A catalytic intermolecular arene C-H borylation process using (H-BBN)2 to make a range of mono-and di-borylated heteroarenes is reported for the first time to our knowledge. Notably, the Aryl-BBN species can be synthesized and utilized in-situ, including in a transformation that is not feasible using the Aryl-BPin compounds that are produced in almost all other catalytic C-H borylation processes. Due to the endergonic nature of the C-H metalation step, for this C-H borylation process to be energetically feasible it requires low barrier -bond metathesis and protonolysis steps. Kinetic studies revealed that the -bond metathesis process proceeds via addition of both H-BBN units in the (H-BBN)2 dimer to the NacNacZn-Aryl complex -i.e., the order of reaction with respect to (H-BBN)2 was found to be 1. This is distinct to conventional bond metatheses which involve one equivalent of a monomeric hydroborane reacting with a M-Y unit of a metal complex. The involvement of both H-BBN units in the turnover limiting process is crucial as this offsets the significant energetic cost of cleaving dimeric (H-BBN)2.