Novel 2,2-difluorovinylzirconocene: A facile synthesis of monosubstituted gem-difluoroolefins via its cross-coupling reaction

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8799-8802

  Ichikawa, Junji ^a   Fujiwara, Masaki ^a   Nawata, Hideyuki ^a   Okauchi, Tatsuo ^a   Minami, Toru ^a  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ORGANOFLUORINE DERIVATIVE; ZIRCONIUM;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030602226     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02035-7     Document Type: Article

References (41)

1. 1. Burton, D. J.; Yang, Z. -Y.; Morken, P. A. Tetrahedron 1994, 50, 2993-3063. Normant, J. F. J. Organomet. Chem. 1990, 400, 19-34.
2. 1. Burton, D. J.; Yang, Z. -Y.; Morken, P. A. Tetrahedron 1994, 50, 2993-3063. Normant, J. F. J. Organomet. Chem. 1990, 400, 19-34.
3. 2. (a) Hudlicky, M. Chemistry of Organic Fluorine Compounds, 2nd ed; Ellis Horwood: Chichester, 1976; Chaps. 5 and 9.
4. (b) Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683.
5. 3. Moore, W. R.; Schatzman, G. L.; Jarvi, E. T.; Gross, R. S.; McCarthy, J. R. J. Am. Chem. Soc. 1992, 114, 360-361. Bey, P.; McCarthy, J. R.; McDonald, I. A. In Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991; pp 105-133.
6. 3. Moore, W. R.; Schatzman, G. L.; Jarvi, E. T.; Gross, R. S.; McCarthy, J. R. J. Am. Chem. Soc. 1992, 114, 360-361. Bey, P.; McCarthy, J. R.; McDonald, I. A. In Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991; pp 105-133.
7. 3: Morken, P. A.; Burton, D. J. J. Org. Chem. 1993, 58, 1167-1172. See also: Jiang, B.; Xu, Y. J. Org. Chem. 1991, 56, 7336-7340. X = aryl: Ishihara, T.; Yamana, M.; Ando, T. Tetrahedron Lett. 1983, 24, 5657-5660. X = O-phosphazene: Allcock, H. R.; Suszko, P. R.; Evans, T. L. Organometallics 1982, 1, 1443-1449.
8. 3: Morken, P. A.; Burton, D. J. J. Org. Chem. 1993, 58, 1167-1172. See also: Jiang, B.; Xu, Y. J. Org. Chem. 1991, 56, 7336-7340. X = aryl: Ishihara, T.; Yamana, M.; Ando, T. Tetrahedron Lett. 1983, 24, 5657-5660. X = O-phosphazene: Allcock, H. R.; Suszko, P. R.; Evans, T. L. Organometallics 1982, 1, 1443-1449.
9. 3: Morken, P. A.; Burton, D. J. J. Org. Chem. 1993, 58, 1167-1172. See also: Jiang, B.; Xu, Y. J. Org. Chem. 1991, 56, 7336-7340. X = aryl: Ishihara, T.; Yamana, M.; Ando, T. Tetrahedron Lett. 1983, 24, 5657-5660. X = O-phosphazene: Allcock, H. R.; Suszko, P. R.; Evans, T. L. Organometallics 1982, 1, 1443-1449.
10. 3: Morken, P. A.; Burton, D. J. J. Org. Chem. 1993, 58, 1167-1172. See also: Jiang, B.; Xu, Y. J. Org. Chem. 1991, 56, 7336-7340. X = aryl: Ishihara, T.; Yamana, M.; Ando, T. Tetrahedron Lett. 1983, 24, 5657-5660. X = O-phosphazene: Allcock, H. R.; Suszko, P. R.; Evans, T. L. Organometallics 1982, 1, 1443-1449.
11. 3: Morken, P. A.; Burton, D. J. J. Org. Chem. 1993, 58, 1167-1172. See also: Jiang, B.; Xu, Y. J. Org. Chem. 1991, 56, 7336-7340. X = aryl: Ishihara, T.; Yamana, M.; Ando, T. Tetrahedron Lett. 1983, 24, 5657-5660. X = O-phosphazene: Allcock, H. R.; Suszko, P. R.; Evans, T. L. Organometallics 1982, 1, 1443-1449.
12. 3: Morken, P. A.; Burton, D. J. J. Org. Chem. 1993, 58, 1167-1172. See also: Jiang, B.; Xu, Y. J. Org. Chem. 1991, 56, 7336-7340. X = aryl: Ishihara, T.; Yamana, M.; Ando, T. Tetrahedron Lett. 1983, 24, 5657-5660. X = O-phosphazene: Allcock, H. R.; Suszko, P. R.; Evans, T. L. Organometallics 1982, 1, 1443-1449.
13. 3: Morken, P. A.; Burton, D. J. J. Org. Chem. 1993, 58, 1167-1172. See also: Jiang, B.; Xu, Y. J. Org. Chem. 1991, 56, 7336-7340. X = aryl: Ishihara, T.; Yamana, M.; Ando, T. Tetrahedron Lett. 1983, 24, 5657-5660. X = O-phosphazene: Allcock, H. R.; Suszko, P. R.; Evans, T. L. Organometallics 1982, 1, 1443-1449.
