Fig. 2. Principal component analysis (PCA) comparing small molecule drugs with products described in synthetic literature reports. (A) shows a principal component analysis used to visualize the physicochemical space occupied by marketed small molecule drugs compounds (grey) and products described in literature reports for the several reaction types evaluated in this work: in red are compounds that were prepared in the seminal Suzuki–Miyaura paper, and in blue are the products formed in leading literature Suzuki–Miyaura reports, recent methods reported for the conversion of aryl pinacol boronates into aryl nitriles and recent Buchwald–Hartwig C–N coupling methods. Representative structures from both the small molecule drugs collection and literature reports are highlighted. Fig. 2B–E depict how properties with the greatest contribution to PC1 and PC2 are mapped by the PCA, with black representing the highest values for each parameter. See ESI† for full details.