palladium diacetate; magnesium oxide; triphenylphosphine in 1,4-dioxane; N,N-dimethyl-formamide T=150°C; 18 h;

(benzyl)-tri-(butyl)-ammonium chloride; potassium carbonate; palladium diacetate in toluene T=110°C; 48 h;

potassium carbonate in methanol 18 h; Heating;

1,10-phenanthroline; palladium diacetate; trifluoroacetic acid in chlorobenzene T=100°C; 12 h;

1: 99 percent / bromine / CH2Cl2 / 4.5 h / 20 °C 2: 100 percent / Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; ethanol; H2O / 18 h / Heating 3: 93 percent / K2CO3 / methanol / 18 h / Heating View Scheme

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 1.2: trimethyl borate / tetrahydrofuran / 0.5 h / -78 °C 1.3: HCl / tetrahydrofuran; H2O 2.1: 100 percent / Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; ethanol; H2O / 18 h / Heating 3.1: 93 percent / K2CO3 / methanol / 18 h / Heating View Scheme

1: 100 percent / Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; ethanol; H2O / 18 h / Heating 2: 93 percent / K2CO3 / methanol / 18 h / Heating View Scheme

1: 100 percent / Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; ethanol; H2O / 18 h / Heating 2: 93 percent / K2CO3 / methanol / 18 h / Heating View Scheme