Reactions were performed on a Chemspeed ISYNTH robotic platform with a solid-dispensing unit to expedite reaction set-up and sampling and off-line LC-MS analysis was used to generate the reaction profile (see supporting information for full experimental details, including workflow schematic diagram). In total, 40 reactions were performed in triplicate, with sampling at four different timepoints, generating 480 reaction profiles. LC-MS alignment and peak picking were performed using automated processing (Progenesis QI) and relative concentrations of the reaction constituents were obtained by normalizing the mass-ion counts over the peaks of interest (see supporting information for full details), resulting in a semi-quantification of the species of interest. This approach allows the study of the variation in amount of these (characterized and uncharacterized) species with changing reaction conditions and is simpler than developing an analytical method to show absolute quantities of all species (which would be a non-viable effort in most academic / industrial settings for reactions of this complexity).