(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; silver(l) oxide in tetrahydrofuran; dichloromethane T=120°C; 18.5 h;

in butan-1-ol T=130°C; 60 h; Sealed vessel; Product distribution / selectivity;

tetrakis(triphenylphosphine) palladium(0); potassium carbonate in ethylene glycol dimethyl ether T=110°C; 48 h; Inert atmosphere;

1: acetic acid / |Reflux 2: triethylamine / dichloromethane / -10 - 0 °C 3: triethylamine / N,N-dimethyl-formamide / 19 h / 20 °C / |Cooling with ice; |Inert atmosphere 4: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethylene glycol dimethyl ether / 48 h / 110 °C / |Inert atmosphere View Scheme

1: triethylamine / N,N-dimethyl-formamide / 19 h / 20 °C / |Cooling with ice; |Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethylene glycol dimethyl ether / 48 h / 110 °C / |Inert atmosphere View Scheme

1: 96 percent / POCl3 / acetonitrile / 2.5 h / Heating 2: 74 percent / H2O / 72 h / 140 °C View Scheme

1: 94.3 percent / hydrazine monohydrate / aq. ethanol / 2 h / Heating 2: 91.1 percent / CuCl2 / acetonitrile / 2 h / Heating 3: 96 percent / POCl3 / acetonitrile / 2.5 h / Heating 4: 74 percent / H2O / 72 h / 140 °C View Scheme