indium(III) chloride; chloro-trimethyl-silane in 1,2-dichloro-ethane T=20°C; 8 h;

2,2'-azo-bisisobutyronitrile in benzene 12 h; Inert atmosphereReflux;

1: pyridine; carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / 20 °C 2: 2,2'-azo-bisisobutyronitrile / benzene / 12 h / Inert atmosphere; Reflux View Scheme

1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C 2: diethylzinc / hexane; dichloromethane / 12 h / -20 °C / Inert atmosphere 3: pyridine; carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / 20 °C 4: 2,2'-azo-bisisobutyronitrile / benzene / 12 h / Inert atmosphere; Reflux View Scheme

1: diethylzinc / hexane; dichloromethane / 12 h / -20 °C / Inert atmosphere 2: pyridine; carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / 20 °C 3: 2,2'-azo-bisisobutyronitrile / benzene / 12 h / Inert atmosphere; Reflux View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere 1.2: 5 h / Reflux 2.1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C 3.1: diethylzinc / hexane; dichloromethane / 12 h / -20 °C / Inert atmosphere 4.1: pyridine; carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / 20 °C 5.1: 2,2'-azo-bisisobutyronitrile / benzene / 12 h / Inert atmosphere; Reflux View Scheme