1.1: 75 percent / DDQ / CH2Cl2 / 3 h / 0 °C 2.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C 2.2: 73 percent / tetrahydrofuran / -78 - 0 °C 3.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 4.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 5.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 6.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme

1.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C 1.2: 73 percent / tetrahydrofuran / -78 - 0 °C 2.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 3.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 4.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 5.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme

1: 83 percent / KOH / methanol / 8 h / Heating 2: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 3: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

1: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 2: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 3: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 4: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 5: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 6: 84 percent / KOH / methanol / 2 h / 20 °C 7: 83 percent / KOH / methanol / 8 h / Heating 8: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 9: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

1: 82 percent / triethylamine; methanesulfonyl chloride / CHCl3 / 25.25 h / 0 - 5 °C 2: 0.7 g / NaI*2H2O / acetone / 6 h / Heating 3: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating 4: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 5: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 6: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 7: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 8: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 9: 84 percent / KOH / methanol / 2 h / 20 °C 10: 83 percent / KOH / methanol / 8 h / Heating 11: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 12: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

1: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 2: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 3: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 4: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 5: 84 percent / KOH / methanol / 2 h / 20 °C 6: 83 percent / KOH / methanol / 8 h / Heating 7: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 8: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

1: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 2: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 3: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 4: 84 percent / KOH / methanol / 2 h / 20 °C 5: 83 percent / KOH / methanol / 8 h / Heating 6: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 7: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

1: 83 percent / KOH / methanol / 8 h / Heating 2: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 3: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

1: 85 percent / triethylamine; methanesulfonyl chloride / CH2Cl2 / 24.17 h / 0 - 5 °C 2: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 3: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 4: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 5: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 6: 84 percent / KOH / methanol / 2 h / 20 °C 7: 83 percent / KOH / methanol / 8 h / Heating 8: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 9: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

1: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 2: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 3: 84 percent / KOH / methanol / 2 h / 20 °C 4: 83 percent / KOH / methanol / 8 h / Heating 5: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 6: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme