1: 2-bromo-pyridine With n-butyllithium in diethyl ether; hexane T=-78 - 0°C; 0.5 h; Inert atmosphere; 2: meta-dibromobenzene With tetrakis(triphenylphosphine) palladium(0); zinc(II) chloride in tetrahydrofuran; diethyl ether; hexane 24 h; Inert atmosphereReflux;

cyclopentadienyl-cyclooctadienyl-cobalt(I) in toluene T=130°C; P=7600 Torr; 72 h;

1: meta-dibromobenzene With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane in N,N-dimethyl-formamide T=20°C; Suzuki-Miyaura coupling; Inert atmosphereHeating; 2: alpha-chloropyridine With water; sodium hydroxide in N,N-dimethyl-formamide Suzuki-Miyaura coupling; 3 h; Inert atmosphereHeating;

tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran 14 h; Reflux;

bis-triphenylphosphine-palladium(II) chloride; copper(II) oxide in N,N-dimethyl-formamide T=160°C; Stille coupling; 0.25 h; Inert atmosphereMicrowave irradiation;

tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; hexane T=20°C; 51 h;

1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 1.2: diethyl ether; hexane 2.1: tetrakis(triphenylphosphine)palladium; copper(I) iodide; potassium hydroxide / 1,2-dimethoxy-ethane / 20 h / Heating View Scheme

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

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 / 51 h / 20 °C View Scheme