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Boronic acids are alkyl or aryl substituted boric acids containing a carbon-boron bond and represented by R-B(OH)2. Generally, boronic acids act as Lewis acids. Boronic acid can easily form reversible covalent complexes with sugars, amino acids, and hydroxamic acids. Owing to its low toxicity and relatively quick degradation in the environment, boronic acid is considered as a green compound. During dehydration, boronic acids give the corresponding boronic anhydrides or boroxines. A six membered heterocyclic ring comprising alternate oxygen and boron atoms is referred to as a boroxine. Boroxines are the cyclotrimeric anhydrides of boronic acids, and isoelectronic to benzene. Examples of boronic anhydrides include trimethylboroxine and triphenylboroxine. Boronic acids and their corresponding boronic anhydrides exist in equilibrium at room temperature.
Boronic acid is a mild organic Lewis acid; their reactivity, stability, and ease of handling have caused them to be significant synthetic intermediates. Boronic acids are often employed in synthetic organic chemistry in the Suzuki reaction, for Chan-Lam coupling, for LiebeskindSrogl coupling, for forming carbon-carbon bonds, carbon-nitrogen bonds, and carbon-oxygen bonds. In supramolecular chemistry, boronic acid is used for the recognition of molecules binding to saccharides and for the fluorescent detection, or selective transport, of saccharides across membranes. Boronic anhydrides are widely used in the production of optics. One of the most common boronic anhydrides used in the methylation of aryl halides by palladium-catalyzed Suzuki-Miyaura coupling reactions is trimethylboroxine. Owing to the presence of covalent chemistry in the boroxine ring, boronic anhydrides find their use in novel molecular architectures and functional materials (Review: Boroxine chemistry and applications: A perspective. Korich, A. L. Dalton Trans., 2010, 39, 1423-1431.