Probing the mechanism of carbon-hydrogen bond activation by photochemically generated hydridotris(pyrazolyl)borato carbonyl rhodium complexes: New experimental and theoretical investigations

Organometallics

Volumn 27, Issue 2, 2008, Pages 189-201

  Blake, Alexander J ^a   George, Michael W ^a   Hall, Michael B ^b   McMaster, Jonathan ^a   Portius, Peter ^a   Sun, Xue Z ^a   Towrie, Michael ^c   Webster, Charles Edwin ^d   Wilson, Claire ^a   Zarić, Snežana D ^e  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b TEXAS A AND M UNIVERSITY   (United States)

^c Harwell Science and Innovation Campus   (United Kingdom)

^d University of Memphis   (United States)

^e UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL HYDRIDE PRODUCTS; HYDRIDOTRIS; PHOTOLYTICALLY ACTIVATED; TIME-RESOLVED INFRARED (TRIR);

CYCLOHEXANE; DENSITY FUNCTIONAL THEORY; ORGANOMETALLICS; PHOTOLYSIS; REACTION KINETICS; RHODIUM;

CHEMICAL BONDS;

EID: 38949165399     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om7008217     Document Type: Article

References (107)

1. (a) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507-514.
2. (b) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154-162.
3. (c) Yang, H.; Kotz, K. T.; Asplund, M. C.; Wilkens, M. J.; Harris, C. B. Acc. Chem. Res. 1999, 32, 551-560.
4. (d) Wasserman, E. P.; Moore, C. B.; Bergman, R. G. Science 1992, 255, 315-318.
5. (e) Jones, W. D. Acc. Chem. Res. 2003, 36, 140-146.
6. (f) Crabtree, R. H. J. Chem. Soc., Dalton Trans. 2001, 2437, 2450.
7. (g) Jones, W. D. Inorg. Chem. 2005, 44, 4475-4484.
8. (h) Hall, M. B.; Fan, H. J. Adv. Inorg. Chem. 2003, 54, 321-349.
9. (i) Niu, S.; Hall, M. B. Chem. Rev. 2000, 100, 353-405.
10. (j) Fan, Y.; Hall, M. B. Organometallics 2005, 24, 3827-3835.
11. (k) Xavier, E. S.; De Almeida, W. B.; Da Silva, J. C. S.; Rocha, W. R. Organometallics 2005, 24, 2262-2268.
12. (l) Bhalla, G.; Periana, R. A. Angew. Chem., Int. Ed. 2005, 44, 1540-1543.
13. (m) Lee, K.; Legzdins, P.; Pamplin, C. B.; Patrick, B. O.; Wada, K. Organometallics 2005, 24, 638-649.
14. (n) Bernskoetter, W. H.; Lobkovsky, E.; Chirik, P. J. Organometallics 2005, 24, 4367-4373.
15. (a) Janowicz, A. H.; Bergman, R. G. J. Am. Chem. Soc. 1982, 104, 352-354.
16. (b) Janowicz, A. H.; Bergman, R. G. J. Am. Chem. Soc. 1983, 105, 3929-3939.
17. (c) Hoyano, J. K. \& Graham, W. A. G. J. Am. Chem. Soc. 1982, 104, 3723-3725.
18. (d) Hoyano, J. K.; McMaster, A. D.; Graham, W. A. G. J. Am. Chem. Soc. 1983, 105, 7190-7191.
19. (e) Jones, W. D.; Feher, F. J. J. Am. Chem. Soc. 1984, 106, 1650.
20. (f) Crabtree, R. H.; Mihelcic, J. M.; Quirk, J. M. J. Am. Chem. Soc. 1979, 101, 7738.
21. (g) Crabtree, R. H.; Mellea, M. F.; Mihelcic, J. M.; Quirk, J. M. J. Am. Chem. Soc. 1982, 104, 107.
