n-butyllithium; N,N,N',N,-tetramethylethylenediamine in tetrahydrofuran; hexane; toluene T=-78 - -15°C;

Raney aluminium-nickel alloy; water; sodium hydroxide in dimethoxymethane T=25°C; 17 h;

1: 3-bromo-aniline With copper diacetate in acetonitrile T=-5°C; 0.25 h; 2: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in acetonitrile T=-5°C; 0.0833333 h; 3: phenylhydrazine in acetonitrile T=-5°C; 3.33333 h;

1: iodobenzene With potassium phosphate; copper(l) iodide; lithium amide in N,N-dimethyl-formamide T=130°C; 6 h; Inert atmosphere; 2: 3-bromo-1-iodobenzene in N,N-dimethyl-formamide T=130°C; 18 h; Inert atmosphere; chemoselective reaction;

1: 3-bromo-aniline With n-butyllithium; ZnCl2*TMEDA in tetrahydrofuran; hexane T=0 - 20°C; 0.5 h; Inert atmosphereSchlenk technique; 2: phenyl-magnesium bromide With N,N'-dimethyl-N,N'-propyleneurea; bis(acetylacetonate)nickel(II); 1,2-dichloro-2-methylpropane in tetrahydrofuran; hexane T=0 - 20°C; 2.5 h; Inert atmosphereSchlenk technique;

1: K2CO3 / Cu / pentan-1-ol / Heating 2: 220 - 240 °C View Scheme

1: K2CO3 / Cu / pentan-1-ol / Heating 2: 220 - 240 °C View Scheme

potassium hydroxide in dimethyl sulfoxide T=130°C; 2 h;

trifluorormethanesulfonic acid T=60°C; 2 h; Yield given. Yields of byproduct given;