hydrogen; Lindlar's catalyst

1: 1.) LDA / 1.) THF, hexane, -10 deg C, 15 min, 2.) THF, hexane, -50 deg C, 6 h 2: Al2O3 / diethyl ether / 6 h / Ambient temperature 3: 99 percent / O2, methylene blue / methanol / 3 h / 0 °C / Irradiation 4: NaBH4, NaHCO3 / H2O / 2 h / Ambient temperature 5: p-TsOH / benzene / Heating 6: 90 percent / H2, quinoline / 5percent Pd/BaSO4 / benzene View Scheme

1: p-TsOH / benzene / Heating 2: 90 percent / H2, quinoline / 5percent Pd/BaSO4 / benzene View Scheme

1: NaBH4, NaHCO3 / H2O / 2 h / Ambient temperature 2: p-TsOH / benzene / Heating 3: 90 percent / H2, quinoline / 5percent Pd/BaSO4 / benzene View Scheme

1: 99 percent / O2, methylene blue / methanol / 3 h / 0 °C / Irradiation 2: NaBH4, NaHCO3 / H2O / 2 h / Ambient temperature 3: p-TsOH / benzene / Heating 4: 90 percent / H2, quinoline / 5percent Pd/BaSO4 / benzene View Scheme

1: Al2O3 / diethyl ether / 6 h / Ambient temperature 2: 99 percent / O2, methylene blue / methanol / 3 h / 0 °C / Irradiation 3: NaBH4, NaHCO3 / H2O / 2 h / Ambient temperature 4: p-TsOH / benzene / Heating 5: 90 percent / H2, quinoline / 5percent Pd/BaSO4 / benzene View Scheme

1: 1.) LDA / 1.) THF, hexane, -10 deg C, 15 min, 2.) THF, hexane, -50 deg C, 6 h 2: Al2O3 / diethyl ether / 6 h / Ambient temperature 3: 99 percent / O2, methylene blue / methanol / 3 h / 0 °C / Irradiation 4: NaBH4, NaHCO3 / H2O / 2 h / Ambient temperature 5: p-TsOH / benzene / Heating 6: 90 percent / H2, quinoline / 5percent Pd/BaSO4 / benzene View Scheme

1: 1) diisopropylamine, n-BuLi / 1) THF, -10 deg C, 30 min; 2) THF, -50 deg C 2: Al2O3 / diethyl ether / 6 h / Ambient temperature 3: 100 percent / O2, methylene blue / methanol / 3 h / 5 °C / Irradiation 4: NaBH4, NaHCO3 / H2O 5: TsOH / benzene / Heating 6: 90 percent / H2 / Lindlar catalyst View Scheme

1: 1.) zinc chips / 1.) THF, 0 deg C, 1 h, 2.) THF, 25 deg C, 1h 2: dimethylsulfoxide / 200 °C 3: 71 percent / lithium amide / liquid ammonia; tetrahydrofuran / 0.75 h 4: 1.) 35percent H2O2, conc. H2SO4, 2.) triethylamine, acetic anhydride / 1.) THF, 20 deg C, 24 h, 2.) 20 deg C, 2 h 5: 71 percent / H2, quinoline / 5percent Pd/C/BaSO4 / hexane View Scheme

1: 71 percent / lithium amide / liquid ammonia; tetrahydrofuran / 0.75 h 2: 1.) 35percent H2O2, conc. H2SO4, 2.) triethylamine, acetic anhydride / 1.) THF, 20 deg C, 24 h, 2.) 20 deg C, 2 h 3: 71 percent / H2, quinoline / 5percent Pd/C/BaSO4 / hexane View Scheme