Activation of B-H, Si-H, and C-F bonds with Tp′Rh(PMe3) complexes: Kinetics, mechanism, and selectivity

Journal of the American Chemical Society

Volumn 137, Issue 3, 2015, Pages 1258-1272

  Procacci, Barbara ^a   Jiao, Yunzhe ^b   Evans, Meagan E ^b   Jones, William D ^b   Perutz, Robin N ^a   Whitwood, Adrian C ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; BENZENE; CHEMICAL ACTIVATION; KINETICS; MIXTURES; PHOTODISSOCIATION; PHOTOLYSIS; RHODIUM COMPOUNDS; SUBSTRATES;

BIMOLECULAR REACTION; CHEMICAL EQUATIONS; COMPETITION REACTIONS; DFT CALCULATION; KINETIC SELECTIVITY; LASER PHOTOLYSIS; PENTAFLUOROPYRIDINE; THERMAL REACTIONS;

SILICON COMPOUNDS;

BENZENE; BORON; CARBON; FLUORINE; HYDROGEN; RHODIUM COMPLEX; SILICON;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DISSOCIATION; HEATING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; PHOTOLYSIS; PHOTOREACTIVITY;

EID: 84921838827     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5113172     Document Type: Article

References (99)

1. (a) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175.
2. (b) Corey, J. Y. Chem. Rev. 2011, 111, 863.
3. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890.
4. Johansson, L.; Tilset, M.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2000, 122, 10846.
5. Clot, E.; Eisenstein, O.; Jasim, N.; Macgregor, S. A.; McGrady, J. E.; Perutz, R. N. Acc. Chem. Res. 2011, 44, 333.
6. (a) Trofimenko, S. Acc. Chem. Res. 1971, 4, 17.
7. (b) Trofimenko, S. Chem. Rev. 1993, 93, 943.
8. Crossley, I. R. Adv. Organomet. Chem. 2008, 56, 199-321.
9. (a) Purwoko, A. A.; Lees, A. J. Inorg. Chem. 1996, 35, 675.
10. (b) Purwoko, A. A.; Drolet, D. P.; Lees, A. J. J. Organomet. Chem. 1995, 504, 107.
11. Lees, A. J. J. Organomet. Chem. 1998, 554, 1.
12. Blake, A. J.; George, M. W.; Hall, M. B.; McMaster, J.; Portius, P.; Sun, X. Z.; Towrie, M.; Webster, C. E.; Wilson, C.; Zaric, S. D. Organometallics 2008, 27, 189.
13. (e) 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.
14. (f) 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.
15. (a) Cristobal, C.; Hernandez, Y. A.; Lopez-Serrano, J.; Paneque, M.; Petronilho, A.; Poveda, M. L.; Salazar, V.; Vattier, F.; Alvarez, E.; Maya, C.; Carmona, E. Chem. - Eur. J. 2013, 19, 4003.
16. (b) Valpuesta, J. E. V.; Alvarez, E.; Lopez-Serrano, J.; Maya, C.; Carmona, E. Chem. - Eur. J. 2012, 18, 13149.
17. Conejero, S.; Esqueda, A. C.; Valpuesta, J. E. V.; Alvarez, E.; Maya, C.; Carmona, E. Inorg. Chim. Acta 2011, 369, 165.
18. Alvarez, E.; Paneque, M.; Petronilho, A. G.; Poveda, M. L.; Santos, L. L.; Carmona, E.; Mereiter, K. Organometallics 2007, 26, 1231.
19. (e) Carmona, E.; Paneque, M.; Santos, L. L.; Salazar, V. Coord. Chem. Rev. 2005, 249, 1729.
20. (f) Paneque, M.; Poveda, M. L.; Carmona, E.; Salazar, V. Dalton Trans. 2005, 1422.
21. (g) Slugovc, C.; Padilla-Martinez, I.; Sirol, S.; Carmona, E. Coord. Chem. Rev. 2001, 213, 129.
22. Hessell, E. T.; Jones, W. D. Organometallics 1992, 11, 1496.
23. Jones, W. D.; Hessell, E. T. J. Am. Chem. Soc. 1993, 115, 554.
24. Wick, D. D.; Jones, W. D. Organometallics 1999, 18, 495.
25. (a) Vetter, A. J.; Flaschenriem, C.; Jones, W. D. J. Am. Chem. Soc. 2005, 127, 12315.
26. (b) Clot, E.; Eisenstein, O.; Jones, W. D. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 6939.
27. Vetter, A. J.; Jones, W. D. Polyhedron 2004, 23, 413.
28. (a) Evans, M. E.; Burke, C. L.; Yaibuathes, S.; Clot, E.; Eisenstein, O.; Jones, W. D. J. Am. Chem. Soc. 2009, 131, 13464.
29. (b) Evans, M. E.; Jones, W. D. Organometallics 2011, 30, 3371.