22. (h) Watson, P. L. J. Am. Chem. Soc. 1983, 106, 6491-6493.
23. (a) Asplund, M. C.; Snee, P. T.; Yeston, J. S.; Wilkens, M. J.; Payne, C. K.; Yang, H.; Kotz, K. T.; Frei, H.; Bergman, R. G.; Harris, C. B. J. Am. Chem. Soc. 2002, 124, 10605-10612.
24. (b) Klei, S. R.; Golden, J. T.; Burger, P.; Bergman, R. G. J. Mol. Catal. A: Chem. 2002, 189, 79-94.
25. (c) Golden, J. T.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 5837-5838.
26. (d) Smith, K. M.; Poli, R.; Harvey, J. N. Chem.-Eur. J. 2001, 7, 1679-1690.
27. (e) McNamara, B. K.; Yeston, J. S.; Bergman, R. G.; Moore, C. B. J. Am. Chem. Soc. 1999, 121, 6437-6443.
28. (f) Alaimo, P. J.; Bergman, R. G. Organometallics 1999, 18, 2707-2717.
29. (g) Asbury, J. B.; Ghosh, H. N.; Yeston, J. S.; Bergman, R. G.; Lian, T. Organometallics 1998, 17, 3417-3419.
30. (h) Tran, E.; Legzdins, P. J. Am. Chem. Soc. 1997, 119, 5071-5072.
31. (i) Dunwoody, N.; Lees, A. J. Organometallics 1997, 16, 5770-5778.
32. (j) Bromberg, S. E.; Lian, T.; Bergman, R. G.; Harris, C. B. J. Am. Chem. Soc. 1996, 118, 2069-2072.
33. (k) Asbury, J. B.; Ghosh, H. N.; Yeston, J. S.; Bergman, R. G.; Lian, T. Organometallics 1998, 17, 3417-3419.
34. (l) Niu, S.; Zaric, S.; Bayse, C. A.; Strout, D. L.; Hall, M. B. Organometallics 1998, 17, 5139-5147.
35. (m) Strout, D. L.; Zarić, S.; Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1996, 118, 6068-6069.
36. (n) Bengali, A. A.; Schultz, R. H.; Moore, C. B.; Bergman, R. G. J. Am Chem. Soc. 1994, 116, 9585-9589.
37. (o) Rest, A. J.; Whitwell, I.; Graham, W. A. G.; Hoyano, J. K.; McMaster, A. D. J. Chem. Soc., Dalton Trans. 1987, 1181, 1190.
38. (p) Belt, S. T.; Grevels, F. W.; Klotzbuecher, W. E.; McCamley, A.; Perutz, R. N. J. Am. Chem. Soc. 1989, 111, 8373-8382.
39. (a) Lees, A. J.; Purwoko, A. A. Coord. Chem. Rev. 1994, 132, 155-160.
40. (b) Purwoko, A. A.; Lees, A. J. Inorg. Chem. 1996, 35, 675-682.
41. (c) Purwoko, A. A.; Tibensky, S. D.; Lees, A. J. Inorg. Chem. 1996, 35, 7049.
42. (d) Pittard, K. A.; Lee, J. P.; Cundari, T. R.; Gunnoe, T. B.; Petersen, J. L. Organometallics 2004, 23, 5514-5523.
43. (e) Bergman, R. G.; Cundari, T. R.; Gillespie, A. M.; Gunnoe, T. B.; Harman, W. D.; Klinckman, T. R.; Temple, M. D.; White, D. P. Organometallics 2003, 22, 2331-2337.
44. (f) Ng, S. M.; Lam, W. H.; Mak, C. C.; Tsang, C. W.; Jia, G.; Lin, Z.; Lau, C. P. Organometallics 2003, 22, 641-651.
45. (g) Tellers, D. M.; Bergman, R. G. Organometallics 2001, 20, 4819-4832.
46. (h) Slugovc, C.; Padilla-Martinez, I.; Sirol, S.; Carmona, E. Coord. Chem. Rev. 2001, 213, 129-157.
47. Webster, C. E.; Hall, M. B. Inorg. Chim. Acta 2002, 330, 268-282, 336, 168.
