Specific C-C coupling of the labile diruthenium bridging methylene complex, Cp2Ru2(μ-CH2)(CO)2(MeCN), with diazoalkanes (R2C=N2) leading to alkenyl complexes, Cp2Ru2(μ-CH=CR2)(μ-H)(CO)2, and alkenes, CH2=CR2

Journal of Organometallic Chemistry

Volumn 569, Issue 1-2, 1998, Pages 71-83

  Akita, Munetaka ^a   Hua, Ruimao ^a   Knox, Selby A R ^a   Moro Oka, Yoshihiko ^a   Nakanishi, Sadahiro ^a   Yates, Michael I ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Alkenyl complexes; C C coupling; Diruthenium

Indexed keywords

EID: 0001924082     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(98)00775-X     Document Type: Article

References (82)

1. (a) J. Falbe, New Synthesis with Carbon Monoxide, Springer, Berlin, 1980.
2. (b) W. Keim, Catalysis in C1 Chemistry, D. Reidel, Dordrecht, 1983.
3. (c) R.B. Anderson, The Fischer-Tropsch Synthesis, Academic Press, London, 1984.
4. (d) H. Pines, The Chemistry of Catalytic Hydrocarbon Conversions, Academic Press, London, 1981.
5. (e) G.A. Somorjai, Introduction to Surface Chemistry and Catalysis, Wiley, New York, 1994.
6. (a) C. Masters, Adv. Organomet. Chem. 19 (1979) 63.
7. (b) E.L. Muetterties, T.N. Rhodin, E. Band, C.F. Brucker, W.R. Pretzer, Chem. Rev. 79 (1979) 79.
8. (c) C.K. Roofer-DePoorter, Chem. Rev. 81 (1981) 447.
9. (d) W.A. Herrmann, Angew. Chem. Int. Ed. Engl. 21 (1982) 117.
10. (e) A.R. Cutler, P.K. Hanna, J.C. Vites, Chem. Rev. 88 (1988) 1363 and references cited therein.
11. For carbide complexes, (f) M. Tachikawa, E.L. Muetterties, Prog. Inorg. Chem. 28 (1981) 203.
12. (g) J.S. Bradley, Adv. Organomet. Chem. 22 (1983) 1.
13. (h) D.F. Shriver, M.J. Sailor, Acc. Chem. Res. 21 (1988) 374.
14. See also (i) W. Beck, B. Niemer, M. Wieser, Angew. Chem. Int. Ed. Engl. 32 (1993) 923.
15. (a) A.F. Dyke, S.A.R. Knox, P.J. Naish, A.G. Orpen, J. Chem. Soc. Chem. Commun. (1980) 441.
16. (b) A.F. Dyke, S.A.R. Knox, P.J. Naish, A.G. Orpen, J. Chem. Soc. Chem. Commun. (1980) 804.
17. (c) D.L. Davies, A.F. Dyke, A. Endesfelder, et al., J. Organomet. Chem. 198 (1980) C43.
18. (d) A.F. Dyke, S.A.R. Knox, K.A. Mead, P. Woodward, J. Chem. Soc. Chem. Commun. (1981) 861.
19. (e) M. Cooke, D.L. Davies, J.E. Guerchais, S.A.R. Knox, K.A. Mead, J. Roué, P. Woodward, J. Chem. Soc. Chem. Commun. (1981) 862.
20. (f) P.Q. Adams, D.L. Davies, A.F. Dyke, S.A.R. Knox, K.A. Mead, P. Woodward, J. Chem. Soc. Chem. Commun. (1983) 222.
21. (g) N.J. Ferrow, S.A.R. Knox, M.J. Morris, A.G. Orpen, J. Chem. Soc. Chem. Commun. (1983) 234.
22. (h) A.F. Dyke, S.A.R. Knox, M.J. Morris, P.J. Naish, J. Chem. Chem. Soc. Dalton Trans. (1983) 1417.
23. (i) R.E. Colborn, A.F. Dyke, S.A.R. Knox, K.A. Mead, P. Woodward, J. Chem. Chem. Soc. Dalton Trans. (1983) 2099.
