β-Bromodifluoromethyl β-enaminoketones: Versatile synthetic intermediates for synthesis of CF2-containing compounds

Tetrahedron Letters

Volumn 46, Issue 32, 2005, Pages 5357-5360

  Wu, Yong Ming ^a   Li, Ya ^a   Deng, Juan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Bromodifluoromethyl; Cyclization; Enaminoketones; Halophilic substitution

Indexed keywords

AMINE; CHLORIDE; FLUORINE DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 21844477870     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.002     Document Type: Article

References (27)

1. S. Fustero, M. Carcía de la Torre, and A. Simón Fuenters J. Org. Chem. 64 1999 5551 5556
2. C. Cimarelli, G. Palmieri, and E. Volpini Tetrahedron Lett. 45 2004 6629 6631
3. H.B. Yu, Q.S. Zhang, and W.Y. Huang Chin. J. Chem. 15 1997 278 282
4. P. Ollinger, W. Remp, and H. Junck Monatch. Chem. 105 1974 346 353
5. C. Cimarelli, and G. Palmieri Res. Dev. Org. Chem. 1 1997 179 189
6. G. Bartoli, G. Cimarelli, and G. Palmieri J. Chem. Soc., Perkin Trans. 1 1994 537 543
7. M.E.F. Braibante, H.S. Braibante, L. Missio, and A. Andricopulo Synthesis 9 1994 898 900
8. P.G. Baraldi, D. Simoni, and S. Manfredini Synthesis 1983 902
9. J.V. Greenhill Chem. Soc. Rev. 6 1977 277 294
10. G. Bartoli, C. Cimarelli, G. Palmieri, M. Bosco, and R. Dalpozzo Synthesis 10 1990 895 897
11. L.W. Hertel, J.S. Kroin, J.W. Misner, and J.M. Tustin J. Org. Chem. 53 1988 2406 2409
12. J. Chen, and Q.M. Hu J. Chem. Soc., Perkin Trans. 1 1994 1111 1114
13. S. Fustero, A. Bartolomé, and J. García Soler Org. Lett. 5 2003 2523 2526
14. A. Suzuki, M. Mae, H. Amii, and K. Uneyama J. Org. Chem. 69 2004 5132 5134
15. D.J. Burton, and Z.Y. Yang Tetrahedron 48 1992 189 275
16. Z.Y. Yang, and D.J. Burton J. Org. Chem. 56 1991 1037 1041
17. Y.M. Wu, Y. Li, and J. Deng J. Fluorine Chem. 126 2005 791 795
18. H.B. Yu, and W.Y. Huang J. Fluorine Chem. 84 1997 65 67
19. S. Fustero, E. Salavert, A. Navarro, and A. Simón Fuentes J. Org. Chem. 67 2002 4667 4679
20. Typical procedure: A flask fitted with a nitrogen inlet was charged with acetophenone (132 mg, 1.1 mmol), N-(p-methoxyphenyl) bromodifluoroacetimidoyl chloride 1 (298 mg, 1 mmol), sodium hydride (80 mg, 60% dispersion in mineral oil, 2 mmol) and 8 mL dry diethyl ether. The mixture was stirred for 24 h at 0°C. After standard work-up, the crude product was purified by flash column chromatography (5% ethyl acetate in petroleum) to give 2a (298 mg, 78%).
21. W.M. Peng, and S.Z. Zhu Tetrahedron 59 2003 4395 4404
22. M. Medebielle, K. Kato, and W.R. Dolbier Jr. Synlett 2002 1541 1543
23. C.D. Burkholder, W.R. Dolbier Jr., and M. Médebielle J. Org. Chem. 63 1998 5385 5394
24. C.D. Burkholder, W.R. Dolbier Jr., and M. Médebielle J. Fluorine Chem. 109 2001 39 48
25. J.V. Greenhill Chem. Soc. Rev. 6 1977 277 294
26. -3.
27. 4, concentrated and subjected to a column chromatography (5% ethyl acetate in petroleum) to give 3a (77 mg, 86%).