Anomalously low yields for cycloheptane-derived trifluoroborates 2{8-10} might be referred to increased lipophilicity of the corresponding fragments, increasing the role of boundary effects in the biphasic system. In summary, the Minisci reaction of gem-difluorinated cycloalkyl trifluoroborates and carboxylic acids is a very promising approach for the C-H modification of heterocyclic systems with gem-diflorocycloalkyl substituents. The corresponding carboxylic acids demonstrates somewhat higher efficiency as the radical sources in the reaction studied under optimized conditions as compared to trifluoroborates. This advantage can be overcome by necessity to use the three-fold excess of the former reagents. Also, trifluoroborates can be advantageous with heterocyclic substrates sensitive to oxidation.