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The Preparation of Gamma- Arylated Ketones via Palladium-Catalyzed Cross-Coupling of Cyclopropanol - Derived Homoenolates with Benzyl Chlorides

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dc.contributor.advisorGarcia, Josue Arturo Orellana
dc.creatorNithiyananthan, Nishanthini
dc.date.accessioned2015-08-28T14:57:19Z
dc.date.available2015-08-28T14:57:19Z
dc.date.copyright2014-08-22
dc.date.issued2015-08-28
dc.date.updated2015-08-28T14:57:19Z
dc.degree.disciplineChemistry
dc.degree.levelMaster's
dc.degree.nameMSc - Master of Science
dc.description.abstractThe first palladium-catalyzed cross-coupling reaction of cyclopropanol-derived ketone homoenolates with benzyl halides, was developed to prepare a variety of γ-arylated ketones. One of the major challenges of this cross-coupling reaction was the competing cleavage of the cyclopropanol starting material to the ring-opened ketone under the reaction conditions. Through systematic optimization studies involving screens of base, ligands, solvents, temperature, Pd sources, conditions for the high yielding cross coupling of 1-phenethylcyclopropanol with 4-methyl benzyl chloride were found. With optimized conditions excellent yields were obtained for the cross-coupling of various electron rich and neutral benzyl chlorides. Moreover, these conditions were also used to successfully cross couple a variety of cyclopropanols to 4-methyl benzyl chloride. This reaction is also shown to work with a low catalyst loading of 1 mol % and in gram-scale without any reduction in yield.
dc.identifier.urihttp://hdl.handle.net/10315/29899
dc.language.isoen
dc.rightsAuthor owns copyright, except where explicitly noted. Please contact the author directly with licensing requests.
dc.subjectChemistry
dc.subject.keywordsPalladium cross-coupling
dc.subject.keywordsHomoenolates
dc.subject.keywordsCyclopropanol
dc.subject.keywordsGamma-arylated ketones
dc.titleThe Preparation of Gamma- Arylated Ketones via Palladium-Catalyzed Cross-Coupling of Cyclopropanol - Derived Homoenolates with Benzyl Chlorides
dc.typeElectronic Thesis or Dissertationen_US

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