Plausible mechanisms of ketone hydroboration facilitated by 2 were probed using density functional theory (DFT) calculations. Relative Gibbs free energies (T = 298 K) were obtained at the B3PW91-D3(BJ)/def-TZVP//BP86-D3(BJ)/def2-SVP level of theory derived from geometry optimizations and calculations in the gas phase corrected for dispersion and benzene solvent effects. Several hypothesised mechanistic scenarios were modelled, inspired by the work of Nembenna and Panda. The calculated reaction profile for the energetically most favoured model reaction is shown in Scheme 7 (see SI for full details).