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

iodine in benzene 12 h; Irradiation;

1: 1.) AlCl3, 2.) CuBr2 / 1.) 75 deg C, 20 h, 2.) acetonitrile, reflux, 5 h 2: 83 percent / DBU / tetrahydrofuran / 4 h / Ambient temperature 3: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 3 h 4: 78 percent / n-BuLi / tetrahydrofuran; hexane / 7 h / -78 - 20 °C 5: 81 percent / NaI, trimethylsilyl chloride / acetonitrile / 3 h / Ambient temperature View Scheme

1: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 3 h 2: 78 percent / n-BuLi / tetrahydrofuran; hexane / 7 h / -78 - 20 °C 3: 81 percent / NaI, trimethylsilyl chloride / acetonitrile / 3 h / Ambient temperature View Scheme

1: 83 percent / DBU / tetrahydrofuran / 4 h / Ambient temperature 2: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 3 h 3: 78 percent / n-BuLi / tetrahydrofuran; hexane / 7 h / -78 - 20 °C 4: 81 percent / NaI, trimethylsilyl chloride / acetonitrile / 3 h / Ambient temperature View Scheme

1: 78 percent / n-BuLi / tetrahydrofuran; hexane / 7 h / -78 - 20 °C 2: 81 percent / NaI, trimethylsilyl chloride / acetonitrile / 3 h / Ambient temperature View Scheme

sulfur T=190 - 220°C;

1: amalgamated zinc; aqueous HCl; toluene 2: sulfur / 190 - 220 °C View Scheme

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