The activation of unreactive aliphatic fluorides is a current challenge. While limited reactions have been reported in literature, an improvement of those methods is desirable. To this end, computational chemistry is seen as a useful aid. First, reported C‒F activation reactions are investigated to elucidate their mechanism. In a second phase, the reactions are optimized by modification of the known reagents and assessing the influence on the thermodynamics and kinetics of the reaction.