Protodeboronation
From Wikipedia, the free encyclopedia
Protodeboronation, or protodeborylation is a chemical reaction involving the protonolysis of a boronic acid (or other organoborane compound) in which a carbon-boron bond is broken and replaced with a carbon-hydrogen bond. Protodeboronation is a well-known undesired side reaction, and frequently associated with metal-catalysed coupling reactions that utilise boronic acids (see Suzuki reaction).[1] For a given boronic acid, the propensity to undergo protodeboronation is highly variable and dependent on various factors, such as the reaction conditions employed and the organic substituent of the boronic acid.
![Thumb image](http://upload.wikimedia.org/wikipedia/commons/thumb/0/04/Simple_protodeboronation_scheme.png/320px-Simple_protodeboronation_scheme.png)
The deliberate protodeboronation of boronic acids (and derivatives) have been applied to some synthetic procedures, such as the installation of a stereospecific proton at chiral centers,[2] and also in purification procedures, such as the removal of unwanted regioisomeric boronic acid by-products.[3]
Recent mechanistic studies have revealed a variety of protodeboronation pathways in aqueous media, and have demonstrated the reaction pH (and subsequently the boronic acid speciation) to be an important factor in understanding the modes of protodeboronation.[4][5]
![A general reaction scheme for the protodeboronation of boronic acids](http://upload.wikimedia.org/wikipedia/commons/thumb/6/64/Protodeboronation_Scheme.png/640px-Protodeboronation_Scheme.png)