An efficient stereoselective preparation of cis-perfluoroalkenylzinc reagents [(E)-RFCF{double bond, long}CFZnCl] by the metallation of 1H,1H-perfluoroalkanes and their derivatization to cis-1-arylperfluoroalkenes [(Z)-RFCF{double bond, long}CFAr]

Journal of Fluorine Chemistry

Volumn 127, Issue 4-5 SPEC. ISS., 2006, Pages 456-470

  Raghavanpillai, Anilkumar ^a   Burton, Donald J ^a  

^a E11 SSH   (United States)

Author keywords

1 Arylperfluoroalkenes; 1 Iodoperfluoroalkenes; 1H,1H Perfluoroalkanes; Dehydrofluorination; LHMDS; Pd(0) coupling; Perfluoroalkenylzinc

Indexed keywords

EID: 33646414808     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2005.12.022     Document Type: Article

References (74)

1. Hiyama T. Organofluorine Compounds: Chemistry and Applications (2000), Springer-Verlag, Berlin pp. 183-233 [Chapter 6]
2. Hiyama T. Organofluorine Compounds: Chemistry and Applications (2000), Springer-Verlag, Berlin pp. 137-177 [Chapter 5]
3. In: Banks R.E., Smart B.E., and Tatlow J.C. (Eds). Organofluorine Chemistry: Principles and Commercial Applications (1994), Plenum Press, New York
4. Schmiegel W.W. In: Hudlicky M., and Pavalath A.E. (Eds). Organic Fluoropolymers in Chemistry of Organic Fluorine Compounds II: A Critical Review, ACS Monograph (1995), ACS 1101-1125
5. Burton D.J., Yang Z.Y., and Qiu W. Chem. Rev. 96 (1996) 1641-1716 and references cited therein
6. Tsai H.J., Thenappan A., and Burton D.J. J. Org. Chem. 59 (1994) 7085-7091
7. Martinet P., Sauvetre R., and Normant J.F. Bull. Soc. Chim. Fr. 127 (1990) 86-92
8. Tozer M.J., and Herpin T.F. Tetrahedron 52 (1996) 8619-8683
9. Leroy J. J. Org. Chem. 46 (1981) 206-209
10. Camps F., Coll J., Fabrias G., and Guerrero A. Tetrahedron 40 (1984) 2871-2878
11. Bessiere Y., Savary D.H., and Schlosser M. Helv. Chim. Acta 60 (1977) 1739-1747
12. McCarthy J.R., Mathews D.P., Stemerick D.M., Huber E.W., Bey P., Lipper B.J., Snyder R.D., and Sunkara P.S. J. Am. Chem. Soc. 113 (1991) 7439-7440
13. Mathews D.P., Millers S.C., Jarvi E.T., Sabol J.S., and McCarthy J.R. Tetrahedron Lett. 34 (1993) 3057-3060
14. Moore W.R., Schatzman G.L., Jarvi E.T., Gross R.S., and McCarthy J.R. J. Am. Chem. Soc. 114 (1992) 360-361
15. Allmendinger T. Tetrahedron 47 (1991) 4905-4914
16. Ctemenceau D., and Cousseau J. Tetrahedron Lett. 34 (1993) 6903-6906
17. Reutrackul V., and Rukachaisririkul V. Tetrahedron Lett. 24 (1983) 725-728
18. Purrington S.T., and Pittman J.H. Tetrahedron Lett. 28 (1987) 3901-3904
19. Boys M.L., Colington E.W., Finch H., Swanson S., and Whitehead J.F. Tetrahedron Lett. 29 (1988) 3365-3368
20. Kawasaki T., Ichige T., and Kitazume T. J. Org. Chem. 63 (1998) 7525-7528
21. Hayashi S., Nakai T., Ishikawa N., Burton D.J., Naae D.G., and Kesling H.S. Chem. Lett. (1979) 983-986
22. Vinson W.A., Prikett K.S., Spanic B., and Ortiz de Montellano P.R. J. Org. Chem. 48 (1983) 4661-4668
23. Ishihara T., and Kuroboshi M. Chem. Lett. (1987) 1145-1148
24. Tellier F., Sauvetre R., and Normant J.F. J. Organometall. Chem. 303 (1986) 309-315
25. Kuroboshi M., Yamada N., Takebe Y., and Hiyama T. Tetrahedron Lett. 36 (1995) 6271-6274
26. Burton D.J., Yang Z.Y., and Morken P.A. Tetrahedron 50 (1994) 2993-3063
27. Xue L., Lu L., Pederson S.D., Liu Q., Narske R.M., and Burton D.J. J. Org. Chem. 62 (1997) 1064-1071
28. Davis C.R., and Burton D.J. J. Org. Chem. 62 (1997) 9217-9222
