triethylsilane; 1,10-phenanthroline; NiII chloride hexahydrate; zinc in N,N-dimethyl-formamide T=100°C; 8 h; Sealed tube; regioselective reaction;

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethanol; water; toluene 12 h; Reflux;

palladium diacetate; potassium carbonate; triphenylphosphine in toluene 12 h; RefluxInert atmosphere;

potassium acetate; 18-crown-6 ether 1.5 h; Ambient temperature; Yield given. Yields of byproduct given;

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethanol; water; toluene 20 h; Inert atmosphereSchlenk techniqueReflux;

1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / |Inert atmosphere; |Schlenk technique 1.2: -78 - 20 °C / |Inert atmosphere; |Schlenk technique 2.1: hydrogenchloride / water / 20 °C / |Inert atmosphere; |Schlenk technique 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; toluene; ethanol / 20 h / |Inert atmosphere; |Schlenk technique; |Reflux View Scheme

Stille coupling;

T=20°C; 24 h; Sealed tube; Overall yield = 64 percent;

hydrogenchloride; sodium nitrite Yield given. Multistep reaction. Yields of byproduct given;