A room temperature direct metal insertion into a nonstrained carbon-carbon bond in solution. C-C vs C-H bond activation

Journal of the American Chemical Society

Volumn 118, Issue 49, 1996, Pages 12406-12415

  Rybtchinski, Boris ^a   Vigalok, Arkadi ^a   Ben David, Yehoshoa ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

IRIDIUM; METAL COMPLEX; RHODIUM;

ARTICLE; COMPLEX FORMATION; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 0030443080     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962253r     Document Type: Article

References (64)

1. For example see: (a) Crabtree, R. H. In The Chemistry of Alkanes and Cycloalkanes; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: New York, 1992; p 653.
2. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245.
3. Amdtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
4. (a) Adams, D. M.; Chatt, J.; Guy, R.; Sheppard, N. J. Chem. Soc. 1961, 738.
5. (b) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108,7346.
6. Hemond, R. C.; Hughes, R. P.; Robinson, D. J.; Rheingold, A. L. Organometallics 1988, 7, 2239.
7. Hughes, R. P.; Trujillo, H. A.; Rheingold, A. L. /. Am. Chem. Soc. 1993, 115, 1583.
8. (e) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647.
9. (f) Li, R. T.; Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1994, 776, 10032.
10. (g) Lu, Z.; Jun, C.'-L.; de Gala, S.; Sigalas, M. P.; Eisenstein, O.; Crabtree, R. H. Organometallics 1994, 114, 1168.
11. (h) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222.
12. Kang, J. W.; Moseley, R.; Maitlis, P. M. J. Am. Chem. Soc. 1969, 91, 5970.
13. (j) Benfield, F. W. C.; Green, M. L. H. J. Chem. Soc., Dalton Trans. 1974, 1324.
14. (k) Eilbracht, P. Chem. Ber. 1980, 113, 542.
15. Hemond, R. C.; Hughes, R. P.; Locker, M. B. Organometallics 1986, 5, 2392.
16. Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1984, 106, 3054.
17. (n) Ibid. 1986, 108, 4679.
18. (o) Hartwig, J. F.; Anderson, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717.
19. (p) Murakami, M.; Amu, H.; Ito, Y. Nature 1994, 370, 540.
20. (q) Suzuki, H.; Takaya, Y.; Takemori, T. J. Am. Chem. Soc. 1994, 776, 10779.
21. (r) Nicholls, J. C.; Spencer, J. L. Organometallics 1994, 73, 1781.
22. (a) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699.
23. (b) Gozin, M.; Aizenberg, M.; Liou, Sh.-Y.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1994, 370, 42.
24. (a) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 777, 9774.
25. (b) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1995, 1965.
26. van der Boom, M. E.; Kraatz, H.-B.; Ben-David, Y.; Milstein, D. J. Chem. Soc., Chem. Commun. 1996, 2167.
27. Shaw, B. L. J. Organomet. Chem. 1980, 200, 307.
28. (a) Bromomethylation: van der Made, A. W.; van der Made, R. H. J. Org. Chem. 1993, 58, 1262. (b)
29. Phosphine synthesis: Moulton, C. J.; Shaw, B. L. J. Chem. Soc., Dallort Trans. 1976, 1020.
30. Nemeh, S.; Jensen, C.; Binamira-Soriaga, E.; Kaska, W. C. Organometallics 1983, 2, 1442.
31. (a) Troughton, P. G. H.; Skapski, A. C. J. Chem. Soc., Chem. Commun. 1968, 575.
32. (b) Takenaka, A.; Syal, S. K.; Sasada, Y.; Omura, T.; Ogoshi, H.; Yoshida, Z.-I. Acta Crystallogr. 1976, B32, 62.
33. van der Zeijden, A. A. H.; van Koten, G.; Ernsting, J. M.; Elsevier, C. J.; Krijnen, B.; Stam, C. H. J. Chem. Soc., Dalton Trans. 1989, 317.
