9, 10 – Diphenylanthracene was synthesized via a multistep synthesis using 9, 10 – dibromoanthracene, a Suzuki coupling was performed using phenylboronic acid over a tetrakis(triphenylphosphine)palladium(0) catalyst to form the title compound:
The mixture of 1,3-dibromobenzene (236 mg, 1.0 mmol), phenylboronic acid (271 mg, 2.2 mmol), and Na2CO3 (424 mg, 4 mmol) was taken up in DMF (2 mL) and then ARF-Pd (300 mg, 0.01 mmol Pd) was added. The mixture was heated under N2 at 110 °C for 2.5 h. After cooling, the mixture was diluted with cold H2O (10 mL) and filtered through a cotton bed. The filtrate was extracted with Et2O (3 × 20 mL) and the combined organic extracts were washed with brine (10 mL), dried (Na2SO4), and evaporated. The residue was purified by column chromatography (silica gel, PE) to give 9,10-Diphenylanthracene (4d), yield 90%. Mp 245-247 °C (Lit.36 245-48 °C). IR (Nujol): 1458, 1377 cm-1. 1H NMR (300 MHz, CDCl3): δ = 7.72-7.66 (m, 4 H), 7.62-7.46 (m, 10 H), 7.34-7.29 (m, 4 H). 13C NMR (75 MHz, CDCl3): δ = 139.1, 137.1, 131.3, 129.8, 128.4, 127.4, 126.9, 125.0.
