I don’t know whether the mechanism of hydrolysis of the boronic acid esters has been studied. However, the dissociative mechanism immediately suggests itself if only by comparison to similar structures.
Since the workup is typically written $\ce{H+/H2O}$, you may consider some buffered source of external protons. These can protonate any of the alcoholates which can then dissociate. (The $\ce{B=O}$ double bond I drew in should be considered no more than additional stabilisation from oxygen lone pairs; boron is electron-deficient by definition.) Another water molecule can associate: the first bond is cleaved. Repeat three times and end up with four molecules of alcohol and tetrahydroxidoborate $\ce{[B(OH)4]-}$.
I don’t know whether the mechanism of hydrolysis of the boronic acid esters has been studied. However, the dissociative mechanism immediately suggests itself if only by comparison to similar structures.
Since the workup is typically written $\ce{H+/H2O}$, you may consider some buffered source of external protons. These can protonate any of the alcoholates which can then dissociate. (The $\ce{B=O}$ double bond I drew in should be considered no more than additional stabilisation from oxygen lone pairs; boron is electron-deficient by definition.) Another water molecule can associate: the first bond is cleaved. Repeat three times and end up with four molecules of alcohol and tetrahydroxidoborate $\ce{[B(OH)4]-}$.
For an acidic work up:
For an acidic work up:
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I don’t know whether the mechanism of hydrolysis of the boronic acid esters has been studied. However, the dissociative mechanism immediately suggests itself if only by comparison to similar structures.
Since the workup is typically written $\ce{H+/H2O}$, you may consider some buffered source of external protons. These can protonate any of the alcoholates which can then dissociate. (The $\ce{B=O}$ double bond I drew in should be considered no more than additional stabilisation from oxygen lone pairs; boron is electron-deficient by definition.) Another water molecule can associate: the first bond is cleaved. Repeat three times and end up with four molecules of alcohol and tetrahydroxidoborate $\ce{[B(OH)4]-}$.
I don’t know whether the mechanism of hydrolysis of the boronic acid esters has been studied. However, the dissociative mechanism immediately suggests itself if only by comparison to similar structures.
Since the workup is typically written $\ce{H+/H2O}$, you may consider some buffered source of external protons. These can protonate any of the alcoholates which can then dissociate. (The $\ce{B=O}$ double bond I drew in should be considered no more than additional stabilisation from oxygen lone pairs; boron is electron-deficient by definition.) Another water molecule can associate: the first bond is cleaved. Repeat three times and end up with four molecules of alcohol and tetrahydroxidoborate $\ce{[B(OH)4]-}$.
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