In the case of aromatic amines with blocked para position, C-H chlorination was instead found to occur in high selectivity at the ortho position (Scheme 2). Notably, di and trisubstituted anilines with electron-donating groups displayed higher reactivity with our protocol, which offered access to products 58-61 in 74-93% yield under the standard conditions. The use of 4-methoxyaniline as a substrate, on the other hand, called for the reaction to be done over an extended time of 18 h at a lower current of 1 mA, in order to afford product 62 in 85% yield alongside 6% dichlorinated byproduct. A similar reactivity was also observed for the reaction between 4-methylaniline and acid chloride 2, which yielded product 63 in 64% with 12% dichlorinated byproduct, when performed with 1 mA current over 18 h. In the case of the electron-deficient 4-chloro and 4fluoroaniline reacting with acid chloride 2, a higher current of 10 mA was required in addition to extended reaction times in order to give 80% and 87% yield of 64 and 4, respectively. However, in these reactions no dichlorinated byproducts were observed. Worthy to note for 3,5-dimethoxy aniline with free para position, C-H chlorination was instead found to occur in high selectivity at the ortho position to afford 65 in 63% yield and without the formation of dichlorinated product.