GENERAL METHODS: 4-bromobenzonitrile (0.5 mmol), 4-ethylphenylboronic acid (0.75 mmol), Cell-NHC-Pd catalyst (0.75 mol%), K2CO3 (1 mmol), and a solvent mixture of DMF:H2O (1:1, 2.5 mL) were sequentially added to a 25 mL round-bottom flask. Depending on the substrate, the reaction mixture was stirred vigorously at 80 °C for a specific time. Upon completion of the reaction, the solid catalyst was removed by filtration. The filtrate was extracted with ethyl acetate (3 x 5 mL), washed three times sequentially with water and saturated saline, and the organic phase was dried with anhydrous MgSO4. After filtration to remove MgSO4, the solvent was concentrated under reduced pressure to remove the solvent. The crude product was purified by preparative thin layer chromatography (TLC) with the eluent of petroleum ether/ethyl acetate (20:1) to give 4'-ethyl-4-cyanobiphenyl and the yield was calculated.
