tributyl-amine; trichlorosilane in xylene Reduction; 3 h; Heating;

sodium hydroxide; tributyl-amine in anhydrous xylene; ethanol; dichloromethane

1: 1.) n-BuLi / 1.) THF, hexane, -70 deg C 2.) -60 deg C to 0 deg C within 2 h 2: 97 percent / 35percent aq. H2O2 / methanol / 1 h / Ambient temperature 3: 1.) LDA 2.) Br2 / 1.) THF, -78 deg C, hexane, 15 min 2.) THF, -70 deg C 4: 97 percent / Cu / dimethylformamide / 4 h / 140 °C 5: 50 percent / HSiCl3, NBu3 / xylene / 3 h / 130 °C View Scheme

1: 97 percent / 35percent aq. H2O2 / methanol / 1 h / Ambient temperature 2: 1.) LDA 2.) Br2 / 1.) THF, -78 deg C, hexane, 15 min 2.) THF, -70 deg C 3: 97 percent / Cu / dimethylformamide / 4 h / 140 °C 4: 50 percent / HSiCl3, NBu3 / xylene / 3 h / 130 °C View Scheme

1: 1.) LDA 2.) Br2 / 1.) THF, -78 deg C, hexane, 15 min 2.) THF, -70 deg C 2: 97 percent / Cu / dimethylformamide / 4 h / 140 °C 3: 50 percent / HSiCl3, NBu3 / xylene / 3 h / 130 °C View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -70 deg C 2.) -60 deg C to 0 deg C within 2 h 2: 97 percent / 35percent aq. H2O2 / methanol / 1 h / Ambient temperature 3: 1.) LDA 2.) Br2 / 1.) THF, -78 deg C, hexane, 15 min 2.) THF, -70 deg C 4: 97 percent / Cu / dimethylformamide / 4 h / 140 °C 5: 50 percent / HSiCl3, NBu3 / xylene / 3 h / 130 °C View Scheme

1: 97 percent / Cu / dimethylformamide / 4 h / 140 °C 2: 50 percent / HSiCl3, NBu3 / xylene / 3 h / 130 °C View Scheme

1: 91 percent / Cu / dimethylformamide / 1 h / Heating 2: 50 percent / HSiCl3, NBu3 / xylene / 3 h / 130 °C View Scheme