bis(trimethyl-silyl)-trifluoroacetamide; trimethylsilyl iodide in dichloromethane T=-20 - 20°C;

1: phosphorus tribromide / 3 h / Heating 2: 1.9 g / toluene / 0.67 h / 0 °C 3: 52 percent / (diethylamido)sulfur trifluoride / Ambient temperature 4: 78 percent / hexamethylphosphoramide, LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C 5: 100 percent / H2 / PdCl2 / ethanol; tetrahydrofuran; methanol / 20 h / 2585.7 Torr 6: 1.29 g / NaHCO3 / H2O; dioxane / 3 h / Ambient temperature 7: 1.19 g / bis(trimethylsilyl)trifluoroacetamide, iodotrimethylsilane / CH2Cl2 / -20 - 20 °C View Scheme

1: 1.9 g / toluene / 0.67 h / 0 °C 2: 52 percent / (diethylamido)sulfur trifluoride / Ambient temperature 3: 78 percent / hexamethylphosphoramide, LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C 4: 100 percent / H2 / PdCl2 / ethanol; tetrahydrofuran; methanol / 20 h / 2585.7 Torr 5: 1.29 g / NaHCO3 / H2O; dioxane / 3 h / Ambient temperature 6: 1.19 g / bis(trimethylsilyl)trifluoroacetamide, iodotrimethylsilane / CH2Cl2 / -20 - 20 °C View Scheme

1: 52 percent / (diethylamido)sulfur trifluoride / Ambient temperature 2: 78 percent / hexamethylphosphoramide, LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C 3: 100 percent / H2 / PdCl2 / ethanol; tetrahydrofuran; methanol / 20 h / 2585.7 Torr 4: 1.29 g / NaHCO3 / H2O; dioxane / 3 h / Ambient temperature 5: 1.19 g / bis(trimethylsilyl)trifluoroacetamide, iodotrimethylsilane / CH2Cl2 / -20 - 20 °C View Scheme

1: 78 percent / hexamethylphosphoramide, LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C 2: 100 percent / H2 / PdCl2 / ethanol; tetrahydrofuran; methanol / 20 h / 2585.7 Torr 3: 1.29 g / NaHCO3 / H2O; dioxane / 3 h / Ambient temperature 4: 1.19 g / bis(trimethylsilyl)trifluoroacetamide, iodotrimethylsilane / CH2Cl2 / -20 - 20 °C View Scheme

1: 100 percent / H2 / PdCl2 / ethanol; tetrahydrofuran; methanol / 20 h / 2585.7 Torr 2: 1.29 g / NaHCO3 / H2O; dioxane / 3 h / Ambient temperature 3: 1.19 g / bis(trimethylsilyl)trifluoroacetamide, iodotrimethylsilane / CH2Cl2 / -20 - 20 °C View Scheme

1: 1.29 g / NaHCO3 / H2O; dioxane / 3 h / Ambient temperature 2: 1.19 g / bis(trimethylsilyl)trifluoroacetamide, iodotrimethylsilane / CH2Cl2 / -20 - 20 °C View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere 2.1: cadmium / N,N-dimethyl-formamide / 3.25 h / 20 °C / Inert atmosphere 2.2: 22 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 20 °C 4.1: trimethylsilyl bromide / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere View Scheme