48. (a) Lian, T.; Bromberg, S. E.; Yang, H.; Bergman, R. G.; Harris, C. B. J. Am. Chem. Soc. 1996, 118, 3769-3770.
49. (b) Bromberg, S. E.; Yang, H.; Asplund, M. C.; Lian, T.; McNamara, B. K.; Kotz, K. T.; Yeston, J. S.; Wilkens, M.; Frei, H.; Bergman, R. G.; Harris, C. B. Science 1997, 278, 260-263.
50. Zarić, S.; Hall, M. B. J. Phys. Chem. A 1998, 102, 1963-1964.
51. (a) Vetter, A. J.; Flaschenriem, C.; Jones, W. D. J. Am. Chem. Soc. 2005, 127, 12315-12322.
52. (b) Clot, E.; Eisenstein, O.; Jones, W. D. Proc. Nat. Acad. Sci. U.S.A. 2007, 104, 6939-6944.
53. Sun, X.-Z.; Grills, D. C.; Nikiforov, S. M.; Poliakoff, M.; George, M. W. J. Am. Chem. Soc. 1997, 119, 7521-7525.
54. (a) Geftakis, S.; Ball, G. E. J. Am. Chem. Soc. 1998, 120, 9953-9944.
55. (b) Lawes, D. J.; Geftakis, S.; Ball, G. E. J. Am. Chem. Soc. 2005, 127, 4134-4135.
56. (c) Lawes, D. J.; Darwish, T. A.; Clark, T.; Harper, J. B.; Ball, G. E. Angew. Chem. 2006, 45, 4486-4490.
57. Ball, G. E.; Brookes, C. M.; Cowan, A. J.; Darwish, T. A.; George, M. W.; Kawanami, H. K.; Portius, P.; Rourke, J. P. Proc. Nat. Acad. Sci. U.S.A. 2007, 104, 6927-6932.
58. Lash, T. D.; Jiao, W. J. Org. Chem. 2003, 68, 3896-3901.
59. Trofimenko, S.; Calabrese, J. C.; Thompson, J. S. Inorg. Chem. 1987, 26, 1507-1514.
60. Trofimenko, S. J. Am. Chem. Soc. 1967, 89, 6288-6294.
61. (a) Towrie, M.; Grills, D. C.; Dyer, J.; Weinstein, J. A.; Matousek, P.; Barton, R.; Bailey, P. D.; Subramaniam, N.; Kwok, W. M.; Ma, C.; Phillips, D.; Parker, A. W.; George, M. W. Appl. Spectrosc. 2003, 57, 367-380.
62. (b) Towrie, M.; Gabrielsson, A.; Matousek, P.; Parker, A. W.; Rodriguez, A. M. B.; Vlcek, A. Appl. Spectrosc. 2005, 59, 467-473.
63. George, M. W.; Poliakoff, M.; Turner, J. J. Analyst 1994, 119, 551-560.
64. Frisch, M. J.; et al. Gaussian 98, Revisions A.6, A.7, A.9, and A11.3; Gaussian, Inc.: Pittsburgh, PA, 1998.
65. Frisch, M. J.; et al. Gaussian 03, Revisions B. and B.05; Gaussian, Inc.: Wallingford, CT, 2004.
66. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
67. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
68. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
69. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824;
70. Phys. Rev. B 1986, 33, 7406-7406.
71. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
72. (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
73. (b) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284-298.
74. Couty, M.; Hall, M. B. J. Comput. Chem. 1996, 17, 1359-1370.
75. Ehlers, M.; Böhme, A. W.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111-114.
76. Dunning, T. H.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; pp 1-28.
77. (a) Dunning, T. H. J. Chem. Phys. 1989, 90, 1007-1023.