30. Jiao, Y. Z.; Evans, M. E.; Morris, J.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2013, 135, 6994.
31. (a) Nishiyama, H.; Horihata, M.; Hirai, T.; Wakamatsu, S.; Itoh, K. Organometallics 1991, 10, 2706.
32. (b) Labinger, J. A.; Osborn, J. A.; Coville, N. J. Inorg. Chem. 1980, 19, 3236.
33. Lau, K. S. Y.; Fries, R. W.; Stille, J. K. J. Am. Chem. Soc. 1974, 96, 4983.
34. Nicasio, M. C.; Paneque, M.; Perez, P. J.; Pizzano, A.; Poveda, M. L.; Rey, L.; Sirol, S.; Taboada, S.; Trujillo, M.; Monge, A.; Ruiz, C.; Carmona, E. Inorg. Chem. 2000, 39, 180.
35. Paneque, N.; Perez, P. J.; Pizzano, A.; Poveda, M. L.; Taboada, S.; Trujillo, M.; Carmona, E. Organometallics 1999, 18, 4304.
36. Wick, D. D.; Jones, W. D. Inorg. Chim. Acta 2009, 362, 4416.
37. (a) Tanabe, T.; Brennessel, W. W.; Clot, E.; Eisenstein, O.; Jones, W. D. Dalton Trans. 2010, 39, 10495.
38. (b) Tanabe, T.; Evans, M. E.; Brennessel, W. W.; Jones, W. D. Organometallics 2011, 30, 834.
39. Jiao, Y. Z.; Morris, J.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2013, 135, 16198.
40. (a) Stoutland, P. O.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. Polyhedron 1988, 7, 1429.
41. (b) Stoutland, P. O.; Bergman, R. G. J. Am. Chem. Soc. 1988, 110, 5732.
42. Campian, M. V.; Harris, J. L.; Jasim, N.; Perutz, R. N.; Marder, T. B.; Whitwood, A. C. Organometallics 2006, 25, 5093.
43. Circu, V.; Fernandes, M. A.; Carlton, L. Inorg. Chem. 2002, 41, 3859.
44. Campian, M. V.; Clot, E.; Eisenstein, O.; Helmstedt, U.; Jasim, N.; Perutz, R. N.; Whitwood, A. C.; Williamson, D. J. Am. Chem. Soc. 2008, 130, 4375.
45. Cook, K. S.; Incarvito, C. D.; Webster, C. E.; Fan, Y. B.; Hall, M. B.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 5474.
46. Callaghan, P. L.; Fernandez-Pacheco, R.; Jasim, N.; Lachaize, S.; Marder, T. B.; Perutz, R. N.; Rivalta, E.; Sabo-Etienne, S. Chem. Commun. 2004, 242.
47. (a) Braunschweig, H.; Colling, M. Coord. Chem. Rev. 2001, 223, 1.
48. (b) Pandey, K. K. Coord. Chem. Rev. 2009, 253, 37.
49. Pandey, K. K. Dalton Trans. 2012, 41, 3278.
50. Lachaize, S.; Sabo-Etienne, S. Eur. J. Inorg. Chem. 2006, 2115.
51. Belt, S. T.; Duckett, S. B.; Helliwell, M.; Perutz, R. N. J. Chem. Soc., Chem. Commun. 1989, 928.
52. Jones, W. D.; Partridge, M. G.; Perutz, R. N. J. Chem. Soc., Chem. Commun. 1991, 264.
53. (a) Jasim, N. A.; Perutz, R. N.; Foxon, S. P.; Walton, P. H. J. Chem. Soc., Dalton Trans. 2001, 1676.
54. (b) Bramananthan, N.; Carmona, M.; Lowe, J. P.; Mahon, M. F.; Poulten, R. C.; Whittlesey, M. K. Organometallics 2014, 33, 1986.
55. Checinska, L.; Grabowski, S. J. Chem. Phys. 2006, 327, 202.
56. Vicente, J.; Gil-Rubio, J.; Bautista, D.; Sironi, A.; Masciocchi, N. Inorg. Chem. 2004, 43, 5665.
57. Macgregor, S. A.; Roe, D. C.; Marshall, W. J.; Bloch, K. M.; Bakhmutov, V. I.; Grushin, V. V. J. Am. Chem. Soc. 2005, 127, 15304.
58. (a) Klahn, A. H.; Oelckers, B.; Godoy, F.; Garland, M. T.; Vega, A.; Perutz, R. N.; Higgitt, C. L. J. Chem. Soc., Dalton Trans. 1998, 3079.
59. 3N·3HF (30 equiv) in THF solution and found 2.5% conversion to 7 at room temperature, increasing to 10% after heating to 60°C for 2 h. The poor yield is consistent with weak hydrogen bonding between the RhF moiety and HF.
60. RhP = 138 Hz). Product ratio: 2:1 for activation at the 3-position.
61. Drolet, D. P.; Lees, A. J. J. Am. Chem. Soc. 1992, 114, 4186.
62. 5N showed formation of 6 after only a few hours of photolysis.
63. The gradients for loss of 1 are given in the Supporting Information. They are close to one another for the three substrates but not identical. We attribute the difference to residual absorption by the substrates which was found to be greatest for pentafluoropyridine. Absorbance at 355 nm and 0.5 mm path length, 0.13 for 1.5 M penta fluoropyridine and 0.54 for 6 mM 1.
