Suzuki-Miyaura Coupling for Terphenyl Synthesis

In a 250 mL round-bottom flask, we added 1.3 g (2 mmol) of compound (7), 0.62 g (2.2 mmol) of [1,1′:3′,1″-terphenyl]-5′-ylboronic acid, 0.91 g (6.5 mmol) of potassium carbonate, and 0.11 g (0.09 mmol) of tetrakis(triphenylphosphine)palladium(0). This mixture was dissolved in 140 mL of anhydrous o-xylene and 30 mL of distilled water and then stirred. The reaction mixture was heated to 110 °C for 20 h under nitrogen. Upon completion of the reaction, it was extracted with dichloromethane and distilled water, and the organic layer was dried with anhydrous MgSO₄. The product was subsequently purified by silica gel column chromatography using the CHCl₃:hexane (2:8) eluent, yielding a white solid (yield: 62%). ¹H NMR (400 MHz, DMSO-d₆): δ(ppm) = 9.13 (d, J = 8.2 Hz, 1H), 9.04 (d, J = 8.6 Hz, 1H), 8.93 (s, 1H), 8.72 (s, 1H), 8.07 (d, J = 8.2 Hz, 1H), 8.03 (s, 1H), 7.89 (s, 2H), 7.87 (s, 4H), 7.79 (d, J = 9.3 Hz, 1H), 7.75–7.62 (m, 4H), 7.49 (t, J = 7.6 Hz, 4H), 7.43–7.37 (m, 4H), 7.25–7.14 (m, 9H), 7.13–7.07 (m, 6H), 7.02 (s, 2H).