Oxidative C-F Cleavage in Metalloenzymes and Model Compounds

Replacement of C-H by C-F bonds provides lipophilicity and chemical stability to organic molecules. These properties make organofluorides interesting compounds in agrochemistry, medicinal chemistry and also in materials. However, the same properties hamper their chemical degradation, resulting in an increasingly concerning environmental persistence, which is fueling the quest for biological and chemical reagents that could cleave the C-F bonds. The first part of this review makes an overview of oxidative enzymes known to defluorinate organic molecules. The second part reviews coordination complexes, originally designed as functional models of oxidative enzymes, that can also engage in related defluorination reactions. The manuscript is hoped to provide ideas for the development of novel catalytic methodologies.

Automated summary

Replacement of C-H by C-F bonds provides lipophilicity and chemical stability to organic molecules, making organofluorides interesting compounds in various fields. However, the environmental persistence due to the same properties leads to a search for biological and chemical reagents that could cleave the C-F bonds. This review discusses oxidative enzymes and coordination complexes as potential solutions for the development of novel catalytic methodologies.