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Thiamine-dependent enzymes catalyze a variety of transformations in nature. We hypothesize that thiamine can also facilitate cross-coupling reactions between carbonyl compounds and alkyl halides, going beyond its natural scope. Preliminary results indicate that the thiamine-dependent enzyme, SucA, catalyzes the coupling of α-ketoglutarate with 1-(bromoethyl)benzene, an unprecedented reaction for these enzymes. To advance our study, we will continue reaction optimization and characterize the enzyme’s selectivity. This will involve conducting reactions and monitoring product formation by liquid chromatography-mass spectrometry. The successful completion of this project will result in a novel pathway to valuable products with high yield and selectivity.