water; hydrogen; palladium on activated charcoal in methanol T=60°C; P=3750.3 Torr; 12 h;

1: 2-(3-trifluoromethylbenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With Pd0(tris(tert-butyl)phosphine)2; cesium fluoride in water; N,N-dimethyl-formamide T=80°C; 0.0166667 h; Inert atmosphereSchlenk technique; 2: methyl iodide in water; N,N-dimethyl-formamide T=80°C; 0.0833333 h; Inert atmosphereSchlenk technique;

triphenylphosphine; bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate in toluene T=140°C; Cyclization; Anti-Markovnikov hydroamination; 48 h;

1: zinc chloride / toluene / 15 h / Heating 2: sodium borohydride / methanol / 0 °C 3: hydrogen; water / 5 percent Pd/C NX-type / methanol / 12 h / 60 °C / 3750.3 Torr View Scheme

iron; hydrogen in 1,3,5-trimethyl-benzene T=20°C; P=7500.75 Torr; 20 h; Autoclave;

triphenylphosphine; bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate in tetrahydrofuran Substitution; Amination; Hydroamination; 20 h; Heating; Title compound not separated from byproducts;

[(dmpp)PtMe3]2 T=100°C; 25 h; Inert atmosphere;

NiCl2[1,2-bis(diphenylphosphine)] in tetrahydrofuran T=20 - 25°C; 3 h;

Cl2Ni(1,2-bis(diphenylphosphino)ethane) in tetrahydrofuran T=20 - 25°C; 3 h;