Bicyclo[1.1.1]pentanes (BCPs) have received much attention as attractive replacements of benzene rings in drug development in an effort to improve a range of properties of importance in the drug development process. Recent years have seen intense activity regarding the synthesis and functionalization of BCPs. While initially this was focused on modification of the BCP bridgehead positions (leading to analogues of para-benzene substituted compounds), bridge-functionalization (to give ortho-benzene analogues) is now firmly in the spotlight. This has included both bridgehead and bridge fluorination methodologies. In this project, we wish to develop novel synthetic methodology based on flow photochemistry for the synthesis of a range of substituted fluorinated bicyclo[1.1.1]pentanes, as well as to investigate important physicochemical properties of the resulting derivatives such as lipophilicity and the potential for intermolecular ligand-protein interactions. We aim to upscale the synthetic methodologies in order to ensure the availability of relevant building blocks for applications in drug discovery in multigram quantities.