A novel synthetic approach to fluorine-containing acetylenic compounds based on Nicholas reaction

Journal of Fluorine Chemistry

Volumn 127, Issue 4-5 SPEC. ISS., 2006, Pages 510-518

  Konno, Tsutomu ^a   Nagai, Go ^a   Ishihara, Takashi ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Dicobaltoctacarbonyl; Fluorine containing alkynes; Nicholas reaction; Propargyl acetates

Indexed keywords

EID: 33646425598     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2005.11.009     Document Type: Article

References (48)

1. For reviews, see
2. Welch J.T., and Eswarakrishnan S. Fluorine in Bioorganic Chemistry (1991), John Wiley and Sons, New York
3. In: Filler R., and Kobayashi Y. (Eds). Biomedicinal Aspects of Fluorine Chemistry (1982), Kodansha Limited/Elsevier Biomedical Press, Tokyo/New York
4. For reviews, see
5. Mikami K., Itoh Y., and Yamanaka M. Chem. Rev. 104 (2004) 1
6. Qiu X.-L., Meng W.-D., and Qing F.-L. Tetrahedron 60 (2004) 6711
7. Dave R., Badet B., and Meffre P. Amino Acids 24 (2003) 245
8. Steenis J.H.V., and Gen A.V.D. J. Chem. Soc., Perkin Trans. 1 (2002) 2117
9. Singh R.P., and Shreeve J.M. Tetrahedron 56 (2000) 7613
10. Prakach G.K.S., and Yudin A.K. Chem. Rev. 97 (1997) 757
11. McClinton M.A., and McClinton D.A. Tetrahedron 32 (1992) 6555
12. T. Konno, J. Chae, T. Tanaka, T. Ishihara, H. Yamanaka, J. Fluorine Chem. 127 (2006) 36.
13. Konno T., Daitoh T., Noiri A., Chae J., Ishihara T., and Yamanaka H. Tetrahedron 61 (2005) 9391
14. Konno T., Daitoh T., Noiri A., Chae J., Ishihara T., and Yamanaka H. Org. Lett. 6 (2004) 933
15. Konno T., Chae J., Tanaka T., Ishihara T., and Yamanaka H. Chem. Commun. (2004) 690
16. Konno T., Takehana T., Chae J., Ishihara T., and Yamanaka H. J. Org. Chem. 69 (2004) 2188
17. Chae J., Konno T., Kanda M., Ishihara T., and Yamanaka H. J. Fluorine Chem. 120 (2003) 185
18. T. Konno, J. Chae, T. Miyabe, T. Ishihara, J. Org. Chem. 74 (2005) 10172.
19. Konno T., Chae J., Ishihara T., and Yamanaka H. Tetrahedron 60 (2004) 11695
20. Konno T., Chae J., Ishihara T., and Yamanaka H. J. Org. Chem. 69 (2004) 8258
21. Chae J., Konno T., Ishihara T., and Yamanaka H. Chem. Lett. 33 (2004) 314
22. Qing F.-L., Gao W.-Z., and Ying J. J. Org. Chem. 65 (2000) 2003
23. Qing F.-L., and Gao W.-Z. Tetrahedron Lett. 41 (2000) 7727
24. Tamura K., Ishihara T., and Yamanaka H. J. Fluorine Chem. 68 (1994) 25
25. Hanamoto T., Hakoshima Y., and Egashira M. Tetrahedron Lett. 45 (2004) 7573
26. Porta P.L., Capuzzi L., and Bettarini F. Synthesis (1994) 287
27. Yamanaka H., Tamura K., Funabiki K., Fukunishi K., and Ishihara T. J. Fluorine Chem. 57 (1992) 177
28. Meazza G., and Zanardi G. J. Fluorine Chem. 55 (1991) 199
29. Hiyama T., and Sato K. Chem. Lett. (1990) 53
30. Allen A.D., Angelini G., Paradisi C., Stevenson A., and Tidwell T.T. Tetrahedron Lett. 30 (1989) 1315
31. Kuwabara M., Fukunishi K., Nomura M., and Yamanaka H. J. Fluorine Chem. 41 (1988) 227
32. Konno T., Chae J., Kanda M., Nagai G., Tamura K., Ishihara T., and Yamanaka H. Tetrahedron 59 (2003) 7571
33. Yoneda N., Matsuoka S., Miyaura N., Fukuhara T., and Suzuki A. Bull. Chem. Soc. Jpn. 63 (1990) 2124
34. Another methods for the preparation of the fluorine-containing alkynes having an aromatic side chain are as follows
35. Bunch J.E., and Bumgardner C.L. J. Fluorine Chem. 36 (1987) 317
36. Hiyama T., Sato K., and Fujita M. Bull. Chem. Soc. Jpn. 62 (1989) 1352
37. Maezza G., Capuzzi L., and Piccardi P. Synthesis (1989) 331
38. Kobayashi Y., Yamashita T., Takahashi K., Kuroda H., and Kumadaki I. Tetrahedron Lett. 23 (1982) 343
39. Brindon A.K., and Crossley I.R. Chem. Commun. (2002) 2420
40. Yamazaki T., Mizutani K., and Kitazume T. J. Org. Chem. 60 (1995) 6046
41. Jennings M.P., Cork E.A., and Ramachandran P.V. J. Org. Chem. 65 (2000) 8763
42. For reviews, see
43. Teobald B.J. Tetrahedron 58 (2002) 4133
44. Fletcher A.J., and Christie S.D.R. J. Chem. Soc., Perkin Trans. 1 (2000) 1657
45. Nicholas K.M. Acc. Chem. Res. 20 (1987) 207
46. Betancort J.M., Martín T., Palazón J.M., and Martín V.S. J. Org. Chem. 68 (2003) 3216
47. Magnus P., Carter R., Davies M., Elliott J., and Pitterna T. Tetrahedron 52 (1996) 6283
48. Magnus P., and Fairhurst R. J. Chem. Soc., Chem. Commun. (1994) 1541