ammonium formate; palladium on activated charcoal in octanol T=25°C;

catalyst: Pd on active carbon in gaseous matrix Hydrogenation in presence of catalyst (10 percent Pd/90 percent active carbon) at 280 °C in H2 stream.;

potassium tetrafluorocobaltate in gaseous matrix T=215 - 225°C; 1.) 3.5-4 h; 2.) 2 h; Further byproducts given;

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 / 0.75 h / -100 °C 1.2: 84 percent / tetrahydrofuran; hexane / cooling 2.1: 98 percent / H2NNH2*H2O / tetrahydrofuran / 2 h / 50 °C 3.1: 89 percent / CuSO4*5H2O / H2O / 2 h / Heating 4.1: 93 percent / ICl 5.1: LDA / tetrahydrofuran / 2.5 h 5.2: 67 percent / H2O / tetrahydrofuran View Scheme

1: triethylamine / dichloromethane / -7 - 20 °C / |Inert atmosphere 2: (η5-cyclopentadienyl)2TiF2; (Ph)2SiH2 / 1,4-dioxane / 18 h / 110 °C / |Inert atmosphere View Scheme

1.1: BuLi / tetrahydrofuran; hexane / 0.75 h / -100 °C 1.2: 84 percent / tetrahydrofuran; hexane / cooling 2.1: 98 percent / H2NNH2*H2O / tetrahydrofuran / 2 h / 50 °C 3.1: 89 percent / CuSO4*5H2O / H2O / 2 h / Heating 4.1: 93 percent / ICl 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 View Scheme

in gas byproducts: polyfluorobromopyridines; Bromination at 685 °C (dwell time 22 s, reactor tube).;

1.1: BuLi / tetrahydrofuran; hexane / 0.75 h / -100 °C 1.2: 84 percent / tetrahydrofuran; hexane / cooling 2.1: 98 percent / H2NNH2*H2O / tetrahydrofuran / 2 h / 50 °C 3.1: 85 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 25 °C 4.1: 71 percent / Br2 / CHCl3 / 3 h / Heating View Scheme