Enhancing catalytic efficiency: Advances with N-heterocyclic carbene ligands and mechanistic insights in cross coupling reactions
Eric Keske
Assistant Professor, Department of Chemistry
Trent University
Thursday, October 31, 2024
9 a.m.
Hybrid: C2-361 and Teams
Abstract: The efficiency of a homogeneous catalytic reaction is often linked to the properties of the catalyst’s supporting ligands. Understanding and controlling these ligand properties can significantly impact both catalyst performance and efficiency. In this context, we argue that N-heterocyclic carbenes (NHCs), commonly utilized as ligands in transition metal catalysis, lack the steric and electronic modularity necessary for effective catalyst tuning. Our group has employed mechanistic tools, including in situ reaction monitoring and density functional theory (DFT) calculations, to investigate ligand effects, potential deactivation mechanisms, and to discover new substrates. We have developed several new sterically modular and tunable NHC ligands and explored their application in cross coupling reactions.1 Additionally, we have identified a previously overlooked side reaction in the Hiyama coupling of aryl halides which we believe contributes significantly to poor catalyst performance in this often-neglected transformation.2 This talk will summarize recent advances from our group focused on the rational design and mechanistic understanding of cross coupling reactions.
References:
- Lim, M. Q.; Brick, K. J.; LeBlanc, J.; Garrard, C.; Keske, E. C., Organometallics 2024, In Revision.
- Brick, K. J.; Lim, M. Q.; Keske, E. C., Organometallics 2023, 42 (22), 3192-3198.