Bathophenanthroline

Typical Procedure: A mixture of bathophenanthroline (7.6 mg, 23 µmol), sodium tert-butoxide (43.3 mg, 0.451 mmol), 4-iodotoluene (48.6 mg, 0.223 mmol) and benzene (2.4 mL, 27 mmol) in a 35 mL oven-dried pressure-resistant tube is stirred at 155 °C for 6 h. After cooling, the reaction mixture is quenched with a 1 N HCl aqueous solution (4 mL) and extracted with Et2O (10 mL × 3). The combined organic layer is dried over MgSO4, filtered, and concentrated in vacuo. Purification with PTLC (silica gel, hexane : EtOAc = 20 : 1) gives the product (28.4 mg, Y. 76%).

Typical procedure: To a vial is added Fe(OAc)2 (4.3 mg), bathophenanthroline (16.6 mg), and KOt-Bu (112 mg). To the vial is then added iodobenzene (102 mg) and benzene (3.9 g). The reaction was stirred vigorously at room temperature for 20 min and then at 80 °C for 20 h. Following cooling, 2 mL of CH2Cl2/hexanes (1:1) is added, and the solution is filtered through silica pad. The pad then rinsed with 15 mL of CH2Cl2/hexanes (1:1). The combined solution is concentrated and the crude mixture is purified by column chromatography (eluent: hexanes) to give biphenyl (68.6 mg, 89 %) as a white solid.