A facile and mild method for the synthesis of terminal bromofluoroolefins via diethylzinc-promoted wittig reaction

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2101-2104

  Lei, Xinsheng ^a   Dutheuil, Guillaume ^a   Pannecoucke, Xavier ^a   Quirion, Jean Charles ^a  

^a Normandie Université   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; CARBONYL DERIVATIVE; KETONE DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CHEMICAL REACTION; HORNER REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 3142694860     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049742d     Document Type: Article

References (21)

1. Yokokoji, O.; Shimizu, T.; Koh, H.; Kumai, S. The 14th International Symposium on Fluorine Chemistry; July 31-Aug. 5, Yokohama, Japan, 1994; P300.
2. Takeuchi, Y.; Yamada, A.; Suzuki, T.; Koizumi, T. Tetrahedron 1996, 52, 225-232.
3. Wnuk, S. F.; Valdez, C. A.; Khan, J.; Moutinho, D.; Robins, M. J.; Yang, X.; Borchardt, R. T.; Balzarini, J.; De Clercq, E. J. Med. Chem. 2000, 43, 1180-1186.
4. Chen, C.; Wilcoxen, K.; Huang, C. Q.; Strack, N.; McCarthy, J. R. J. Fluorine Chem. 2000, 101, 285-290.
5. Zhang, X.; Burton, D. J. J. Fluorine Chem. 2001, 112, 47-54.
6. Xu, J.; Burton, D. J. Org. Lett. 2002, 4, 831-833.
7. Shimizu, M.; Yamada, N.; Takebe, Y.; Hata, T.; Kuroboshi, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1998, 71, 2903-2921.
8. Burton, D. J.; Yang, Z.-Y.; Qiu, W. Chem. Rev. 1996, 96, 1641-1715.
9. Eddarir, S.; Francesch, C.; Mestdagh, H.; Rolando, C. Bull. Soc. Chim. Fr. 1997, 134, 741-755.
10. Kuroboshi, M.; Yamada, N.; Takebe, Y.; Hiyama, T. Tetrahedron Lett. 1995, 36, 6271-6274.
11. Burton, D. J. J. Fluorine Chem. 1983, 23, 339-357.
12. Vanderhaar, R. W.; Burton, D. J.; Naae, D. G. J. Fluorine Chem. 1971/1972, 1, 381-383.
13. Naae, D. G.; Kesling, H. S.; Burton, D. J. Tetrahedron Lett. 1975, 3789-3792.
14. Hata, T.; Kitagawa, H.; Shimizu, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 1691-1695.
15. Aggarwal, V. K.; Ali, A.; Coogan, M. P. J. Org. Chem. 1997, 62, 8628-8629.
16. To a solution of triphenylphosphine (2.4 mmol, 1.2 equiv), tribromofluoromethane (2.4 mmol, 1.2 equiv), and an appropriate aldehyde or ketone (2.0 mmol, 1.0 equiv) in anhydrous THF (30-40 mL) was added a solution of diethylzinc in hexanes or toluene (2.4 mmol, 1.2 equiv) dropwise via a syringe pump over 30 min at room temperature under argon. The mixture was stirred at room temperature for 30 min. The resulting solution was then quenched with methanol (10 mL), stirred for 30 min, and concentrated under reduced pressure. The residue was then chromatographed on silica gel (eluent: cyclohexane/ethyl acetate), affording the desired bromofluoroolefins.
17. Xu, J.; Burton, D. J. Tetrahedron Lett. 2002, 43, 2877-2879.
18. Chen, C.; Wilcoxen, K.; Huang, C. Q.; Strack, N.; McCarthy, J. R. J. Fluorine Chem. 2000, 101, 285-290.
19. Chen, C.; Wilcoxen, K.; Strack, N.; McCarthy, J. R. Tetrahedron Lett. 1999, 40, 827-830.
20. Ratovelomanana, V.; Rollin, Y.; Gébéhenne, C.; Gosmini, C.; Perichon, J. Tetrahedron Lett. 1994, 35, 4777-4780.
21. Xu, J.; Burton, D. J. J. Fluorine Chem. 2001, 112, 47-54.