1: 94 percent / Et3N / benzene / 2 h 2: 84 percent / LiCl; NaBH4 / tetrahydrofuran; ethanol / 16 h / 20 °C 3: 70 percent / PPh3; DEAD; diphenylphosphoryl azide / tetrahydrofuran / 24 h / 20 °C 4: tristrimethylsilane; AIBN / benzene / 5 h / Heating 5: 73.6 mg / NaCNBH3 / acetonitrile / 0.25 h / 20 °C 6: 83 percent / NH3; Na / tetrahydrofuran / 0.2 h / -50 °C View Scheme

1.1: CuI; triethylamine / PdCl2(PPh3)2 / tetrahydrofuran / 12 h / 20 °C 2.1: BuLi / diethyl ether; hexane / 0.5 h / 0 - 20 °C 2.2: ZnCl2 / toluene / 2 h / 120 °C 2.3: 97 percent / NH4Cl / toluene; H2O View Scheme

in dichloromethane T=20°C;

1.1: acetic acid / water; acetonitrile / 0.5 h / 20 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: pyridine; potassium tert-butylate / 0.18 h / 20 - 160 °C / Inert atmosphere; Microwave irradiation 3.1: BaMnO4 / dichloromethane / 12 h / 45 °C / Inert atmosphere View Scheme

copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride in N,N-dimethyl-formamide T=20°C; Sonogashira coupling; 12 h;

1.1: 100 percent / CuI; triethylamine / PdCl2(PPh3)2 / tetrahydrofuran / 12 h / 20 °C 2.1: BuLi / diethyl ether; hexane / 0.5 h / 0 - 20 °C 2.2: ZnCl2 / toluene / 1 h / 120 °C 2.3: 100 percent / NH4Cl / toluene; H2O View Scheme

K2S; copper(I) bromide in 1-methyl-pyrrolidin-2-one T=120°C; 1 h; Inert atmosphere;