Under argon protection, 1.4 mg (0.005 mmol) of dichlorobis(trimethylphosphine)nickel (NiCl2(PMe3)2), 77.4 mg (0.5 mmol) of 4-chlorobenzamide, 152 mg (1.0 mmol) of cesium fluoride (CsF), 140 mg (0.55 mmol) of bis(pinacolato)bis(boronic acid) ( B2pin2), 180 mg (1.05 mmol) trimethyl (2,2,5,5-tetrafluoroethoxy) silane (TMSEF), and 0.5 mL 1,4-dioxane. The reaction vessel was sealed and the mixture was stirred and reacted at 100°C for 12 hours. Upon completion of the reaction, the reaction vessel was cooled to room temperature and the reaction was quenched by the addition of 1 mL of saturated aqueous ammonium chloride. The mixture was extracted three times with 8 mL of ethyl acetate and the organic phases were combined. The solvent was removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography (eluent gradient: hexane/chloroform/ethyl acetate = 4:1:0 to 4:1:1) to afford 92 mg (75% yield) of the target product 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide as a white solid.
