Following up on the remarkable activity of catalyst 3 in the halide-abstraction reaction, it was next employed in the nitro-Michael addition reaction of 5-methoxy-indole with trans-nitrostyrene (Scheme 3), which had not been catalyzed by neutral halogen bonding organocatalysts before (and in which a iodotriazolium-based dicationic halogen bond donor had also previously failed). Scheme 3: Benchmark nitro-Michael reaction for evaluation of XB catalysts.