potassium carbonate; potassium iodide in N,N-dimethyl-formamide T=20°C; Inert atmosphere;

1: para-iodobenzonitrile With iso-propylmagnesium bromide in tetrahydrofuran T=-35°C; 1 h; 2: With zinc(II) chloride in tetrahydrofuran T=-35°C; 0.166667 h; 3: Bn2N-OBz With copper (I) trifluoromethane sulfonate benzene in tetrahydrofuran T=25°C; 1 h;

1,1'-bis-(diphenylphosphino)ferrocene; n-butyllithium; lithium tert-butylate; nickel on carbon in hexane; toluene 7 h; Heating;

copper(l) iodide; biphenyl-2-yl-di-tert-butyl-phosphane; lithium tert-butylate in 1,4-dioxane T=20°C; 4 h; Inert atmosphereSchlenk technique;

1: para-bromobenzonitrile With isopropylmagnesium chloride lithium chloride complex in tetrahydrofuran T=0°C; 3 h; 2: N-chloro(dibenzyl)amine With N,N,N',N,-tetramethylethylenediamine in tetrahydrofuran T=-40 - 0°C; chemoselective reaction;

potassium hexamethylsilazane in 1,4-dioxane T=100°C; metal-free Buchwald-Hartwig amination; 0.166667 h; Inert atmosphere;

1.1: 66 percent / dipotassium hydrogen phosphate / dimethylformamide / 24 h / 20 °C 2.1: iso-propyl magnesium bromide / tetrahydrofuran / 1 h / -35 °C 2.2: zinc chloride / tetrahydrofuran / 0.17 h / -35 °C 2.3: 96 percent / copper(I) trifluoromethanesulfonate benzene complex / tetrahydrofuran / 1 h / 20 °C View Scheme

aluminum oxide; zeolite K-Y in benzene 5 h; Heating; Yield given. Yields of byproduct given;

(i) NH2OH*HCl, Py, (ii) DCC, CuSO4*5H2O, Et3N; Multistep reaction;