To a suspension of potassium phenyltriflfluoroborate (92.3 mg, 0.5 mmol), 1-bromonapthalene (103.5 mg, 0.5 mmol), and K2CO3 (204.5 mg, 1. 5 mmol) in MeOH (0.75 mL) was added Pd(OAc)2 in methanol (1.25 mL, 2 × 10–3 M) and then the reaction mixture was stirred and heated at reflflux for 2 h. The mixture was cooled to room temperature and diluted with water (10 mL). The aqueous phase was extracted with CH2Cl2 (3 × 4 mL). The combined organic extracts were washed with brine (10 mL) and dried (MgSO4). The crude product was then purifified via chromatography (silica gel) eluting with hexane to deliver 76.1 mg (75%) of 1-phenylnaphthalene. Reference: Molander, G. A.; Biolatto, B. J. Org. Chem. 2003, 68, 4302−4314.
