Authors:

Nicholas Colvin

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About Paper:

Catalytic hydrogenation reactions are an important step in many organic synthesis pathways and are used in both commercial and academic settings. These reactions typically utilize a heterogeneous catalyst made up of a metal, which activates the hydrogen, and a support, which stabilizes the metal and provides a high surface area. Since some diastereomers have different properties, certain applications of this reaction require facial selectivity of hydride addition, referred to as directed hydrogenation, which is often achieved using a directing group on the substrate that binds to the catalyst to guide facially selective hydride addition to the molecule. By alloying second metal with the catalytically active metal in heterogeneous catalysts, we can further tune the active surface to increase product selectivity, which we then utilize in congruence with the inherent robustness and high activity of heterogeneous systems to hydrogenate tetrasubstituted olefins, a historically challenging transformation. In this work, we synthesize a series of cyclopentenols bearing a tetrasubstituted olefin and test these on our optimized catalyst. We find that not only is our catalyst capable of hydrogenating these substrates with high conversion and diastereoselectivity, but we also observe improved chemoselectivity in our system compared to a commercially available catalyst. This research can have significant impacts in medicinal and fine chemical production, but more work needs to be done to further expand the substrate scope and elucidate the nature of the active site.

Source:

Purdue University / 2023

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Co-authors:

Nicholas Colvin