triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide T=20°C; 96 h;

1.1: n-BuLi / diethyl ether / 3 h / -78 °C 1.2: 84 percent / I2 / diethyl ether 2.1: 93 percent / Et3N / [PdCl2(PPh3)2]; CuI / 96 h / 20 °C View Scheme

1.1: 89 percent / SnCl2*2H2O / ethanol; tetrahydrofuran / 20 h / 20 °C 2.1: H2SO4; NaNO2 / 2 h / 0 °C 2.2: 70 percent / KI / 0.25 h / 80 °C 3.1: 91 percent / CuI; Et3N / (Ph3P)2PdCl2 / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: H2SO4; NaNO2 / 2 h / 0 °C 1.2: 70 percent / KI / 0.25 h / 80 °C 2.1: 91 percent / CuI; Et3N / (Ph3P)2PdCl2 / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: 80 percent / H2SO4; NaNO2 / ethanol / 36 h / 90 °C 2.1: 89 percent / SnCl2*2H2O / ethanol; tetrahydrofuran / 20 h / 20 °C 3.1: H2SO4; NaNO2 / 2 h / 0 °C 3.2: 70 percent / KI / 0.25 h / 80 °C 4.1: 91 percent / CuI; Et3N / (Ph3P)2PdCl2 / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: 97 percent / Br2 / acetic acid / 4 h / 65 °C 2.1: 80 percent / H2SO4; NaNO2 / ethanol / 36 h / 90 °C 3.1: 89 percent / SnCl2*2H2O / ethanol; tetrahydrofuran / 20 h / 20 °C 4.1: H2SO4; NaNO2 / 2 h / 0 °C 4.2: 70 percent / KI / 0.25 h / 80 °C 5.1: 91 percent / CuI; Et3N / (Ph3P)2PdCl2 / tetrahydrofuran / 48 h / 20 °C View Scheme