Fluoride ion-initiated α-fluorovinylation of carbonyl compounds with α-fluorovinyldiphenylmethylsilane

Abstract

α-Fluorovinyldiphenylmethylsilane was synthesized in one step from 1,1-difluoroethylene; the TBAF-initiated reaction of the silane with carbonyl compounds smoothly proceeded to give the corresponding α-fluoroallylic alcohols in good yields.

References

1. T. Allmendinger, C. Angst and H. Karfunkel, J. Fluorine Chem., 1995, 72, 247.
2. D. J. Burton, Z.-Y. Yang and P. A. Morken, Tetrahedron, 1994, 50, 2993.
3. The synthesis of α-fluorovinyltributyltin has been reported. However, no reaction with carbonyl compounds has been reported D. P. Matthews, P. P. Waid, J. S. Sabol and J. R. McCarthy, Tetrahedron Lett., 1994, 35, 5177.
4. A use of a similar methodology has been reported M. Fujita, M. Obayashi and T. Hiyama, Tetrahedron, 1988, 44, 4135; G. K. S. Prakash, R. Krishnamurti and G. A. Olah, J. Am. Chem. Soc., 1989, 111, 393.
5. Alternative methods to prepare α-fluoroallylic alcohols have been reported T. Ernet and G. Haufe, Synthesis, 1997, 953; T. Dubuffet, C. Bidon, P. Martinet, R. Sauvêtre and J.-F. Normant, J. Organomet. Chem., 1990, 393, 161.
6. T. Hanamoto, Y. Kiguchi, K. Shindo, M. Matsuoka and M. Kondo, Chem. Commun, 1999, 151.
7. We modified the preparation of the phenyldimethylsilyllithium reagent I. Fleming, R. S. Roberts and S. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1998, 1209.
8. S. A. Fontana, C. R. Davis, Y.-B. He and D. J. Burton, Tetrahedron, 1996, 52, 37.