Carbon-hydrogen bond cleavage reaction in 5-coordinate bis(2,6- dimethylbenzenethiolato)ruthenium(II) complexes

Organometallics

Volumn 29, Issue 14, 2010, Pages 3146-3159

  Hirano, Masafumi ^a   Togashi, Sayaka ^a   Ito, Muneaki ^a   Sakaguchi, Yuko ^a   Komine, Nobuyuki ^a   Komiya, Sanshiro ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

C-H BOND CLEAVAGE; CARBON-HYDROGEN BOND; CONCERTED MECHANISM; KINETIC STUDY; LIGAND DISPLACEMENT; ROOM TEMPERATURE; RUTHENIUM COMPLEXES;

BENZENE; HYDROGEN; HYDROGEN BONDS; METHANOL; RUTHENIUM; SUBSTITUTION REACTIONS;

RUTHENIUM COMPOUNDS;

EID: 77955906602     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100249s     Document Type: Article

References (68)

1. Chatt, J.; Davidson, J. M. J. Chem. Soc. 1965, 843.
2. (a) Murai, S., Ed., Activation of Unreactive Bonds and Organic Synthesis, Springer: Berlin, 1999.
3. (b) Arndtsen, B. A.; Bergman, R. G.; Moley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
4. (c) Crabtree, R. H. Chem. Rev. 1985, 85, 254.
5. (d) Shilov, A. E.; Shteinman, A. A. Cord. Chem. Rev. 1977, 24, 97.
6. (d) Shilov, A. E. The Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reidel: Dordrecht, The Netherlands, 1984.
7. (e) Wasserman, E. P.; Moore, C. B.; Bergman, R. G. Sience 1992, 255, 315.
8. (f) Homogeneous Transition Metal Catalyzed Reactions; Moser, W. R., Slocum, D. W., Eds.; Advances in Chemistry 230; American Chemical Society: Washington, DC.; 1992.
9. (g) Naota, T.; Takaya, H.; Murahashi, S. Chem. Rev. 1998, 98, 2599.
10. (h) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
11. (i) Fundamentals of Molecular Catalysis; Kurosawa, H.; Yamamoto, A., Eds.; Elsevier: Amsterdam, 2003.
12. (j) Murahashi, S., Ed. Ruthenium in Organic Synthesis; Wiley: New York; 2004.
13. (k) Komiya, S.; Hirano, M. Dlton Trans. 2003, 1439.
14. Djukic, J.-P.; Sortais, J.-B.; Barloy, L.; Pfeffer, M. Eur. J. Inorg. Chem. 2009, 817.
15. Lewis, L. N.; Smith, J. F. J. Am. Chem. Soc. 1986, 108, 2728.
16. Hsu, G. C.; Kosar, W. P.; Jones, W. D. Organometallics 1994, 13, 385.
17. (a) Komiya, S.; Ito, T.; Cowie, M.; Yamamoto, A.; Ibers, J. A. J. Am. Chem. Soc. 1976, 98, 3874.
18. (b) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
19. (a) Ozawa, F.; Yamagami, I.; Yamamoto, A. J. Organomet. Chem. 1994, 473, 265.
20. (b) Kanaya, S.; Imai, Y.; Komine, N.; Hirano, M.; Komiya, S. Organometallics 2005, 24, 1059.
21. (a) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. J. Am. Chem. Soc. 1991, 113, 3404.
22. (b) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. J. Am. Chem. Soc. 1991, 113, 6499.
23. (c) Hirano, M.; Sato, H.; Kurata, N.; Komine, N.; Komiiya, S. Organometallics 2007, 26, 2005.
24. Kanaya, S.; Komine, N.; Hirano, M.; Komiya, S. Chem. Lett. 2001, 1284.
25. (a) Yi, C. S.; Yun, S. Y. J. Am. Chem. Soc. 2005, 127, 17000.
26. (b) Pastine, S. J.; Gribkov, D. V.; Sames, D. J. Am. Chem. Soc. 2006, 128, 14220.
27. Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimer, S. J. Am. Chem. Soc. 1992, 114, 5888.
28. Thompson, M. E.; Baxter, S. M.; Bulls, A. R.; Burger, B. J.; Nolan, M. C.; Santarsiero, B. D.; Schofer, W. P.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 203.
29. (a) Gunnoe T. B. Eur. J. Inorg. Chem. 2007 1185.
30. (b) DeYonker N. J.; Foley, N. A.; Cundari, T. R.; Gunnoe, T. B.; Petersen, J. L. Organometallics 2007, 26, 6604.
31. (c) Feng, Y.; Lail, M.; Foley, N. A.; Gunnoe, T. B.; Barakat, K. A.; Cundari, T. R.; Petersen, J. L. J. Am. Chem. Soc. 2006, 128, 7982.
32. (d) Feng, Y.; Gunnoe, T. B.; Grimes, T. V.; Cundari, T. R. Organometallics 2006 25 5456.
33. (e) Feng Y.; Lail M.; Barakat K. A.; Cundari T. R.; Gunnoe T. B.; Petersen J. L. J. Am. Chem. Soc. 2005 127 14174.
34. Davies D. L.; Donald S. M. A.; Al-Duaij O.; Macgregor S. A.; Polleth M. J. Am. Chem. Soc. 2006 128 4210.
35. Snelgrove J. L.; Conrad J. C.; Yap G. P. A.; Fogg D. E. Inorg. Chim. Acta 2003 345 268.
36. (a) Oxgaard J.; Tenn W. J.; III.; Nielsen R. J.; Periana R. A.; Goddard W. A. Organometallics 2007 26 1565.
37. (b) Tenn W. J. III.; Young K. J. H.; Oxgaard J.; Nielsen R. J.; Goddard W. A. Periana R. A. Organometallics 2006 25 5173.
38. (b) Tenn W. J. III; Young K. J. H.; Bhalla G.; Oxgaard J.; Goddard W. A. III J. Am. Chem. Soc. 2005 127 14172.
