Protodeboronation

Protodeboronation, or protodeborylation is a chemical reaction involving the <a href="/facts/Protonolysis/6FhgouNz">protonolysis</a> of a <a href="/facts/Boronic_acid/BtN4s5B4">boronic acid</a> (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 <a href="/facts/Side_reaction/HMJ8CYxH">side reaction</a>, and frequently associated with metal-catalysed <a href="/facts/Coupling_reaction/L464wvvk">coupling reactions</a> that utilise boronic acids (see <a href="/facts/Suzuki_reaction/aRISucCH">Suzuki reaction</a>). 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.
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, and also in purification procedures, such as the removal of unwanted regioisomeric boronic acid by-products.
Recent mechanistic studies have revealed a variety of protodeboronation pathways in aqueous media, and have demonstrated the reaction <a href="/facts/PH/RnSv8D7y">pH</a> (and subsequently the boronic acid speciation) to be an important factor in understanding the modes of protodeboronation.

Protodeboronation open-in-new

Protodeboronation