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Progress in Selective Hydrogenation: Reactivity Trends in PdAu Heterogeneous Catalysts & Developing Chiral Building Blocks for New Homogeneous Catalysts

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Title:Progress in Selective Hydrogenation: Reactivity Trends in PdAu Heterogeneous Catalysts & Developing Chiral Building Blocks for New Homogeneous Catalysts
Authors:Chinen, Amy
Contributors:Cain, Matthew (advisor)
Chemistry (department)
Keywords:selective hydrogenation
heterogeneous catalysis
biorenewable chemicals
asymmetric hydrogenation
homogeneous catalysis
show 1 moreP-stereogenic ligands
show less
Date Issued:May 2017
Publisher:University of Hawaii at Manoa
Abstract:Selective hydrogenation is an essential method for converting cheap starting materials into more valuable chemical building blocks. Whether regioselectivity or diastereoselectivity is desired, catalysts are often employed to aid in this transformation. This work explores possibilities for finetuning both homogeneous and heterogeneous catalysts. Previously, bimetallic PdAu catalysts were used to enable the conversion of biologically produced 4-hydroxycoumarin (4HC) to pharmaceutically relevant coumarin and dihydroxycoumarin (DHC), but the subtleties of catalyst preparation and the effect of Pd loading were not known. Part I focuses on identifying reactivity trends resulting from variations in PdAu catalysts. Several PdAu catalysts with varying Pd:Au ratios were prepared by controlled surface reactions (CSR) or incipient wetness impregnation (IWI). Using high performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GCMS), we determined the effects of the preparation method and Pd loading on reactivity, selectivity, and resistance to deactivation for the selective hydrogenation of 4HC to DHC. Part II aims to develop chiral building blocks for C1-symmetric, P-stereogenic ligands that will be used in the asymmetric hydrogenation of heavily functionalized substrates. To date, a new diastereoselective method of adding RO-H across a P=P double bond was identified and a new sterically dominating R group was generated. The results were analyzed by nuclear magnetic resonance (NMR) spectroscopy.
Pages/Duration:34 pages
URI:http://hdl.handle.net/10125/56523
Rights:All UHM Honors Projects are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission from the copyright owner.
Appears in Collections: Honors Projects for Chemistry


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