One of the major advantages of PC electrodes is their durability which allows for easy recyclability, especially compared to RVC. In a brief series of experiments, the same set of PC electrodes were used in five sequential Kolbe homocoupling reactions (5, Table ) and simply rinsing and wiping each electrode in between runs. No visible degradation occurred, and yields were consistent across all runs. A set of RVC electrodes were exposed to the same conditions and, while reactivity also remained consistent, handling the RVC was a delicate process. Extreme care was required to not break the fragile electrode in between runs which, due to the macroporous nature of RVC, could not be simply rinsed and required sonication for adequate cleaning, resulting in some physical degradation (See SI for details). The reactivity of PC electrodes was explored alongside comparative runs performed with RVC as a benchmark, GC as an amorphous carbon electrode devoid of a 3D structure, and simple graphite as a control. Comparable reactivity to RVC and GC was found in both homo-and hetero Kolbe coupling (Table ). Notably, graphite reactivity under the conditions yielded no desired product, confirming that the CVD coating is crucial to exhibit unique rAP reactivity. Perhaps the most valuable function of this new electrode material is its translatability to large-scale parallel plate flow reactors, where RVC fails due to fragility and GC is non-ideal due to its high cost similar to noble metal electrodes. Of particular interest to us was attempting decagram synthesis of 4, an adipic acid derivative used in cosmetics and polymer chemistry (Table ). Currently, this simple compound is procured from petroleum feedstocks, whereas this route provides a sustainable alternative as the starting material, monomethyl succinic acid can be derived from bio-based succinate (mass produced via fermentation). A 280 mmol (~37 g) scale synthesis was carried out utilizing a parallel plate reactor with custom PC electrodes (Figure ). Some additional optimization was explored (See Flow FAQ in SI) when translating the reaction conditions from small-scale to take into consideration possible safety concerns as well as address equipment limitations. Tetramethylammonium hydroxide, which served as an electrolyte, was substituted with an innocuous solution of potassium carbonate and formic acid. This aqueous solution also contributed a small percentage of water to the system to increase conductivity. A parallel plate flow reactor that has been previously described by our group was employed with a slight modification of the reactor design in order to reduce the electrode distance. Electric current was delivered with a combination of waveform amplifier and a signal generator (see SI for full details of flow setup). Due to the limit of the waveform amplifier, the overall current on large-scale was lower than the expected value estimated from the small-scale runs; this was accounted for by decreasing rAP frequency (i.e. pulse duration was increased to 200 ms). Under these conditions 12.5 g of the desired product were obtained after 40 hrs of electrolysis, demonstrating PC's utility on large-scale. Encouraged by the success of flow rAP Kolbe coupling with PC electrodes, a more synthetically challenging transformation was evaluated on scale. Thus, trifluoromethylated compound 22 was targeted due to the growing interest of N-methylated unnatural amino acids as an important building unit for peptide-based therapeutics. It was envisioned that aspartate derivative 20 would serve as a simple precursor to such compounds through rAP hetero-Kolbe coupling followed by reductive oxazolidinone ring cleavage (Table ). Gratifyingly, under the conditions reported in the original heterocoupling procedure, 20 was cleanly converted into 21 with only 1.4 F/mol, demonstrating highly practical nature of this coupling (54% yield). The downstream transformations of 21 via silane-based reduction followed by the attachment of Fmoc group (chromophore for chiral HPLC analysis) revealed that 22 was enantiopure (60%, >99% ee).