gem-Diflurination pattern has a significant impact on the reaction outcome. Thus, 4,4-difluorinated cycloalkyl building blocks have nearly the same efficiency as their non-fluorinated counterparts, while 3,3and especially 2,2-difluorinated analogs demonstrate diminished activity. Oxidation potentials obtained from cyclic voltammograms of the trifluoroborates studied are considerably higher for the fluorinated compounds; therefore, they may be only partially responsible for the observed effects. Other factors like radical nucleophilicity or the cycloalkyl fragment lipophilicity (e.g., for cycloheptane derivatives) should be also taken into account.