Mechanism of Palladium‐Catalyzed Suzuki–Miyaura Reactions: Multiple and Antagonistic Roles of Anionic “Bases” and Their Countercations

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Abstract
In Suzuki–Miyaura reactions, anionic bases F− and OH− (used as is or generated from CO32− in water) play multiple antagonistic roles. Two are positive: 1) formation of trans‐[Pd(Ar)F(L)2] or trans‐[Pd(Ar)‐ (L)2(OH)] (L=PPh3) that react with Ar′B(OH)2 in the rate‐determining step (rds) transmetallation and 2) catalysis of the reductive elimination from intermediate trans‐[Pd(Ar)(Ar′)(L)2]. Two roles are negative: 1) formation of unreactive arylborates (or fluoroborates) and 2) complexation of the OH group of [Pd(Ar)(L)2(OH)] by the countercation of the base (Na+, Cs+, K+).
Funding Information
  • Centre National de la Recherche Scientifique
  • CNRS
  • Ministère de la Recherche

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