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Manganese-catalyzed carbonylation of alkyl iodides

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dc.contributor.advisor Stephen L. Buchwald. en_US Westerhaus, Felix Alexander en_US
dc.contributor.other Massachusetts Institute of Technology. Dept. of Chemistry. en_US 2010-05-25T20:42:33Z 2010-05-25T20:42:33Z 2009 en_US 2009 en_US
dc.description Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2009. en_US
dc.description Vita. Cataloged from PDF version of thesis. en_US
dc.description Includes bibliographical references (p. 121-125). en_US
dc.description.abstract The palladium-catalyzed cross-coupling of aryl bromides with zirconocene-benzyne complexes has been investigated by S.L. Buchwald and coworkers. This method allows the formation of substituted biphenyls and terphenyls, however only two ortho-substituents are tolerated in this transformation. The studies reportd herein aimed at the synthesis of tri- and tetra substituted biaryls, since they are important precursors to biaryl phosphine ligands. The project did not succeed due to stability problems of the formed substituted zirconium biaryl. A general method for the manganese-catalyzed carbonylation of alkyl iodides while using a variety of nucleophiles was developed. The method concerns the alkoxy and amino carbonylation as well as the use of more unconventional nucleophiles such as thiols, azide and hydride. The method employs alkyl iodides although bromides are also feasible substrates through in situ Finkelstein reaction with catalytic to substoichiometric amounts of sodium iodide. The functional group tolerance is high and the conditions for the transformation are mild using only 40 psi of carbon monoxide pressure and temperatures between r.t. and 90°C for more difficult cases. en_US
dc.description.statementofresponsibility by Felix Alexander Westerhaus. en_US
dc.format.extent 126 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 Manganese-catalyzed carbonylation of alkyl iodides 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 589162702 en_US

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