1.1: potassium tert-butylate / dimethyl sulfoxide / 1 h / 20 °C 1.2: 20 °C 2.1: hydrogenchloride / diethyl ether; acetonitrile View Scheme

1.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: potassium carbonate / water / 0.08 h 2.2: Inert atmosphere 3.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme

1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 2.1: dichloromethane; water / 0 - 10 °C 3.1: borane-THF / tetrahydrofuran / 20 - 50 °C 3.2: 0.25 h / 0 - 5 °C 3.3: 2.5 h / 0 °C / Reflux 4.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 4.2: 2 h / 20 °C 5.1: potassium carbonate / water / 0.08 h 5.2: Inert atmosphere 6.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme

1.1: hydrogenchloride / dichloromethane; water / 0.33 h 2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 3.1: dichloromethane; water / 0 - 10 °C 4.1: borane-THF / tetrahydrofuran / 20 - 50 °C 4.2: 0.25 h / 0 - 5 °C 4.3: 2.5 h / 0 °C / Reflux 5.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: potassium carbonate / water / 0.08 h 6.2: Inert atmosphere 7.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme

1.1: borane-THF / tetrahydrofuran / 20 - 50 °C 1.2: 0.25 h / 0 - 5 °C 1.3: 2.5 h / 0 °C / Reflux 2.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 2.2: 2 h / 20 °C 3.1: potassium carbonate / water / 0.08 h 3.2: Inert atmosphere 4.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme

1.1: dichloromethane; water / 0 - 10 °C 2.1: borane-THF / tetrahydrofuran / 20 - 50 °C 2.2: 0.25 h / 0 - 5 °C 2.3: 2.5 h / 0 °C / Reflux 3.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 3.2: 2 h / 20 °C 4.1: potassium carbonate / water / 0.08 h 4.2: Inert atmosphere 5.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme

1.1: potassium carbonate / water / 0.08 h 1.2: Inert atmosphere 2.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme

sodium hydroxide in water Product distribution / selectivity;