34. The synthesis and characterization of the (tert-butylethylene)rhodium dimer will be reported elsewhere.
35. Wilkins, R. G. Kinetics and Mechanism of Reactions of Transition Metal Complexes, 2nd ed.; VCH: Weinheim, 1991; p 236.
36. 1H} NMR follow-up shows that in the case of the ethylenerhodium dimer 2b the substitution step is also rate determining for the overall process.
37. Fryzuk, M. D.; MacNeil, P.; Rettig, S. J. Organometallics 1986,5, 2469.
38. (a) Mann, B. E.; Taylor, B. F. I3C NMR Data for Organometaallic Compounds; Academic Press: New York, 1981.
39. (b) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724.
40. C-C bond cleavage of 5,5-dimethyIcyclopentadiene to generate a methyliridium cyclopentadienyl complex was reported (see ref 2h).
41. McMillen, D. F.; Golden, D. M. Rev. Phys. Chem. 1982, 33, 492.
42. (a) Bryndza, H. E.; Fong, L. K.; Paciello, R. A.; Tarn, W.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 1444.
43. (b) Nolan, S. R; Hoff, C. D.; Stoutland, P. O.; Newman, L. J.; Buchanan, J. M.; Bergman, R. G.; Yang, G. K.; Peters, K. S. J. Am. Chem. Soc. 1987,109, 3143.
44. Stoutland, P. O.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. Polyhedron 1988, 7, 1429.
45. 8 solution of the products of indium-promoted C-C and C-H activation in THF showed that they are identical to those in benzene (6a and 7a; the analogous complex to 6a containing coordinated THF is not obtained), which permits the estimation of the solvent effect on the C-C and C-H activation processes.
46. (a) Fryzuk, M. D.; McConville, D. H.; Rettig, S. J. J. Organomet. Chem. 1993,445, 245.
47. (b) Hofmann, R; Meier, C; Englert, U.; Schmidt, M. U. Chem. Ber. 1992, 725, 353.
48. (a) Frost, A. A.; Pearson, R. G. Kinetics and Mechanism; John Wiley & Sons: New York, 1961.
49. (b) Laidler, K. J. Chemical Kinetics; Harper Collins: New York, 1987.
50. For example see: Wolf, J.; Lass, R. W.; Manger, M.; Werner, H. Organometallics 1995, 14, 2649.
51. Ryabov, A. D. Chem. Rev. 1990, 90, 403.
52. The electron-donating methoxy substituent is expected to cause significant retardation of a nucleophilic substitution reaction rate when the cleaved bond is in direct polar conjugation to it. For an example of oxidative addition reaction rate correlated with Hammett constants see: Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1665.
53. (a) Jones, W. D. In Activation and Functionalization of Alkenes; Hill, C. L., Ed.; John Wiley & Sons: New York, 1989; p 111.
54. (b) Selmeczy, A. D.; Jones, W. D.; Osman, R.; Perutz, R. N. Organometallics 1995, 14, 5677.
55. (a) Jones, W. D.; Feher, F. J. Ace. Chem. Res. 1989, 22, 91.
56. (b) Jones, W. D.; Feher, F. J. J. Am. Chem. Soc. 1985, 107, 620.
57. Lavin, M.; Holt, E. M.; Crabtree, R. H. Organometallics 1989, 8, 99.
58. (a) Low, J. J.; Goddard, W. A., III. J. Am. Chem. Soc. 1984, 106, 10779.
59. (b) Blomberg, M. R. A.; Siegbahn, P. E. M.; Nagashima, U.; Wennerberg, J. J. Am. Chem. Soc. 1991,113,424.
60. Siegbahn, P. E. M.; Blomberg, M. J. Am. Chem. Soc. 1992, 114, 10548.
61. Crabtree, R. H.; Holt, E. M.; Lavin, M.; Morenhouse, S. M. Inorg. Chem. 1985, 24, 1986.
62. Herde, J. L.; Senoff, C. V.Inorg. Nucl. Chem. Lett. 1971, 7, 1029.
63. Cramer, R. Inorg. Chem. 1962, 1, 722.
64. Bennett, M. A.; Saxby, J. D. Inorg. Chem. 1968, 7, 321.