Asym. Nuc. C(sp3)-Fluorination under Synergistic Organocat.

Organofluorine compounds are omnipresent in modern life and have found a plethora of applications. Besides notable examples such as refrigerants and plastics (e.g., Teflon), approximately 35% of agrochemicals and 20% of marketed drugs contain at least one carbon-fluorine bond. These bonds offer unique properties in terms of stability as well as polarity and thus can be used to improve pharmacological properties of drugs. Moreover, pharmaceuticals containing small amounts of radioactive fluorine can be traced in patients using a PET scan and are helping to diagnose and localise diseases as well as enable personalised treatments. However, the great utility of organofluorine compounds comes at a cost: Their preparation involves highly hazardous chemicals such as hydrogen fluoride (a highly toxic, corrosive gas) that has been responsible for severe accidents in the past. Replacing these substances by safe, cost-efficient and readily available fluoride sources is the primary goal for future innovations in fluorine chemistry. The group of Prof. Gouverneur at the University of Oxford is known for their world-leading expertise and cutting-edge discoveries in the synthesis of fluorinated molecules. An example is the concept of Hydrogen-Bonding Phase Transfer Catalysis which was developed in the group in recent years. This subtype of organocatalysis enables the utilisation of cheap and safe alkali metal fluorides by urea-based catalysts. It has been found that this methodology can fine-tune the reactivity of fluoride leading to highly selective reactions. In this fashion, the fluorination process increases efficiency, supresses side reactions and reduces the amount of waste in comparison to previous methods. The aim of this project will be the expansion of this principle towards less reactive, but pharmacologically very relevant starting materials in order to broaden the scope of this catalytic concept further.