29. Liu Q., and Burton D.J. Org. Lett. 4 (2002) 1483-1485
30. Lim C., Burton D.J., and Wesolowski C.A. J. Fluorine Chem. 119 (2003) 21-26
31. Burdon J., Coe P.L., Haslock I.B., and Powell R.L. Chem. Commun. (1996) 49-50
32. Burdon J., Coe P.L., Haslock I.B., and Powell R.L. J. Fluorine Chem. 99 (1999) 127-131
33. Anilkumar R., and Burton D.J. Tetrahedron Lett. 43 (2002) 2731-2733
34. Raghavanpillai A., and Burton D.J. J. Org. Chem. 69 (2004) 7083-7091
35. Anilkumar R., and Burton D.J. Tetrahedron Lett. 43 (2002) 6979-6982
36. Anilkumar R., and Burton D.J. J. Fluorine Chem. 126 (2005) 833-841
37. Anilkumar R., and Burton D.J. J. Fluorine Chem. 125 (2004) 561-566
38. Anilkumar R., and Burton D.J. J. Fluorine Chem. 126 (2005) 455-461
39. Dixon S. J. Org. Chem. 21 (1956) 400-403
40. Knunyants I.L., German L.S., and Dyatkin B.L. Izv. Akad. Nauk. SSSR, Ser. Khim. (1960) 221-230
41. Fialkaov Yu.A., and Yagupolskii L.M. Zhurn. Obshch. Khim. 36 (1966) 1968-1976
42. Dmowski W. J. Fluorine Chem. 18 (1981) 25-30
43. Albadri R., Moreau P., and Commeyras A. Nouveu J. Chim. 6 (1982) 581-587
44. Moreau P., Albadri R., and Commeyras A. Nouveu J. Chim. 1 (1977) 497-502
45. Dmowski W. J. Fluorine Chem. 15 (1980) 299-313
46. Dmowski W. J. Fluorine Chem. 21 (1982) 201-219
47. Dmowski W. J. Fluorine Chem. 26 (1984) 223-241
48. Dmowski W. J. Fluorine Chem. 29 (1985) 273-286
49. Dmowski W. J. Fluorine Chem. 29 (1985) 287-296
50. Dmowski W. J. Fluorine Chem. 26 (1984) 379-394
51. Dmowski W. Polish J. Chem. 60 (1986) 129-141
52. Nguyen T., Rubienstein M., and Wakselman C. J. Fluorine Chem. 11 (1978) 573-589
53. Heinze P.L., and Burton D.J. J. Fluorine Chem. 31 (1986) 115-119
54. Heinze P.L., and Burton D.J. J. Org. Chem. 53 (1988) 2714-2720
55. Hansen S.W., Spawn D.T., and Burton D.J. J. Fluorine Chem. 35 (1987) 415-420
56. Kuroboshi M., and Hiyama T. Chem. Lett. (1990) 1607-1610
57. Anilkumar R., and Burton D.J. Tetrahedron Lett. 44 (2003) 6661-6664
58. Anilkumar R., and Burton D.J. J. Fluorine Chem. 126 (2005) 1174-1184
59. Burton D.J., Spawn T.D., Heinze P.L., Bailey A.R., and Shin-Ya S. J. Fluorine Chem. 44 (1989) 167-174
60. Burton D.J., Shin-Ya S., and Howells R.D. J. Am. Chem. Soc. 101 (1979) 3689-3690
61. Burton D.J., and Cox D.G. J. Am. Chem. Soc. 105 (1983) 650-651
62. Burton D.J., Shin-Ya S., and Howells R.D. J. Fluorine Chem. 15 (1980) 543-546
63. Filyakova T.I., Belen'kii G.G., Lur'e E.P., Zapevalov A.Ya., Kolenko I.P., and German L.S. Izv. Akad. Nauk. SSSR, Ser. Khim. (1979) 681-683
64. Filyakova T.I., Zapevalov A.I., Kodess M.I., Kurykin M.A., and German L.S. Izv. Akad. Nauk. SSSR, Ser. Khim. (1994) 1614-1619
65. Frohn H.-J., and Bardin V.V.Z. Anorg. Allg. Chem. 627 (2001) 2499-2505
66. Frohn H.-J., and Bardin V.V.Z. J. Fluorine Chem. 123 (2004) 43-49
67. T. Mitsuru, N. Yoshitaka, F. Satoshi, JP 88-321935 (1990) (Chem. Abstr. 113: 190741).
68. Mikami K., Itoh Y., and Yamanaka M. Chem. Rev. 104 (2004) 1-16 and references cited therein
69. Brace N.O., Marshall L.W., Pinson C.J., and Wingerden G. J. Org. Chem. 49 (1984) 2361-2368
70. Hahnfeld J.L., and Burton D.J. Tetrahedron Lett. (1975) 773-776
71. Heinze P.L., Spawn T.D., Burton D.J., and Shin-Ya S. J. Fluorine Chem. 38 (1988) 131-134
72. Howells R.D., and Gilman H. J. Fluorine Chem. 5 (1975) 99-114
73. Thoai N. J. Fluorine Chem. 5 (1975) 115-125
74. Coulson D.R. Inorg. Synth. 13 (1972) 121-124