boron tribromide in dichloromethane T=-78 - 0°C; 2 h;

boron tribromide in dichloromethane T=-78 - -20°C; 1.5 h; Inert atmosphere;

boron tribromide in dichloromethane T=-78 - -20°C; 1.5 h; Inert atmosphere;

hydrogen; sodium formate; palladium on activated charcoal in tetrahydrofuran; methanol 6 h; Ambient temperature; Yield given;

1: SOCl2 / 2 h / Ambient temperature 2: H2, sodium formate / 5percent Pd/C / tetrahydrofuran; methanol / 6 h / Ambient temperature View Scheme

1: pyridine / 1.) 35 deg C, 1 h, 2.) r.t., 10 h 2: p-TsOH*H2O / methanol / 5 h / 60 °C 3: pyridine / 2 h / Ambient temperature 4: benzylamine, diethylamine 5: SOCl2 / 2 h / Ambient temperature 6: H2, sodium formate / 5percent Pd/C / tetrahydrofuran; methanol / 6 h / Ambient temperature View Scheme

1: benzylamine, diethylamine 2: SOCl2 / 2 h / Ambient temperature 3: H2, sodium formate / 5percent Pd/C / tetrahydrofuran; methanol / 6 h / Ambient temperature View Scheme

1: caesium carbonate / toluene / 1 h / 20 °C / Inert atmosphere 2: potassium hydroxide / methanol; water / 1 h / 20 °C 3: ammonium cerium (IV) nitrate; sodium hydrogencarbonate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 4: boron tribromide / dichloromethane / 1.5 h / -78 - -20 °C / Inert atmosphere View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 °C / Inert atmosphere 1.3: -78 - 20 °C / Inert atmosphere 2.1: ammonium cerium (IV) nitrate / water; acetonitrile / 1 h / 0 °C 3.1: sodium azide / tetrahydrofuran; water / 1 h / 20 °C 4.1: caesium carbonate / toluene / 1 h / 20 °C / Inert atmosphere 5.1: potassium hydroxide / methanol; water / 1 h / 20 °C 6.1: ammonium cerium (IV) nitrate; sodium hydrogencarbonate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 7.1: boron tribromide / dichloromethane / 1.5 h / -78 - -20 °C / Inert atmosphere View Scheme

1: ammonium cerium (IV) nitrate / water; acetonitrile / 1 h / 0 °C 2: sodium azide / tetrahydrofuran; water / 1 h / 20 °C 3: caesium carbonate / toluene / 1 h / 20 °C / Inert atmosphere 4: potassium hydroxide / methanol; water / 1 h / 20 °C 5: ammonium cerium (IV) nitrate; sodium hydrogencarbonate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 6: boron tribromide / dichloromethane / 1.5 h / -78 - -20 °C / Inert atmosphere View Scheme