Organotrifluoroborate hydrolysis: Boronic acid release mechanism and an acid–base paradox in cross-coupling
AJJ Lennox, GC Lloyd-Jones - Journal of the American Chemical …, 2012 - ACS Publications
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,
thereby minimizing side reactions such as oxidative homocoupling and protodeboronation …
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,
thereby minimizing side reactions such as oxidative homocoupling and protodeboronation …
[引用][C] Organotrifluoroborate Hydrolysis: Boronic Acid Release Mechanism and an Acid–Base Paradox in Cross-Coupling
LA JJ - 2012
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