General Description
4-Acetylphenylboronic acid is a boronate, belongs to a class of synthetic organic compounds. It reacts rapidly with peroxynitrite (ONOO(-)) to form stable hydroxy derivatives. It undergoes Suzuki coupling with 4-bromotriphenylamine catalyzed by dichlorobis(triphenylphosphine)Pd(II), during the synthesis of dendrimers.
Synthesis
The general procedure for the synthesis of (R)-1-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-ol and 4-acetylphenylboronic acid from 1-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-ol was carried out in the following manner: under aseptic conditions, the appropriate racemic alcohol ( 0.5 mmol) was dissolved in dimethylformamide (2 mL) and added to a 500 mL conical flask containing 8.2 g of wet cells (resuspended in 100 mL of phosphate buffer, pH 7.0, 100 mmol/L). The reaction was carried out at 20°C and 400 rpm for 120 hours. After completion of the reaction, the reaction mixture was extracted for 24 h using a continuous liquid-liquid extractor and dichloromethane (300 mL). The organic layer was dried with anhydrous magnesium sulfate followed by evaporation of the solvent under reduced pressure. The crude product was purified by column chromatography using hexane/ethyl acetate as eluent.
References
[1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 110, p. 117 - 125