14. 3: Morken, P. A.; Burton, D. J. J. Org. Chem. 1993, 58, 1167-1172. See also: Jiang, B.; Xu, Y. J. Org. Chem. 1991, 56, 7336-7340. X = aryl: Ishihara, T.; Yamana, M.; Ando, T. Tetrahedron Lett. 1983, 24, 5657-5660. X = O-phosphazene: Allcock, H. R.; Suszko, P. R.; Evans, T. L. Organometallics 1982, 1, 1443-1449.
15. 3: Morken, P. A.; Burton, D. J. J. Org. Chem. 1993, 58, 1167-1172. See also: Jiang, B.; Xu, Y. J. Org. Chem. 1991, 56, 7336-7340. X = aryl: Ishihara, T.; Yamana, M.; Ando, T. Tetrahedron Lett. 1983, 24, 5657-5660. X = O-phosphazene: Allcock, H. R.; Suszko, P. R.; Evans, T. L. Organometallics 1982, 1, 1443-1449.
16. 3: Morken, P. A.; Burton, D. J. J. Org. Chem. 1993, 58, 1167-1172. See also: Jiang, B.; Xu, Y. J. Org. Chem. 1991, 56, 7336-7340. X = aryl: Ishihara, T.; Yamana, M.; Ando, T. Tetrahedron Lett. 1983, 24, 5657-5660. X = O-phosphazene: Allcock, H. R.; Suszko, P. R.; Evans, T. L. Organometallics 1982, 1, 1443-1449.
17. 5. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 5437-5438. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379-6382. Ichikawa, J.; Moriya, T.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1991, 961-964. Ichikawa, J.; Hamada, S.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 337-340. Ichikawa, J.; Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 3779-3782. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739-740. Ichikawa, J.; Yonemaru, S.; Minami, T. Synlett 1992, 833-834. Ichikawa, J.; Ikeura, C.; Minami, T. J. Fluorine Chem. 1993, 63, 281-285. Ichikawa, J.; Miyazaki, S.; Fujiwara, M.; Minami, T. J. Org. Chem. 1995, 60, 2320-2321.
18. 5. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 5437-5438. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379-6382. Ichikawa, J.; Moriya, T.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1991, 961-964. Ichikawa, J.; Hamada, S.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 337-340. Ichikawa, J.; Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 3779-3782. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739-740. Ichikawa, J.; Yonemaru, S.; Minami, T. Synlett 1992, 833-834. Ichikawa, J.; Ikeura, C.; Minami, T. J. Fluorine Chem. 1993, 63, 281-285. Ichikawa, J.; Miyazaki, S.; Fujiwara, M.; Minami, T. J. Org. Chem. 1995, 60, 2320-2321.
19. 5. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 5437-5438. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379-6382. Ichikawa, J.; Moriya, T.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1991, 961-964. Ichikawa, J.; Hamada, S.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 337-340. Ichikawa, J.; Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 3779-3782. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739-740. Ichikawa, J.; Yonemaru, S.; Minami, T. Synlett 1992, 833-834. Ichikawa, J.; Ikeura, C.; Minami, T. J. Fluorine Chem. 1993, 63, 281-285. Ichikawa, J.; Miyazaki, S.; Fujiwara, M.; Minami, T. J. Org. Chem. 1995, 60, 2320-2321.
20. 5. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 5437-5438. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379-6382. Ichikawa, J.; Moriya, T.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1991, 961-964. Ichikawa, J.; Hamada, S.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 337-340. Ichikawa, J.; Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 3779-3782. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739-740. Ichikawa, J.; Yonemaru, S.; Minami, T. Synlett 1992, 833-834. Ichikawa, J.; Ikeura, C.; Minami, T. J. Fluorine Chem. 1993, 63, 281-285. Ichikawa, J.; Miyazaki, S.; Fujiwara, M.; Minami, T. J. Org. Chem. 1995, 60, 2320-2321.
21. 5. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 5437-5438. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379-6382. Ichikawa, J.; Moriya, T.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1991, 961-964. Ichikawa, J.; Hamada, S.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 337-340. Ichikawa, J.; Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 3779-3782. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739-740. Ichikawa, J.; Yonemaru, S.; Minami, T. Synlett 1992, 833-834. Ichikawa, J.; Ikeura, C.; Minami, T. J. Fluorine Chem. 1993, 63, 281-285. Ichikawa, J.; Miyazaki, S.; Fujiwara, M.; Minami, T. J. Org. Chem. 1995, 60, 2320-2321.
22. 5. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 5437-5438. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379-6382. Ichikawa, J.; Moriya, T.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1991, 961-964. Ichikawa, J.; Hamada, S.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 337-340. Ichikawa, J.; Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 3779-3782. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739-740. Ichikawa, J.; Yonemaru, S.; Minami, T. Synlett 1992, 833-834. Ichikawa, J.; Ikeura, C.; Minami, T. J. Fluorine Chem. 1993, 63, 281-285. Ichikawa, J.; Miyazaki, S.; Fujiwara, M.; Minami, T. J. Org. Chem. 1995, 60, 2320-2321.
