[bmim]PF6; triethylamine; bis-triphenylphosphine-palladium(II) chloride in water T=100°C; P=15001.2 Torr; 30 h;

tetrabutyl ammonium fluoride; palladium dichloride in tetrahydrofuran T=65°C; Hiyama coupling; 9 h; stereoselective reaction;

1: potassium carbonate; copper(l) iodide; N-methyl-2-(methylamino)ethylamine / tetrahydrofuran / 18 h / 80 °C / |Inert atmosphere 2: copper(ll) bromide; tetrabutylammomium bromide; dipotassium peroxodisulfate; 3-pyridinecarboxylic acid ethyl ester / acetonitrile / 24 h / 20 °C / |Inert atmosphere View Scheme

1: With iron (+/-)-(N,N'-bis(pyridin-2-ylmethylene)cyclohexane-1,2-diamine)dichloride in tetrahydrofuran T=-20°C; 0.25 h; 2: With LiH3BNMe2 in tetrahydrofuran T=-20 - 20°C; 16 h;

copper(l) iodide; [bmim]BF4; proline potassium salt T=110°C; 10 h;

tetrakis(triphenylphosphine) palladium(0); triethylamine T=90°C; Substitution; 1 h;

iron (+/-)-(N,N'-bis(pyridin-2-ylmethylene)cyclohexane-1,2-diamine)dichloride in tetrahydrofuran T=-20°C; 0.25 h;