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Boronic esters (RB(OR)2), also referred to as boronate esters, are formed between a boronic acid and an alcohol. Boronate esters are stable compounds, although the -C-B- bond of boronic ester is slightly longer than C-C single bonds. Boronic acid esters can undergo saponification and racemize optically active compounds. Boronic acid esters coordinate with basic molecules to form stable tetra-coordinated adducts. Boronic acid esters are considered as compounds for the designing of new drugs and drug delivery devices, more particularly as boron carriers for neutron capture therapy.
Boronic esters are very easy to purify and characterize. They have enhanced reactivity, higher compatibility with many reagents, better solubility in organic solvents, and are also used as good protecting groups to eliminate unwanted side reactions. Boronic acid ester molecules are used in pharmaceuticals, agrochemicals, and high-tech materials.
With their excellent ability to construct C-C bonds via metal-catalyzed cross coupling, boronic esters have received much attention for use in organic synthesis. The boronic esters are widely used for carrying out cross coupling reactions. Boronic acid esters are used in the Suzuki-Miyaura coupling reaction for synthesizing unsymmetrical biaryls, which has wide use in pharmaceuticals and agrochemical industries. Chiral alpha-Haloalkylboronic esters as reagents for asymmetric synthesis (reviewed in Boronic Esters in Asymmetric Synthesis, Matteson, D. S. J. Org. Chem., 2013, 78 (20), 1000910023) have been reported to yield diastereomeric ratios exceeding 1000. (alpha-Amidoalkyl)boronic acids include the biochemically significant serine protease inhibitors, which are used for the treatment of multiple myeloma and mantle cell lymphoma.