Abstract
Carbon-fluorine (C-F) bonds are notoriously robust. The strength of the C-F bond, its high dipole moment and the small size of the F atom give a range of valuable chemical, physical and biological properties to organofluorides making them suitable for various applications, e.g. polymers and materials, specialty solvents, performance fluids, active ingredients of pharmaceuticals and agrochemicals. In accordance with this the selective synthesis of organofluorides is an important and contemporary research area. Many electrophilic, nucleophilic and radical fluorinations have been developed in the past but efficiently introducing fluorine atoms remains a challenge today. Radical fluorination is less explored in comparison to the other two types and typically suffers from competitive electrophilic fluorination and oxidative processes. In the framework of this project a first goal is to explore a novel fluorinating agent acting as non-electrophilic fluorine radical donor. Besides the selective introduction of a fluorine atom, defluorinative functionalization of geminal fluorinated systems is an attractive alternative but seldomly explored approach to obtain challenging tertiary alkyl fluorides. Given the homolytic bond dissociation energy of unactivated C(sp3)-F is high and increases in geminal fluorinated systems this is not surprising. During this project novel selective defluorinative routes which should overcome this high bond strength obstacle will be explored.
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