This highlights the importance of considering the correct speciation of the hydroborane when designing borylation processes using (H-BBN)2, as this has a considerable impact on the energy profile for a catalytic cycle. In this case, the ability of the metal complex to interact with two H-BBN units is enabled by ligand non-innocence, specifically interaction of the NacNac C position with one of the H-BBN units derived from (H-BBN)2. The second H-BBN unit then effects the -bond metathesis with the M-Aryl unit. Thus, NacNac ligand non-innocence is essential for low barrier -bond metathesis and protonolysis phases, which is crucial for enabling borylation catalysis given the endergonic nature of the C-H metalation phase. Thus, this study showcases the benefits of ligating main group metals with non-innocent NacNac ligands, the dramatic impact (H-BBN)2 has on mechanism relative to monomeric boronate esters (e.g., HBPin), and the utility of extending catalytic C-H borylation beyond the synthesis of the aryl-boronate esters that currently dominate this field.