Aliphatic azacycles are essential motifs in drug discovery, with 59% of unique small-mol. drugs approved by the FDA containing at least one nitrogen heterocycle.1 Of these, the piperidine motif is the most prevalent nitrogen ring-system, highlighting the importance of this heterocycle in small-mol. drug discovery. Simple piperidines are readily available; hence, methods for the straightforward late-stage diversification of this ring-system, ideally exploiting C-H functionalization, are valuable tools for medicinal chem. In this presentation, we wish to report the successful realization of the α-oxidation2 of aza-unsaturated rings using cheap and available iodine in mild conditions; as well as β-functionalization of piperidine rings to form cyclic enaminyl sulfones, and the use of the installed functionality as a unique nucleophile for wider functionalization.3 In the same report, we wish to also report a new approach to access polysubstituted piperidinones from simple, com. available or easy to prepare starting materials using HAT chem.