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dc.contributor.advisorGregory C. Fu.en_US
dc.contributor.authorBencivenga, Nicholas Ernesten_US
dc.contributor.otherMassachusetts Institute of Technology. Dept. of Chemistry.en_US
dc.date.accessioned2012-09-27T18:12:01Z
dc.date.available2012-09-27T18:12:01Z
dc.date.copyright2012en_US
dc.date.issued2012en_US
dc.identifier.urihttp://hdl.handle.net/1721.1/73437
dc.descriptionThesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2012.en_US
dc.descriptionCataloged from PDF version of thesis.en_US
dc.descriptionIncludes bibliographical references (p. 26-27).en_US
dc.description.abstractA method for the nickel-catalyzed cross-coupling between benzoxazole and secondary halides was explored. This method was to make use of the activated C-H bond found in benzoxazole at the 2-position to generate the nucleophilic species in situ. After an extensive survey of parameters no such method could be found. However, it was found that copper(I) salts promoted the coupling of benzoxazole and benzylic bromides in high yield, albeit in a racemic fashion. Additionally a method to cross-couple terminal alkynes with secondary halides employing nickel-catalysis was explored. After surveying a number of alkynylmetal species, generated in situ, alkynyl borates were found to cross-couple with allylic chlorides to furnish product with the best enantioselectivity (enantiomeric excess ca. 70%), however in low yield.en_US
dc.description.statementofresponsibilityby Nicholas Ernest Bencivenga.en_US
dc.format.extentiii, 57 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.titleEnantioselective nickel catalysis : exploiting activated C-H bondsen_US
dc.typeThesisen_US
dc.description.degreeS.M.en_US
dc.contributor.departmentMassachusetts Institute of Technology. Dept. of Chemistry.en_US
dc.identifier.oclc809934144en_US


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