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Kinetic Data for the Transmetalation/Reductive Elimination in Palladium-Catalyzed Suzuki–Miyaura Reactions: Unexpected Triple Role of Hydroxide Ions Used as Base

✍ Scribed by Dr. Christian Amatore; Dr. Anny Jutand; Gaëtan Le Duc


Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
379 KB
Volume
17
Category
Article
ISSN
0947-6539

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✦ Synopsis


Dedicated to Professor Marc Julia

, which generates ArAr' and a Pd 0 species. Conversely, the base OH À disfavors the reaction by formation of the unreactive anionic Ar'B(OH) 3

À . As a consequence of these antagonistic effects of OH À , the overall reactivity is controlled by the concentration of OH À and passes through a maximum as the concentration of OH À is increased. Therefore, the base favors the rate-determining transmetalation and unexpectedly also the reductive elimination.