1: 2-bromo-pyridine With tert.-butyl lithium in tetrahydrofuran T=-78°C; 1.5 h; Inert atmosphere; 2: With zinc(II) chloride−TMEDA in tetrahydrofuran T=20°C; 1 h; Inert atmosphere; 3: 1,3,5-tribromo benzene With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran 17 h; Reflux;

bis-triphenylphosphine-palladium(II) chloride; lithium chloride in toluene T=150°C; 48 h; Inert atmosphere;

copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium hydroxide in ethylene glycol dimethyl ether Suzuki coupling; 20 h; Reflux;

bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran 23 h; Heating;

tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; hexane T=20°C; 24 h;

1.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -86 °C 1.2: 2 h / -86 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / hexane; tetrahydrofuran / 24 h / 20 °C View Scheme

1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.5 h; 2: With boric acid trimethyl ester in tetrahydrofuran; hexane T=-78°C; 1 h;

n-butyllithium; oxonium in not given by a react. of B-contg. compd. with Br-contg. compd.;