An improved synthesis of fluorinated imidoylsilanes

Synthesis

Volumn , Issue 11, 2006, Pages 1836-1840

  Akamatsu, Chie ^a   Yamauchi, Atsushi ^a   Kobayashi, Takeshi ^a   Ozeki, Yu ^a   Takagi, Jun ^a   Amii, Hideki ^a   Uneyama, Kenji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Fluorine; Imidoylsilane; Imines; Magnesium; Umpolung

Indexed keywords

BROMINE COMPOUNDS; CHEMICAL BONDS; CHLORINE COMPOUNDS; FLUORINE; FLUORINE COMPOUNDS; MAGNESIUM PRINTING PLATES; SYNTHESIS (CHEMICAL);

C-BR BONDS; IMIDOYLSILANE; IMINES; UMPOLUNG;

SILANES;

BROMIDE; CHLORIDE; IMIDOYLSILANE DERIVATIVE; N (2,2,3,3,4,4,4 HEPTAFLUORO 1 TRIMETHYLSILYLBUTYLIDENE) N (4 METHOXYPHENYL)AMINE; N (4 METHOXYPHENYL) N (2,2 DIFLUORO 1 TRIMETHYLSILYLETHYLIDENE)AMINE; N (4 METHOXYPHENYL) N (2,2,2 TRIFLUORO 1 TRIETHYLSILYLETHYLYLIDENE)AMINE; N (4 METHOXYPHENYL) N (2,2,2 TRIFLUORO 1 TRIMETHYLSILYLETHYLIDENE)AMINE; N (4 METHOXYPHENYL) N (2,2,3,3,3 ENTAFLUORO 1 TRIMETHYLSILYLPROPYLIDENE)AMINE; N (4 METHOXYPHENYL) N (PENTAFLUOROPHENYLTRIMETHYLSILYLMETHYLENE)AMINE; SILANE DERIVATIVE; TRIFLUOROACETAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; FLUORINATION; SILYLATION; SYNTHESIS;

EID: 33745170388     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942361     Document Type: Article

References (52)

