A new platinum complex catalyzed reaction involving nucleophilic substitution at the central carbon atom of the π-allyl ligand

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7523-7527

  Kadota, Joji ^a   Komori, Shinji ^a   Fukumoto, Yoshiya ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; PLATINUM COMPLEX;

ARTICLE; CATALYSIS; COMPLEX FORMATION; ISOMERISM; LIGAND BINDING; SYNTHESIS;

EID: 0033215351     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990845x     Document Type: Article

References (36)

1. Trost, B. M.; Verhoven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Vol. 8, p 799.
2. (a) Ephritikhine, M.; Green, M. L. H.; Mackenzie, R. E. J. Chem. Soc., Chem. Commun. 1976, 619.
3. (b) Ephritikhine, M.; Francis, B. R.; Green, M. L. H.; Mackenzie, R. E.; Smith, M. J. J. Chem. Soc., Dalton Trans. 1977, 1131.
4. (c) Adam, G. J. A.; Davies, S. G.; Ford, K. A.; Ephritikhine, M.; Todd, P. F.; Green, M. L. H. J. Mol. Catal. 1980, 8, 15.
5. (d) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1984, 106, 7272.
6. (e) McGhee, W. D.; Bergman, R. G. J. Am. Chem. Soc. 1985, 107, 3388.
7. (f) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346.
8. (g) Tjaden, E. B.; Stryker, J. M. J. Am. Chem. Soc. 1990, 112, 6420.
9. (h) Wakefield, J. B.; Stryker, J. M. J. Am. Chem. Soc. 1991, 113, 7057.
10. (i) Tjaden, E. B.; Stryker, J. M. Organometallics 1992, 11, 16.
11. (j) Tjaden, E. B.; Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1992, 114, 1100.
12. (k) Schwiebert, K. E.; Stryker, J. M. Organometallics 1993, 12, 600.
13. (l) Tjaden, E. B.; Stryker, J. M. J. Am. Chem. Soc. 1993, 115, 2083.
14. (a) Hegedus, L. S.; Danlington, W. H.; Russell, C. E. J. Org. Chem. 1980, 45, 5193.
15. (b) Carfagna, C.; Maniani, L.; Musco, A.; Sallese, G.; Santi, R. J. Org. Chem. 1991, 56, 3924.
16. (c) Carfagna, C.; Galarini, R.; Musco, A.; Santi, R. Organometallics 1991, 10, 3956.
17. (d) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 234.
18. (e) Wilde, A.; Otte, A. R; Hoffmann, H. M. R. J. Chem. Soc., Chem. Commun. 1993, 615.
19. (f) Formica, M.; Musco, A.; Pontellini, R.; Linn, K.; Mealli, C. J. Organomet. Chem. 1993, 448, C6.
20. (g) Carfagna, C.; Galarini, R.; Linn, K.; López, J. A.; Mealli, C.; Musco, A. Organometallics 1993, 12, 3019.
21. (h) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 100.
22. (i) Satake, A.; Nakata, T. J. Am. Chem. Soc. 1998, 120, 10391.
23. (j) Satake, A.; Koshino, H.; Nakata, T. Chem. Lett. 1999, 49.
24. Ohe, K; Matsuda, H.; Morimoto, T.; Ogoshi, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1994, 116, 4125.
25. (a) Castaño, A. M.; Aranyos, A.; Szabó, K. J.; Bäckvall, J. E. Angew. Chem., Int. Ed. Engl. 1995, 34, 2551.
26. (b) Aranyos, A.; Szabó, K. J.; Castaño, A. M.; Bäckvall, J. E. Organometallics 1997, 16, 1058.
27. Tsai, F.-Y.; Chen, H.-W.; Chen, J.-T.; Lee, G.-H.; Wang, Y. Organometallics 1997, 16, 822.
28. (a) Organ, M. G.; Miller, M. Tetrahedron Lett. 1997, 38, 8181.
29. (b) Organ, M. G.; Miller, M.; Konstantinou, Z. J. Am. Chem. Soc. 1998, 120, 9283.
30. The lack of reaction appears to be due to stable trimethylenemethane-plainum complex formation through nucleophilic substitution at the central carbon atom of the π-allyl ligand, followed by deprotonation. Actually, the stoichiometric reaction of 2-chloro-(π-allyl) platinum complex with sodium diethyl malonate gave a trimethylenemethane-platinum complex in 21% yield.
31. A preliminary result of a similar reaction using sodium ethyl benzoyl acetate has been reported; see ref 4.
32. 1H NMR spectrum). This result is not understood as of now and must be investigated in detail.
33. Cook, C. D.; Jauhal, G. S. J. Am. Chem. Soc. 1968, 90, 1464.
34. Maitlis, P. M.; Moseley, K. J. Chem. Soc., Chem. Commun. 1971, 982.
35. Hutchins, R. O.; Kandasamy, D. J. Org. Chem. 1975, 40, 2530.
36. Skattebøl, L. J. Org. Chem. 1866, 31, 1554.