[bis(acetoxy)iodo]benzene; iodine in 1,2-dichloro-ethane T=30 - 40°C; 3 h; ultrasonic irradiation;

triethylamine in dichloromethane T=20°C; 15 h;

1.1: 74 percent / n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C 2.1: 83 percent / i-Bu2AlH / CH2Cl2; hexane / 1 h / -78 - -40 °C 3.1: 83 percent / citric acid monohydrate / toluene / 6 h / Heating 4.1: 67 percent / Pd(OAc)2; triphenylphosphine; K2CO3 / dimethylformamide / 16 h / 110 °C 5.1: 87 percent / H2 / Pd/C / ethanol / 15 h / 20 °C 6.1: lithium; NH3 / tetrahydrofuran / 3 h / -78 °C 6.2: 88 percent / NH4Cl 7.1: 82 percent / triethylamine / CH2Cl2 / 15 h / 20 °C View Scheme

1.1: 87 percent / H2 / Pd/C / ethanol / 15 h / 20 °C 2.1: lithium; NH3 / tetrahydrofuran / 3 h / -78 °C 2.2: 88 percent / NH4Cl 3.1: 82 percent / triethylamine / CH2Cl2 / 15 h / 20 °C View Scheme

1.1: 67 percent / Pd(OAc)2; triphenylphosphine; K2CO3 / dimethylformamide / 16 h / 110 °C 2.1: 87 percent / H2 / Pd/C / ethanol / 15 h / 20 °C 3.1: lithium; NH3 / tetrahydrofuran / 3 h / -78 °C 3.2: 88 percent / NH4Cl 4.1: 82 percent / triethylamine / CH2Cl2 / 15 h / 20 °C View Scheme

1.1: 83 percent / i-Bu2AlH / CH2Cl2; hexane / 1 h / -78 - -40 °C 2.1: 83 percent / citric acid monohydrate / toluene / 6 h / Heating 3.1: 67 percent / Pd(OAc)2; triphenylphosphine; K2CO3 / dimethylformamide / 16 h / 110 °C 4.1: 87 percent / H2 / Pd/C / ethanol / 15 h / 20 °C 5.1: lithium; NH3 / tetrahydrofuran / 3 h / -78 °C 5.2: 88 percent / NH4Cl 6.1: 82 percent / triethylamine / CH2Cl2 / 15 h / 20 °C View Scheme

1.1: 83 percent / citric acid monohydrate / toluene / 6 h / Heating 2.1: 67 percent / Pd(OAc)2; triphenylphosphine; K2CO3 / dimethylformamide / 16 h / 110 °C 3.1: 87 percent / H2 / Pd/C / ethanol / 15 h / 20 °C 4.1: lithium; NH3 / tetrahydrofuran / 3 h / -78 °C 4.2: 88 percent / NH4Cl 5.1: 82 percent / triethylamine / CH2Cl2 / 15 h / 20 °C View Scheme

hydrogen; palladium dihydroxide T=20°C;

1.1: lithium; NH3 / tetrahydrofuran / 3 h / -78 °C 1.2: 88 percent / NH4Cl 2.1: 82 percent / triethylamine / CH2Cl2 / 15 h / 20 °C View Scheme

1: platinum; acetic acid anhydride / Hydrogenation.Behandlung des Reaktionsprodukts mit wss. Salzsaeure 2: aqueous alkaline solution; benzene View Scheme