Bimetallic alloy nanoparticles are important catalysts for selective heterogeneous hydrogenation reactions, particularly to achieve chemoselectivity in the presence of other reducible functionality. Our group recently showed that a well-defined bimetallic surface is capable of achieving stereoselective hydrogenation of olefins through a directing group strategy. Taking inspiration from molecular catalysts for directed hydrogenation, we utilize a bimetallic alloy comprising a noble metal and a base metal wherein the base metal adsorbs a heteroatom directing group on the substrate and the noble metal binds the olefin and activates hydrogen. Because of the bifunctional substrate adsorption, hydrogen is selectively delivered from the same face as the directing group. We show that heteroatom-directed heterogeneous hydrogenation is highly diastereoselective for a wide range of substrate classes, including hindered olefins and arenes that are unreactive in the presence of molecular hydrogenation catalysts. We also utilize colloidal synthesis, CO DRIFTS, and catalytic kinetics to elucidate the active site ensemble required for heterogeneous directed hydrogenation. We show that a ~3:1 ratio of the noble metal to the base metal is necessary to achieve high diastereoselectivity.

Bimetallic alloy nanoparticles for stereoselective heterogeneous hydrogenation

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