Ba(OH)2·8H2O; palladium diacetate; tris-(o-tolyl)phosphine in ethylene glycol dimethyl ether; water T=50°C; 1.5 h; Inert atmosphere;

sulfuric acid in acetic acid T=25°C; 2 h;

lithium aluminium tetrahydride; oxalic acid T=120°C;

1: N-bromosuccinmide; hexafluoroisopropyl alcohol / dichloromethane / 0.5 h 2: Ba(OH)2·8H2O; palladium diacetate; tris-(o-tolyl)phosphine / ethylene glycol dimethyl ether; water / 1.5 h / 50 °C / Inert atmosphere View Scheme

1: PPh3 gold(I) chloro complex; silver hexafluoroantimonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2: N-bromosuccinmide; hexafluoroisopropyl alcohol / dichloromethane / 0.5 h 3: Ba(OH)2·8H2O; palladium diacetate; tris-(o-tolyl)phosphine / ethylene glycol dimethyl ether; water / 1.5 h / 50 °C / Inert atmosphere View Scheme

1.1: magnesium / tetrahydrofuran / 0.12 h / 0 °C 1.2: 84 percent / tetrahydrofuran / 1 h / -40 - 20 °C 2.1: magnesium / diethyl ether / 0 °C 2.2: 83 percent / diethyl ether / 0.5 h / 0 °C 3.1: 86 percent / thionyl chloride; DMAP / pyridine / 0.02 h / 0 °C 4.1: 65 percent / sodium methoxide / dimethylsulfoxide / 1.5 h / 20 °C 5.1: NbCl5; LiAlH4 / dioxane / 2 h / Heating View Scheme

1.1: magnesium / diethyl ether / 0 °C 1.2: 83 percent / diethyl ether / 0.5 h / 0 °C 2.1: 86 percent / thionyl chloride; DMAP / pyridine / 0.02 h / 0 °C 3.1: 65 percent / sodium methoxide / dimethylsulfoxide / 1.5 h / 20 °C 4.1: NbCl5; LiAlH4 / dioxane / 2 h / Heating View Scheme

1.1: magnesium / diethyl ether / 0 °C 1.2: 83 percent / diethyl ether / 0.5 h / 0 °C 2.1: 86 percent / thionyl chloride; DMAP / pyridine / 0.02 h / 0 °C 3.1: 65 percent / sodium methoxide / dimethylsulfoxide / 1.5 h / 20 °C 4.1: NbCl5; LiAlH4 / dioxane / 2 h / Heating View Scheme

1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 1.2: 1 h / -78 °C 2.1: PPh3 gold(I) chloro complex; silver hexafluoroantimonate / dichloromethane / 2 h / 20 °C 3.1: hexafluoroisopropyl alcohol; N-bromosuccinmide / dichloromethane 4.1: palladium diacetate; tris-(o-tolyl)phosphine; Ba(OH)2 View Scheme

T=500 - 550°C; by/at 122 degree Celsius melting form;