Authors:

Benedict G Grill

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In multi-arene systems, the potential for selective catalyzed hydrogenation is one that has many applications to pharmaceutical and materials research. Current research on selective hydrogenation of bi- arenes through directing groups has the potential for late-stage selective saturation of single aromatic rings, possibly increasing drug libraries and allowing for higher drug potency to be achieved. Different functional groups, like amines, have their binding abilities to catalyst surfaces change based on ranging polarity of solvents. Our goal in this project was to determine the effects that solvents can have on adsorption of specific groups on to the catalyst binding sites to further determine the most applicable solvent to use for multi-arene hydrogenation, specifically suppression of rings with non-directing functional groups to allow for selective hydrogenation. We assessed the solvent's role in selective hydrogenation of directing group bearing substrates by analyzing the turnover frequency and conversion percentage of these hydrogenation reactions to determine the solvent effects. Four solvents were studied: ethanol, cyclohexane, tetrahydrofuran (THF), and dimethylformaldehyde (DMF). Analyzation of each compound with respective solvents were studied in both singularity and in competition with each other. Less polar solvents, such as THF and Cyclohexane were found to suppress substrates with non-polar functional groups in competition with substrates with polar functional groups, while more polar solvents such as Ethanol were less suppressive of the non-polar functional groups in competition. This research will be further applied to multi-arene hydrogenation based on the efficiency of the solvent in selective hydrogenation. Keywords: Selective Hydrogenation; Catalyzed Hydrogenation; Solvent Effects

Source:

Purdue University / 2025

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Co-authors:

Benedict G Grill