1,1'-Bis(diphenylphosphino)ferrocene (8.9 mg, 0.016 mmol, 4 mol%) and the corresponding hydrazone (0.40 mmol, 1.0 eq. of non-liquid hydrazone) were loaded into dry Schlenk tubes (25 mL) containing a stirring bar, and the reaction tubes were transferred to a glove box; the reaction tubes were purified with [Ru(p-cymene)Cl2]2 ( 4.9 mg, 0.008 mmol, 2 mol%), Cs2CO3 (169 mg, 0.52 mmol, 1.3 eq.), and CsF (24 mg, 0.16 mmol, 0.4 eq.) into the reaction tube. The reaction tube was removed from the glove box, evacuated and backfilled with CO2 three times. Subsequently, anhydrous DMF (1 mL), the corresponding perylene (0.40 mmol, 1.0 equiv. of liquid substrate) were added to the reaction mixture via syringe under CO2 atmosphere. The Schlenk tube was sealed at CO2 atm (1 atm). The resulting mixture was stirred at 80 C (380 r/min) for 24 h. The reaction mixture was cooled to room temperature. The resulting mixture was diluted with 2 mL of EtOAc, the reaction was quenched with 2 mL of 2N HCl, and the reaction mixture was extracted with EtOAc (3 x 5 mL). The combined organic phases were concentrated in vacuum; the residue was purified by fast column chromatography on short silica gel (0.1% AcOH/petroleum ether/EtOAc 10/1~5/1) to afford the target product 3-bromophenylacetic acid.
