Probing the dynamics and reactivity of a stereochemically nonrigid Cp*Ru(h)(κ2-P,carbene) complex

Organometallics

Volumn 28, Issue 1, 2009, Pages 74-83

  Rankin, Matthew A ^a   Maclean, Darren F ^a   Mcdonald, Robert ^b   Ferguson, Michael J ^b   Lumsden, Michael D ^a   Stradiotto, Mark ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RATE CONSTANTS;

ADDITION PRODUCTS; ANALOGOUS REACTIONS; CARBENE; CO-ORDINATIVELY UNSATURATED; COMPLEX 1; CRYSTALLOGRAPHIC CHARACTERIZATIONS; DYNAMIC PROCESS; EN ROUTES; HYDRIDE ELIMINATIONS; QUANTITATIVE FORMATIONS; REACTION MECHANISMS; SPECTROSCOPIC INVESTIGATIONS;

ADDITION REACTIONS;

EID: 61849146221     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800761c     Document Type: Article

References (86)

1. For selected recent reports and reviews, see: (a) Ito, M.; Ikariya, T. Chem. Commun. 2007, 5134.
2. (b) Ito, M.; Sakaguchi, A.; Kobayashi, C.; Ikariya, T. J. Am. Chem. Soc. 2007, 129, 290.
3. (c) Palacios, M. D.; Puerta, M. C.; Valerga, P.; Lledós, A.; Veilly, E. Inorg. Chem. 2007, 46, 6958.
4. (d) Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393.
5. (e) Bruneau, C.; Renaud, J.-L.; Demerseman, B. Chem.-Eur. J. 2006, 12, 5178.
6. (f) Trost, B. M.; Frederiksen, M. U.; Rudd, M. T. Angew. Chem., Int. Ed. 2005, 44, 6630.
7. (g) Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P. Eur. J. Inorg. Chem. 2004, 17.
8. (h) Nagashima, H.; Kondo, H.; Hayashida, T.; Yamaguchi, Y.; Gondo, M.; Masuda, S.; Miyazaki, K.; Matsubara, K.; Kirchner, K. Coord. Chem. Rev. 2003, 245, 177.
9. (i) Glaser, P. B.; Tilley, T. D. J. Am. Chem. Soc. 2003, 125, 13640.
10. (j) Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Inorg. Chem. 1990, 30, 1.
11. For some prominent examples featuring alternative Ru complexes, see: (a) Gunanathan, C.; Ben-David, Y.; Milstein, D. Science 2007, 317, 790.
12. (b) Grubbs, R. H. Angew. Chem., Int. Ed. 2006, 45, 3760.
13. (c) Chauvin, Y. Angew. Chem., Int. Ed. 2006, 45, 3741.
14. (d) Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008.
15. (a) Rankin, M. A.; Hesp, K. D.; Schatte, G.; McDonald, R.; Stradiotto, M. Chem. Commun. 2008, 250.
16. (b) Lundgren, R. J.; Rankin, M. A.; McDonald, R.; Stradiotto, M. Organometallics 2008, 27, 254.
17. (c) Rankin, M. A.; MacLean, D. F.; Schatte, G.; McDonald, R.; Stradiotto, M. J.. Am. Chem. Soc. 2007, 129, 15855.
18. (d) Rankin, M. A.; Schatte, G.; McDonald, R.; Stradiotto, M. J. Am. Chem. Soc. 2007, 129, 6390.
19. (e) Lundgren, R. J.; Rankin, M. A.; McDonald, R.; Schatte, G.; Stradiotto, M. Angew. Chem., Int. Ed. 2007, 46, 4732.
20. (f) Rankin, M. A.; McDonald, R.; Ferguson, M. J.; Stradiotto, M. Organometallics 2005, 24, 4981.
21. (g) Rankin, M. A.; McDonald, R.; Ferguson, M. J.; Stradiotto, M. Angew. Chem., Int. Ed. 2005, 44, 3603.
22. For recent discussions of M-alkyl/M-alkylidene and related equilibria in late metal chemistry, see: (a) Álvarez, E.; Paneque, M.; Petronilho, A. G.; Poveda, M. L.; Santos, L. L.; Carmona, E.; Mereiter, K. Organometallics 2007, 26, 1231.