23. 5. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 5437-5438. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379-6382. Ichikawa, J.; Moriya, T.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1991, 961-964. Ichikawa, J.; Hamada, S.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 337-340. Ichikawa, J.; Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 3779-3782. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739-740. Ichikawa, J.; Yonemaru, S.; Minami, T. Synlett 1992, 833-834. Ichikawa, J.; Ikeura, C.; Minami, T. J. Fluorine Chem. 1993, 63, 281-285. Ichikawa, J.; Miyazaki, S.; Fujiwara, M.; Minami, T. J. Org. Chem. 1995, 60, 2320-2321.
24. 5. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 5437-5438. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379-6382. Ichikawa, J.; Moriya, T.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1991, 961-964. Ichikawa, J.; Hamada, S.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 337-340. Ichikawa, J.; Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 3779-3782. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739-740. Ichikawa, J.; Yonemaru, S.; Minami, T. Synlett 1992, 833-834. Ichikawa, J.; Ikeura, C.; Minami, T. J. Fluorine Chem. 1993, 63, 281-285. Ichikawa, J.; Miyazaki, S.; Fujiwara, M.; Minami, T. J. Org. Chem. 1995, 60, 2320-2321.
25. 5. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 5437-5438. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379-6382. Ichikawa, J.; Moriya, T.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1991, 961-964. Ichikawa, J.; Hamada, S.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 337-340. Ichikawa, J.; Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 3779-3782. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739-740. Ichikawa, J.; Yonemaru, S.; Minami, T. Synlett 1992, 833-834. Ichikawa, J.; Ikeura, C.; Minami, T. J. Fluorine Chem. 1993, 63, 281-285. Ichikawa, J.; Miyazaki, S.; Fujiwara, M.; Minami, T. J. Org. Chem. 1995, 60, 2320-2321.
26. 5. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 5437-5438. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 6379-6382. Ichikawa, J.; Moriya, T.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1991, 961-964. Ichikawa, J.; Hamada, S.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 337-340. Ichikawa, J.; Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 3779-3782. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739-740. Ichikawa, J.; Yonemaru, S.; Minami, T. Synlett 1992, 833-834. Ichikawa, J.; Ikeura, C.; Minami, T. J. Fluorine Chem. 1993, 63, 281-285. Ichikawa, J.; Miyazaki, S.; Fujiwara, M.; Minami, T. J. Org. Chem. 1995, 60, 2320-2321.
27. 6. Electrophiles with which 2,2-difluorovinyllithium reacts are limited to carbonyl compounds. Gillet, J. P.; Sauvêtre, R.; Normant, J. F. Synthesis 1982, 297-301. Sauvêtre, R.; Normant, J. F. Tetrahedron Lett. 1982, 23, 4325-4328. Drakesmith, F. G.; Richardson, R. D.; Stewart, O. J.; Tarrant, P. J. Org. Chem. 1968, 35, 286-291.
28. 6. Electrophiles with which 2,2-difluorovinyllithium reacts are limited to carbonyl compounds. Gillet, J. P.; Sauvêtre, R.; Normant, J. F. Synthesis 1982, 297-301. Sauvêtre, R.; Normant, J. F. Tetrahedron Lett. 1982, 23, 4325-4328. Drakesmith, F. G.; Richardson, R. D.; Stewart, O. J.; Tarrant, P. J. Org. Chem. 1968, 35, 286-291.
29. 6. Electrophiles with which 2,2-difluorovinyllithium reacts are limited to carbonyl compounds. Gillet, J. P.; Sauvêtre, R.; Normant, J. F. Synthesis 1982, 297-301. Sauvêtre, R.; Normant, J. F. Tetrahedron Lett. 1982, 23, 4325-4328. Drakesmith, F. G.; Richardson, R. D.; Stewart, O. J.; Tarrant, P. J. Org. Chem. 1968, 35, 286-291.
30. 7. Gillet, J. P.; Sauvêtre, R.; Normant, J. F. Synthesis 1986, 538-543.
31. 8. Hanzawa, Y.; Ito, H.; Taguchi, T. Synlett 1995, 299-305 and references therein.
32. 9. (a) Ito, H.; Nakamura, T.; Taguchi, T.; Hanzawa, Y. Tetrahedron 1995, 51, 4507-4518.
33. (b) Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040. See also:
34. (c) Takahashi, T.; Kondakov, D. Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871-5872 and references therein.
35. 9b
36. 11. Butyllithium should be added dropwise over 10 min to a THF solution of 1 at -78 °C.
37. 12. Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829-2832.
38. 13. For the reports on transmetalation of organozirconiums, see: Zr to Cu: Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154-5155 and references therein. Zr to Zn: Negishi, E.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 100, 2254-2256.
39. 13. For the reports on transmetalation of organozirconiums, see: Zr to Cu: Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154-5155 and references therein. Zr to Zn: Negishi, E.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 100, 2254-2256.
40. +); found 185.0333.
41. 2Zr" probably acted as a chloride source to generate 8.