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Enantioselective nickel catalysis : exploiting activated C-H bonds

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dc.contributor.advisor Gregory C. Fu. en_US Bencivenga, Nicholas Ernest en_US
dc.contributor.other Massachusetts Institute of Technology. Dept. of Chemistry. en_US 2012-09-27T18:12:01Z 2012-09-27T18:12:01Z 2012 en_US 2012 en_US
dc.description Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2012. en_US
dc.description Cataloged from PDF version of thesis. en_US
dc.description Includes bibliographical references (p. 26-27). en_US
dc.description.abstract A 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.statementofresponsibility by Nicholas Ernest Bencivenga. en_US
dc.format.extent iii, 57 p. en_US
dc.language.iso eng en_US
dc.publisher Massachusetts Institute of Technology en_US
dc.rights M.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.uri en_US
dc.subject Chemistry. en_US
dc.title Enantioselective nickel catalysis : exploiting activated C-H bonds en_US
dc.type Thesis en_US S.M. en_US
dc.contributor.department Massachusetts Institute of Technology. Dept. of Chemistry. en_US
dc.identifier.oclc 809934144 en_US

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