Degree Type

Thesis

Date of Award

2018

Degree Name

Master of Science

Department

Chemistry

Major

Organic Chemistry

First Advisor

Levi M. Stanley

Abstract

In this thesis, heterogeneous frameworks are explored and examined for their use in recyclable catalysis. Specifically, metal-organic-frameworks (MOFs) and covalent-organic-frameworks (COFs) containing bidentate nitrogen ligands are pursued for their use in transition metal catalysis.

Palladium(II)-functionalized COF (Pd@TpBpy COF) is demonstrated as a recyclable, heterogeneous catalyst for palladium-catalyzed conjugate addition of arylboronic acids to β,β-disubstituted enones to form ketone products containing all-carbon quaternary centers in aqueous 50 mM NaTFA as the reaction medium. A wide range of arylboronic acids are added to various β,β-disubstituted enones in moderate-to-high yields.

Pyridine oxazoline derivatives are designed and synthesized for incorporation into MOFs through varying methods including amide coupling, amine coupling, and solvent-assisted ligand incorporation (SALI). Preliminary data shows potential for palladium-catalyzed, enantioselective conjugate addition of phenylboronic acid to β,β-disubstituted enones to form ketone products.

Copyright Owner

Brian Schumacher

Language

en

File Format

application/pdf

File Size

55 pages

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