Reaction Steps
Racemic iodide 12i (101 mg, 0.28 mmol), 2-methoxyphenylboronic acid (86 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 (0.24 mL, 0.70 mmol). Argon was bubbled through the resulting mixture for 10 minutes, and the system was heated to reflux for 14 h. The reaction mixture 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. Gradient flash column chromatography (silica gel, 98:2→95:5 hexane/EtOAc) afforded 57 (83 mg, 87%) as an orange oil that solidified on standing: Rf 0.19 (95:5 hexane/EtOAc); mp 92-93° C. (hexane); IR (KBr) vmax 3082, 2941, 2833, 2776, 1597, 1450, 1411 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.09 (dd, 1H, J=7.5, 1.8 Hz), 7.26 (td, 1H, J=7.8, 1.8 Hz), 7.02 (td, 1H, J=7.5, 0.9 Hz), 6.87 (d, 1H, J=8.4 Hz), 4.27 (t, 1H, J=3.6 Hz), 4.24 (s, 5H), 4.09 (t, 1H, J=2.1 Hz), 4.05 (t, 1H, J=2.7 Hz), 3.79 (s, 3H), 2.47 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 157.5, 132.6, 127.5, 127.0, 120.0, 113.1, 110.5, 75.5, 68.9, 66.8, 62.0, 56.8, 55.6, 44.1; EIMS [m/z (%)] 335 (M+, 100), 229 (24); HRMS (EI) calcd for C19H21NO88Fe: 335.0972. Found 335.0978.
