Pyridine-4-boronic acid is a kind of boronic acid derivative. It is useful building blocks in crystal engineering. It can also be used as a catalyst to act as a dehydrative condensation agent to synthesize amides using carboxylic acid and amines as raw materials. Its derivative, polystyrene-bound 4-pyridineboronic acid, is a useful catalyst for amidation reaction and esterification of alpha-hydrocarboxylic acids.
Under argon protection, 4-bromopyridine (1.5 g, 10 mmol) was placed in a 200 mL Schlenk flask and 40 mL of anhydrous deoxytetrahydrofuran was added. After cooling the reaction mixture to -78 °C, 5 mL (2.2 M, 11 mmol) of n-butyllithium solution was slowly added dropwise and the reaction was maintained at this temperature for 1 hour. Subsequently, 4 mL of trimethyl borate was added and the reaction continued at -78 °C for 1 hour. Upon completion of the reaction, the mixture was slowly warmed to room temperature and stirred overnight. The reaction was quenched with 2 mol/L hydrochloric acid solution and purified by recrystallization from hexane to give pyridine-4-boronic acid hydrochloride (0.8 g, 65% yield).
http://www.wako-chem.co.jp/english/labchem/product/Org/pyridineboronic/
José J. CamposGaxiola et al. "Pyridineboronic Acids as Useful Building Blocks in Combination with Perchloroplatinate(II) and -(IV) Salts: 1D, 2D, and 3D Hydrogen-Bonded Networks Containing X-H•••Cl2Pt− (X = C, N+), B(OH)2•••Cl2Pt−, and B(OH)2•••(HO)2B Synthons." Crystal Growth & Design 10.7(2010).
Kara, H., A. G. Orpen, and T. J. Podesta. "Pyridine boronic acids as building blocks in crystal engineering." Acta Crystallographica 61.Suppl (2001): C357.
