palladium diacetate; potassium carbonate; triphenylphosphine in methanol; acetonitrile T=50°C; Suzuki Coupling; 24 h; Inert atmosphere; regioselective reaction;

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in water; toluene T=80°C; 40.5 h; Inert atmosphere;

1: 5-bromo-2-iodopyridine With zinc in tetrahydrofuran T=0 - 20°C; Negishi coupling reaction; Inert atmosphere; 2: para-iodoanisole With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=20°C; Negishi coupling reaction; 24 h; Inert atmosphere; chemoselective reaction;

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in water; N,N-dimethyl-formamide T=90°C;

1: tetrahydrofuran / 0.25 h / -20 °C 2: 2) o-chloranil / 1) THF, -20 deg C, 15 min, 2) toluene, reflux, 6 h View Scheme

3,4,5,6-tetrachloro-1,2-benzoquinone 1) THF, -20 deg C, 15 min, 2) toluene, reflux, 6 h; Multistep reaction;