The combination of the [Cp*Co(CO)I 2 ] catalyst with various additives and solvents at different temperatures for different durations has led to a considerable increase in the amount of research regarding the catalysis of C−H functionalization via high-valent Co, owing to the unique reactivity of the catalyst. Our study presents, for the first time, a data-driven approach toward reported reactions catalyzed using [Cp*Co-(CO)I 2 ]. We analyze distinct solvents, additives, reaction times, temperatures, and directing groups with their associated mean yields, which accelerates the screening process in the laboratory to yield favorable combinations. We demonstrate the effects of reaction conditions and directing groups on the reaction performance by integrating data from the reaction. Additionally, we examine the reactions based on their yields using principal component analysis and the t-stochastic neighbor embedding method. These exploratory investigations may be very useful for synthetic chemists as a starting point in catalytic studies.