copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran T=20°C; 3 h;

1: 2-octynoic acid With silver(l) oxide in N,N-dimethyl-formamide T=20°C; 0.0833333 h; Inert atmosphere; 2: 4-iodobenzoic acid ethyl ester With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine; lithium iodide in N,N-dimethyl-formamide T=70°C; Sonogashira coupling; 2.5 h; Inert atmosphere;

hydrogenchloride Combinatorial reaction / High throughput screening (HTS);

1: H2 / 10percent Pd/C / ethanol / 12 h / 20 °C / atmospheric pressure 2: lithium aluminum hydride / diethyl ether / 2 h / 0 °C 3: 636 mg / manganese oxide / CH2Cl2 / 2 h / 20 °C View Scheme