SHAPING ORGANIC SYNTHESIS WITH LIGHT-DRIVEN PROCESSES

The use of photons to perform photochemical transformations has become an important research topic. The selective and mild generation of highly reactive intermediates, such as radicals, has led to the development of synthetic methods active also on complex molecules. The presented thesis is divided into four chapters and an appendix. The first chapter provides an introduction to the reactivity of radical intermediates, the main methods for generating radicals using light, and the principal mechanisms involved. The second chapter discusses the stereoselective α-amination of aldehydes using a direct excitation method. The formation of C–N bonds in the α-position of ketones has also been investigated but yielded unsatisfactory results. The third chapter reports two methods for introducing oxazolidinone moieties into heterocycles. The first method employs extremely mild reaction conditions (sodium bicarbonate in water) through an EDA complex pathway. The second method, still to be clarified, involves an aggregation-induced photochemical transformation. The fourth chapter presents a photocatalytic transformation using a synthetic photocatalyst to synthesize biaryl systems through a novel mechanism based on proton-coupled electron transfer. The appendix describes the work I carried out during my six-month traineeship in the Noël research group, where I focused on developing a method to analyze the kinetic isotope effect (KIE) through Raman spectroscopy in flow conditions.