Interestingly, by increasing the equivalents of the acid chloride partner and extending the reaction time, it proved possible to direct this electrochemical cascade towards the formation of dichlorinated products as the main products (Scheme 3). The reactions between acid chloride and various aniline showed similar accelerating effect by the presence of electron-donating groups to the aniline on the dichlorination reaction, as demonstrated by the entries giving products 83-87 in 67-96% yield. In the case of phenylenediamines as substrates, we were able to achieve diacylation in parallel to dichlorination by modifying the reaction conditions. When the reaction was performed with meta-phenylenediamine and 4 equiv. of the acid chloride 2, it was possible to isolate product 88 in 96% yield after 3 h. From ortho-phenylenediamine, we could generate product 89 in 67% yield with 2 equiv. of acid chloride 2 when the reaction was carried out at a lower current (5 mA) for 6 h. To our delight, highly efficient dichlorination was also observed for the naphthyl scaffold, furnishing product 90 in 67% yield when the reaction was performed for 3 h. As was demonstrated with aniline as the aromatic amine partner, this dichlorination strategy also display a broad tolerance towards different acid chlorides. Here, the 2,4-dichlorinated amide products 91-99 were obtained in synthetically useful yields ranging between 52-91% following reaction times of 15-45 h. The corresponding dichlorination with ethyl chloroformate as the reaction partner, on the other hand, was found to be less efficient and the carbamate product 100 was obtained in 40% yield after 17 h.