The generation of the reaction data set for Miniscitype alkylation reactions involved the experimental evaluation of a diverse array of electron-deficient heterocyclic fragments in combination with various sp 3rich carboxylic acids. A total of 80 common medicinal chemistry fragments (e.g., pyridines, pyrimidines, quinolines, benzoxazoles, F1-F80, Supplementary Information [SI]4.1) and 59 carboxylic acids (A1-A59, SI4.2) were selected, resulting in a chemical space of 4,720 possible combinations (Figure ). Data analysis using the Simple User-Friendly Reaction Format (SURF) revealed variable reactivity dependent on different silver salts and additives while maintaining consistent oxidant and solvent systems. Consequently, each fragment-acid combination was assessed with different catalysts and additives in a 24-well plate format (Figure ).