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

J Ichikawa, M Fujiwara, H Nawata, T Okauchi…

Index: Ichikawa, Junji; Fujiwara, Masaki; Nawata, Hideyuki; Okauchi, Tatsuo; Minami, Toru Tetrahedron Letters, 1996 , vol. 37, # 48 p. 8799 - 8802

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Citation Number: 40

Abstract

2, 2-Difluorovinyl p-toluenesulfonate, readily obtained from 2, 2, 2-trifluoroethanol, is treated with zirconocene equivalent “Cp2Zr” to generate the remarkably themostable nonsubstituted 2, 2-difluorovinylzirconocene, which in turn couples with aryliodides in the presence of palladium catalyst and zinc iodide to afford monosubstituted gem-difluoroolefins in high yields. The reaction proceeds via 2, 2-difluorovinylzinc as confirmed by 19F-NMR ...