23. (b) Kuznetsov, V. F.; Abdur-Rashid, K.; Lough, A. J.; Gusev, D. G. J. Am. Chem. Soc. 2006, 128, 14388.
24. (c) Salem, H.; Ben-David, Y.; Shimon, L. J. W.; Milstein, D. Organometallics 2006, 25, 2292.
25. (d) Clot, E.; Chen, J.; Lee, D.-H.; Sung, S. Y.; Appelhans, L. N.; Faller, J. W.; Crabtree, R. H.; Eisenstein, O. J. Am. Chem. Soc. 2004, 126, 8795.
26. (e) Carmona, E.; Paneque, M.; Poveda, M. L. Dalton Trans. 2003, 4022.
27. (f) Caulton, K. G. J. Organomet. Chem. 2001, 617-618, 56.
28. Reports providing quantitative rate data for reversible a-hydride elimination processes are scarce: (a) Morton, L. A.; Wang, R.; Yu, X.; Campana, C. F.; Guzei, I. A.; Yap, G. P. A.; Xue, Z.-L. Organometallics 2006, 25, 427.
29. (b) Schrock, R. R.; Seidel, S. W.; Mösch-Zanetti, N. C.; Shih, K.-Y.; O'Donoghue, M. B.; Davis, W. M.; Reiff, W. M. J. Am. Chem. Soc. 1997, 119, 11876.
30. (c) Threlkel, R. S.; Bercaw, i. E. J. Am. Chem. Soc. 1981, 103, 2650.
31. (a) Bain, A. D. Prog. Nucl. Magn. Reson. 2003, 43, 63.
32. (b) Bain, A. D.; Cramer, J. A. J. Magn. Res. A 1996, 118, 21.
33. (c) Bain, A. D.; Cramer, J. A. J. Magn. Reson. A 1993, 103, 217.
34. (d) Bain, A. D.; Cramer, J. A. J. Phys. Chem. 1993, 97, 2884.
35. Ingleson, M. J.; Yang, X.; Pink, M.; Caulton, K. G. J. Am. Chem. Soc. 2005, 127, 10846.
36. For selected reports and reviews, see: (a) Lachaize, S.; Sabo-Etienne, S. Eur. J. Inorg. Chem. 2006, 2115.
37. (b) Osipov, A. L.; Vyboishchikov, S. F.; Dorogov, K. Y.; Kuzmina, L. G.; Howard, J. A. K.; Lemenovskii, D. A.; Nikonov, G. I. Chem. Comtnun. 2005, 3349.
38. (c) Osipov, A. L.; Gerdov, S. M.; Kuzmina, L. G.; Howard, J. A. K.; Nikonov, G. I. Organometallics 2005, 24, 587.
39. (d) Takao, T.; Amako, M.; Suzuki, H. Organometallics 2001, 20, 3406.
40. (e) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175.
41. (f) Shelby, Q. D.; Lin, W.; Girolami, G. S. Organometallics 1999, 18, 1904.
42. (g) Lemke, F. R.; Galat, K. J.; Youngs, W. J. Organometallics 1999, 18, 1419.
43. (h) Tobita, H.; Kurita, H.; Ogino, H. Organometallics 1998, 17, 2850.
44. (i) Wada, H.; Tobita, H.; Ogino, H. Organometallics 1997, 16, 3870.
45. (j) Mitchell, G. P.; Tilley, T. D. J.. Am. Chem. Soc. 1997, 119, 11236.
46. (k) Campion, B. K.; Heyn, R. H.; Tilley, T. D. Chem. Commun. 1992, 1201.
47. Campion, B. K.; Heyn, R. H.; Tilley, T. D. Organometallics 1992, 11, 3918.
48. (m) Straus, D. A.; Zhang, C.; Quimbita, G. E.; Grumbine, S. D.; Heyn, R. H.; Tilley, T. D.; Rheingold, A. L.; Geib, S. J. J. Am. Chem. Soc. 1990, 112, 2673.
49. (n) Straus, D. A.; Tilley, T. D.; Rheingold, A. L.; Geib, S. J. J. Am. Chem. Soc. 1987, 109, 5872.
50. (o) References li and 3a,c,d herein.
51. 22) species has been observed previously: Gusev, D. G.; Nadasdi, T. T.; Caulton, K. G. Inorg. Chem. 1996, 35, 6772.
52. 1H} NMR: δ 47.9, 47.8.
53. The addition of Si-H across Ru=C may represent an elementary reaction step in hydrosilylation chemistry employing Ru=C precatalysts: (a) Menozzi, C.; Dalko, P. I.; Cossy, J. J. Org. Chem. 2005, 70, 10717.
