With the purpose of tuning the reactivity of transition metal catalysts, asymmetric [O,O,N,N] ligands were synthesized via benzoxazine intermediates. Composed of a benzene ring fused with an oxazine ring, benzoxazines are organic compounds that have been demonstrated as useful in the synthesis of polymers due to their reactive ortho positions. Substituents installed at the ortho and para positions relative to the phenol are used to avoid typical benzoxazine electrophilic aromatic substitution (EAS) polymerizations allowing for the synthesis of discrete asymmetric ligands. These ligands will chelate to metal centers to make chiral titanium complexes which were tested in the formation of polylactic acid. All of the titanium complexes synthesized demonstrated catalytic activity when converting lactide to polylactic acid. Since this ligand class is produced at a relatively low cost, the implications of this research would be beneficial in terms of cost-effective advancements in catalytic design.

Synthesis, analysis, and metalation of asymmetric [O,O,N,N] amine bis(phenolate) ligands from benzoxazine intermediates

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