In this intricate ballet of fleeting radical intermediates, we realized that a careful balance between the XAT, the radical addition and the final HAT steps was crucial to avoid parasitic reaction pathways. Accordingly, we also evaluated the possibility for these intermediates to undergo competitive, yet non-productive pathways, including the direct addition of LBR I onto dimethyl maleate 2d with formation of a new B-C bond (through TS4) and the reduction of the cyclohexyl radical II to cyclohexane (through TS5). However, our computational analysis revealed that both steps occur with higher activation energies and less negative energy gains compared to those describing the desired process.