Utilization of tetrabutylammonium triphenyldifluorosilicate as a fluoride source for silicon-carbon bond cleavage

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 6901-6905

  Pilcher, Anthony S ^a   DeShong, Philip ^a  

^a UNIVERSITY OF MARYLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001443339     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960922d     Document Type: Article

References (32)

1. Schlosser, M.; Lipshutz, B. H. In Organometallics in Synthesis; Schlosser, M., Ed.; J. Wiley & Sons: New York, 1994; Chapters 1 and 4 and references cited therein.
2. (a) Furin, G. G.; Vyazankina, O. A.; Gostevsky, B. A.; Vyazankin, N. S. Tetrahedron 1988, 44, 2675.
3. (b) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371.
4. Pilcher, A. S.; Ammon, H. L.; DeShong, P. J. Am Chem. Soc. 1995, 117, 5166.
5. (a) Schwesinger, R.; Link, R.; Thiele, G.; Rotter, H.; Honert, D.; Limbach, H.; Männle, F. Angew. Chem., Int. Ed. Engl. 1991, 30, 1372.
6. (b) Chen, S. F.; Mariano, P. S. Tetrahedron 1988, 44, 7013.
7. (c) Ricci, A.; Degl'Innocenti, A.; Fiorenza, M.; Taddei, M.; Spartera, M. A.; Walton, D. R. M. Tetrahedron Lett. 1982, 23, 577.
8. Cox, D. P.; Terpinsky, J.; Lawrynowicz, W. J. Org. Chem. 1984, 49, 3216.
9. Some of the TMS ethers resulting from condensation are hydrolytically unstable. For these products, the standard workup procedures involving exposure of the crude products to dilute acid resulted in removal of the TMS ether.
10. In a control experiment, treatment of hexanal with TBAT under the described conditions in the absence of allyltrimethylsilane did not produce aldol products.
11. (a) Hosomi, A.; Shirahata, A.; Sakurai, H. Tetrahedron Lett. 1978, 3043.
12. (b) Sakurai, H. Pure App. Chem. 1982, 54, 1.
13. (c) Sakurai, H.; Hosomi, A.; Saito, M. Sasaki, K.; Iguchi, H.; Sasaki, J.; Araki, Y. Tetrahedron 1983, 39, 883 and references cited therein.
14. (d) Sakurai has also reported the fluoride-catalyzed condensation of crotyltrifluorosilane derivatives with aldehydes: Kira, M.; Kobayashi, M.; Sakurai, H. Tetrahedron Lett. 1987, 28, 4081. (e) Sakurai, H. Synlett 1990, 1 and references cited therein.
15. (d) Sakurai has also reported the fluoride-catalyzed condensation of crotyltrifluorosilane derivatives with aldehydes: Kira, M.; Kobayashi, M.; Sakurai, H. Tetrahedron Lett. 1987, 28, 4081. (e) Sakurai, H. Synlett 1990, 1 and references cited therein.
16. 1H NMR chemical shifts of the methyl group: (Guyon, R.; Villa, P. Bull. Soc. Chim. Fr. 1972, 1375).
17. 1H NMR chemical shifts of the methyl group: (Guyon, R.; Villa, P. Bull. Soc. Chim. Fr. 1972, 1375).
18. This is the first example of fluoride-initiated intermolecular coupling between allyltrimethylsilane and an imine derivative. For an example of an alkoxide-induced reaction between an imine and a benzylsilane derivative, see: Shimizu, S.; Ogata, M. Synth.Commun. 1989, 19, 2219.
19. (a) Chtara, R. A.; Moreau, J. L.; Gaudemar, M. C. R. Acad. Sci., Ser. C 1975, 250, 3115 and references cited therein.
20. (b) Yamamoto, Y.; Ito, W.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 1131 and references cited therein.
21. (c) Keck, G. E.; Enholm, E. J. J. Org. Chem. 1985, 50, 146.
22. (d) Wuts, P. G. M.; Jung, Y. W. Tetrahedron Lett. 1986, 27, 2079.
23. (e) Yamamoto, Y. Alrichimica Acta 1987, 20, 45 and references cited therein.
24. (f) Hoffmann, R. W.; Endesfelder, A. Liebigs Ann. Chem. 1987, 215 and references cited therein.
25. (g) Ciufolini, M. A.; Spencer, G. O. J. Org. Chem. 1989, 54, 4739.
26. (a) Heerding, D. A.; Hong, C. Y.; Kado, N.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 11028 and references cited therein.
27. (b) Hiemstra, H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014 and references cited therein.
28. (c) Kercher, T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200.
29. For an account of the reaction between imines and allenyl silanes, see: Jin, J.; Smith, D. T.; Weinreb, S. M. J. Org. Chem. 1995, 60, 5366. Borzilleri, R. M.; Weinreb, S. M.; Parzez, M. J. Am Chem. Soc. 1994, 116, 9789.
30. For an account of the reaction between imines and allenyl silanes, see: Jin, J.; Smith, D. T.; Weinreb, S. M. J. Org. Chem. 1995, 60, 5366. Borzilleri, R. M.; Weinreb, S. M.; Parzez, M. J. Am Chem. Soc. 1994, 116, 9789.
31. Unpublished results, A. S. Pilcher, P. Loeszos, J. W. Schwantes, V. Lee, and A. L. Slover.
32. Ashby, E. C.; DePriest, R. N. Tetrahedron Lett. 1982, 23, 5251.