1: piperazine-1-carboxylic acid tert-butyl ester With rac-2, 2'-bis(diphenylphosphine)-1,1'-binaphthyl; sodium t-butanolate; palladium diacetate in tetrahydrofuran T=20°C; 0.5 h; 2: 4-Bromo-benzoic acid methyl ester With hydrogenchloride in tetrahydrofuran T=70°C; 14 h;

1: 92 percent / PdCl2(PPh3)2; CuI; Et3N / 24 h / 50 °C 2: LiAlH4 / tetrahydrofuran / 2 h / 23 °C 3: 1.01 g / K2CO3; MeOH / 22 h / 23 °C View Scheme

diethylenetriamine-N,N,N',N'',N''-pentaacetic acid; ammonia; copper(II) oxide; potassium hydroxide in water T=100°C; 12 h;

1.1: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'- binaphthyl / toluene / 20 - 120 °C / Inert atmosphere 2.1: potassium hydroxide / ethanol; water / 20 - 100 °C / Inert atmosphere 2.2: 0 °C / pH 2 / Inert atmosphere View Scheme

palladium diacetate; caesium carbonate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl in 1,4-dioxane T=100°C; 2 h;

1: 82.8 percent / PdCl2, PPh3, CuI, Et2NH / 72 h / Ambient temperature 2: 61 percent / conc. H2SO4, Hg(OAc)2 / H2O / 2 h / Heating View Scheme

1.1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; triethylamine / tetrahydrofuran / 0.33 h / 20 °C / |Inert atmosphere 1.2: 15 h / 20 °C / |Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere 3.1: 1H-imidazole / tetrahydrofuran / 15 h / 0 - 20 °C / |Inert atmosphere 4.1: potassium carbonate; methanol / 2 h / 20 °C / |Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / |Inert atmosphere 5.2: 0.5 h / 20 °C / |Inert atmosphere 6.1: hydrogen; palladium 10 on activated carbon / ethyl acetate / 15001.5 Torr 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere 8.1: triethylamine / dichloromethane / 0.5 h / 0 °C / |Inert atmosphere 9.1: sodium iodide / acetone / 0.25 h / 20 °C 10.1: N,N-dimethyl-formamide / 2 h / 20 °C / |Inert atmosphere 11.1: sodium hydroxide; water / 4 h / |Reflux View Scheme

2: silver sulfate; nitrobenzene / Umsetzen des Reaktionsprodukts mit verd. Natronlauge View Scheme

1: 92 percent / PdCl2(PPh3)2; CuI; Et3N / 24 h / 50 °C 2: LiAlH4 / tetrahydrofuran / 2 h / 23 °C View Scheme

hydrogenchloride in tetrahydrofuran; methanol; Petroleum ether