1. (a) Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641.
2. (b) Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 5437.
3. (c) Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379.
4. (d) Ichikawa, J.; Moriya, T.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1991, 961.
5. (e) Ichikawa, J.; Hamada, S.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 337.
6. (f) Okada, Y.; Minami, T.; Yamamoto, T.; Ichikawa, J. Chem. Lett. 1992, 547.
7. (g) Ichikawa, J.; Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 3779.
8. (h) Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739.
9. Ichikawa, J.; Yonemaru, S.; Minami, T. Synlett 1992, 833.
10. (a) Patel, S. T.; Percy, J. M.; Wilkens, R. D. Tetrahedron 1995, 51, 9201.
11. (b) Howarth, J. A.; Owton, W.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1995, 757.
12. (c) Howarth, J. A.; Owton, W.; Percy, J. M.; Rock, M. H. Tetrahedron 1995, 51, 10289.
13. (d) Crowley, P. J.; Howarth, J. A.; Owton, W.; Percy, J. M.; Stansfield, K. Tetrahedron Lett. 1996, 37, 5975.
14. (e) Crowley, P. J.; Percy, J. M.; Stansfield, K. Tetrahedron Lett. 1996, 37, 8233.
15. (f) Crowley, P. J.; Percy, J. M.; Stansfield, K. Tetrahedron Lett. 1996, 37, 8237.
16. (g) Balnaves, A. S.; Gelbrich, T.; Hursthouse, M. B.; Light, M. E.; Palmer, M. J.; Percy, J. M. J. Chem. Soc., Perkin Trans. 1 1999, 2525.
17. (h) DeBoos, G. A.; Fullbrook, J. J.; Owton, W. M.; Percy, J. M.; Thomas, A. C. Synlett 2000, 963.
18. (i) DeBoos, G. A.; Fullbrook, J. J.; Percy, J. M. Org. Lett. 2001, 3, 2859.
19. (j) Garayt, M. R.; Percy, J. M. Tetrahedron Lett. 2001, 42, 6377.
20. (k) Cox, L. R.; DeBoos, G. A.; Fullbrook, J. J.; Percy, J. M.; Spencer, N. S.; Tolley, M. Org. Lett. 2003, 5, 337.
21. (a) Jin, F.; Jiang, B.; Xu, Y. Tetrahedron Lett. 1992, 33, 1221.
22. (b) Jin, F.; Xu, Y.; Huang, W. J. Chem. Soc., Perkin Trans. 1 1993, 795.
23. (c) Jin, F.; Xu, Y. J. Fluorine Chem. 1993, 62, 207.
24. (d) Jin, F.; Xu, Y.; Huang, W. J. Chem. Soc., Chem Commun. 1993, 814.
25. Bordeau, M.; Clavel, P.; Barba, A.; Berlande, M.; Biran, C.; Roques, N. Tetrahedron Lett. 2003, 44, 3741.
26. (a) Higashiya S., Lim D. S., Ngo S. C., Toscano P. J., Welch J. T.; Abstracts of Papers, 222nd National Meeting of the American Chemical Society, Chicago IL, Aug 26-30, 2001; American Chemical Society: Washington D.C., 2001; ORGN 41
27. (b) Ngo, S. C.; Chung, W. J.; Lim, D. S.; Shigashiya, S.; Welch, J. T. J. Fluorine Chem. 2002, 117, 207.
28. (c) Chung, W. J.; Higashiya, S.; Oba, Y.; Welch, J. T. Tetrahedron 2003, 59, 10031.
29. (d) Chung, W. J.; Welch, J. T. J. Fluorine Chem. 2004, 125, 543.
30. (e) Chung, W. J.; Ngo, S. C.; Higashiya, S.; Welch, J. T. Tetrahedron Lett. 2004, 45, 5403.
31. (a) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941.
32. (b) Tamura, K.; Yan, F.-Y.; Sakai, T.; Uneyama, K. Bull. Chem. Soc. Jpn. 1994, 67, 300.
33. (c) Watanabe, H.; Yan, F.-Y.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758.
34. Uneyama, K.; Noritake, C.; Sadamune, K. J. Org. Chem. 1996, 61, 6055.
35. A carbene-type intermediate has been proposed for benzoyl lithium, see: (a) Trzupek, L. S.; Newirth, T. L.; Kelly, E. G.; Nudelman, N. S.; Whitesides, G. M. J. Am. Chem. Soc. 1973, 95, 8118.
36. (b) Nudelman, N. S.; Vitale, A. A. J. Org. Chem. 1981, 46, 4625.
37. (c) Seyferth, D.; Weinstein, R. M. J. Am. Chem. Soc. 1982, 104, 5534.
38. (d) Aminocarbene structure: Butters, M. Comprehensive Organic Functional Group Transformations, Vol. 5; Katrizky, A. R.; Meth-Cohn, O.; Rees, C. W.; Moody, C. J., Eds.; Pergamon Press: Oxford, 1995, 783-804.
39. Preparation of (non-fluorinated) imidoylsilanes from imidoyl chlorides: (a) Bourgeois, P. J. Organomet. Chem. 1974, 76, C1.
40. (b) Niznik, G. E.; Morrison, W. H.; Walborsky, H. M. J. Org. Chem. 1974, 39, 600.
41. Generation of (non-fluorinated) imidoyl lithiums from the corresponding imidoyl chlorides: Alonso, E.; Ramón, D. J.; Yus, M. Tetrahedron 1998, 54, 12007.
42. (a) Amii, H.; Kobayashi, T.; Hatamoto, Y.; Uneyama, K. Chem. Commun. 1999, 1323.
43. (b) Amii, H.; Kobayashi, T.; Uneyama, K. Synthesis 2000, 2001.
44. (c) Mae, M.; Amii, H.; Uneyama, K. Tetrahedron Lett. 2000, 41, 7893.
45. (d) Amii, H.; Kobayashi, T.; Terasawa, H.; Uneyama, K. Org. Lett. 2001, 3, 3103.
46. (e) Amii, H.; Hatamoto, Y.; Seo, M.; Uneyama, K. J. Org. Chem. 2001, 66, 7216.
47. (f) Hata, H.; Kobayashi, T.; Amii, H.; Uneyama, K.; Welch, J. T. Tetrahedron Lett. 2002, 43, 6099.
48. Kobayashi, T.; Nakagawa, T.; Amii, H.; Uneyama, K. Org. Lett. 2003, 5, 4297.
49. (a) Wakefield, B. J. Organomagnesium Methods in Organic Synthesis; Academic Press: London, 1995.
50. (b) Pearson, D. E.; Cowan, D.; Beckler, J. D. J. Org. Chem. 1958, 24, 504.
51. (c) Garst, J. F.; Ungvary, F.; Batlaw, R.; Lawrence, K. E. J. Am. Chem. Soc. 1991, 113, 6697.
52. Tamura, K.; Mizukami, H.; Maeda, K.; Watanabe, H.; Uneyama, K. J. Org. Chem. 1993, 58, 32.