Reaction Steps
Racemic iodide 12i (102 mg, 0.29 mmol), PhB(OH)2 (78 mg, 0.57 mmol) and Pd(PPh3)4 (33 mg, 2.86×10−2 mmol) were added to a dry Schlenk flask, followed by DME (3 mL) and an aqueous solution of 3 M aqueous NaOH (0.25 mL, 0.70 mmol). Argon was bubbled through the resulting mixture for 10 minutes, and the system was heated at reflux for 17 h. The reaction was allowed to cool to room temperature, diluted with Et2O, washed with water (1×5 mL), brine (1×5 mL), dried over Na2SO4, filtered, and all volatiles were removed in vacuo. Flash column chromatography (silica gel, 98:2 hexane/EtOAc) afforded 56 (85 mg, 93%) as an orange oil: Rf 0.41 (90:10 hexane/EtOAc); IR (KBr, CHCl3) vmax 3093, 2940, 2848, 2778, 1605, 1487, 1452, 1416 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.61 (d, 1H, J=7.8 Hz), 7.49 (s, 1H), 7.23 (t, 1H, J=7.5 Hz), 7.04 (d, 1H, J=7.5 Hz), 4.23 (s, 1H), 4.18 (s, 5H), 4.11 (s, 1H), 4.02 (t, 1H, J=2.7 Hz), 2.52 (s, 6H), 2.39 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 139.0, 137.1, 129.0, 127.7, 126.7, 125.7, 112.4, 77.9, 69.1, 66.7, 62.2, 58.1, 44.6, 21.5; EIMS [m/z (%)] 319 (M+, 100); HRMS (EI) calcd for C19H21N56Fe: 319.1023. Found 319.1025.
