Hybrid Surfactants with N-Heterocyclic Carbene Heads as a Multifunctional Platform for Interfacial Catalysis

Processing of substrates with different solvent compatibility is a persistent problem in homogeneous catalysis, in particular when one starting compound is water soluble and the other is not. A tempting concept found in literature is micellar catalysis. However, developing catalysts, which are surfactants at the same time, stands at its beginning. We report the synthesis of a new surfactant system with a N-heterocyclic carbene (NHC) moiety as a head group. Characteristic surfactant properties such as the formation of micelles or liquid crystals is documented. The new surfactant ligand forms coordination compounds with various metals, most importantly Pd2+ in square planar geometry. The Pd-NHC compound as well shows surfactant features, and can be used successfully for C-C cross coupling reactions (Suzuki, Heck). The boost in catalytic activity by one order of magnitude compared to analogous, but non-amphiphilic species is reported.