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- Title
Mechanism of Palladium-Catalyzed Suzuki-Miyaura Reactions: Multiple and Antagonistic Roles of Anionic 'Bases' and Their Countercations.
- Authors
Amatore, Christian; Le Duc, Gaëtan; Jutand, Anny
- 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+).
- Subjects
SUZUKI reaction; PALLADIUM catalysts; ANIONS; CHEMICAL inhibitors; CATALYSIS; FLUOBORATES; COMPLEXATION reactions; METAL complexes
- Publication
Chemistry - A European Journal, 2013, Vol 19, Issue 31, p10082
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201300177