Pentafluoroethylated Compounds of Silicon, Germanium and Tin

In this contribution we present an account on pentafluoroethylated compounds of silicon, germanium and tin. The pronounced electron-withdrawing effect of the pentafluoroethyl group leads to a markedly increased Lewis acidity at the central atom which results in the stabilization of hypervalent complexes, anionic element(II) species as well as remarkable reactivities of element-element and element-hydrogen bonds. By addition to unsaturated C-C bonds or by reaction with organic halides as well as transition-metal complexes the molecules bearing a pentafluoroethyl-element group are readily accessible. Moreover, the utilization of pentafluoroethyl groups facilitates the formation of donor-stabilized germylenes and stannylenes. A series of such compounds serves as suitable pentafluoroethylation reagents. Conversely to the well-studied trifluoromethyl derivatives these compounds frequently exhibit a higher thermostability, which allows a more convenient handling.