potassium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; ethanol; water Suzuki coupling; 16 h; Heating;

sodium hydroxide in ethanol; water T=70°C; 16 h;

1.1: 95 percent / Et3N; CuI / Pd*PPh3)2Cl2 / 24 h / Heating 2.1: NaNO2; 6N HCl / H2O / 0.5 h / 0 °C 2.2: 73 percent / 3 h / Heating 3.1: 77 percent / POCl3 / pyridine; chlorobenzene / 1 h / Heating 4.1: 86 percent / 2M K2CO3 / Pd(PPh3)4 / H2O; ethanol; 1,2-dimethoxy-ethane / 16 h / Heating View Scheme

1.1: NaNO2; 6N HCl / H2O / 0.5 h / 0 °C 1.2: 73 percent / 3 h / Heating 2.1: 77 percent / POCl3 / pyridine; chlorobenzene / 1 h / Heating 3.1: 86 percent / 2M K2CO3 / Pd(PPh3)4 / H2O; ethanol; 1,2-dimethoxy-ethane / 16 h / Heating View Scheme

1: 77 percent / POCl3 / pyridine; chlorobenzene / 1 h / Heating 2: 86 percent / 2M K2CO3 / Pd(PPh3)4 / H2O; ethanol; 1,2-dimethoxy-ethane / 16 h / Heating View Scheme

1: palladium diacetate; caesium carbonate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl / toluene / 18 h / 100 °C / Inert atmosphere 2: sodium hydroxide / ethanol; water / 16 h / 70 °C View Scheme

1: N-chloro-succinimide / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere 2: palladium diacetate; caesium carbonate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl / toluene / 18 h / 100 °C / Inert atmosphere 3: sodium hydroxide / ethanol; water / 16 h / 70 °C View Scheme

1: copper(l) iodide; potassium carbonate; N-methyl-2-(methylamino)ethylamine / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 2: N-chloro-succinimide / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere 3: palladium diacetate; caesium carbonate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl / toluene / 18 h / 100 °C / Inert atmosphere 4: sodium hydroxide / ethanol; water / 16 h / 70 °C View Scheme

hydrogenchloride; sodium nitrite

1: sulfuric acid 2: hydrochloric acid; sodium nitrite View Scheme