Since the first synthesis of an ylide and their use in Wittig-type reactions these compounds have been applied in a variety of important reactions. In recent years, bisylidic compounds such as carbodiphosphoranes have found renewed interest due to their unique electronic structure and donor properties. While the bonding situation in these compounds is still under debate, their strong donor capacity has been demonstrated such as by the coordination of small molecules or ions such as CO2, BH3 or GeCl+, or their use in bond activation reactions. Our group has become interested in the class of metalated ylides, the so-called yldiides. They can be viewed as the anionic congeners of bisylides, formed by replacement of one positively charged onium moiety (e.g. a phosphonium group) by a neutral substituent. Comparable to bisylides, metalated ylides possess two pairs of electrons at the central carbon atom and can thus act as monoanionic X,L-type σ- and π-donor ligands (Figure 1). In the past years, we were able to demonstrate that also metalated ylides are readily isolable ligands with fascinating donor properties. In this presentation, the preparation and electronic structure of metalated ylides as well as synthetic applications will be discussed.

Metalated ylides: Unique donor ligands for main group chemistry

255th National Meeting (2018)

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