Synthesis and reactivity of Ru(PPh3)3(CO)HF and the N-heterocyclic carbene derivatives Ru(NHC)(PPh3)2(CO)HF

Organometallics

Volumn 26, Issue 14, 2007, Pages 3484-3491

  Reade, Steven P ^a   Nama, Devendrababu ^b   Mahon, Mary F ^a   Pregosin, Paul S ^b   Whittlesey, Michael K ^a  

^a University of Bath Claverton Down   (United Kingdom)

^b LABORATORY OF INORGANIC CHEMISTRY   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; MOLECULAR STRUCTURE; RUTHENIUM COMPOUNDS; THERMAL EFFECTS; X RAY CRYSTALLOGRAPHY;

HETEROCYCLIC CARBENES; HYDRIDE FLUORIDE COMPLEXES;

ORGANOMETALLICS;

EID: 34547327910     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om070164p     Document Type: Article

References (80)

1. (a) Doherty, N.; Hoffman, N. W. Chem. Rev. 1991, 91, 553.
2. (b) Murphy, E. F.; Murugavel, R.; Roesky, H. W. Chem. Rev. 1997, 97, 3425.
3. (c) Clark, H. C. S.; Holloway, J. H. In Advanced Inorganic fluorides: Synthesis, Characterization and Applications; Nakajima, T., Zemva, B., Tressaud, A., Eds.; Elsevier: Amsterdam, 2000; p 51.
4. (d) Grushin, V. V. Chem. Eur. J. 2002, 8, 1006.
5. Grushin, V. V.; Marshall, W. J. Angew. Chem., Int. Ed. 2002, 41, 4476.
6. (a) Jones, W. D.; Partridge, M. G.; Perutz, R. N. J. Chem. Soc., Chem. Commun. 1991, 264.
7. (b) Anderson, C. M.; Crespo, M.; Ferguson, G.; Lough, A. J.; Puddephatt, R. J. Organometallics 1992, 11, 1177.
8. (c) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373.
9. (d) Burdeniuc, J.; Jedlicka, B.; Crabtree, R. H. Chem. Ber.-Recl. 1997, 130, 145.
10. (e) Richmond, T. G. Top. Organomet. Chem. 1999, 3, 243.
11. (f) Archibald, S. J.; Braun, T.; Gaunt, J. A.; Hobson, J. E.; Perutz, R. N. Dalton Trans. 2000, 2013.
12. (g) Braun, T.; Cronin, L.; Higgitt, C. L.; McGrady, J. E.; Perutz, R. N.; Reinhold, M. New J. Chem. 2001, 25, 19.
13. (h) Braun, T.; Noveski, D.; Neumann, B.; Stammler, H.-G. Angew. Chem., Int. Ed. 2002, 41, 2745.
14. (i) Ferrando-Miguel, G.; Gerard, H.; Eisenstein, O.; Caulton, K. G. Inorg. Chem. 2002, 41, 6440.
15. (j) Reinhold, M.; McGrady, J. E.; Perutz, R. N. J. Am. Chem. Soc. 2004, 126, 5268.
16. (k) Burling, S.; Elliott, P. I. P.; Jasim, N. A.; Lindup, R. J.; McKenna, J.; Perutz, R. N.; Archibald, S. J.; Whitwood, A. C. Dalton Trans. 2005, 3686.
17. (l) Torrens, H. Coord. Chem. Rev. 2005, 249, 1975.
18. (m) Braun, T.; Perutz, R. N. In Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, D. M. P., Eds.; Elsevier: Oxford, U.K., 2006; Vol. 1, Chapter 1.26, p 725.
19. (a) Braun, T.; Foxon, S. P.; Perutz, R. N.; Walton, P. H. Angew. Chem., Int. Ed. 1999, 38, 3326.
20. (b) Braun, T.; Perutz, R. N. Chem. Commun. 2002, 2749.
21. Kirkham, M. S.; Mahon, M. F.; Whittlesey, M. K. Chem. Commun. 2001, 813.
22. (a) Whittlesey, M. K.; Perutz, R. N.; Greener, B.; Moore, M. F. Chem. Commun. 1997, 187.
