1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 10 - 50 °C / Inert atmosphere; Darkness 1.2: 0 - 35 °C / pH 12 - 13 2.1: N,N-dimethyl-formamide / 95 - 100 °C 2.2: 0 - 5 °C / pH 8 - 9 3.1: N-ethyl-N,N-diisopropylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 90 - 95 °C / Inert atmosphere 4.1: water; sodium carbonate; methanol / 2 h / 25 - 30 °C 5.1: hydrogen; methanesulfonic acid / 5 palladium on charcoal / acetone / 20 °C / 2585.81 Torr 5.2: 0.5 h / 25 - 30 °C 6.1: hydrogen bromide / dichloromethane; water; ethylene glycol / 0.5 h / 5 - 10 °C / Inert atmosphere View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 60 °C / Reflux 2.1: isopropyl alcohol; water / 4 h / 20 - 35 °C 3.1: potassium hydroxide / toluene; water / 0.25 h / 21 - 25 °C 3.2: 4 h / 100 °C 4.1: triethylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 5 h / 115 °C 5.1: potassium carbonate; water / methanol 6.1: hydrogen bromide / water / pH 1.5 7.1: hydrogen / 5 Pd(II)/C(eggshell) / water / 20 - 50 °C / Autoclave View Scheme

1.1: oxalyl dichloride / N,N-dimethyl-formamide; toluene / 2.5 h / 20 - 25 °C 2.1: methyl-magnesium chloride / tert-butyl methyl ether; tetrahydrofuran / 0.75 h / 20 °C 2.2: 0.5 h / 3 - 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 60 °C / Reflux 4.1: isopropyl alcohol; water / 4 h / 20 - 35 °C 5.1: potassium hydroxide / toluene; water / 0.25 h / 21 - 25 °C 5.2: 4 h / 100 °C 6.1: triethylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 5 h / 115 °C 7.1: potassium carbonate; water / methanol 8.1: hydrogen bromide / water / pH 1.5 9.1: hydrogen / 5 Pd(II)/C(eggshell) / water / 20 - 50 °C / Autoclave View Scheme

1.1: methyl-magnesium chloride / tert-butyl methyl ether; tetrahydrofuran / 0.75 h / 20 °C 1.2: 0.5 h / 3 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 60 °C / Reflux 3.1: isopropyl alcohol; water / 4 h / 20 - 35 °C 4.1: potassium hydroxide / toluene; water / 0.25 h / 21 - 25 °C 4.2: 4 h / 100 °C 5.1: triethylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 5 h / 115 °C 6.1: potassium carbonate; water / methanol 7.1: hydrogen bromide / water / pH 1.5 8.1: hydrogen / 5 Pd(II)/C(eggshell) / water / 20 - 50 °C / Autoclave View Scheme

1: With ammonia in tert-butyl methyl ether; water pH=10.5 - 11.0; 2: With sodium carbonate in tert-butyl methyl ether; water 3: With hydrogen bromide in ipa; acetone pH=6.6 - 7.5; Product distribution / selectivity;

1.1: triethylamine / N,N-dimethyl-formamide / 2 h / 90 - 100 °C 1.2: 3 h / Reflux 2.1: water; sodium carbonate; methanol / 2 h / 25 - 30 °C 3.1: hydrogen; methanesulfonic acid / 5 palladium on charcoal / acetone / 20 °C / 2585.81 Torr 3.2: 0.5 h / 25 - 30 °C 4.1: hydrogen bromide / dichloromethane; water; ethylene glycol / 0.5 h / 5 - 10 °C / Inert atmosphere View Scheme

1.1: potassium hydroxide / toluene; water / 0.25 h / 21 - 25 °C 1.2: 4 h / 100 °C 2.1: triethylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 5 h / 115 °C 3.1: potassium carbonate; water / methanol 4.1: hydrogen bromide / water / pH 1.5 5.1: hydrogen / 5 Pd(II)/C(eggshell) / water / 20 - 50 °C / Autoclave View Scheme

1.1: triethylamine / palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 75 - 80 °C 2.1: hydrogen / palladium 10 on activated carbon / methanol / 40 °C / 3677.86 Torr 2.2: 5 h / 25 - 70 °C View Scheme