Building on this versatility, we employed this general C-H anti-Friedel-Crafts strategy to regioselectively functionalise a range of pharmaceutical and agrochemical compounds. The late-stage alkylation with N-Boc 4-methylpyperidine was selected as piperidines are the most common nitrogen heterocycle found in drug molecules. This included: the antiretroviral Neviparine (46); the fungicide Boscalid (47); and the steroid biosynthesis inhibitor Metyrapone (48) in moderate yield (Fig. ). Notably, the excess of electron-poor aromatic radical acceptors was largely recovered, such that all pharmaceutical acceptors were purified in high yield based on recovered starting material (77-88 %), thus making the use of excess reagent non-prohibitive for late-stage or expensive substrates. Furthermore, we employed a redox-active ester of Gemfibrozil, a lipid-regulating fibrate, in the C-H alkylation of 3fluoropicolinonitrile in good yield (49, 66 %). This shows the ability of this methodology to not only alkylate aromatic molecules but furnish carboxylic acid drug molecules with aromatic groups. These results highlight the methodology's practical applicability in the late- To better understand the EDA complexation, mechanistic pathway and selectivity for this methodology, we performed DFT calculations to elucidate the mechanism of this anti-Friedel-Crafts C-H functionalisation. The model system (Entry 1, Table ) was selected based on its optimal reactivity, and the calculations were carried out at ωB97XD/6-31g(d,p) level of theory (see Supplementary Information for details).