In conclusion, neutral multidentate halogen bonding organocatalysts based on iodocarborane moieties were introduced. Binding data in solution suggested superior Lewis acidity compared to established fluorinated analogs, which was confirmed by their strong catalytic activity. The tridentate variant 3, in particular, excelled in a halide abstraction reaction, surpassing even the performance of strong dicationic halogen bond donors, and facilitated for the first time the activation of a nitro group with a neutral halogen bonding based organocatalyst. To the best of our knowledge, these new systems represent the strongest neutral multidentate halogen bond donors available.