After successfully applying a reactivity classification step, we proceeded with the interrogation of the regioselectivity for both the Hayashi-Heck and hydroformylation reactions (Fig. , Step 2) by regressing ligand parameters to the experimentally measured ΔΔG ‡ using MLR. For the Hayashi-Heck reaction, regioselectivity (i.e., formation of olefin 4 vs 5) was correlated to two electronic parameters, aniso 31 P NMR and P-C σ* occupancy, the computed anisotropic phosphorus NMR shielding and the occupancy of the σ* orbitals of the P-C bonds, respectively (Fig. ). It should be noted that robust models could only be found when ligands were first curated using the yield threshold. MLR was also used successfully to examine the enantioselectivity for this transformation (see SI Fig. ).