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Substrate-directed Heterogeneous Hydrogenation of Olefins Using Bimetallic Nanoparticles.
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Substrate-directed Heterogeneous Hydrogenation of Olefins Using Bimetallic Nanoparticles.
자료유형  
 학위논문
Control Number  
0017163778
International Standard Book Number  
9798342123235
Dewey Decimal Classification Number  
600
Main Entry-Personal Name  
Swann, William A.
Publication, Distribution, etc. (Imprint  
[S.l.] : Purdue University., 2024
Publication, Distribution, etc. (Imprint  
Ann Arbor : ProQuest Dissertations & Theses, 2024
Physical Description  
354 p.
General Note  
Source: Dissertations Abstracts International, Volume: 86-04, Section: B.
General Note  
Advisor: Li, Christina W.;Bart, Suzanne Doucette;Marinero-Caceres, Ernesto;Wei, Alexander.
Dissertation Note  
Thesis (Ph.D.)--Purdue University, 2024.
Summary, Etc.  
요약Directed hydrogenation, in which product geometric selectivity is dictated by the binding of an ancillary directing group on the substrate to the catalyst, is typically achieved by homogeneous Rh and Ir complexes. No heterogeneous catalyst has been able to achieve equivalently high directivity due to a lack of control over substrate binding orientation at the catalyst surface. In this work, we demonstrate through structure-activity studies that careful control of surface ensemble geometry in bimetallic nanoparticle catalysts can confer hydroxyl-directed selectivity in heterogeneous double bond hydrogenation. We postulate that the oxophilic alloy component binds hydroxyl groups to pre-orient the molecule on the surface, while proximal noble metal atoms impart facially selective addition of hydride to the olefin. We found that controlling the degree of surface alloying between oxophilic and noble metal component as well as alloy component identity is critical to maximizing reaction selectivity and starting material conversion. Our optimized catalysts exhibit good functional group tolerance on a variety of cyclohexenol and cyclopentenol scaffolds, with Pd-Cu and Pt-Ni systems being developed for the diastereoselective hydrogenation of tri- and more challenging tetra-substituted olefins, respectively. The applicability of this method is then demonstrated in a four-step synthesis of a fine fragrance compound, (1R,2S)- (+)-cis-methyldihydrojasmonate (Paradisone®), with high yield and enantiopurity.
Subject Added Entry-Topical Term  
Hydrogen.
Subject Added Entry-Topical Term  
Alcohol.
Subject Added Entry-Topical Term  
Particle size.
Subject Added Entry-Topical Term  
Hydrogenation.
Subject Added Entry-Topical Term  
Catalysis.
Subject Added Entry-Topical Term  
Alloys.
Subject Added Entry-Topical Term  
Nanoparticles.
Subject Added Entry-Topical Term  
Natural products.
Subject Added Entry-Topical Term  
Solvents.
Subject Added Entry-Topical Term  
Adsorption.
Subject Added Entry-Topical Term  
Materials science.
Subject Added Entry-Topical Term  
Nanotechnology.
Subject Added Entry-Topical Term  
Organic chemistry.
Added Entry-Corporate Name  
Purdue University.
Host Item Entry  
Dissertations Abstracts International. 86-04B.
Electronic Location and Access  
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Control Number  
joongbu:658329
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