39. (c) Oxgaard J.; Muller R. P.; Goddard W. A. III Periana R A J. Am. Chem. Soc. 2004 126 352
40. Koike T.; Ikariya T. Organometallics 2005 24 724
41. Hirano M.; Sakaguchi Y.; Yajima T.; Kurata N.; Komine N.; Komiya S. Organometallics 2005 24 4799.
42. Yamamoto, A. in Organotransition Metal Chemistry, Fundamental Concepts and Applications; Wiley: New York, 1986, pp 190.
43. 4-1, 5-COD) (TDPME) (4b'). One of the reasonable explanations is that a protic species catalyzes the isomerization from 1, 5-COD to the more stable 1, 3-COD Hirano, M.; Shibasaki, T.; Komiya, S.; Bennett, M. A. Organometallics 2002, 21, 5738.
44. 2 were reported Field, L. D.; Hmbley, T. W.; Ya, B. C. K. Inorg. Chem. 1994, 33, 2009.
45. (a) Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 3rd Ed.; Wiley: New York, 2001; pp 268.
46. (b) Yamamoto, A. Organotransition Metal Chemistry, Fundamental Concepts and Applications; Wiley: New York, 1986; pp 189.
47. The P (1)-Ru (1)-S (2) angle is slightly smaller than the P (3.-Ru (1)-S (2) angle for 2d, while they are comparable for 2a. The reason for the favor of S (2) in 2d to be such biased position is not clear so far.
48. Riehl, J.-F.; Jean, Y.; Eisenstein, O.; Pélissier, M. Organometallics 1992, 11, 729.
49. Kamata, M.; Hirotsu, K.; Higuchi, T.; Tatsumi, K.; Hoffmann, R.; Yoshida, T.; Otsuka, S. J. Am. Chem. Soc. 1981, 103, 5772.
50. 3) 2 (2.476 A), and 1a (2.429 å)
51. [ref 12]. (a) Mashima, K.; Mikami, A.; Nakamura, A. Nakamura, ACem. Lett. 1992, 1473.
52. (b) Jessop, P. G.; Rettig, S. L.; James, B. R. J. Chem. Soc. Chem. Commun. 1991, 773.
53. (c) Jessop, P. G.; Rettig, S. L.; Lee., C.-L.; James, B. R. Inorg. Chem. 1991, 30, 4617.
54. The stereochemical description is based on the 1990 IUPAC Inorganic Rules: Block, B. P.; Powell, W. H.; Ernelius, W. C. Inorganic Chemical Nomenclature: Principles and Practice, ACS Professional Reference Book; American Chemical Society, Washington, DC, 1990; pp 143.
55. 1H} NMR spectra of the octahedral TRIPHOS complexes, we cannot rule out unexpected upfield shift of the central PPh in 1a. cf. George, T. A.; Tisdale, R. C. J. Am. Chem. Soc. 1985, 107, 5157.
56. Because separation of these stereochemical isomers was difficult, the isomeric mixture was employed for the hydrogenolysis reaction. The reaction completely proceeded but the hydride species corresponding to the minor species was not observed at all.
57. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 3rd Ed.; Wiley: New York, 2001; pp 6.
58. One of the ortho methyl resonances in 9d appears in significantly high field at δ 1.57, while another ortho methyl group resonates at the comparable region to the related cis-bis (2, 6-dimethylbenzenethiolato) ruthenium (II) complexes such as 2a (δ 2.11), 2b (δ 2.46), 2d (δ 2.55), and free 2, 6-dimethylbenzenethiol (δ 2.48). Because 9d is a coordinatively unsaturated complex, this fact may be caused by the lone pair electrons on the S atom attached to the saturated Ru center, or the ring current effect of the aromatic ring.
59. 3 (170°). Tolman, C. A. Chem. Rev. 1977, 77, 313.
60. Gordon, A. J.; Ford, R. A. The Chemist's Companion: A Handbook of Practical Data, Techniques, and References; Wiley: New York, 1972; pp 6.
61. We have found Brønsted acid promote the C-H bond cleavage reaction in aryloxoruthenium (II) complex. The present C-H bond cleavage reaction from 2 in the presence of Brønsted acid will be reported elsewhere. Hirano, M.; Kuga, T.; Kitamura, M.; Kanaya, S.; Komine, N.; Komiya, S. Organometallics 2008, 27, 3635.
62. Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC: New York, 2003; pp 31,.
63. Kosolapoff, G. M.; Maier, L. In Organic Phosphorus Compounds, Vol. 1; Wiley: New York, 1972; p 32.
64. Itoh, K.; Nagashima, H.; Ohshima, T.; Oshima, N.; Nishiyama J. Ognaomet. Chem. 1984, 272, 179.
65. Bennett, M. A.; Neumann, M.; Thomas, M.; Wang, X.-Q. Organometallics 1991, 10, 3237.
66. Hallman, P. S.; McCarvey, B. R.; Wilkinson, G. J. Chem. Soc. A 1968, 3143.
67. Rohr, M.; Günther, M.; Jutz, F.; Grunwaldt, J.-D.; Emerich, H.; Beek, W. V.; Baiker, A. Apl. Catal., A 2005, 296, 238.
68. Jones, R. A.; Real, F. M.; Wilkinson, G.; Galas, A. M. R.; Hursthouse, M. B.; Malik, K. M. A. J. Chem. Soc. Dalton Trans. 1980, 511.