Palladium-Catalyzed Acyl Suzuki–Miyaura Coupling from Carboxylic Acids In Situ Activated by HATU: An Efficient Way to Ketones Laid by Nitrogen Coordination

Abstract

A palladium-catalyzed acyl Suzuki–Miyaura coupling between carboxylic acids and organoboronic acids has been developed, employing hexafluorophosphate azabenzotriazole tetramethyl uronium as an in situ activator. Using Pd₂(dba)₃/PCy₃ as the catalyst and K₂CO₃ as the base, the reaction accommodates a broad range of both aliphatic and aromatic carboxylic acids. Controlled experiments and density functional theory calculations reveal that the pyridine nitrogen plays a critical role in the catalytic cycle.