| This thesis focuses on expeditious and robust modes of fluorination. One such route is microwave-accelerated fluorodenitration and another is a nickel-mediated oxidative addition of fluorine. A background review of the literature is presented with a particular emphasis on certain reactions and methodologies of note. These pathways were then experimentally applied to other substrates in an effort to use them as a model for more complex molecules, like natural products.;Indoles and oxindoles are common motifs in natural products, anticancer therapeutics and CNS agents. A common plant in the Amazon, called Uncaria tomentosa or commonly known as uña de gato, is rich in pentacyclic oxindole alkaloids. Oxindole extractions have shown in vivo and in vitro efficacy against HIV transciptase, cancer growth and recovery and the central Wnt-signalling pathway. Indigenous people of the Amazon have been using this plant for centuries as a common health elixir and as the pharmacological relevance of these compounds has been numerously reported, it was decided to study them further by investigating possible ways of radiolabeling them.;One method studied, nitrodehalogenation followed by fluorodenitration, proved a robust and efficacious method for activated aromatic substrates. Another method utilized a nickel-mediated intermediate and the final fluorination step could be done under aqueous conditions. It was found that the nitrodehalogenation followed by fluorodenitration was more effective and robust on a wide range of substrates. The latter nickel-mediated pathway was sensitive and in our hands did not show good substrate diversity. |
