1: With methanesulfonic acid; hydrogen; 5 palladium on charcoal in acetone 2: With ammonia in dichloromethane; water 3: With hydrogen bromide in dichloromethane; water T=20°C; 0.5 h;

1: With hydrogen; palladium 10 on activated carbon in methanol T=40°C; P=3677.86 Torr; 2: With hydrogen bromide in isopropyl alcohol T=25 - 70°C; 5 h; Product distribution / selectivity;

hydrogen bromide in acetone T=20°C; 0.25 h; Product distribution / selectivity;

1.1: potassium carbonate; methanol / 25 - 35 °C 1.2: 25 - 30 °C 2.1: hydrogen / 5 Pd(II)/C(eggshell) / water; acetone / 25 - 35 °C / Inert atmosphere 3.1: sodium hydroxide / ethyl acetate; water / 0.33 h / 25 - 30 °C / pH 7 - 10 3.2: 10.5 h / 20 - 25 °C View Scheme

1.1: isopropyl alcohol; water / 4 h / 20 - 35 °C 2.1: potassium hydroxide / toluene; water / 0.25 h / 21 - 25 °C 2.2: 4 h / 100 °C 3.1: triethylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 5 h / 115 °C 4.1: potassium carbonate; water / methanol 5.1: hydrogen bromide / water / pH 1.5 6.1: hydrogen / 5 Pd(II)/C(eggshell) / water / 20 - 50 °C / Autoclave View Scheme

1: triethylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 5 h / 115 °C 2: potassium carbonate; water / methanol 3: hydrogen bromide / water / pH 1.5 4: hydrogen / 5 Pd(II)/C(eggshell) / water / 20 - 50 °C / Autoclave View Scheme

1: With sodium hydroxide in water; ethyl acetate T=25 - 30°C; pH=7 - 10; 0.333333 h; 2: With hydrogen bromide in water; acetone T=20 - 25°C; 10.5 h; Product distribution / selectivity;

in water; acetone T=20°C; 120 h; Product distribution / selectivity;

1.1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 3 h / Reflux 2.1: ethylmagnesium bromide; zinc(II) chloride / dichloromethane; tetrahydrofuran / 5 - 30 °C 2.2: -10 - 25 °C 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 10 - 50 °C / Inert atmosphere; Darkness 3.2: 0 - 35 °C / pH 12 - 13 4.1: N,N-dimethyl-formamide / 95 - 100 °C 4.2: 0 - 5 °C / pH 8 - 9 5.1: N-ethyl-N,N-diisopropylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 90 - 95 °C / Inert atmosphere 6.1: water; sodium carbonate; methanol / 2 h / 25 - 30 °C 7.1: hydrogen; methanesulfonic acid / 5 palladium on charcoal / acetone / 20 °C / 2585.81 Torr 7.2: 0.5 h / 25 - 30 °C 8.1: hydrogen bromide / dichloromethane; water; ethylene glycol / 0.5 h / 5 - 10 °C / Inert atmosphere View Scheme

1.1: ethylmagnesium bromide; zinc(II) chloride / dichloromethane; tetrahydrofuran / 5 - 30 °C 1.2: -10 - 25 °C 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 10 - 50 °C / Inert atmosphere; Darkness 2.2: 0 - 35 °C / pH 12 - 13 3.1: N,N-dimethyl-formamide / 95 - 100 °C 3.2: 0 - 5 °C / pH 8 - 9 4.1: N-ethyl-N,N-diisopropylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 90 - 95 °C / Inert atmosphere 5.1: water; sodium carbonate; methanol / 2 h / 25 - 30 °C 6.1: hydrogen; methanesulfonic acid / 5 palladium on charcoal / acetone / 20 °C / 2585.81 Torr 6.2: 0.5 h / 25 - 30 °C 7.1: hydrogen bromide / dichloromethane; water; ethylene glycol / 0.5 h / 5 - 10 °C / Inert atmosphere View Scheme