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    Iron-catalyzed decarboxylative cross coupling reactions and palladium-catalyzed sp2-sp3 coupling of coumarins.

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    Trivedi_ku_0099M_10695_DATA_1.pdf (1.831Mb)
    Issue Date
    2009-12-15
    Author
    Trivedi, Rushi
    Publisher
    University of Kansas
    Format
    111 pages
    Type
    Thesis
    Degree Level
    M.S.
    Discipline
    Medicinal Chemistry
    Rights
    This item is protected by copyright and unless otherwise specified the copyright of this thesis/dissertation is held by the author.
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    Abstract
    The thesis details the development of a decarboxylative synthesis of aryl ethers using a relatively new Iron catalyst and a novel decarboxylative coupling of coumarins catalyzed by palladium. Aryl allyl carbonates underwent facile decarboxylative coupling in presence of a new iron catalyst. The allylation is found to be regioselective rather than regiospecific. This suggests that the allylation proceeds through π-allyl iron intermediates in contrast to related allylations of carbon nucleophiles that proceed via σ-allyl complexes. The reason we looked at iron as a catalyst was to offset the cost of expensive palladium catalyst usually used in these types of reactions. The second project involved allyl esters of 3-carboxylcoumarins, which underwent facile decarboxylative coupling at just 25−50 °C in moderate to good yields. This represents the first extension of decarboxylative C−C bond-forming reactions to the coupling of aromatics with sp3-hybridized electrophiles. Finally, the same concept can be applied to the sp2−sp3 couplings of pyrones and thiocoumarins. A variety of biologically important heteroaromatics can be readily functionalized without the need for strong bases or stoichiometric organometallics that are typically required for more standard cross-coupling reactions.
    URI
    http://hdl.handle.net/1808/6177
    Collections
    • Medicinal Chemistry Dissertations and Theses [80]
    • Theses [3828]

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    785-864-8983

    KU Libraries
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    Lawrence, KS 66045
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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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