Phenylboronic acid is used in numerous cross coupling reactions. In 1979, Miyarura and Suzuki found a carbon-carbon bond forming reaction (now called a Suzuki reaction) using alkenyl boranes, aryl halides, catalytic Pd(0), and base to produce arylated alkene products. This method was generalized to a route producing biaryls by coupling phenylboronic acid with aryl halides.
More C-C bond forming processes commonly use phenylboronic acid as a reagent. Alpha-amino acids can be generated using the uncatalyzed reaction between alpha-ketoacids, amines, and phenylboronic acid. Heck-type cross coupling of phenylboronic acid to alkenes and alkynes. This unique C-C bond forming reaction has the ability to couple a terminal olefin with boronic acid using a transition metal catalyst. Aryl azides and nitroaromatics can also be generated using phenylboronic acid.PhB(OH)2 can be used as a protecting group for diols and diamines. Phenylboronic acid can also be regioselectively halodeboronated using aqueous bromine, chlorine, or iodine.
PhB(OH)2 + Br2 + H2O → PhBr + B(OH)3 + HBr
Phenylboronic acid is used in biology schemes as receptors and sensors for carbohydrates, antimicrobial agents and enzyme inhibitors, neutron capture therapy for cancer, transmembrane transport, and bioconjugation and labeling of proteins and cell surface.
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