E-selective allyl transfer reaction in a μ-η1: η2-crotylplatinum-cobalt complex

Organometallics

Volumn 27, Issue 9, 2008, Pages 2145-2148

  Komine, Nobuyuki ^a   Hirota, Takuma ^a   Hirano, Masafumi ^a   Komiya, Sanshiro ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; ISOMERS; OXIDATION; PLATINUM COMPOUNDS;

ALLYL TRANSFER REACTION; OXIDATIVE ADDITION; SITE EXCHANGE;

COBALT COMPOUNDS;

EID: 44449091588     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om701062g     Document Type: Article

References (40)

1. (a) Braunstein, P.; Oro, L. A.; Raithby, P. R., Eds. Metal Clusters in Chemistry; Wiley-VCH: Weinheim, Germany, 1999.
2. (b) Adams, R. D., Cotton, F. A., Eds. Catalysis by Di- and Polynuclear Metal Cluster Complexes; Wiley-VCH: New York, 1998.
3. Chetcuti, M. J. In Comprehensive Organometallic Chemistry II; Adams, R. D., Ed.; Pergamon Press: Oxford, U.K., 1995; Vol. 10.
4. Shriver, D. F.; Kaesz, H., Adams, R. D., Eds. The Chemistry of Metal Cluster Complexes; VCH: New York, 1990.
5. (e) Ritleng, V.; Chetcuti, M. J. Chem. Rev. 2007, 107, 797.
6. (a) Komiya, S.; Endo, I. Chem. Lett. 1988, 1709.
7. (b) Miki, K.; Kasai, N.; Endo, I.; Komiya, S. Bull. Chem. Soc. Jpn. 1989, 62, 4033.
8. (c) Fukuoka, A.; Sadashima, T.; Endo, I.; Ohashi, N.; Kambara, Y.; Sugiura, T.; Komiya, S. Organometallics 1994, 13, 4033.
9. (d) Fukuoka, A.; Sadashima, T.; Sugiura, T.; Wu, X.; Mizuho, Y.; Komiya, S. J. Organomet. Chem. 1994, 473, 139.
10. (e) Komiya, S.; Endo, I.; Fukuoka, A.; Hirano, M. Trends Organomet. Chem. 1994, 1, 223.
11. (f) Fukuoka, A.; Sugiura, T.; Yasuda, T.; Taguchi, T.; Hirano, M.; Komiya, S. Chem. Lett. 1997, 329.
12. (g) Fukuoka, A.; Fukagawa, S.; Hirano, M.; Komiya, S. Chem. Lett. 1997, 377.
13. (h) Yasuda, T.; Fukuoka, A.; Hirano, M.; Komiya, S. Chem. Lett. 1998, 29.
14. (i) Komiya, S.; Yasuda, T.; Fukuoka, A.; Hirano, M. J. Mol. Catal. A 2000, 159, 63.
15. (j) Komiya, S.; Muroi, S.; Furuya, M.; Hirano, M. J. Am. Chem. Soc. 2000, 122, 170.
16. (k) Komine, N.; Hoh, H.; Hirano, M.; Komiya, S. Organometallics 2000, 19, 5251.
17. (l) Fukuoka, A.; Fukagawa, S.; Hirano, M.; Koga, N.; Komiya, S. Organometallics 2001, 20, 2065.
18. (m) Furuya, M.; Tsutsuminai, S.; Nagasawa, H.; Komine, N.; Hirano, M.; Komiya, S. Chem. Commun. 2003, 2046.
19. (n) Tsutsuminai, S.; Komine, N.; Hirano, M.; Komiya, S. Organometallics 2003, 22, 4238.
20. (o) Tsutsuminai, S; Komine, N.; Hirano, M.; Komiya, S. Organometallics 2004, 23, 44.
21. (p) Komine, N.; Tanaka, S.; Tsutsuminai, S.; Akahane, Y.; Hirano, M.; Komiya, S. Chem. Lett. 2004, 33, 858.
22. (q) Kuramoto, A.; Nakanishi, K.; Kawabata, T.; Komine, N.; Hirano, M.; Komiya, S. Organometallics 2006, 25, 311.
23. (r) Komine, N.; Tsutsuminai, S.; Hoh, H.; Yasuda, T.;. Hirano, M.; Komiya, S. Inorg. Chem. Acta 2006, 359, 3699.
24. (s) Tanaka, S.; Hoh, H.; Akahane, Y.; Tsutsuminai, S.; Komine, N.; Hirano, M.; Komiya, S. J. Organomet. Chem. 2007, 692, 26.
25. (t) Komine, N.; Tsutsuminai, S.; Hirano, M.; Komiya, S. J. Organomet. Chem. 2007, 692, 4486.
26. Alper, H.; Abbayes, H. D.; Roches, D. D. J. Organomet. Chem. 1976, 121, C31.
27. 2 has been suggested: Osakada, K.; Chiba, T.; Nakamura, Y.; Yamamoto, T.; Yamamoto, A. Organometallics 1989, 8, 2602.
28. 3-allenyl/propargyl dinuclear complex is also known: Ogoshi, S.; Nishida, T.; Shinagawa, T.; Kurosawa, H. J. Am. Chem. Soc. 2001, 123, 7164.
29. 3-crotylcobalt complex is much slower,
30. 3, in which the negative charge on the cobalt atom is stabilized by carbonyl ligands.
31. gNMR Version 4.0.1; Ivory Soft/Cherwell Scientific Publishing: Oxford, 1998.
32. 6, ε = 21).
33. 6.
34. (a) Boyle, R. C.; Pool, D.; Jacobsen, H.; Fink, M. J. J. Am. Chem. Soc. 2007, 128, 9054.
35. (b) Danny, C.; Simon, B. D.; Sarah, L. H.; Iman, G. K.; Robin, N. P.; Sylviane, S.-E.; Philippa, L. T. Organometallics 2004, 23, 5744.
36. (c) Boyle, R. C.; Mague, J. T.; Fink, M. J. J. Am. Chem. Soc. 2003, 125, 3228.
37. (d) Bars, O.; Braunstein, P.; Geoffroy, G. L.; Metz, B. Organometallics 1986, 5, 2021.
38. (a) An alternative possible mechanism involves twist-rotation via a pseudotetrahedral transition state: Obora, Y.; Tsuji, Y.; Nishiyama, Y.; Ebihara, M.; Kawamura, T. J. Am. Chem. Soc. 1996, 118, 10922.
39. (b) Tsuji, Y.; Nishiyama, K.; Hori, S.; Ebihara, M.; Kawamura, T. Organometallics 1998, 17, 507.
40. (c) Ozawa, F.; Kamite, J. Organometallics 1998, 17, 5630. However, we consider that this mechanism is less probable because il is difficult to explain specific dynamic processes of the E-isomer with this mechanism.