 1999, 121, 11603-11604
86. (b) D. S. La, E. S. Sattely, J. G. Ford, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2001, 123, 7767-7778.
87. For a related case, see: S. Chang, L. Jones, C. Wang, L. M. Henling and R. H. Grubbs, Organometallics, 1998, 17, 3460-3465.
88. J. J. Van Veldhuizen, D. G. Gillingham, S. B. Garber, O. Kataoka and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 12502-12508.
89. K. Grela, S. Harutyunyan and A. Michrowska, Angew. Chem., Int. Ed., 2002, 41, 4038-4040.
90. K. Grela and M. Kim, Eur. J. Org. Chem., 2003, 963-966.
91. H. Wakamatsu and S. Blechert, Angew. Chem., Int. Ed., 2002, 41, 2403-2405.
92. M. S. Sanford, L. M. Henling, M. W. Day and R. H. Grubbs, Angew. Chem., Int. Ed., 2000, 39, 3451-3453.
93. For representative reports on Mo-catalyzed AROM/CM, see: (a) G. S. Weatherhead, J. G. Ford, E. J. Alexanian, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2000, 122, 1828-1829; (b) Ref. 51b
94. (c) W. C. P. Tsang, J. A. Jernelius, G. A. Cortez, G. S. Weatherhead, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 1255, 2591-2596.
95. For examples of Mo-catalyzed ARCM, see: (a) J. B. Alexander, D. S. La, D. R. Cefalo, A. H. Hoveyda and R. R. Schrock, J. Am. Chem. Soc., 1998, 120, 4041-4042
96. (b) D. S. La, J. B. Alexander, D. R. Cefalo, D. D. Graf, A. H. Hoveyda and R. R. Schrock, J. Am. Chem. Soc., 1998, 120, 9720-9721
97. (c) S. S. Zhu, D. R. Cefalo, D. S. La, J. Y. Jamieson, W. M. Davis, A. H. Hoveyda and R. R. Schrock, J. Am. Chem. Soc., 1999, 121, 8251-8259
98. (d) D. R. Cefalo, A. F. Kiely, M. Wuchrer, J. Y. Jamieson, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2001, 123, 3139-3140
99. (e) A. F. Keily, J. A. Jernelius, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 2868-2869.
100. For a recent report where Ru catalyst 2 is reported to be an "especially effective" initiator in polymer synthesis, see: S. Demel, S. Riegler, K. Wewerka, W. Schoefberger, C. Slugovc and F. Selzer, Inorg. Chim. Acta, 2003, 345, 363-366.