Pd black; potassium carbonate in water T=60°C; Sonogashira Cross-Coupling; 5 h; Green chemistry;

1: 3-pyrrol-1-yl-propionic acid 1-methyl-prop-2-ynyl ester in acetonitrile Electrochemical reaction; 2: para-iodoanisole With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide T=20°C; Sonogashira reaction; 12 h; 3: With sodium methylate in tetrahydrofuran; methanol T=20°C; 1 h;

1: ZTK-2-125 With n-butyllithium in tetrahydrofuran T=-78°C; 0.25 h; 2: acetaldehyde in tetrahydrofuran T=20°C; 0.333333 h;

1: 4-ethynyl-1-methoxy-benzene With n-butyllithium in tetrahydrofuran T=-78°C; 0.5 h; Inert atmosphere; 2: acetaldehyde in tetrahydrofuran T=-78 - 20°C; 0.5 h; Inert atmosphere;

sodium tetrahydroborate in ethanol T=0°C; 1 h;

1.1: nBuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 1.2: 82 percent / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C 2.1: NaBH4 / ethanol / 1 h / 0 °C View Scheme

1.1: 99 percent / PPh3 / CH2Cl2 / 0.17 h / 20 °C 2.1: n-BuLi / tetrahydrofuran / 0.25 h / -78 °C 2.2: 79 percent / tetrahydrofuran / 0.33 h / 20 °C View Scheme

Iron (III) nitrate nonahydrate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxygen; sodium chloride in toluene T=20°C; 4.2 h;