2-[(dimethylamino)methyl]-1-thiophenolato-copper(I); potassium carbonate in dimethyl sulfoxide T=160°C; 16 h; Inert atmosphere; chemoselective reaction;

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C 1.2: zinc chloride / tetrahydrofuran; hexane / -78 - 20 °C 1.3: 85 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 12 h / Heating 2.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C 2.2: zinc chloride / tetrahydrofuran; hexane / -78 - 20 °C 2.3: 62 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 12 h / Heating 3.1: pyridinium hydrochloride View Scheme

potassium hydroxide in methanol; dimethyl sulfoxide

copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine in toluene T=60°C; Sonogashira cross-coupling;