Mild and Selective Palladium-Catalyzed Pyridylic Allylation of 4-Alkylpyridines

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dc.contributor.advisorOrellana Garcia, Josue Arturo
dc.contributor.authorRasheed, Faizan
dc.date.accessioned2020-08-11T12:34:43Z
dc.date.available2020-08-11T12:34:43Z
dc.date.copyright2019-03
dc.date.issued2020-08-11
dc.date.updated2020-08-11T12:34:43Z
dc.degree.disciplineChemistry
dc.degree.levelMaster's
dc.degree.nameMSc - Master of Science
dc.description.abstractPyridines and related heterocycles enjoy widespread occurrence in biologically relevant natural products and drug-like molecules. Therefore, new methods that facilitate their synthesis and incorporation into drug-like structures will likely have a significant impact on the drug development process. This is especially true when these methods accomplish selective functionalization and allow a broad functional group tolerance. Reported herein is a new strategy for the selective allylation of 4-alkylpyridine derivatives. Our methodology exploits well-established alkylidene dihydropyridine intermediates as substrates for a Pd-catalyzed decarboxylative allylation reaction, which installs a synthetically versatile allyl group at the 4-pyridylic position. The use of a weak base and the absence of a Lewis acid in our method enables the allylation of 4-alkylpyridines with exceptional functional group tolerance. Moreover, the compatibility of the proposed pyridylic allylation strategy extends beyond simple 4-alkylpyridines to more sophisticated 3- and 4-disubstituted pyridines.
dc.identifier.urihttp://hdl.handle.net/10315/37663
dc.languageen
dc.rightsAuthor owns copyright, except where explicitly noted. Please contact the author directly with licensing requests.
dc.subject.keywordsOrganic chemistry
dc.subject.keywordsTransition metal
dc.subject.keywordsPalladium
dc.subject.keywordsPyridine
dc.subject.keywordsCross coupling
dc.subject.keywordsOrganometallic chemistry
dc.subject.keywordsDrug discovery
dc.titleMild and Selective Palladium-Catalyzed Pyridylic Allylation of 4-Alkylpyridines
dc.typeElectronic Thesis or Dissertation

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