Over the last few decades, fluorinated scaffolds have become an integral part of the drug discovery process as a convenient and valuable tool for fine-tuning the compound's physicochemical properties (acidity/basicity, lipophilicity, or solubility). Introduction of the fluorine-containing fragment often shows a significant impact on the compound's affinity to the desired biological target and its general metabolic stability. On the other hand, an evident trend for an increased use of sp -enriched structures in drug discovery gave rise to an intense investigation of fluorinated saturated (hetero)cycles. Since aromatic ring systems nevertheless remain essential and most popular structural elements of drug molecules, the synthetic methods allowing their decoration with fluorinated sp -enriched fragments are of high demand (Figure ). To date, various strategies to introduce the fluorinated cycloalkyl fragment into the aromatic core are known in the literature, including either fluorination of a pre-formed scaffold or the construction of a complex structure using fluorinated building blocks via common or recently (re-)introduced chemical transformations. The latter strategy can be especially promising since in many cases, C(sp 2 )-C(sp ) bond formation is possible. In particular, the radical C-H functionalization of aromatic heterocycles has become recognized as an effective instrument for late-stage modification of electron-deficient heteroaromatic species. While the seminal report on such transformations was made by Minisci and co-workers as early as in 1970s (Scheme 1, A), only with recent developments by the groups of Baran, Molander, and others, the Minisci reaction and its boron variant received a broad attention of the chemical community.