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Organo trifluoroborates are the class of compounds generally represented by [RBF3]-. Owing to their strong nucleophilic nature, organo trifluoroborates can react with electrophiles even in the absence of transition-metal catalysts. Organo trifluoroborates can withstand many reaction conditions and therefore can replace boronic acids, boronate esters and organo boranes in many organic transformations. The organo trifluoroborates are used as substrates in various organic transformations such as oxidations, Wittig and related alkenation reactions, condensation reactions, reductive aminations, substitution reactions, metalhalogen exchange reactions, 1,3-dipolar cycloadditions and cross-coupling reactions.
Organo trifluoroborates are involved in Suzuki-Miyaura coupling reaction which contributes to pharmaceutical research, pilot plant technologies, and drug manufacturing. The coupling of an aryltrifluoroborate with an aryl halide proceeds with high efficiency and avoids the extensive generation of undesired phenolic and homocoupling side products (Butters, M.; Harvey, J. N.; Jover, J.; Lennox, A. J. J.; Lloyd-Jones, G. C.; Murray, P. M. Aryl Trifluoroborates in SuzukiMiyaura Coupling: The Roles of Endogenous Aryl Boronic Acid and Fluoride. Angew. Chem. Int. Ed. 2010, 49, 5156-5160). Due to the presence of an empty p-orbital in trivalent Boron atom, organo trifluoroborates can interact with targets and therefore has more biological applications such as enzyme-inhibition assays. The aryl potassium trifluoroborate compounds are more active than the corresponding boronic acids against alpha-chymotrypsin and trypsin. The greater ligand/receptor binding properties of dipeptidyl organo trifluroborate compounds are due to the presence of additional hydrophilic elements and hydrophobic moieties.