sodium tetrahydroborate; sodium hydroxide in methanol; water T=60 - 70°C;

1: 95.3 percent / BF3*Et2O / diethyl ether / 14 h / 20 °C 2: 91 percent / H2 / 5percent Pd/C / ethanol / 30 h / 20 - 25 °C / 760 Torr View Scheme

sodium sulfate in dichloromethane 1 h; Ambient temperature;

[Ir(μ-Cl)(cyclooctene)2]2; diethylesilane in dichloromethane T=23°C; 0.5 h; Inert atmosphere;

1: 10 palladium on activated charcoal; ammonium formate 2: potassium carbonate / methanol / 20 °C View Scheme

1: sulfuric acid / 0 °C / Reflux 2: 10 palladium on activated charcoal; ammonium formate 3: potassium carbonate / methanol / 20 °C View Scheme

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 4 h / -78 °C / Inert atmosphere 1.3: Saturated solution 2.1: sulfuric acid / 0 °C / Reflux 3.1: 10 palladium on activated charcoal; ammonium formate 4.1: potassium carbonate / methanol / 20 °C View Scheme