The unique stereoelectronic properties of the α-halocarbonyl system serves as a guiding tool, with methods to generate stabilised α-radicals readily achieved using visible light. 12a,21 Access via direct excitation or activation of Lewis base derived electron donor-acceptor (EDA) complexes (Figure ) enables the practitioner to combine this mild activation mode with other reactivity platforms for the controlled construction of sp 3 carbon centres. Given the structural similarities of α-halo boron systems (p-orbital vs. π*), we were intrigued to find that similar activation had thus far been unexplored, presumably due to formidable complications that arise by undesired boron p-orbital activation in the presence of Lewis basic additives. Should this obstacle be overcome, we envisaged that the conformation and stereoelectronic properties could give rise to a weakened C-X bond creating a prominent precursor for mild, catalyst-free generation of α-boryl radicals.