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Abstract A synthetic method for the palladium‐catalyzed cyanation of aryl boronic acids using bench stable and non‐toxicN‐cyanosuccinimide has been developed. High‐throughput experimentation facilitated the screen of 90 different ligands and the resultant statistical data analysis identified that ligand σ‐donation, π‐acidity and sterics are key drivers that govern yield. Categorization into three ligand groups – monophosphines, bisphosphines and miscellaneous – was performed before the analysis. For the monophosphines, the yield of the reaction increases for strong σ‐donating, weak π‐accepting ligands, with flexible pendant substituents. For the bisphosphines, the yield predominantly correlates with ligand lability. The applicability of the designed reaction to a wider substrate scope was investigated, showing good functional group tolerance in particular with boronic acids bearing electron‐withdrawing substituents. This work outlines the development of a novel reaction, coupled with a fast and efficient workflow to gain understanding of the optimal ligand properties for the design of improved palladium cross‐coupling catalysts.