To gain a comprehensive understanding of the mechanism, density functional theory (DFT) calculations at the B3LYP-D3/cc-pVTZ(-f)/LACV3P//B3LYP-D3/6-31G**/LACVP level of theory were conducted. Our investigation began with the 16-electron complex A1 using 1-hexene and CsOAc as the reactant and base, respectively. Two plausible mechanistic scenarios were considered, as depicted in Scheme 2: The first scenario, depicted by the black trace, initiates with the formation of an amide followed by subsequent olefin insertion. The second scenario, illustrated by the blue and green traces, follows a pathway through nitrene formation, involving the concerted creation of both C-N bonds. We ruled out the possibility of a direct concerted metalation-deprotonation (CMD) of the olefin due to its unrealistically high energy demand (see SI for details).