Organotrifluoroborate hydrolysis: boronic acid release mechanism and an acid-base paradox in cross-coupling.
摘要：
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. The study reveals that the hydrolysis rates (THF, H2O, Cs2CO3, 55 °C) depend on a number of variables, resulting in complex solvolytic profiles with some RBF3K reagents. For example, those based on p-F-phenyl, naphthyl, furyl, and benzyl moieties are found to require acid catalysis for efficient hydrolysis. This acid–base paradox assures their slow hydrolysis under basic Suzuki–Miyaura coupling conditions. However, partial phase-splitting of the THF/H2O induced by the Cs2CO3, res...
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DOI：
10.1021/ja300236k
被引量：
年份：
2012
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