hydrogen; palladium dichloride in tetrahydrofuran; methanol; ethanol P=2585.7 Torr; 20 h;

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 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 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 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 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