24. (j) R.E. Colborn, D.L. Davies, A.F. Dyke, A. Endesfelder, et al., J. Chem. Soc. Dalton Trans. (1983) 2661.
25. (k) S.A.R. Knox, Pure Appl. Chem. 56 (1984) 81.
26. (l) N.J. Ferrow, S.A.R. Knox, J. Chem. Soc. Chem. Commun. (1984) 679.
27. (m) D.L. Davis, B.P. Gracey, V. Guerchais, S.A.R. Knox, A.G. Orpen, J. Chem. Soc. Chem. Commun. (1984) 841.
28. (n) D.L. Davies, S.A.R. Knox, K.A. Mead, M.J. Morris, P. Woodward, J. Chem. Soc. Dalton Trans. (1984) 2293.
29. (o) N.G. Connelly, N.J. Ferrow, B.P. Gracey, S.A.R. Knox, A.G. Orpen, J. Chem. Soc. Chem. Commun. (1985) 14.
30. (p) N.G. Connelly, N.J. Ferrow, S.A.R. Knox, K.A. Macpherson, A.G. Orpen, J. Chem. Soc. Chem. Commun. (1985) 16.
31. (q) N.M. Doherty, J.A.K. Howard, S.A.R. Knox, N.J. Terrill, M.I. Yates, J. Chem. Soc. Chem. Commun. (1989) 638.
32. (r) J.A.K. Howard, S.A.R. Knox, N.J. Terrill, M.I. Yates, J. Chem. Soc. Chem. Commun. (1989) 640.
33. (s) M.J. Fildes, S.A.R. Knox, A.G. Orpen, M.L. Turner, M.I. Yates, J. Chem. Soc. Chem. Commun. (1989) 1680.
34. (t) R.E. Colborn, D.L. Davies, A.F. Dyke, S.A.R. Knox, K.A. Mead, A.G. Orpen, J. Chem. Soc. Dalton Trans. (1989) 1799.
35. (u) S.A.R. Knox, K.A. Macpherson, A.G. Orpen, M.C. Rendle, J. Chem. Soc. Dalton Trans. (1989) 1807.
36. (v) G.C. Bruce, S.A.R. Knox, A.J. Phillips, J. Chem. Soc. Chem. Commun. (1990) 716.
37. (w) G.C. Bruce, B. Gangnus, S.E. Garbar, S.A.R. Knox, A.G. Orpen, A.J. Philiiips, J. Chem. Soc. Chem. Commun. (1990) 1360.
38. (x) R.E. Colborn, A.F. Dyke, B.P. Gracey, et al., J. Chem. Soc. Dalton Trans. (1990) 761.
39. (y) S.A.R. Knox, J. Organomet. Chem. 400 (1990) 255.
40. (a) M. Akita, T. Oku, Y. Moro-oka, J. Chem. Soc. Chem. Commun. (1992) 1031.
41. (b) M. Akita, T. Oku, R. Hua, Y. Moro-oka, J. Chem. Soc. Chem. Commun. (1993) 1670.
42. (c) M. Akita, R. Hua, Y. Moro-oka, J. Chem. Soc. Chem. Commun. (1996) 541.
43. (d) M. Akita, R. Hua, T. Oku, Y. Moro-oka, Organometallics 15 (1996) 2548.
44. (e) M. Akita, R. Hua, T. Oku, M. Tanaka, Y. Moro-oka, Organometallics 15 (1996) 4162.
45. (f) R. Hua, M. Akita, Y. Moro-oka, Inorg. Chim. Acta 250 (1996) 177.
46. (g) M. Akita, R. Hua, Y. Moro-oka, J. Organomet. Chem. 539 (1997) 205.
47. (h) M. Akita, R. Hua, S. Nakanishi, M. Tanaka, Y. Moro-oka, Organometallics 16 (1997) 5572.
48. (a) W.A. Herrmann, Adv. Organomet. Chem. 20 (1982) 159.
49. (b) W.A. Herrmann, J. Organomet. Chem. 250 (1983) 319.
50. (c) I.M. Saez, D.G. Andrews, P.M. Maitlis, Polyhedron 7 (1988) 827.
51. (d) R.J. Puddephatt, Polyhedron 7 (1988) 767.
52. (a) J.P. Collman, L.S. Hegedus, J.R. Norton, R.G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, 1987.