54. (b) Maifeld, S. V.; Iran, M. N.; Lee, D. Tetrahedron Lett. 2005, 46, 105.
55. (c) Aricó, C. S.; Cox, L. R. Org. Biomol. Chem. 2004, 2, 2558.
56. (a) Schmidt, B. Eur. J. Org. Chem. 2004, 1865.
57. (b) Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312.
58. Jutzi, P.; Müller, C.; Stammler, A.; Stammler, H.-G. Organometallics 2000, 19, 1442.
59. (a) Braunschweig, H.; Kollann, C.; Rais, D. Angew. Chem., Int. Ed. 2006, 45, 5254.
60. (b) Aldridge, S.; Coombs, D. L. Coord. Chem. Rev. 2004, 248, 535.
61. (c) Crudden, C. M.; Edwards, D. Eur. J. Org. Chem. 2003, 4695.
62. (d) Braunschweig, H.; Colling, M. Coord. Chem. Rev. 2001, 223, 1.
63. (e) Piers, W. E. Angew. Chem., Int. Ed. 2000, 39, 1923.
64. (f) Braunschweig, H. Angew. Chem., Int. Ed. 1998, 37, 1786.
65. (g) Irvine, G. J.; Lesley, M. J. G.; Marder, T. B.; Norman, N. C.; Rice, C. R.; Robins, E. G.; Roper, W. R.; Whittell, G. R.; Wright, L. J. Chem. Rev. 1998, 98, 2685.
66. (h) Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957.
67. n complexes, see: (a) Hesp, K. D.; Rankin, M. A.; McDonald, R.; Stradiotto, M. Inorg. Chem. 2008, 47, 7471.
68. (b) Kawano, Y.; Hashiva, M.; Shimoi, M. Organometallics 2006, 25, 4420.
69. (c) Saito, T.; Kuwata, S.; Ikariya, T. Chem. Lett. 2006, 35, 1224.
70. (d) Kuan, S. L.; Leong, W. K.; Goh, L. Y.; Webster, R. D. J. Organomet. Chem. 2006, 691, 907.
71. (e) Murphy, J. M.; Lawrence, J. D.; Kawamura, K.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 13684.
72. (f) Kuan, S. L.; Leong, W. K.; Goh, L. Y.; Webster, R. D. Organometallics 2005, 24, 4639.
73. (g) Merle, N.; Frost, C. G.; Koicok-Kohn, G.; Willis, M. C.; Weller, A. S. J. Organomet. Chem. 2005, 690, 2829.
74. (h) Merle, N.; Koicok-Köhn, G.; Mahon, M. F.; Frost, C. G.; Ruggerio, G. D.; Weller, A. S.; Willis, M. C. Dalton Trans. 2004, 3883.
75. (i) Waltz, K. M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 11358.
76. (j) Hartwig, J. F.; Bhandari, S.; Rablen, P. R. J. Am. Chem. Soc. 1994, 116, 1839.
77. Rickard, C. E. F.; Roper, W. R.; Williamson, A.; Wright, L. J. Organometallics 2000, 19, 4344.
78. For some other crystallographically characterized complexes featuring a Ru-H-B bridging motif, see: (a) Alcaraz, G.; Clot, E.; Helmstedt, U.; Vendier, L.; Sabo-Etienne, S. J. Am. Chem. Soc. 2007, 129, 8704.
79. (b) Lachaize, S.; Essalah, K.; Montiel-Palma, V.; Vendier, L.; Chaudret, B.; Barthelat, J.-C.; Sabo-Etienne, S. Organometallics 2005, 24, 2935.
80. (c) Montiel-Palma, V.; Lumbierres, M.; Donnadieu, B.; Sabo-Etienne, S.; Chaudret, B. J. Am. Chem. Soc. 2002, 124, 5624.
81. (d) Baker, R. T.; Calabrese, J. C.; Westcott, S. A.; Marder, T. B. J. Am. Chem. Soc. 1995, 117, 8777.
82. (e) References 15a-d and 15f-h herein.
83. (a) Smith, K.; Pelter, A.; Jin, Z. Angew. Chem., Int. Ed. 1994, 33, 851.
84. (b) Pelter, A.; Smith, K.; Buss, D.; Jin, Z. Heteroat. Chem. 1992, 3, 275.
85. Meissner, A.; Sørensen, O. W. Magn. Reson. Chem. 2001, 39, 49.
86. Farrugia, L. J. ORTEP-3 for Windows version 1.074. J. Appl. Crystallogr. 1997, 30, 565.