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Please use this identifier to cite or link to this item: http://hdl.handle.net/1807/24253

Title: Investigations in Transition Metal Catalysis: Development of a Palladium Catalyzed Carboesterification of Olefins and Synthesis of Chiral Sulfoxide Pincer Ligands
Authors: Jardine, Katherine Jane
Advisor: Dong, Vy Maria
Department: Chemistry
Keywords: Transition Metal Catalysis
Pincer ligands
Carboesterification
Issue Date: 6-Apr-2010
Abstract: The development of a palladium-catalyzed intramolecular carboesterification of unactivated olefins is described. Olefin difunctionalization is a powerful tool for adding complexity to a molecule, and this formal [3+2] cycloaddition generates highly functionalized fused ring systems. Initially discovered by Dr. Yang Li in our group, it was found that when propiolic acids with a pendant terminal olefin were treated with 1 mol % Pd(MeCN)2Cl2, 3 equivalents of copper (II) chloride, and 3 equivalents of lithium chloride in acetonitrile at 50 °C, cyclization occurred in up to 90% yield. The optimization of this reaction and the extension to propiolamides and propargyl alcohols is described in this thesis. A mechanism involving a novel palladium-carboxylate species is proposed. Preliminary investigations into the synthesis of chiral sulfoxide pincer ligands are also described. The nucleophilic aromatic substitution of 1,3-dibromobenzene and 2,6-dichloropyridine with various thiols, followed by oxidation of the sulfides to sulfoxides is investigated as a route to the desired proligands.
URI: http://hdl.handle.net/1807/24253
Appears in Collections:Master
Department of Chemistry - Master theses

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