The oxidation of Au(I) complexes featuring two hemilabile ligands was investigated. The phosphine-amine (P ∧ N) and mesoionic N-heterocyclic carbenepyridine (C ∧ N) ligands were shown to stabilize the ensuing Au(III) complexes by chelation. Oxidation of (MeDalphos)AuCl with PhICl 2 directly affords the corresponding P ∧ N-chelated cationic Au(III) complex without requiring a chloride abstractor. The C ∧ N hemilabile ligand is shown to efficiently chelate Au(III), but not Au(I). Cationization of the (C ∧ N)AuCl complex 3 affords the dinuclear complex 4 with the C ∧ N ligand bridging two Au centers. Oxidation of 3 with PhICl 2 does not spontaneously enforce coordination of the pyridine side arm, as with the P ∧ N ligand. However, cationization of the resulting AuCl 3 complex 5 with a chloride abstractor successfully promoted pyridine chelation. The structures of all complexes have been ascertained by NMR spectroscopy and X-ray diffraction analyses.