1: PPh3; iPr2NH; CuI / Pd(OAc)2 / Heating 2: 88 percent / K2CO3 / methanol / 20 °C View Scheme

1: 73.7 percent / H2SO4; I2; (NH4)2S2O8 / AcOH / H2O / 1 h / 20 - 80 °C 2: 83.9 percent / PPh3; CuI; Et3N / PdCl2 / 3 h / 80 °C 3: 89.1 percent / potassium hydroxide / toluene / 3 h / Heating View Scheme

1: 83.9 percent / PPh3; CuI; Et3N / PdCl2 / 3 h / 80 °C 2: 89.1 percent / potassium hydroxide / toluene / 3 h / Heating View Scheme

(i) PCl5, (ii) NaNH2, liq. NH3, Fe(NO3)3*H2O; Multistep reaction;

in acetone