bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine in tetrahydrofuran T=45°C; Inert atmosphereSchlenk technique;

1: 75 percent / HIO3/I2/H2SO4 / acetic acid; H2O; CCl4 / 2 h / 40 °C 2: 57 percent / Pd(OAc)2, PPh3 / 24 h View Scheme

palladium diacetate; triphenylphosphine 24 h;

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -70 °C / |Inert atmosphere; |Schlenk technique 1.2: 0.5 h / |Inert atmosphere; |Schlenk technique 2.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 45 °C / |Inert atmosphere; |Schlenk technique View Scheme

1.1: N-bromosuccinmide / |Inert atmosphere; |Schlenk technique 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -70 °C / |Inert atmosphere; |Schlenk technique 2.2: 0.5 h / |Inert atmosphere; |Schlenk technique 3.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 45 °C / |Inert atmosphere; |Schlenk technique View Scheme

1: 1) BuLi / ether, hexane 2: 90 percent / KF*2H2O / dimethylformamide View Scheme