While the classical Minisci reaction involves the use of carboxylic acids as the radical precursors (which was later demonstrated for a wide range of both aromatic and aliphatic substrates), boronic acid derivatives (in particular, trifluoroborates) have received much attention as a promising alternative (Scheme 1, B). Silver species have been widely used as an oxidant (especially in catalytic amounts in the presence of a stoichiometric co-oxidant, e.g. AgNO3/K2S2O8 or AgNO3/Selectfluor 53 ) to generate the corresponding radical intermediate; other reagents included molecular oxygen, CuCl2, Mn(OAc)3, etc. Photoredox methods are also worth outlining, both metalo- and organocatalytic. While the reactivity and selectivity of various (cyclo)alkyl radical sources and heteroaromatic partners in the Minisci reaction was studied, fluorinated substituents were largely underexplored at these conditions. Thus, several examples of the photocatalytic C-H activation involving 4,4-difluorocyclohexanecarboxylic acid as the radical source were reported. In this regard, achievements of Baran and co-workers on the C-H functionalization of heterocyclic rings with fluorinated sulfinates can be also mentioned. In this work, we evaluate the reactivity of gem-difluorinated cycloalkane building blocks (carboxylic acids and triflurooborates, C4 to C7) as the radical sources in the Minisci reaction under parallel synthesis conditions (Scheme 1, C). In particular, a small compound library following the design principles shown in Figure , A has been prepared. In addition to that, an attempted rationalization of the obtained results based on cyclic voltammetry experiments and molecular geometry data is provided.