copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran T=20°C; 10 h;

1: 92 percent / potassium carbonate / tetrahydrofuran; ethanol / 22 h / 20 °C 2: 49 percent / CuI; Et3N / PdCl2(PPh3)2 / tetrahydrofuran / 10 h / 20 °C View Scheme

1.1: n-BuLi / diethyl ether; hexane / 2.5 h / -78 °C 1.2: diethyl ether; hexane / -78 - 20 °C 1.3: 88 percent / NH4Cl / diethyl ether; hexane / 5 h / 20 °C 2.1: 92 percent / potassium carbonate / tetrahydrofuran; ethanol / 22 h / 20 °C 3.1: 49 percent / CuI; Et3N / PdCl2(PPh3)2 / tetrahydrofuran / 10 h / 20 °C View Scheme