23. (b) Fraser, S. L.; Antipin, M. Yu.; Khroustalyov, V. N.; Grushin, V. V. J. Am. Chem. Soc. 1997, 119, 4769.
24. (c) Marshall, W. J.; Grushin, V. V. Organometallics 2004, 23, 3343.
25. (d) Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2004, 126, 3068.
26. (e) Noveski, D.; Braun, T.; Krückemeier, S. J. Fluorine Chem. 2004, 125, 959.
27. Holloway, J. H.; Hope, E. G. J. Fluorine Chem. 1996, 76, 209.
28. (a) Blake, A. J.; Cockman, R. W.; Ebsworth, E. A. V.; Holloway, J. H. J. Chem. Soc., Chem. Commun. 1988, 529.
29. (b) Brewer, S. A.; Holloway, J. H.; Hope, E. G. J. Chem. Soc., Dalton Trans. 1994, 1067.
30. (c) Brewer, S. A.; Coleman, K. S.; Fawcett, J.; Holloway, J. H.; Hope, E. G.; Russell, D. R.; Watson, P. G. J. Chem. Soc., Dalton Trans. 1995, 1073.
31. (d) Coleman, K. S.; Holloway, J. H.; Hope, E. G. J. Chem. Soc., Dalton Trans. 1997, 1713.
32. (e) Coleman, K. S.; Holloway, J. H.; Hope, E. G.; Langer, J. J. Chem. Soc., Dalton Trans. 1997, 4555.
33. (f) Yahav, A.; Goldberg, I.; Vigalok, A. J. Am. Chem. Soc. 2003, 125, 13634.
34. (g) Yahav, A.; Goldberg, I.; Vigalok, A. Inorg. Chem. 2005, 44, 1547.
35. Caulton, K. G. New J. Chem. 1994, 18, 25.
36. (a) Mezzetti, A.; Becker, C. Helv. Chim. Acta 2002, 85, 2686.
37. (b) Becker, C.; Kieltsch, I.; Broggini, D.; Mezzetti, A. Inorg. Chem. 2003, 42, 8417.
38. (a) Grushin, V. V. Angew. Chem., Int. Ed. 1998, 37, 994.
39. (b) Ishii, Y.; Chatani, N.; Yorimitsu, S.; Murai, S. Chem. Lett. 1998, 157.
40. (c) Barthazy, P.; Hintermann, L.; Stoop, R. M.; Wörle, M.; Mezzetti, A.; Togni, A. Helv. Chim. Acta 1999, 82, 2448.
41. (d) Barthazy, P.; Stoop, R. M.; Wörle, M.; Togni, A.; Mezzetti, A. Organometallics 2000, 19, 2844.
42. (e) Braun, T.; Perutz, R. N.; Sladek, M. I. Chem. Commun. 2001, 2254.
43. (f) Sladek, M. I.; Braun, T.; Neumann, B.; Stammler, H.-G. Dalton Trans. 2002, 297.
44. (g) Kuhl, S.; Schneider, R.; Fort, Y. Adv. Synth. Catal. 2003, 345, 241.
45. (a) Blum, O.; Frolow, F.; Milstein, D. J. Chem. Soc., Chem. Commun. 1991, 258.
46. (b) den Reijer, C. J.; Wörle, M.; Pregosin, P. S. Organometallics 2000, 19, 309.
47. (c) Jasim, N. A.; Perutz, R. N.; Whitwood, A. C.; Braun, T.; Izundu, J.; Neumann, B.; Rothfeld, S.; Stammler, H.-G. Organometallics 2004, 23, 6140.
48. (d) 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.
49. (a) Scott, N. M.; Nolan, S. P. Eur. J. Inorg. Chem. 2005, 1815.
50. (b) N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
51. (c) Glorius. F. A. Top. Organomet. Chem. 2007, 21, 1.
52. Burling, S.; Kociok-Köhn, G.; Mahon, M. F.; Whittlesey, M. K.; Williams, J. M. J. Organometallics 2005, 24, 5868. See also ref 26.
53. Chatwin, S. L.; Davidson, M. G.; Doherty, C.; Donald, S. M.; Jazzar, R. F. R.; Macgregor, S. A.; McIntyre, G. J.; Mahon, M. F.; Whittlesey, M. K. Organometallics 2006, 25, 99.
