Titanocene-catalyzed carbosilylation of alkenes and dienes using alkyl halides and chlorosilanes

Journal of Organic Chemistry

Volumn 65, Issue 17, 2000, Pages 5291-5297

  Nii, Shinsuke ^a   Terao, Jun ^a   Kambe, Nobuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE DERIVATIVE; RADICAL; REAGENT; TITANOCENE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS;

EID: 0034714405     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000483p     Document Type: Article

References (29)

1. Asao, N.; Yoshikawa, E.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4874-4875.
2. Pd-catalyzed carbosilylation: (a) Chatani, N.; Hanafusa, T. J. Chem. Soc., Chem. Commun. 1985, 838-839.
3. (b) Sakurai, H.; Kamiyama, Y.; Nakadaira, Y. J. Am. Chem. Soc. 1977, 99, 3879-3880.
4. (c) Saso, H.; Ando, W. Chem. Lett. 1988, 1567-1570.
5. (d) Sakurai, H.; Imai, T. Chem. Lett. 1975, 891-894.
6. (e) Chatani, N.; Amishiro, N.; Murai, S. J. Am. Chem. Soc. 1991, 113, 7778-7780.
7. (f) Chatani, N.; Amishiro, N.; Morii, T.; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834-1840.
8. Obora, Y.; Tauji, Y.; Kawamura, T. J. Am. Chem. Soc. 1995, 117, 9814-9821.
9. Wu, M.; Yang, F.; Cheng, C. J. Org. Chem. 1999, 64, 2471-2474.
10. (a) Terao, J.; Saito, K; Nii, S.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1998, 120, 11822-11823.
11. (b) Terao, J.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1998, 39, 9697-9698.
12. (a) Terao, J.; Torii, K.; Saito, K.; Kambe, N.; Baba, A.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 2653-2656.
13. (b) Terao, J.; Watanabe, T.; Saito, K.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1998, 39, 9201-9204.
14. 2 and alkyl Grignard reagents, see: Martin, H. A.; Jellinek, F. J. Organomet. Chem. 1968, 12, 149-161.
15. nPrMgBr, see:
16. (b) Luinstra, G. A.; ten Cate, L. C.; Heeres, H. J.; Pattiasina, J. W.; Meetsma, A.; Teuben, J. H. Organometallics 1991, 10, 3227-3237.
17. iPrMgBr. Rilatt, J. A.; Kitching, W. Organometallics 1982, 1, 1089-1093.
18. It is reported that 14 decomposes rapidly at -50 °C forming 15 along with a 1:1 mixture of n-butane and butenes. McDermott, J. X.; Wilson, M. E.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 6529-6536.
19. iPrMgBr is known. Gao, Y.; Sato, F. J. Chem. Soc., Chem. Commun. 1995, 659-660.
20. Brintzinger, H. H. J. Am. Chem. Soc. 1967, 89, 6871-6877.
21. Maillard, B.; Forrest, D.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 7024-7026.
22. Citterio, A.; Arnoldi, A.; Minisci, F. J. Org. Chem. 1979, 44, 2674-2682.
23. Silver, M. S.; Shafer, P. R.; Nordlander, J. E.; Ruchardt, C.; Roberts, J. D. J. Am. Chem. Soc. 1960, 82, 2646-2647.
24. 2) complex has been isolated and well catalyzed. The crystal structure of this complex is more similar to a (titanacyclopropane) δ-coordination rather than a π-coordination structure, see: Cohen, S. A.; Auburn, P. R.; Bercaw, J. E. J. Am. Chem. Soc. 1983, 705, 1136-1143.
25. Martin, H. A.; Jellinek, F. Angew. Chem. 1964, 76, 274. Chen, J.; Kai, Y.; Kasai, N.; Yasuda, H.; Yamamoto, H.; Nakamura, A. J. Organomet. Chem. 1991, 407, 191-205.
26. Martin, H. A.; Jellinek, F. Angew. Chem. 1964, 76, 274. Chen, J.; Kai, Y.; Kasai, N.; Yasuda, H.; Yamamoto, H.; Nakamura, A. J. Organomet. Chem. 1991, 407, 191-205.
27. nBuMgCl was used.
28. 2 as the catalyst (unpublished result). The details will be published in due course.
29. Li, X.; Singh, S. M.; Labrie, F. Synth. Commun. 1994, 24, 733-743.