64. Wick, D. D.; Reynolds, K. A.; Jones, W. D. J. Am. Chem. Soc. 1999, 121, 3974.
65. Luo, Y. Comprehensive Handbook of Chemical Bond Energies; CRC Press: Boca Raton, FL, 2007.
66. Levy, C. J.; Puddephatt, R. J. Organometallics 1997, 16, 4115.
67. Chan, D.; Duckett, S. B.; Heath, S. L.; Khazal, I. G.; Perutz, R. N.; Sabo-Etienne, S.; Timmins, P. L. Organometallics 2004, 23, 5744.
68. Rablen, P. R.; Hartwig, J. F.; Nolan, S. P. J. Am. Chem. Soc. 1994, 116, 4121.
69. Lam, K. C.; Lin, Z. Y.; Marder, T. B. Organometallics 2007, 26, 3149.
70. Nova, A.; Reinhold, M.; Perutz, R. N.; Macgregor, S. A.; McGrady, J. E. Organometallics 2010, 29, 1824.
71. Zhu, J.; Lin, Z. Y.; Marder, T. B. Inorg. Chem. 2005, 44, 9384.
72. (a) Raza, A. L.; Panetier, J. A.; Teltewskoi, M.; Macgregor, S. A.; Braun, T. Organometallics 2013, 32, 3795.
73. (b) Teltewskoi, M.; Panetier, J. A.; Macgregor, S. A.; Braun, T. Angew. Chem., Int. Ed. 2010, 49, 3947.
74. Cronin, L.; Higgitt, C. L.; Karch, R.; Perutz, R. N. Organometallics 1997, 16, 4920.
75. (a) Procacci, B.; Blagg, R. J.; Perutz, R. N.; Rendon, N.; Whitwood, A. C. Organometallics 2014, 33, 45.
76. (b) Noveski, D.; Braun, T.; Neumann, B.; Stammler, A.; Stammler, H. G. Dalton Trans. 2004, 4106.
77. Selmeczy, A. D.; Jones, W. D.; Partridge, M. G.; Perutz, R. N. Organometallics 1994, 13, 522.
78. (a) Lindup, R. J.; Marder, T. B.; Perutz, R. N.; Whitwood, A. C. Chem. Commun. 2007, 3664.
79. (b) Archibald, S. J.; Braun, T.; Gaunt, J. A.; Hobson, J. E.; Perutz, R. N. J. Chem. Soc., Dalton Trans. 2000, 2013.
80. Jones, W. D. Inorg. Chem. 2005, 44, 6138.
81. (a) Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864.
82. (b) Alcaraz, G.; Sabo-Etienne, S. Coord. Chem. Rev. 2008, 252, 2395.
83. Perutz, R. N.; Sabo-Etienne, S. Angew. Chem., Int. Ed. 2007, 46, 2578.
84. Campian, M. V.; Perutz, R. N.; Procacci, B.; Thatcher, R. J.; Torres, O.; Whitwood, A. C. J. Am. Chem. Soc. 2012, 134, 3480.
85. (a) Osman, R.; Perutz, R. N.; Rooney, A. D.; Langley, A. J. J. Phys. Chem. 1994, 98, 3562.
86. (b) Colombo, M.; George, M. W.; Moore, J. N.; Pattison, D. I.; Perutz, R. N.; Virrels, I. G.; Ye, T. Q. J. Chem. Soc., Dalton Trans. 1997, 2857.
87. Evans, M. E.; Li, T.; Vetter, A. J.; Rieth, R. D.; Jones, W. D. J. Org. Chem. 2009, 74, 6907.
88. Calladine, J. A.; Duckett, S. B.; George, M. W.; Matthews, S. L.; Perutz, R. N.; Torres, O.; Khuong, Q. V. J. Am. Chem. Soc. 2011, 133, 2303.
89. Linden, H. B. Eur. J. Mass Spectrom. 2004, 10, 459.
90. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.
91. Frieden, C. KINSIM/FITSIM; Washington University School of Medicine: St. Louis, MO, 1997; http://www.biochem.wustl.edu/cflab/message.html.
92. Peng, C. Y.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49.
93. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
94. (b) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
95. Frisch, M. J.; et al. Gaussian 03; Gaussian, Inc.: Wallingford, CT, 2004.
96. Ehlers, A. W.; Bohme, M.; Dapprich, S.; Gobbi, A.; Hollwarth, A.; Jonas, V.; Kohler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111.
97. Hollwarth, A.; Bohme, M.; Dapprich, S.; Ehlers, A. W.; Gobbi, A.; Jonas, V.; Kohler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237.
98. Hehre, W. J.; Ditchfie, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
99. Choi, G.; Morris, J.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2012, 134, 9276.