The Optimization of Reaction Conditions in the Synthesis and Analysis of Asymmetric [O,N,O] Amine bis(phenolate) Ligands

ONU McIntosh Center; Activities Room

Through benzoxazine intermediates, asymmetric [O,O,N,O] ligands were synthesized with the purpose of tuning the reactivity of transition metal catalysts. While there is often difficulty associated with synthesizing large, complex ligands, benzoxazines have been demonstrated as useful in synthesizing asymmetric ligands. To avoid the typical benzoxazine polymerizations, substituents were installed at positions ortho and para to the phenol. By blocking electrophilic aromatic substitution (EAS) reactions at multiple ortho and para positions, a discrete asymmetric ligand can be synthesized from the benzoxazine and a phenol. A subsequent reaction with a new phenol results in the asymmetric ligand. Implications of this research include potential advancements in catalytic design, which would contribute to the growth of research in renewably sourced polymers. Considering that this ligand class is relatively low-cost to produce, it is especially of interest.