Boronic acid derivatives have also been used to suppress protodeboronation.
2.
Many efforts have been put towards mitigating undesired protodeboronation in cross-coupling reactions.
3.
This increases the rate of productive reaction and thus subdues unwanted decomposition pathways such as protodeboronation.
4.
Beyond this synthetic application, protodeboronation was rarely noted or valued in other chemical processes throughout the early 20th century.
5.
However, in more recent years, protodeboronation has emerged as a problematic side reaction with many chemical processes that utilise boronic acids.
6.
This has resulted in an increased usage of boronic acids, and subsequently followed by an increased number of reports concerning problematic protodeboronation.
7.
Conversely, basic heteroaromatic boronic acids ( boronic acids that contain a basic nitrogen atom, such as 2-pyridine boronic acid ) display new protodeboronation mechanisms.
8.
One of the earliest reports of protodeboronation was made by Ainley and Challenger, who were the first researchers to explore the reactivity of boronic acids with common chemical reagents.
9.
In fact, the addition of acid ( H + ) or hydroxide ( OH-) acts to attenuate protodeboronation by shifting the speciation away from the reactive zwitterion.
10.
For the 2-pyridine boronic acid, the zwitterionic compound is responsible for its rapid protodeboronation under neutral pH, through a unimolecular fragmentation of the C-B bond.
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