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With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃;
To a hot (100 0C) solution of intermediate A.ii (18.5 g, 81.8 mmol), K2CO3 (14.7 g, 106 mmol), trans-2-phenylboronic acid (13.7 g, 90 mmol) in dioxane (320 mL) and water (80 mL) was added Pd(PPh3 )4 (4.77 g, 5 mol%). The resulting mixture was stirred at 1000C over night. After cooling, the reaction mixture was diluted with water (300 mL). The volatiles were removed in vacuo and the residue was taken up in EA (300 mL). The two layers were separated and the aq. layer was extracted one more with EA (300 mL). The combined org. layers were washed with brine, dried over MgSO4, filtered and <n="39"/>concentrated to dryness. The residue was chromatographed (EA-Hept 1 :2) to afford the title compound as a yellow solid (17.79 g, 87% yield).1H NMR (CDCl3) delta: 8.89 (d, J = 4.6 Hz, IH); 8.16 (dd, J = 9.5, 5.5 Hz, IH); 7.83 (dd, J = 2.7, 9.5 Hz, IH); 7.70-7.63 (m, 4H); 7.55-7.34 (m, 5H).
With tetraethylammonium hydroxide;tetrakis(triphenylphosphine) palladium(0); In N,N'-dimethylacetamide (DMA); at 110℃; for 24h;
1b) 2,8-Bis-((E)-styryl)-dibenzofuran Tetrethylamine hydroxide (13.6 g, 18.4 mmol), tetrakis(triphenylphosphine)palladium(0) (142 mg) and trans-2-phenylvinylboronic acid (2.3 g, 15.3 mmol) are added to a solution of the product from example 1a) (2.00 g, 6.14 mmol) in N,N'-Dimethylacetamide (DMA) (30 ml). The mixture is then stirred at 110° C. for 24 hours. The reaction mixture is cooled to room temperature and poured into H2O. A gray crude product is obtained after filtration and washing with n-hexane. The crude product is purified by silicagel column chromatography with CH2Cl2, which result in a white solid (71percent yield, mp.: 226° C.). 1H-NMR (CDCl3, ppm): 7.26-7.30 (m, 6H), 7.39 (t, 4H), 7.54-7.58 (m, 6H), 7.65 (dd, 2H), 8.12 (d, 2H)
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