Formation of a palladalactone complex by C-O bond cleavage of diketene promoted by a zerovalent palladium complex

Chemistry Letters

Volumn , Issue 7, 1999, Pages 685-686

  Kakino, Ryuki ^a   Nagayama, Kazuhiro ^a   Kayaki, Yoshihito ^a   Shimizu, Isao ^a   Yamamoto, Akio ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033245527     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.685     Document Type: Article

References (28)

1. a) A. Yamamoto, Adv. Organometal. Chem., 34, 111 (1992).
2. b) Y. -S. Lin, and A. Yamamoto, "Topics in Organometallic Chemistry," ed by S. Murai, Springer, Berlin (1999), Vol. 3, pp. 161-192.
3. a) K. Nagayama, F. Kawataka, M. Sakamoto, I. Shimizu, and A. Yamamoto, Chem. Lett., 1995, 367.
4. b) K. Nagayama, I. Shimizu, and A. Yamamoto, Chem. Lett., 1998, 1143.
5. c) K. Nagayama, F. Kawataka, M. Sakamoto, I. Shimizu, and A. Yamamoto, Bull. Chem. Soc. Jpn., 72, 573 (1999).
6. d) K. Nagayama, I. Shimizu, and A. Yamamoto, Bull. Chem. Soc. Jpn., 72, 799 (1999).
7. R. J. Clemens, Chem. Rev., 86, 241 (1986).
8. a) C. E. Garrett and G. C. Fu, J. Am. Chem. Soc., 120, 7479 (1998).
9. b) J. C. Ruble and G. C. Fu, J. Org. Chem., 61, 7230 (1996).
10. c) I. Shibata, M. Nishio, A. Baba, and H. Matsuda, J. Chem. Soc., Chem. Commun., 1993, 1067.
11. d) M. Hayashi, T. Inoue, and N. Oguni, J. Chem. Soc., Chem. Commun., 1994, 341.
12. e) M. Hayashi, T. Inoue, Y. Miyamoto, and N. Oguni, Tetrahedron. 50, 4385 (1994).
13. Y. Abe, M. Sato, H. Goto, R. Sugawara, E. Takahashi, and T. Kato, Chem. Pham. Bull., 31, 4346 (1983).
14. b) Y. Abe, H. Goto, M. Sato, and T. Kato, Chem. Pham. Bull., 31, 1108 (1983).
15. c) T. Fujisawa, T. Sato, Y. Gotoh, M. Kawashima, and T. Kawara, Bull. Chem. Soc. Jpn., 55, 3555 (1982).
16. d) K. Itoh, M. Fukui, and Y. Kurachi, J. Chem. Soc., Chem. Commun., 1977, 500.
17. e) K. Itoh, T. Yogo, and Y. Ishii, Chem. Lett., 1977, 103.
18. T. Yamamoto, J. Ishizu, and A. Yamamoto, Bull. Chem. Soc. Jpn., 55, 623 (1982).
19. a) Y. -J. Kim, K. Osakada, A. Takenaka, and A. Yamamoto, J. Am. Chem. Soc., 112, 1096 (1990).
20. b) K. Osakada, Y. Ozawa, and A. Yamamoto, J. Organomet. Chem., 399, 341 (1990).
21. -1.
22. 2Pd: C, 35.05; H, 6.47%. Found: C, 35.18; H, 6.78%.
23. 0)). A crystal with approximate dimensions of 0.20 × 0.20 × 0.15 mm was used for analysis. The structure was solved by direct methods (SIR 92) and refined by full-matrix least-squares calculations. Final R and R values were 0.020 and 0.025, respectively.
24. 2(styrene)] gives a five-membered palladalactone complex. The complex was characterized by single-crystal X-ray analysis. K. Osakada, M. -K. Doh, F. Ozawa, and A. Yamamoto, Organometallics, 9, 2197 (1990).
25. Palladalactone complexes with four and six-membercd rings have been prepared using kelene and their molecular structures have been determined by X-ray diffraction. S. Baba, T. Ogura, and S. Kawaguchi, J. Chem. Soc., Chem. Commun., 1972, 910.
26. Complexes 3 - 7 have been characterized by spectroscopic means and elemental analysis.
27. 3 ligands in complex 2 was stripped away by action of dimethyl acetylenedicarboxylate to give monophosphine complex 7.
28. T. Yamamoto, K. Sano, K. Osakada, S. Komiya, A. Yamamoto, Y. Kushi, andT. Tada, Organometallics, 9, 2369 (1990)