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Palladium-catalyzed C-N cross-coupling reactions toward the synthesis of drug-like molecules

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dc.contributor.advisor Stephen L. Buchwald and K. Dane Wittrup. en_US
dc.contributor.author McAvoy, Camille Z en_US
dc.contributor.other Massachusetts Institute of Technology. Dept. of Chemical Engineering. en_US
dc.date.accessioned 2012-09-27T15:27:58Z
dc.date.available 2012-09-27T15:27:58Z
dc.date.copyright 2012 en_US
dc.date.issued 2012 en_US
dc.identifier.uri http://hdl.handle.net/1721.1/73388
dc.description Thesis (S.B.)--Massachusetts Institute of Technology, Dept. of Chemistry; and, (S.B.)--Massachusetts Institute of Technology, Dept. of Chemical Engineering, 2012. en_US
dc.description Cataloged from PDF version of thesis. en_US
dc.description Includes bibliographical references (p. ). en_US
dc.description.abstract The development of methodologies for C-N bond formation reactions is an important scientific challenge because of many academic and industrial applications. This work will focus particularly on palladium-catalyzed cross-couplings of amine-containing compounds with aryl halides. The scope of the BrettPhos precatalyst for the cross-coupling of ortho-substituted aryl iodides with amides is studied using substrates with a variety of functional groups. Due to potential metal-chelating issues with some of the substrates used in this study, a proposed ligand synthesis is discussed in which one of the methoxy groups of BrettPhos is replaced with a morpholine capable of occupying palladium's open coordination site during its catalytic cycle. A final C-N bond formation study focuses on the cross-coupling of aryl halides with amidine salts. For this cross-coupling, a methodology has been developed that can be applied to various electron-rich, electron-poor, and electron-neutral substrates. Furthermore, the products of this cross-coupling can be used for a subsequent electrocyclization through a reaction with aldehyde, demonstrating that a relatively simple two-pot methodology can be used to make relatively complex substrates with pharmaceutical applications. Both amides and amidines are common moieties in drug-like molecules because of the various biological activities of these functional groups. Potential medicinal applications of the developed cross-coupling of amidine salts with aryl halides methodology are described. Thus, methodologies for various palladium-catalyzed, C-N cross-couplings as well as a potential ligand synthesis to be used for palladium catalysis are herein discussed. en_US
dc.description.statementofresponsibility by Camille Z. McAvoy. en_US
dc.format.extent 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 http://dspace.mit.edu/handle/1721.1/7582 en_US
dc.subject Chemistry. en_US
dc.subject Chemical Engineering. en_US
dc.title Palladium-catalyzed C-N cross-coupling reactions toward the synthesis of drug-like molecules en_US
dc.type Thesis en_US
dc.description.degree S.B. en_US
dc.contributor.department Massachusetts Institute of Technology. Dept. of Chemistry. en_US
dc.contributor.department Massachusetts Institute of Technology. Dept. of Chemical Engineering. en_US
dc.identifier.oclc 809804704 en_US


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