ammonium formate; palladium on activated charcoal in octanol T=75°C; 4 h;

copper(II) sulfate in water 0.416667 h; Heating;

in deuterated toluene T=20°C; 16 h; Inert atmosphere; regioselective reaction;

1: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 50 °C 2: 85 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 25 °C 3: 51 percent / aq. CuSO4 / 0.42 h / Heating View Scheme

1: 85 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 25 °C 2: 51 percent / aq. CuSO4 / 0.42 h / Heating View Scheme

1: 79 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 2 h / 150 °C 2: 77 percent / HCOONH4 / Pd/C / octan-1-ol / 4 h / 75 °C View Scheme

1: 91 percent / BuLi / tetrahydrofuran; hexane / 1 h / -75 °C 2: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 50 °C 3: 85 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 25 °C 4: 51 percent / aq. CuSO4 / 0.42 h / Heating View Scheme

1.1: BuLi / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: 80 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane / 1 h / -75 °C 2.1: 79 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 2 h / 150 °C 3.1: 77 percent / HCOONH4 / Pd/C / octan-1-ol / 4 h / 75 °C View Scheme

1.1: BuLi; i-Pr2NH / tetrahydrofuran; hexane 1.2: 85 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane 2.1: BuLi / tetrahydrofuran; hexane / 2 h / -75 °C 2.2: 80 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane / 1 h / -75 °C 3.1: 79 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 2 h / 150 °C 4.1: 77 percent / HCOONH4 / Pd/C / octan-1-ol / 4 h / 75 °C View Scheme

1: 85 percent / HCOONH4 / Pd/C / octan-1-ol / 25 °C 2: 91 percent / BuLi / tetrahydrofuran; hexane / 1 h / -75 °C 3: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 50 °C 4: 85 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 25 °C 5: 51 percent / aq. CuSO4 / 0.42 h / Heating View Scheme