sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethanol; water; toluene 5.5 h; Heating / reflux;

1: With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in tetrahydrofuran; cyclohexane T=-78°C; 1 h; Inert atmosphere; 2: With 3,4,5,6-tetrachloro-1,2-benzoquinone; acetic acid in tetrahydrofuran; cyclohexane T=-78 - 20°C; Inert atmosphere; chemoselective reaction;

1: 3-bromo-pyridine With n-butyllithium in diethyl ether; hexane T=-90°C; 0.5 h; 2: With tributyltin chloride in diethyl ether; hexane T=-70°C; 4 h; 3: ortho-iodochlorobenzene With palladium diacetate; triphenylphosphine in N,N-dimethyl-formamide T=120°C; 144 h;

1.1: potassium phosphate; CuSO4‵5H2O; 1,10-phenanthroline / toluene / 48 h / Inert atmosphere; Reflux 2.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere View Scheme

potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide in tetrahydrofuran 3 h; Heating;

1 h; Ambient temperatureIrradiation; Title compound not separated from byproducts;