The prevalence of saturated N-heterocycle moieties within biologically active molecules has led to their widespread application as scaffolds in medicinal chemistry, with over half of all FDA approved pharmaceuticals containing an amine heterocycle. While the cross-coupling toolbox allows for the simple functionalisation of aromatic N-heterocycle building blocks, saturated equivalents present a further set of challenges. Methods for their N-alkylation/arylation often require reagents that may generate quaternary ammonium salts or potentially cause issues downstream in pharmaceutical processes due to genotoxicity, while functionalisation at other positions on the ring requires sp C-H activation chemistry. The saturation of these molecules also necessitates consideration of asymmetry as molecules of pharmaceutical interest are designed for application in a chiral environment.