On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5

Wiesemann M, Klösener J, Neumann B, Stammler H-G, Hoge B (2018)
CHEMISTRY-A EUROPEAN JOURNAL 24(8): 1838-1843.

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Abstract
Pentafluoroethyllithium, LiC2F5, has been established as an efficient and versatile reagent for the transfer of the pentafluoroethyl unit to a number of electrophiles. Here, the stability of this species up to -40 degrees C is of advantage, particularly in comparison to its smaller congener LiCF3. The usual production of LiC2F5, however, from gaseous HC2F5 or IC2F5 and strong bases requires specially designed apparatuses, which severely impeded its value as a laboratory reagent. In this contribution we communicate an alternative gas-free and highly efficient protocol for the synthesis of LiC2F5 from the already commercialized stannate salt [PPh4][Sn(C2F5)(5)]. The [Sn(C2F5)(5)](-) anion represents not only the first example of a structurally characterized hypervalent pentaalkylstannate but also serves as a precursor for the synthesis of the homoleptic tetrakis(pentafluoroethyl)stannane, Sn(C2F5)(4). The reaction of the latter with n-butyllithium provides an insight into the mechanism of LiC2F5 generation.
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Wiesemann M, Klösener J, Neumann B, Stammler H-G, Hoge B. On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5. CHEMISTRY-A EUROPEAN JOURNAL. 2018;24(8):1838-1843.
Wiesemann, M., Klösener, J., Neumann, B., Stammler, H. - G., & Hoge, B. (2018). On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5. CHEMISTRY-A EUROPEAN JOURNAL, 24(8), 1838-1843. doi:10.1002/chem.201704807
Wiesemann, M., Klösener, J., Neumann, B., Stammler, H. - G., and Hoge, B. (2018). On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5. CHEMISTRY-A EUROPEAN JOURNAL 24, 1838-1843.
Wiesemann, M., et al., 2018. On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5. CHEMISTRY-A EUROPEAN JOURNAL, 24(8), p 1838-1843.
M. Wiesemann, et al., “On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 24, 2018, pp. 1838-1843.
Wiesemann, M., Klösener, J., Neumann, B., Stammler, H.-G., Hoge, B.: On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5. CHEMISTRY-A EUROPEAN JOURNAL. 24, 1838-1843 (2018).
Wiesemann, Markus, Klösener, Johannes, Neumann, Beate, Stammler, Hans-Georg, and Hoge, Berthold. “On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)(5)](-), and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5”. CHEMISTRY-A EUROPEAN JOURNAL 24.8 (2018): 1838-1843.
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