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dc.contributor.advisorStephen L. Buchwald.en_US
dc.contributor.authorDavis, Nicole R. (Nicole Rose)en_US
dc.contributor.otherMassachusetts Institute of Technology. Dept. of Chemistry.en_US
dc.date.accessioned2010-05-25T20:42:18Z
dc.date.available2010-05-25T20:42:18Z
dc.date.copyright2009en_US
dc.date.issued2009en_US
dc.identifier.urihttp://hdl.handle.net/1721.1/55101
dc.descriptionThesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2009.en_US
dc.descriptionVita. Cataloged from PDF version of thesis.en_US
dc.descriptionIncludes bibliographical references.en_US
dc.description.abstractA new ligand, AdBrettPhos, was synthesized and its use, along with tBuBrettPhos, in C-O coupling reactions at low temperatures was investigated. Using Pd catalysts containing these ligands, electron-neutral aryl bromides were coupled with phenols at room temperature for the first time. A variety of electron-deficient aryl halides and phenols were also coupled at moderate temperatures in good yields. In order to probe how the structural features of the ligand affect the catalytic activity of Pd catalysts containing dialkylbiarylphosphines, a series of novel ligands was synthesized and their utility in Pd-catalyzed C-N couplings was investigated. All of these ligands provided competent catalysts for the cross-coupling reactions of aryl halides with primary alkyl or aryl amines. However, in general these catalysts cannot match the rates and low catalyst loadings achieved by BrettPhos-supported Pd-catalysts, with the exception of L8, which was shown to be superior to BrettPhos in terms of rate and yield for the coupling of methylamine. The high selectivity for monoarylation of primary amines exhibited by these catalysts indicates that the methoxy substituent ortho to phosphorous plays an important role in regulating this selectivity.en_US
dc.description.statementofresponsibilityby Nicole R. Davis.en_US
dc.format.extent98 p.en_US
dc.language.isoengen_US
dc.publisherMassachusetts Institute of Technologyen_US
dc.rightsM.I.T. theses 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. See provided URL for inquiries about permission.en_US
dc.rights.urihttp://dspace.mit.edu/handle/1721.1/7582en_US
dc.subjectChemistry.en_US
dc.titleSynthesis and study of ligands for Pd-catalyzed C-O and C-N couplingen_US
dc.typeThesisen_US
dc.description.degreeS.M.en_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistry
dc.identifier.oclc589008175en_US


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