1: 1.) lithium hexamethylsilylamide (LHDS) / 1.) THF, -80 deg C, 2.) THF 2: 80 percent / H2 / Pd/C / ethyl acetate View Scheme

1.1: potassium hexamethyldisilazane / toluene; tetrahydrofuran / 0.25 h / -70 °C 1.2: 47 percent / toluene; tetrahydrofuran / 0.5 h / -70 °C 2.1: potassium hexamethyldisilazane / toluene; tetrahydrofuran / 0.5 h / -70 °C 2.2: 13 percent / oxodiperoxymolybdenum(pyridine)(HMPTA) / toluene; tetrahydrofuran / 2 h / -70 °C 3.1: 86 percent / H2 / Pd-C / ethyl acetate / 2 h / 20 °C View Scheme

1: 1.) lithium hexamethylsilylamide (LHDS) / 1.) THF, -80 deg C, 2.) THF 2: 66 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 3: 76 percent / H2 / Pd/C / ethyl acetate View Scheme

Multi-step reaction with 4 steps 1: 1.) lithium hexamethyldisilylamide (LHDS) / 1.) benzene, 2.) benzene, 0 deg C, 5 min2: 78 percent / 60percent aq. perchloric acid / acetic acid; CH2Cl2 / 4.5 h / Ambient temperature3: 80 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature4: 81 percent / H2 / Pd/C / ethyl acetate / 18 h / 2280 Torr / Ambient temperature  

Multi-step reaction with 2 steps 1: 1.) lithium hexamethylsilylamide (LHDS) / 1.) THF, -80 deg C, 2.) THF2: 66 percent / LiAlH4 / tetrahydrofuran / Ambient temperature  

Multi-step reaction with 2 steps 1.1: potassium hexamethyldisilazane / toluene; tetrahydrofuran / 0.25 h / -70 °C1.2: 47 percent / toluene; tetrahydrofuran / 0.5 h / -70 °C2.1: potassium hexamethyldisilazane / toluene; tetrahydrofuran / 0.5 h / -70 °C2.2: 13 percent / oxodiperoxymolybdenum(pyridine)(HMPTA) / toluene; tetrahydrofuran / 2 h / -70 °C