Synthesis of Electron-Rich β-Fluoroamines: Alkene Aminofluorination Using N,N-Dialkylhydroxylamines

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2019

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Fluorine in modern pharmaceuticals has enabled development of drugs with enhanced therapeutic value through the selective modulation of a variety of pharmacological parameters. Therefore, methods to prepare molecular scaffolds which contain the fluorine atom are of critical importance for the continued success of novel drug discovery. In this thesis, the regioselective intermolecular aminofluorination of alkenes has been achieved with N,N-dialkylhydroxylamines and nucleophilic fluorine. With this copper-catalyzed approach, a variety of pharmaceutically relevant β-fluorophenethylamines have been prepared. Additionally, through the systematic evaluation of substituted alkenes and electronically varied O-substituted-N-hydroxylmorpholines, the limitations of the method have been discovered. Mechanistic experiments have also revealed the presence of a radical intermediate, which suggests the transformation occurs through a nitrogen-initiated pathway.

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Ku, Colton Kawika Sam (2019). Synthesis of Electron-Rich β-Fluoroamines: Alkene Aminofluorination Using N,N-Dialkylhydroxylamines. Master's thesis, Duke University. Retrieved from https://hdl.handle.net/10161/19786.

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