m-1-H 20% 16h <1% For the most active bidentate catalyst m-1 and several comparison compounds, kinetic profiles of the reaction were obtained via quenching with sodium methanolate in regular intervals. The corresponding plot (Figure ) once again illustrates vividly that the difference between bidentate and monodentate catalysts (even when the same number of iodine centers are present; grey versus green line). Interestingly, more than twice the catalyst loading (10 mol-%) of bidentate fluorinated halogen bond donor m-2 is needed to roughly replicate the performance of the monodentate carborane (with 4 mol-%; blue versus green line). Next, the tridentate catalyst 3 was tested in the same reaction. Based on the titration data with chloride, approximately the same performance as m-1 could have been expected, whereas the corresponding fluorinated tridentate halogen bond donor 4 typically considerably outperformed its bidentate analog m-2. At 0.5% catalyst loading of 3, full conversion was observed already after just 1 h (Table , entry 10), which is in stark contrast to the 79% yield obtained with m-1 after 16 h (entry 6). The corresponding kinetic profile (which was inevitably somewhat noisy given the short reaction times) indicated that almost complete conversion was indeed already achieved after about 10 minutes (Figure ). This strong catalytic activity surpasses even that of our previously strongest iodine-based di-cationic catalyst 6. It hints at the great potential of catalyst 3 for its use in other reactions, but also demonstrates that catalytic performance cannot satisfyingly be extrapolated from simple binding data alone. In a direct comparison between the catalysts 3, 4 and 6 under identical conditions, quenched after 1 h reaction time, carboranederived catalyst 3 outperformed the other catalysts as shown below.