Control of ambident nucleophiles

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The addition of nucleophiles to electrophiles is a common step in the synthesis of agrochemical and pharmaceuticals. However, the use of ambident nucleophiles, as for example in cyproconazole (a fungal growth inhibitor) and thiamethoxam (a neonicotinoid insecticide), always presents a challenge, irrespective of whether the nucleophile is simple or complex. Selectivity less than 100%, by necessity, makes a process less economic; the unwanted isomer must be separated or eliminated - e.g., by isomerisation - all of which costs time and materials. This project will apply physical organic techniques to elucidate the fundamental mechanistic aspects that control the regioselectivity of such processes, with the goal of engendering binary control by mechanistic switch, using catalysis.