To demonstrate the power of our complimentary divergent process, we looked to probe our reaction at larger scale, and explore subsequent reactivity of the corresponding isomers (Scheme 4). Despite an apparent dependence on photon flux, the reaction was unperturbed on 1 mmol scale enabling efficient formation of E-13 and Z-13 in 85% and 66% respectively. Both isomers could be easily transformed to the trifluoroborate (E-44 and Z-44) with retention of stereochemistry. Similarly, stereospecific allylation with an electron-deficient aldehyde was successful with both isomers to access anti-45 and syn-45 in good yields. In summary, we have developed an efficient, operationally simple method for the in situ generation of α-boryl radicals using only light, α-halo boronic and an inexpensive additive. When exposed to styrenes, this platform enables the rapid construction synthetically useful E-allylic esters. Capitalising on the benign activation the inclusion of a sensitiser facilitated a stereodivergent approach to the Z-isomer. The translation of this protocol for the mild generation of α-boryl radicals to other catalysis platforms may prove expansive for the future construction of highly desirable 3D organoboron scaffolds.