To answer this question, we selected a series of aromatic and aliphatic amines with different pKa values (Figure ), three representative ones of which are shown in Figure (PhNH2, DBU and TEA with an ascending order of nucleophilicity), to examine whether stronger Lewis bases (compared to THF) could chemically react with ADBr. It has to be noted that the experiment using amine controls cannot possibly produce an identical condition compared with the previous solvent one to allow for accurate NMR on the one hand, the ADBr benzyl group deprotonation was not observed, since a loss of the methylene proton results in an ylide with diminished NMR signal due to its diradical nature, as has been previously reported suing a much stronger base, e.g., t-BuOK. On the other hand, the NMR spectrum of ADBr/TEA also varies substantially from that of ADBr/THF, where the signal of the proton para to the N atom at  = 10.3 ppm disappears, along with an ensembled high-field shift of aromatic protons from  > 8 ppm to 6.9-7.5 ppm (Figure ). The NMR results point to a highly likely event of chemical reaction between TEA and ADBr.