Bio-Inspired Tishchenko Reaction



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Synthesized a biocatalyst that acts like a Tishchenko reaction able to react with di-aldehydes to form cyclic esters, lactones. Lactones have many beneficial biological features such as being anti-microbial and anti-tumor agents. Thus, synthesized iridium catalysts with different substituents and electron groups. Ir1 is the model catalyst that was then modified by changing the substituent to a butylamino and variations with different electron groups to form Ir2, Ir3, and Ir4. A kinematics study was performed on each catalyst. Looking at the GC-MS chromatograms, we are able to determine that Ir3 was the fastest reacting catalyst followed by Ir1. A possible intermediate was observed in the GC-MS which would require more testing to characterize and identify its role. Second experiment focused on limiting the sodium formate, which activates the iridium catalyst. By limiting sodium formate, we are able to determine the rate-determining step and gain an idea about the mechanistic approach of the catalyst. As the first step consists of reducing one aldehyde, then either another reduction occurs or an oxidation reaction. H-NMR standards were used to determine the ratios of the compounds present. More testing is required to make a proper conclusion of how limiting sodium formate affects the reaction and the catalyst.