selenium(IV) oxide in 1,4-dioxane T=80°C; 18 h;

1: With diisobutylaluminium hydride in tetrahydrofuran; dichloromethane T=-78°C; 3 h; 2: With hydrogenchloride in tetrahydrofuran; dichloromethane; water

1: [palladium(II)(bis(triphenylphosphanyl))dichloride]; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: ammonia / ethanol / 2 h / 80 °C / |Sealed tube View Scheme

copper(l) iodide T=50°C; 0.166667 h; Ionic liquidInert atmosphereMicrowave irradiationSealed tube;

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: KF*2H2O / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3: hydrogen / ethyl acetate / 2 h / 20 °C View Scheme

1.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / tetrahydrofuran / |Inert atmosphere; |Reflux 2.1: 5 palladium on charcoal; hydrogen / ethyl acetate / 2 h / 10343.2 Torr / |Autoclave 3.1: manganese(IV) oxide / benzene / 12 h / 20 °C / |Inert atmosphere 4.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 2 h / 25 °C / |Inert atmosphere 4.2: |Inert atmosphere 5.1: manganese(IV) oxide / benzene / 12 h / 25 °C / |Inert atmosphere View Scheme