palladium 10 on activated carbon; hydrogen in methanol T=20°C; 12 h;

sulfuric acid Heating;

in diethyl ether; dichloromethane T=0 - 20°C;

1: 99 percent / NaOH / PdCl2 2: 84 percent / conc. HCl / 12 h / Heating View Scheme

oxygen in toluene T=80°C; 24 h;

ammonium formate; silica gel; palladium dichloride in formic acid; water 0.133333 h; microwave irradiation;

1: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, 0 deg C, 0.5 h, 2) 0 deg C 2: 95 percent / LiAlH4 / diethyl ether / 0 °C 3: 81 percent / CrO3, pyridine / CH2Cl2 / Ambient temperature 4: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C 6: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 7: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 8: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 9: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 10: 64 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 11: 88 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, 0 deg C, 0.5 h, 2) 0 deg C 2: 95 percent / LiAlH4 / diethyl ether / 0 °C 3: 81 percent / CrO3, pyridine / CH2Cl2 / Ambient temperature 4: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C 6: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 7: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 8: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 9: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 10: 58 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 11: 90 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 78 percent / NaH, Bu4NI / tetrahydrofuran / 13 h / Ambient temperature 2: 80 percent / LDA / tetrahydrofuran / 1.) from 0 deg C to r.t.; 2.) reflux, 30 min 3: 81 percent / TMEDA, NaH / dimethylsulfoxide / 0.75 h 4: catecholborane / tetrahydrofuran / 4.5 h / -23 °C 5: Raney-Ni / ethanol / 0.5 h / Ambient temperature View Scheme

sodium tetrahydroborate in water 8 h; Ambient temperature;