chloro-trimethyl-silane; sodium iodide in acetonitrile 3 h; Ambient temperature;

tetrabutyl-ammonium chloride; palladium diacetate; caesium carbonate; triphenylphosphine in N,N-dimethyl-formamide T=85 - 90°C; Inert atmosphere;

barium dihydroxide; copper T=300°C; P=25 Torr;

1: 1.) t-BuNH2, Br2, 2.) 4-(dimethylamino)pyridine / 1.) toluene, CH2Cl2, -78 to RT, 5 h, 2.) pyridine, room temp., 24 h 2: 95 percent / n-BuLi / tetrahydrofuran / 10 h / -78 - 20 °C 3: 54 percent / conc. HCl / methanol / 3 h / Heating 5: 72 percent / n-BuLi / tetrahydrofuran; hexane / 7 h / -78 - 20 °C 6: 88 percent / NaI, trimethylsilyl chloride / acetonitrile / 3 h / Ambient temperature View Scheme

2: 72 percent / n-BuLi / tetrahydrofuran; hexane / 7 h / -78 - 20 °C 3: 88 percent / NaI, trimethylsilyl chloride / acetonitrile / 3 h / Ambient temperature View Scheme

1: 54 percent / conc. HCl / methanol / 3 h / Heating 3: 72 percent / n-BuLi / tetrahydrofuran; hexane / 7 h / -78 - 20 °C 4: 88 percent / NaI, trimethylsilyl chloride / acetonitrile / 3 h / Ambient temperature View Scheme

1: 95 percent / n-BuLi / tetrahydrofuran / 10 h / -78 - 20 °C 2: 54 percent / conc. HCl / methanol / 3 h / Heating 4: 72 percent / n-BuLi / tetrahydrofuran; hexane / 7 h / -78 - 20 °C 5: 88 percent / NaI, trimethylsilyl chloride / acetonitrile / 3 h / Ambient temperature View Scheme

1: 72 percent / n-BuLi / tetrahydrofuran; hexane / 7 h / -78 - 20 °C 2: 88 percent / NaI, trimethylsilyl chloride / acetonitrile / 3 h / Ambient temperature View Scheme

selenium