78. (b) Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1994, 100, 2975-2988.
79. Davidson, E. R. Chem. Phys. Lett. 1996, 260, 514-518.
80. (a) Harvey, J. N.; Aschi, M.; Schwarz, H.; Koch, W. Theor. Chem. Acc. 1998, 99, 95.
81. (b) Harvey, J. N.; Aschi, M. Phys. Chem. Chem. Phys. 1999, 1, 5555-5563.
82. (c) Harvey, J. N. J. Am. Chem. Soc. 2000, 122, 12401-12402.
83. (d) Harvey, J. N. In Spin-Forbidden Reactions in Transition-Metal Chemistry; Cundari, T. R., Ed.; Marcel Dekker, Inc.: New York, 2001.
84. (e) Smith, K. M.; Poli, R.; Harvey, J. N. Chem.-Eur. J. 2001, 7, 1679-1690.
85. (f) Smith, K. M.; Poli, R.; Harvey, J. N. New J. Chem. 2000, 24, 77-80.
86. (g) Carreon-Macedo, J. L.; Harvey, J. N. J. Am. Chem. Soc. 2004, 126, 5789-5797.
87. (a) Fonseca Guerra, C.; Snijders, J. G.; Velde, G. T.; Baerends, E. J. Theor. Chem. Acc. 1998, 99, 391-403.
88. (b) Velde, G. T.; Bickelhaupt, F. M.; van Gisbergen, S. J. A.; Fonseca Guerra, C.; Baerends, E. J.; Snijders, J. G.; Ziegler, T. J. Comput. Chem. 2001, 22, 931-967.
89. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211.
90. (a) Ohta, K.; Hashimoto, M.; Takahashi, Y.; Hikichi, S.; Akita, M.; Moro-oka, Y. Organometallics 1999, 18, 3234-3240.
91. (b) Del Ministro, E.; Renn, O.; Rueegger, H.; Venanzi, L. M.; Burckhardt, U.; Gramlich, V. Inorg. Chim. Acta 1995, 240, 631-639.
92. (c) Rheingold, A. L.; Ostrander, R. L.; Haggerty, B. S.; Trofimenko, S. Inorg. Chem. 1994, 33, 3666-3676.
93. (d) Moszner, M.; Wolowiec, S.; Trosch, A.; Vahrenkamp, H. J. Organomet. Chem. 2000, 595, 178-185.
94. -1, which decayed on a similar time scale. The origin of this band is still unclear.
95. Yeston, J. S.; McNamara, B. K.; Bergman, R. G.; Moore, C. B. Organometallics 2000, 19, 3442-3446.
96. (a) Fan, Y.; Hall, M. B. Chem.-Eur. J. 2004, 10, 1805-1814.
97. (b) Cavallo, L.; Jacobsen, H. Eur. J. Inorg. Chem. 2003, 892, 902.
98. (c) de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. J. Am. Chem. Soc. 2002, 124, 11809-11826.
99. (d) de Visser, S. P.; Ogliaro, F.; Harris, N.; Shaik, S. J. Am. Chem. Soc. 2001, 123, 3037-3047.
100. (e) Harris, N.; Cohen, S.; Filatov, M.; Ogliaro, F.; Shaik, S. Angew. Chem., Int. Ed. 2000, 39, 2003-2007.
101. (f) Schroder, D.; Shaik, S.; Schwarz, H. Acc. Chem. Res. 2000, 33, 139-145.
102. (g) Harvey, J. N. Struct. Bonding (Berlin) 2004, 112, 151-183.
103. (h) Salomon, O.; Reiher, M.; Hess, B. A. J. Chem. Phys. 2002, 117, 4729-4737.
104. Hall, M. B.; Fan, H.-J. Adv. Inorg. Chem. 2003, 54, 321-349.
105. (a) Chan, A. S. C.; Pluth, J. J.; Halpern, J. J. Am. Chem. Soc. 1980, 102, 5952-5954.
106. (b) Halpern, J. Science 1982, 217, 401-407.
107. (c) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754.