UC San Diego

Aromatic compounds are ubiquitous in everyday life as they are commonly found in the composition of materials, technologies, energy, and medicines. The functionalization of these compounds via C-H Functionalization strategies are particularly useful in order to access a variety of new compounds, and in regards to medicinal chemistry increasing the capacity to synthesize lead aromatic compounds without the need for de novo syntheses. Radical C-H functionalization in particular has become increasing popular due to the resurgence of photochemistry allowing for the generation of more reactive-radical or charged open-shell intermediates. C-H Functionalization as a whole enables Late-stage functionalization of more complex molecules, allowing for the facile transformation of specific C-H bonds and increased diversification of compounds. However, a current limitation in the field is the lack of regio-control on aromatic substrates, known to produce mixtures of constitutional isomers in many reaction methodologies. Our lab has developed radical strategies for the functionalization of aromatic compounds, which is discussed in two manuscripts in Chapter 1 and 2. We also are developing a regioselective-catalyst controlled Lewis base perfluoroalkylation of anilides which is discussed in Chapter 3. We believe these works can be utilized in the functionalization of aromatic compounds and relevant for use towards drug discovery efforts.