type, we obtained three structural isomers, 2aa, 2ab, 2ad, and the decarbonylated product, 2ac. Overall, the total yield of insertion products increased with stronger electron-withdrawing properties of the PG. Selective formation of 2ac was achieved by introducing the Boc-group. Interestingly, 2ac was the exclusive decarboxylation product, and no other structural isomer was observed. Introducing the Ac-group resulted in a mixture of 2aa, 2ab, and 2ac. Notably, using TCA as the PG led to an 80% yield with the selective production of the para-insertion product, 2ad. Similarly, TFA yielded only 2ad as the sole product, indicating a preference for electron-withdrawing PG for para-insertion.