To a solution of 2-fluoro-1-iodo-3-(trifluoromethoxy)benzene (25 g, 81 mmol) in dry toluene (200 mL) was added Cs2CO3 (38.7 g, 120 mmol), Pd2(dba)3 (7.42 g, 8.1 mmol), BINAP (10.8 g, 16.2 mmol) and benzhydrylideneamine (19.6 g, 108 mmol). The reaction mixture was refluxed for 8 h with stirring and then cooled to RT. The organic layer was washed with water and brine and then dried over MgSO4. After removal of solvent in vacuo, the residue was purified by column chromatography on silica gel (solvent gradient from 100% n-hexane to n-hexane/EtOAc 20:1) to afford the title compound as a pale yellow oil. 1H NMR (CDCl3, 400 MHz): δ 7.72 (s, 1H, ArH,), 7.70 (s, 1H, ArH), 7.45-7.42 (m, 1H, ArH,), 7.37-7.33 (m, 2H, ArH), 7.25-7.17 (m, 3H, ArH), 7.06 (s, 1H, ArH), 7.05 (s, 1H, ArH,), 6.84 (t, 1H, J=8 Hz, ArH), 6.78 (t, 1H, J=8 Hz, ArH), 6.67-6.64 (m, 1H, ArH).
