potassium permanganate; sulfuric acid T=100°C;

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethanol; water; toluene Suzuki coupling; Inert atmosphereReflux;

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; water T=95°C; Suzuki Coupling; 20 h;

1: 3-iodo-α,α,α-trifluorotoluene With isopropylmagnesium chloride lithium chloride complex in tetrahydrofuran T=-20°C; 1 h; Inert atmosphere; 2: With lithium chlorozincate in tetrahydrofuran Inert atmosphere; 3: 4-bromo-aniline With bis(dibenzylideneacetone)-palladium(0); dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine in tetrahydrofuran T=25°C; Negishi cross-coupling reaction; 0.0833333 h; Inert atmosphere;

tin(ll) chloride in ethanol; ethyl acetate Heating;

1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -100 - -78 °C 1.2: ZnCl2 / tetrahydrofuran; hexane / 1 h 1.3: 65 percent / Pd(PPh3)4 / tetrahydrofuran; hexane / 18 h 2.1: 95 percent / SnCl2*2H2O / ethanol; ethyl acetate / Heating View Scheme

1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -100 - -78 °C 1.2: ZnCl2 / tetrahydrofuran; hexane / 1 h 1.3: 65 percent / Pd(PPh3)4 / tetrahydrofuran; hexane / 18 h 2.1: 95 percent / SnCl2*2H2O / ethanol; ethyl acetate / Heating View Scheme

1: acetic acid; H2SO4; fuming HNO3 2: tin; aq.-ethanolic HCl View Scheme

1: acetic acid; mixture of gaseous nitrogen oxides / Behandeln des Reaktionsprodukts mit Benzol 2: acetic acid; H2SO4; fuming HNO3 3: tin; aq.-ethanolic HCl View Scheme