Organotrifluoroborate Hydrolysis: Boronic Acid Release Mechanism and an Acid–Base Paradox in Cross-Coupling

AJJ Lennox, GC Lloyd-Jones

Index: Lennox, Alastair J. J.; Lloyd-Jones, Guy C. Journal of the American Chemical Society, 2012 , vol. 134, # 17 p. 7431 - 7441

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Citation Number: 95

Abstract

The hydrolysis of potassium organotrifluoroborate (RBF3K) reagents to the corresponding boronic acids (RB (OH) 2) has been studied in the context of their application in Suzuki– Miyaura coupling. The “slow release” strategy in such SM couplings is only viable if there is an appropriate gearing of the hydrolysis rate of the RBF3K reagent with the rate of catalytic turnover. In such cases, the boronic acid RB (OH) 2 does not substantially accumulate, ...