To bypass the generation of a carbene radical cation, we set out to explore an alternative strategy for the oxidation of bis(imino)carbene 1. We envisaged a two-step approach, first by carbene coordination to a two-electron oxidant, then removing the oxidant along with two electrons. Accordingly, treating 1 with I2 as the two-electron oxidant formed the (iodo)carbenium ion as evidenced by in-situ 1 H NMR (Fig. , Fig. ) . However, all attempts to abstract both iodides were unsuccessful, possibly due to the strong halophilicity of the target carbene dication (vide infra). This prompted us to exchange the iodides for O 2-, which could be easily achieved through a one-pot procedure from 1. Thus, treating 1 with I2 and then NaOSiMe3 afforded the neutral bis(imino)carbonyl compound 2 . Gratifyingly, subjecting 2 to triflic anhydride as the O 2-abstracting agent led to a new species . The 1 H NMR spectrum displays only one set of signals associated with the two NHI units. The central carbon signal appears at 119.8 ppm in the 13 C{ 1 H} NMR, in excellent agreement with DFT calculations for the target carbene dication 1 2+ (PBE0/def2-TZVPP//r 2 SCAN-3c; 124.8 ppm). The 19 F NMR spectrum shows only one signal at -77.9 ppm which is in the typical range observed for an uncoordinated triflate anion.