Yield given. Multistep reaction. Yields of byproduct given;

Yield given. Multistep reaction. Yields of byproduct given;

pyridine; tetrabutyl-ammonium chloride; palladium diacetate in N,N-dimethyl-formamide T=120°C; 4 h;

tributyl-amine in diethylene glycol dimethyl ether T=150°C; 12 h;

tetrachloromethane; triphenylphosphine in dichloromethane T=20°C; 5 h; Inert atmosphere;

1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 0 - 20 °C 2.1: sodium hydride / 0 - 20 °C 2.2: 20 °C 2.3: 150 °C 3.1: water; sodium chloride / dimethyl sulfoxide / 150 °C 4.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / -50 °C 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C 5.2: -78 - 20 °C View Scheme

copper(l) chloride

1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 0 - 20 °C 2.1: sodium hydride / 0 - 20 °C 2.2: 20 °C 2.3: 150 °C View Scheme

1.1: Et3N / CH2Cl2 / 0 - 20 °C 2.1: NaI / acetone / Heating 3.1: n-BuLi; i-Pr2NH / hexane; tetrahydrofuran / 1 h / -78 °C 3.2: tetrahydrofuran; hexane / -78 - 20 °C 4.1: 69 percent Spectr. / PPh3; Et3N / Pd(OAc)2 / dimethylformamide; H2O / 24 h / 130 °C View Scheme