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Asymmetric catalysis, where a metal catalyst is used to transform a substrate into a single enantiomer of product, has become a popular synthetic technique in both academic and industrial settings. An enantiomer is a single molecule with a unique three-dimensional shape with a mirror image not superimposable on the original. The chirality, or right or left-handedness, of compounds lead to applications important in the pharmaceutical and agrochemical industries. Commonly, a metal complex’s ability to create a product of a certain enantiomer relies on a chiral group being attached to the metal. However, having the chirality of a metal complex depend on the attached ligands being unsymmetrical is an underexplored area. Such a complex would be considered “chiral-at-metal,” where the metal itself would become a chiral center. This type of complex would allow for the usage of achiral phosphines, which are cheaper and easier to synthesize than chiral phosphines. Ruthenium complexes have shown great catalytic activity in transfer hydrogenation reactions, demonstrating product yields of 100% in one study. Such complexes can thus be analyzed in asymmetric catalysis with differing ligands. We will synthesize chiral-at-metal complexes and their catalytic success will be explored through the transfer hydrogenation of acetophenone. The future of this research lies in creating effective complexes using metals such as ruthenium, and eventually iron and cobalt or other more affordable metals.
Catalysis, Enantiomers, Hydrogenation, Acetophenone
Fritz, Nora, "Synthesis of Transfer Hydrogenation Catalysts Containing Unsymmetrical Bisphosphines" (2021). Undergraduate Research Symposium 2021. 2.
Faculty Mentor: Dr. Bryan Nell