triethylsilane; trichloroacetic acid in toluene T=70°C;

potassium hydroxide in neat (no solvent) T=150°C; 18 h; regioselective reaction;

hydrogen; palladium on activated charcoal in ethanol T=20°C; 2 h;

1: copper(II) acetate / palladium(II) acetate / dimethylformamide; dimethylsulfoxide / 18 h / 70 °C 2: 0.14 g / hydrogen / palladium on carbon / ethanol / 2 h / 20 °C View Scheme

1: copper(II) acetate / palladium(II) acetate / dimethylformamide; dimethylsulfoxide / 18 h / 70 °C 2: 0.14 g / hydrogen / palladium on carbon / ethanol / 2 h / 20 °C View Scheme

hydrogenchloride in methanol; water T=20°C; 2 h;

palladium (II) trifluoroacetate; oxygen; bis[2-(diphenylphosphino)phenyl] ether in toluene T=140°C; 8 h; regioselective reaction;

1.1: 97 percent / H2 / 10 percent Pd/C / ethanol / 72 h / 100 °C / 38786.1 Torr 2.1: 57 percent / aq. KOH; BnEt3NCl / CH2Cl2 / Heating 3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 3.2: 73 percent / HMPA / tetrahydrofuran; hexane / -78 - 20 °C 4.1: AIBN / acetonitrile / 0.25 h / 100 °C 5.1: Raney-Ni / ethanol View Scheme

1.1: 57 percent / aq. KOH; BnEt3NCl / CH2Cl2 / Heating 2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 73 percent / HMPA / tetrahydrofuran; hexane / -78 - 20 °C 3.1: AIBN / acetonitrile / 0.25 h / 100 °C 4.1: Raney-Ni / ethanol View Scheme

1.1: 84 percent / KF / tetrahydrofuran / 2 h / 40 °C 2.1: 97 percent / H2 / 10 percent Pd/C / ethanol / 72 h / 100 °C / 38786.1 Torr 3.1: 57 percent / aq. KOH; BnEt3NCl / CH2Cl2 / Heating 4.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 4.2: 73 percent / HMPA / tetrahydrofuran; hexane / -78 - 20 °C 5.1: AIBN / acetonitrile / 0.25 h / 100 °C 6.1: Raney-Ni / ethanol View Scheme