Automated reaction preparation was carried out on an Opentrons liquid-handling platform (OT-2), 28 with the deck containing a 24-well plate of each precursor stock solution, a 6well solvent plate, and a 48-well reaction plate. A general OT-2 Python input protocol script was adapted to include the solvent calibrated gantry, aspirate and dispense speeds, along with the stock/solvent locations and move commands dictionaries (full details given in the Supporting Information S2). The reaction plate was subsequently removed from the deck, sealed and stirred at 70 °C for 17 h. A 20 μL sample was then taken, dissolved in MeCN, and taken for HRMS analysis. The bulk reaction mixture solvent was removed with a 48-well EquaVAP and redissolved in acetonitrile-d3 for 1 H NMR analysis. Overall, 24 combinations were screened under the same reaction conditions (overall concentration: 0.0092 M, total volume: 1 mL, MeCN, 70 °C, 17 hours) in 2 mL capped vials with stirrer bars, and repeated to check reproducibility.