Finally, to probe the scalability of this reaction, a 100 mmol scale synthesis of unnatural amino acids 1 and 38 was pursued utilizing recirculating flow (Figure ). Additionally, given the inconvenience of synthesizing and isolating 100 mmol of the necessary RAE, an in situ protocol was targeted to avoid an intermediate purification step en route to multigram quantities of 1 and 38. In practice, 100 mmol (ca. 34 g) of glutamic acid derived 87/88 was activated in THF with DIC and NHPI for 3 h. Given the empirical observation that the urea byproducts from in situ activation can hinder the performance of the reaction, a means by which to remove this byproduct was needed in order to carry out this large scale reaction open to air. Fortunately, the diisopropylurea is not completely soluble in THF and can simply be filtered off using filter paper as the RAE is being transferred to the round bottom flask containing the nickel catalyst and the iodoarene coupling partner together with lithium chloride as a supporting electrolyte. Once the addition was complete, the key silver nitrate additive was added directly to the flask as solids. A peristaltic pump was enlisted to recirculate the reaction mixture through the reactor bearing a sacrificial magnesium plate anode and carbon felt cathode (see SI for full details and graphical guide). In the initial hour of the reaction, the reaction mixture progressed from a heterogenous suspension of silver halide salts to a homogenous green solution as the silver is plated within the electrode chamber on the carbon felt cathode. After electrolysis at 1 A for 12 hours, the reaction mixture was worked up following the standard protocol and 1 and 38 were accessed in 15 grams (43%) and 18 grams (49%) respectively.