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With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; under 760.051 Torr; for 4h;Schlenk technique;
General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained
With copper(I) oxide; caesium carbonate; imidazole-4-carboxylic acid; In acetonitrile; at 80℃; for 24h;
General procedure: To a screw-capped vial (4-mL) were added Cs2CO3 (1.0 mmol, 325 mg), Cu2O (0.005 mmol, 0.7 mg), 1H-imidazole-4-carboxylic acid (0.01 mmol, 1.1 mg) and acetonitrile (0.25 mL). The vial was sealed with septum and allowed to stir for a while; the iodoarene (0.5 mmol) and phenol (0.6 mmol) were then injected into the reaction mixture via a syringe. The septum was removed, and the vial was sealed with a screw cap. The reaction mixture was stirred at 80 oC for 24 h. The crude reaction mixture was diluted with CH2Cl2, filtered through a thin Celite pad, and concentrated in vacuo. The residue was isolated through a column chromatography by using hexane and ethyl acetate as eluent to give the pure product. Products 3a-v were obtained according to this procedure. The known structures were characterized by the 1H NMR and 13C NMR of reported literatures.1-3 Spectral data, 1H NMR and 13C NMR spectra for all the new compounds are listed below.
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; for 18h;Inert atmosphere; Reflux;
A solution of toluene (450 mL) and ethanol (150 mL) was bubbled with nitrogen gas for 10 min. Triphenylen-2-ylboronic acid (10.0 g g, 36.7 mmol), 1,2-diiodobenzene (36.4 g, 110 mmol), tetrakis(triphenylphosphine)palladium(0) (2.1 g, 1.8 mmol), and tripotassium phosphate (39.0 g, 184 mmol) were added. The mixture was bubbled with nitrogen gas for 15 minutes and refluxed for 18 hours. After cooling (22 C.), the reaction mixture was filtered through a silica pad and washed with toluene. The solvent was removed in vacuo and the residue was purified by flash column chromatography using hexane to 30% DCM in hexane to yield the desired product 2-(2-iodophenyl)triphenylene (9.2 g, 21.4 mmol, 58.2% yield) as a pale yellow solid.
General procedure: Under an N2 atmosphere, substrate 1 (0.2 mmol) and 1,2-diiodobenzene(IV) (0.1 mmol) were placed in a dry glass tube. Heptane (10 mL)was added and the well-stirred mixture was irradiated under UV light(300 nm) until the reaction was complete (TLC monitoring). The solvent was removed in vacuo and the residue was purified by silica gel column chromatography to afford the coupling product 2.
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