N-Heterocyclic Olefins: An Investigation into a Developing Class of Ligands
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Abstract
An investigation into the relatively new carbene class, N-heterocyclic olefins (NHOs) was completed. An improved synthesis of the ligand was developed. NHOs were tested as ligands for late transition metal complexes. Specifically complexes with rhodium, gold and palladium were synthesized and characterized. The rhodium complex allowed for investigation into the donor strength and bonding mode. It was determined that NHOs are good σ-donors and very poor π-acceptors. Comparing the NHOs to the ubiquitous N-heterocyclic carbenes (NHCs) showed NHOs to be weaker donors. The NHO-palladium complexes were tested as catalysts for Suzuki-Miyauri cross-coupling reactions. The complexes were active catalysts, but fell short of the currently used NHC complexes.