Faculty Advisor

Boisvert, Luc

Area of Study

Science and Mathematics

Publication Date

Summer 2013

Abstract

Industrially, alkene and carbonyl hydrogenation reactions are catalyzed by iridium, rhodium and ruthenium-centered catalysts. These highly toxic metals are very expensive, both to attain and to dispose of after degradation. This ongoing research seeks to investigate cleaner and more economical alternative catalysts by synthesizing and testing a bipyridine-derived iron catalyst utilizing the unconventional ligand-assisted heterolytic cleavage of hydrogen mechanism to facilitate double bond hydrogenation. In the time allotted, this segment of research sought to synthesize the two catalyst ligands 6-hydroxy-2,2’-bipyrdine and 6,6’-dihydroxy-2,2’-bipyridine, and to model ligand-iron attachment using commercially available iron complexes. The former of the two ligands was synthesized completely, primarily by Suzuki-Miyaura cross-coupling, while the 6,6’-dimethoxy-2,2’-bipyridine precursor to the latter ligand was synthesized by Ullman coupling but never successfully purified. Ligand-iron attachment test reactions between XFe(CO)2I (X = Cp, Cp*) and 2,2’-bipryidine (bpy) resulted consistently in [XFe(CO)(bpy)]I rather than the desired XFe(bpy)I despite the application of photolysis and bubbling nitrogen gas. Future research goals include cleaner, complete synthesis of 6,6’-dihydroxy-2,2’-bipyridine, attachment of ligands to iron center, and catalytic testing.

Publisher

University of Puget Sound

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