Palladium(II) Acetate

Typical Procedure:
Palladium(II) acetate (9.6 mg, 0.048 mmol), 1,4-benzoquinone (23.7 mg, 0.22 mmol), silver(I) carbonate (237.2 mg, 0.86 mmol) and benzo[h]quinoline (0.43 mmol) are weighed into a 20 mL scintillation vial. After adding 1,2-dichlorobenzene (3.75 mL), 125 µL of DMSO (1.45 mmol) is added. The resulting mixture is sealed with a teflon-lined cap, and vigorously stirred at 130 °C. The reaction mixture turns grey/brown upon heating. The reaction is cooled to room temperature, filtered through a plug of silica, and the silica is washed with copious AcOEt (150 mL). The filtrate is concentrated and then evaporated to dryness under high vacuum, and the resulting residue is purified by column chromatography (SiO₂, AcOEt : hexane = 2 : 98) to afford the desired product as a pale yellow solid (130 mg, Y. 93%).

Typical procedure:
A 10 mL oven-dried Schlenk tube is charged with Pd(OAc)2 (0.005 mmol), 1,3-bis(diphenylphosphino)propane (0.0075 mmol), and potassium ethyl oxalate (0.75 mmol). The tube is evacuated and backfilled with argon. Bromobenzene (0.5 mmol) and 1-methyl-2-pyrrolidone (1.0 mL), are added by syringe at room temperature. The tube is then sealed and the mixture is allowed to stir under 1 atm of argon at 150°C for 24 h (the tube is connected to the Schlenk line which is filled with argon so that CO2 can be released to air).