1: 95 percent / PdCl2, PPh3, CuI / triethylamine; dimethylformamide 2: 58 percent / BBr3 / CH2Cl2 / 0.25 h / -70 °C 3: 91 percent / Ambient temperature; macroelectrolysis: mercury pool working electrode, tetraethylammonium p-toluenesulfonate supporting electrolyte View Scheme

1: With n-butyllithium in tetrahydrofuran; hexane T=-95°C; 0.0833333 h; 2: With iodine in tetrahydrofuran; hexane T=-95°C; Further stages.;

N-ethyl-N,N-diisopropylamine in dichloromethane 0.666667 h; Ambient temperature;

1.1: 92 percent / K2CO3 / acetone / 3 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -95 °C 2.2: 84 percent / I2 / tetrahydrofuran; hexane / -95 °C View Scheme

n-butyllithium; iodine in diethyl ether

1: NaH / tetrahydrofuran 2: BuLi; I2 / diethyl ether View Scheme

N,N,N',N,-tetramethylethylenediamine; tert.-butyl lithium; ethylene iodochloride in diethyl ether T=-78°C; without TMEDA, other solvent and temperature; Product distribution;

chloro-trimethyl-silane; sodium iodide in acetonitrile