N-phosphanyl-imidazolin-2-ylidenes: Novel stable carbenes as bidentate ligands for late transition metals

•Stable, free N-phosphanyl-imidazolin-2-ylidene carbenes have been prepared.•The carbenes form stable complexes with Ag(I).•The Ag(I) complexes can transfer the carbene ligands to other metal centres (Cu, Au).

N-phosphorylated, N-heterocyclic carbenes (NHC) based on the imidazoline skeleton have been prepared for the first time. The free carbenes feature good stability and in best cases they can be stored in the solid state for months at ambient temperature without decomposition. The carbenes are capable of acting as ligands towards late transition metal centres such as silver(I). The resulting complexes are stable and can be employed as reagents for the preparation of complexes of other group 11 metals upon transmetallation. The complexes, one carbene ligand and related compounds have all been structurally characterized.

Graphical abstractThe title carbenes have been prepared for the first time: they feature good stability and are capable of acting as ligands towards group 11 metal centres forming dinuclear complexes. Figure optionsDownload full-size imageDownload as PowerPoint slide