Hypervalent iodine(III) reagents have garnered widespread interest from the synthetic community, due to their low toxicity and high selectivity, reactivity and functional-group compatibility in mild-condition syntheses. These compounds exhibit broad electrophilicity, wherein a ligand bound to a central iodonium atom is readily transferred to a nucleophile. This method is amenable to a wide variety of nucleophiles, yielding arylated, alkynylated and vinylated products. Diaryliodonium salts (Ar2IX), bearing two aryl groups, are a common reagent class; as bench-stable, easy to synthesize, and non-hazardous arylation agents, they allow for reaction pathways reminiscent of metal-mediated transformations but without need for expensive, scarce, and toxic transition-metal catalysts. The Olofsson group has developed a diarylation strategy whereby both aryl ligand-groups can be transferred from Ar2IX. This methodology has found wide applicability, with the most recent being the synthesis α-diarylated quaternary centres from stabilized carbon nucleophiles. Previous experimental and computational studies support a mechanistic pathway consistent with a stepwise SnAr reaction followed by an intramolecular aryl transfer for S-nucleophiles. The goal of the present project is thus to explore the mechanisms of the diarylation for other nucleophiles, and compare the energies for alternative pathways like ligand coupling, to gain fundamental expertise on the reactivity of diaryliodonium salts. This will be achieved through computational modelling, utilizing Density Functional Theory in Gaussian 16. Here, the potential energy landscape of the reactions will be evaluated to identify relevant ground-state intermediates and transition states.