53. (b) M. Brookhart and W. B. Studabaker, Chem. Rev. 87 (1987) 411.
54. (c) E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, ch. 5.1-5.5.
55. (d) B. Cornils, W.A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds (2 vols.), VCH, Weinheim, 1996.
56. (e) G.W. Parshal, S.D. Ittel, Homogeneous Catalysis, 2nd ed., Wiley-Interscience, New York, 1992.
57. (a) H. Berke, R. Hoffmann, J. Am. Chem. Soc. 100 (1978) 7224.
58. (b) B.E.R. Schilling, R. Hoffmann, D.L. Lichtenberger, J. Am. Chem. Soc. 101 (1979) 585.
59. (c) N.M. Kostic, R.F. Fenske, J. Am. Chem. Soc. 104 (1982) 3879.
60. A part of the results were already reported in a preliminary communication. M. Akita, R. Hua, S.A.R. Knox, Y. Moro-oka, S. Nakanishi, M.I. Yates, J. Chem. Soc. Chem. Commun. (1997) 51.
61. 2 but insoluble in other organic solvents such as benzene and ether. However, the reaction with diazoalkane is so fast that it makes the system homogeneous within a few minutes.
62. 2.
63. See, for example, T. Takao, S. Yoshida, S. Suzuki, M. Tanaka, Organometallics 14 (1995) 3856 and references cited therein.
64. The ease of the C-H reductive elimination (2→7) is dependent on the substituent of the μ-alkenyl part. The interconversion between 2e and 2e′ is explained in terms of free rotation of the Ru-Ru bond in 7.
65. See 4 (c,h) and references cited therein.
66. Shapley J.R., Sievert A.C., Churchill M.R., Wassermann H.J. J. Am. Chem. Soc. 103:1981;6975.
67. Lewandos G.S., Doherty N.M., Knox S.A.R., Macpherson K.A., Orpen A.G. Polyhedron. 7:1988;837.
68. See, for example, (a) K.D. Schramm, J.A. Ibers, J. Am. Chem. Soc. 100 (1978) 2932.
69. (b) G.L. Hillhouse, B.L. Haymore, W.A. Herrmann, Inorg. Chem. 18 (1979) 2423.
70. (c) L. Messerle, M.D. Curtis, J. Am. Chem. Soc. 104 (1982) 889.
71. (d) M.D. Curtis, L. Messerle, J.J. D'Errico, W.M. Butler, M.S. Hay, Organometallics 5 (1986) 2283.
72. (e) A. Nakamura, T. Yoshida, M. Cowie, S. Otsuka, J.A. Ibers, J. Am. Chem. Soc. 99 (1977) 2108.
73. P.M. Maitlis, H.C. Long, R. Quyoum, M.L. Turner, Z.-Q. Wang, J. Chem. Soc. Chem. Commun. (1996) 1.
74. T.J. DeBoer, H.J. Backer, Org. Synth. Collect. 4 (1963) 250.
75. A.F. Mckay, W.L. Ott, G.W. Taylor, M.N. Buchanan, J.F. Crooker, Can. J. Res. Sect. B 28 (1950) 683.
76. N.E. Searle, Org. Synth. Collect. vol. 4 (1963) 424.
77. Holton T.L., Shechter H. J. Org. Chem. 60:1995;4725.
78. Farnum D.G. J. Org. Chem. 28:1963;870.
79. Nenitzescu C.D., Solomonica E. Org. Synth. Collect. 2:1943;496.
80. Kopinski R.P., Pinhey J. Aust. J. Chem. 36:1983;311.
81. Neuenschwander M., Farrni H.P., Lehmann H., Vögeli R. Chimia. 28:1974;115.
82. International Tables for X-Ray Crystallography, vol. 4, Kynoch Press, Birmingham, 1975.