54. An interaction between ruthenium and an o-fluorine substituent in the fluorinated NHC 1,3-bis(2,6-difluorophenyl)imidazol-2-ylidene has recently been reported: Ritter, T.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 11768.
55. Laitar, D. S.; Müller, T. G.; Gray, T. G.; Sadighi, J. P. Organometallics 2005, 24, 4503.
56. (a) Schaub, T.; Radius, U. Chem. Eur. J. 2005, 11, 5024.
57. (b) Schaub, T.; Backes, M.; Radius, U. J. Am. Chem. Soc. 2006, 128, 15964.
58. 8e
59. FP coupling constants of 23.0 Hz to be determined in both cases.
60. Huang, D. J.; Koren, P. R.; Folting, K.; Davidson, E. R.; Caulton, K. G. J. Am. Chem. Soc. 2000, 122, 8916.
61. Levison, J. J.; Robinson, S. D. J. Chem. Soc. A 1970, 2947.
62. Santos, A.; López, J.; Montoya, J.; Noheda, P.; Romero, A.; Echavarren, A. M. Organometallics 1994, 13, 3605.
63. Sánchez-Delgado, R. A.; Thewalt, U.; Valencia, N.; Andriollo, A.; Márquez-Silva, R.-L.; Puga, J.; Schöllhorn, H.; Klein, H.-P.; Fontal, B. Inorg. Chem. 1986, 25, 1097.
64. 2HF has been reported by Caulton and co-workers and found to have a high-frequency hydride chemical shift: Poulton, J. T.; Sigalas, M. P.; Folting, K.; Streib, W. E.; Eisenstein, O.; Caulton, K. G. Organometallics 1994, 13, 1476.
65. 2 in a very different way: Burling, S.; Mahon, M. F.; Powell, R. E.; Whittlesey, M. K.; Williams, J. M. J. J. Am. Chem. Soc. 2006, 128, 13702.
66. Junk, P. C.; Steed, J. W. J. Organomet. Chem. 1999, 587, 191.
67. 19F NMR spectra, prompting us to suggest that these species are hydrolysis products resulting from reaction of Ru-F with traces of water on glassware or cannula or in the solvent.
68. (a) Pilon, M. C.; Grushin, V. V. Organometallics 1998, 17, 1774.
69. (b) Roe, D. C.; Marshall, W. J.; Davidson, F.; Soper, P. D.; Grushin, V. V. Organometallics 2000, 19, 4575.
70. (a) Jasim, N. A.; Perutz, R. N. J. Am. Chem. Soc. 2000, 122, 8685.
71. (b) Jasim, N. A.; Perutz, R. N.; Foxon, S. P.: Walton, P. H. Dalton Trans. 2001, 1676.
72. (a) Coulson, D. R. J. Am. Chem. Soc. 1976, 95, 3111.
73. (b) Murphy, V. J.; Hascall, T.; Chen, J. Y.; Parkin, G. J. Am. Chem. Soc. 1996, 118, 7428.
74. (c) Murphy, V. J.; Rabinovich, D.; Hascall, T.; Klooster, W. T.; Koetzle, T. F.; Parkin, G. J. Am. Chem. Soc. 1998, 120, 4372.
75. (d) GilRubio, J.; Weberndörfer, B.; Werner, H. J. Chem. Soc., Dalton Trans. 1999, 1437.
76. (e) Vicente, J.; Gil-Rubio, J.; Bautista, D.; Sironi, A.; Masciocchi, N. Inorg. Chem. 2004, 43, 5665.
77. Ahmad, N.; Levison, J. J.; Robinson, S. D.; Uttley, M. F. Inorg. Synth. 1974, 15, 48.
78. Kühn, N.; Kratz, T. Synthesis 1993, 561.
79. Nolan, S. P. Personal communication.
80. Sheldrick, G. M. Acta Crystallogr. 1990, 467-473, A46. Sheldrick, G. M. SHELXL-97, a Computer Program for Crystal Structure Refinement; University of Göttingen, Göttingen, Germany, 1997.