hydrogen; palladium on activated charcoal in methanol; ethyl acetate atmospheric pressure;

1: 92 percent / Cs2CO3; KI / dimethylformamide / 8 h / 20 °C 2: 100 percent / sodium borohydride / methanol; CHCl3 / 1 h / 0 °C 3: 81 percent / TFA; triethylsilane / CH2Cl2 / 0.25 h / 0 °C 4: 73 percent / MgBr2*OEt2 / toluene; diethyl ether / Heating 5: 91 percent / K2CO3 / acetone / 8 h / Heating 6: 100 percent / hydrogen / Pd/C / methanol; ethyl acetate / atmospheric pressure View Scheme

1: 91 percent / K2CO3 / acetone / 8 h / Heating 2: 100 percent / hydrogen / Pd/C / methanol; ethyl acetate / atmospheric pressure View Scheme

1: 73 percent / MgBr2*OEt2 / toluene; diethyl ether / Heating 2: 91 percent / K2CO3 / acetone / 8 h / Heating 3: 100 percent / hydrogen / Pd/C / methanol; ethyl acetate / atmospheric pressure View Scheme

1: 100 percent / sodium borohydride / methanol; CHCl3 / 1 h / 0 °C 2: 81 percent / TFA; triethylsilane / CH2Cl2 / 0.25 h / 0 °C 3: 73 percent / MgBr2*OEt2 / toluene; diethyl ether / Heating 4: 91 percent / K2CO3 / acetone / 8 h / Heating 5: 100 percent / hydrogen / Pd/C / methanol; ethyl acetate / atmospheric pressure View Scheme

1: 81 percent / TFA; triethylsilane / CH2Cl2 / 0.25 h / 0 °C 2: 73 percent / MgBr2*OEt2 / toluene; diethyl ether / Heating 3: 91 percent / K2CO3 / acetone / 8 h / Heating 4: 100 percent / hydrogen / Pd/C / methanol; ethyl acetate / atmospheric pressure View Scheme

1: KOH / H2O / 3 h / Heating 2: 25 percent / dicyclohexylurea / tetrahydrofuran / 10 h / Heating 3: 92 percent / Cs2CO3; KI / dimethylformamide / 8 h / 20 °C 4: 100 percent / sodium borohydride / methanol; CHCl3 / 1 h / 0 °C 5: 81 percent / TFA; triethylsilane / CH2Cl2 / 0.25 h / 0 °C 6: 73 percent / MgBr2*OEt2 / toluene; diethyl ether / Heating 7: 91 percent / K2CO3 / acetone / 8 h / Heating 8: 100 percent / hydrogen / Pd/C / methanol; ethyl acetate / atmospheric pressure View Scheme

1: palladium diacetate; copper diacetate / toluene / |Reflux 2: palladium 10 on activated carbon; hydrogen / methanol; ethyl acetate / 4 h / 20 °C / 2068.65 Torr View Scheme

1: potassium carbonate / acetone / |Inert atmosphere 2: methanol / 48 h / 20 °C / |Inert atmosphere 3: sodium tetrahydroborate / methanol / 1 h / 0 °C / |Inert atmosphere 4: palladium diacetate; copper diacetate / toluene / |Reflux 5: palladium 10 on activated carbon; hydrogen / methanol; ethyl acetate / 4 h / 20 °C / 2068.65 Torr View Scheme

bromine; sodium acetate; acetic acid T=20°C; 0.5 h;