copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride 4 h; Heating;

piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) Sonogashira-Hagihara coupling; Heating;

1: 86 percent / K2CO3 / dimethylformamide / 6 h / 60 °C 2: 82 percent / silica gel-supported nitric acid / CH2Cl2 / 0.25 h 3: 92 percent / hydrazine monohydrate; graphite / ethanol / 12 h / Heating 4: 85 percent / aq. HBF4; t-butyl nitrite / CH2Cl2; tetrahydrofuran / 0.17 h / 10 - 15 °C 5: 88 percent / potassium acetate; 18-crown-6; I2 / CHCl3 / 6 h 6: 85 percent / NEt3; CuI / bis(triphenylphosphine)palladium(II)dichloride / 4 h / Heating View Scheme

1: 86 percent / K2CO3 / dimethylformamide / 6 h / 60 °C 2: 82 percent / silica gel-supported nitric acid / CH2Cl2 / 0.25 h 3: 92 percent / hydrazine monohydrate; graphite / ethanol / 12 h / Heating 4: 85 percent / aq. HBF4; t-butyl nitrite / CH2Cl2; tetrahydrofuran / 0.17 h / 10 - 15 °C 5: 88 percent / potassium acetate; 18-crown-6; I2 / CHCl3 / 6 h 6: 85 percent / NEt3; CuI / bis(triphenylphosphine)palladium(II)dichloride / 4 h / Heating View Scheme

1: 3.4 g / BBr3 / CH2Cl2 / 31 h / -78 - 20 °C 2: 7.31 g / K2CO3 / dimethylformamide / 4 h / 60 °C 3: 92.5 percent / Pd(PPh3)4; CuI; piperidine / Heating View Scheme

1: 7.31 g / K2CO3 / dimethylformamide / 4 h / 60 °C 2: 92.5 percent / Pd(PPh3)4; CuI; piperidine / Heating View Scheme