Synthesis of Primary Arylamines Using Bulky Palladium N-heterocyclic Carbene Precatalysts

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dc.contributor.advisorOrgan, Michael George
dc.creatorLombardi, Christopher Daniel
dc.date.accessioned2017-07-27T13:34:21Z
dc.date.available2017-07-27T13:34:21Z
dc.date.copyright2017-01-17
dc.date.issued2017-07-27
dc.date.updated2017-07-27T13:34:21Z
dc.degree.disciplineChemistry
dc.degree.levelMaster's
dc.degree.nameMSc - Master of Science
dc.description.abstractThe reaction between aryl halides and ammonia was investigated using N-heterocyclic carbene (NHC) ligated palladium pre-catalysts. The use of NHCs is well documented for coupling of alkyl and arylamines, but there is little precedent for the coupling of ammonia. A new, rationally designed, pre-catalyst (DiMeIHeptCl)Pd(allyl)Cl featuring highly-branched alkyl chains has been shown to be effective in selective aminations across a range of challenging substrates, including nitrogen-containing heterocycles and those featuring base-sensitive functionality. The less bulky Pd-PEPPSI-IPentCl pre-catalyst performs well for ortho substituted aryl halides giving monoarylated products in high yield with good selectivity.
dc.identifier.urihttp://hdl.handle.net/10315/33513
dc.language.isoen
dc.rightsAuthor owns copyright, except where explicitly noted. Please contact the author directly with licensing requests.
dc.subjectChemistry
dc.subject.keywordsPalladium
dc.subject.keywordsCatalysis
dc.subject.keywordsNHC
dc.subject.keywordsAmination
dc.subject.keywordsBuchwald-Hartwig amination
dc.subject.keywordsAmmonia
dc.subject.keywordsAminotriphenysilane
dc.titleSynthesis of Primary Arylamines Using Bulky Palladium N-heterocyclic Carbene Precatalysts
dc.typeElectronic Thesis or Dissertation

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