First, we chose to investigate the impact of the aniline substitution pattern on the reaction performance. Here, a wide range of aniline derivatives having both one and multiple substituents in the meta and ortho positions were surveyed using cyclohexanecarbonyl chloride (2) as the acid chloride. The substituents on the aniline moiety were found to have a profound effect on the rate of the cascade process in several of the cases, which can be ascribed to their influence on the C-H chlorination process that occur at the aromatic ring belonging to the aniline reagent.