Electronic and steric tuning of N-heterocyclic carbene ligands: Effect on palladium-catalyzed cross-coupling reactions

ORGN 374

Eric Assen B. Kantchev, organ@yorku.ca, Niloufar Hadei, Christopher J. O'Brien, Cory Valente, Lawrence Montgomery, and Michael G. Organ. Department of Chemistry, York University, 4700 Keele Street, Toronto, ON M3J 1P3, Canada
Recently, N-heterocyclic carbenes (NHC) have attracted considerable interest as ligands for transition metal homogeneous catalysis. The excellent σ-donor properties of NHC impart excellent activity and thermal stability to the catalysts formed. Study of the effects of ligand structure with respect to electronic and steric effects is important for discovery of new catalytic protocols and providing further mechanistic insights. We have prepared an array of ligand precursors incorporating electron-withdrawing (F) and electrondonating (OMe) substituents into 1,3-diarylimidazolidinium (1,2) and 1,3-di(1-adamantyl)benzimidazolidinium (3) scaffolds, as well as the novel ligand precursor 4. Effects of ring size will also be explored using ligand series 5, 6 and 7. The synthesis of 1-7 and their use in palladium-catalyzed cross coupling reactions will be reported.