Removal of a palladium-bound tertiary phosphine ligand with silver(I) salts to generate cationic monoorganopalladium(II) complexes having one trimethylphosphine ligand

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 5, 1997, Pages 1135-1140

  Kayaki, Yoshihito ^a   Shimizu, Isao ^a   Yamamoto, Akio ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DINUCLEAR; EQUIMOLAR AMOUNT; HALIDE COMPLEXES; HALIDE LIGAND; MONOPHOSPHINE COMPLEX; NMR SPECTRUM; PALLADIUM COMPLEXES; PHOSPHINE COMPLEX; SILVER SALTS; TERTIARY PHOSPHINES; TRIMETHYLPHOSPHINES;

CHLORINE COMPOUNDS; COMPLEXATION; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS COMPOUNDS; SALTS; SILVER COMPOUNDS;

PALLADIUM COMPOUNDS;

EID: 0000412715     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.70.1135     Document Type: Article

References (37)

1. J. Tsuji, "Palladium Reagents: Innovations in Organic Synthesis", Wiley, Chichester (1995);
2. J. P. Collman, L. S. Hegedus, J. R. Norton, and R. G. Finke, "Principle and Applications of Organotransition Metal Chemistry", University Science Books, Mill Valley, California (1987);
3. R. H. Crabtree, "The Organometallic Chemistry of the Transition Metals", Wiley Interscience, New York (1994);
4. A. Yamamoto, "Organotransition Metal Chemistry", Wiley Interscience, New York (1986).
5. M. Bochmann, J. Chem. Soc, Dalton Trans., 1996, 255, and papers cited therein.
6. A. Yamamoto, J. Organomet. Chem., 500, 337 (1995).
7. A. Sen, Acc. Chem. Res., 26, 303 (1993);
8. E. Drent and P. H. M. Budzelaar, Chem. Rev., 96, 663 (1996);
9. L. K. Johnson, S. Mecking, and M. Brookhart, J. Am. Chem. Soc., 118, 267 (1996), and papers cited therein.
10. General reviews of Heck reactions: a) G. D. Davis, Jr., and A. Hallberg, Chem. Rev., 89, 1433 (1989);
11. A. de Meijere and F. E. Meyer, Angew. Chem., Int. Ed. Engl., 33, 2379 (1994);
12. W. Cabri and I. Candiani, Acc. Chem. Res., 28, 2 (1995), and references cited therein.
13. F. Kawataka, I. Shimizu, and A. Yamamoto, Bull. Chem. Soc. Jpn., 68, 654 (1995).
14. Y. Kayaki, F. Kawataka, I. Shimizu, and A. Yamamoto, Chem. Lett., 1994, 2171;
15. Y. Kayaki, I. Shimizu, and A. Yamamoto, Chem. Lett, 1995, 1089.
16. Y. Kayaki, I. Shimizu, and A. Yamamoto, Bull. Chem. Soc. Jpn., 70, 917 (1997).
17. G. K. Anderson, Organometallics, 2, 665 (1983);
18. F. T. Ladipo and G. K. Anderson, Organometallics, 13, 303 (1994), and references cited therein.
19. Y. Hayashi, K. Isobe, Y. Nakamura, and S. Okeya, J. Organomet. Chem., 310, 127 (1986).
20. M. S. Driver and J. F. Hartwig, J. Am. Chem. Soc., 117, 4708 (1995);
21. J. F. Hartwig and F. Paul, J. Am. Chem. Soc., 117, 5373 (1995);
22. F. Paul, J. Patt, and J. F. Hartwig, Organometallics, 14, 3030 (1995);
23. R. A. Widenhoefer, H. A. Zhong, and S. L. Buchwald, Organometallics, 15, 2745 (1996);
24. R. A. Widenhoefer and S. L. Buchwald, Organometallics, 15, 2755 (1996).
25. V. V. Grushin, C. Bensimon, and H. Alper, Organometallics, 14, 3259 (1995).
26. R. B. King, Inorg. Chem., 2, 936 (1963);
27. J. M. Jenkins and B. L. Shaw, J. Chem. Soc. A, 1966, 770.
28. 3) have been isolated by R. G. Goel et al. R. G. Goel and P. Pilon, Inorg. Chem., 17, 2876 (1978), and references cited therein.
29. A. J. Cheney, B. E. Mann, and B. L. Shaw, J. Chem. Soc., Chem. Commun., 1971, 431, and references cited therein.
30. According to a theoretical study using ab initio calculation, the path for the migratory CO insertion requires a coordination site cis to the methyl ligand whereas an insertion pathway through a fivecoordinate intermediate is a high-energy process: H. Tachikawa, Advanced Research Center for Science and Engineering, Waseda University, a private communication.
31. 4/Ni has been ascribed to formation of a monophosphine arylnickel complex, although the mono-phosphine complex has not been well characterized. Y. Ishimura, K. Maruya, Y. Nakamura, T. Mizoroki, and A. Ozaki, Bull. Chem. Soc. Jpn., 56, 818 (1983).
32. 2] with a silver salt has been briefly mentioned. M. Wada and K. Oguro, Inorg. Chem., 15, 2346 (1976).
33. F. Kawataka, Y. Kayaki, I. Shimizu, and A. Yamamoto, Organometallics, 13, 3517 (1994).
34. G. P. C. M. Dekker, C. J. Elservier, K. Vrieze, and P. W. N. M. van Leeuwen, Organometallics, 11, 1598 (1992).
35. Y.-J. Kim, K. Osakada, A. Takenaka, and A. Yamamoto, J. Am. Chem. Soc., 112, 1096 (1990).
36. R. E. Rülke, J. M. Ernsting, A. L. Spek, C. J. Elsevier, P. W. N. M. van Leeuwen, and K. Vriese, Inorg. Chem., 32, 5769 (1993).
37. J. Chatt and L. M. Venanzi, J. Chem. Soc., 1957, 2351.