potassium acetate; bis(dibenzylideneacetone)-palladium(0); tri-cyclo-hexyl-phosphine in 1,4-dioxane T=80°C; 72 h; Inert atmosphere;

tetrakis(triphenylphosphine) palladium(0) in toluene T=110°C; Stille Cross Coupling; 12 h; Inert atmosphere; chemoselective reaction;

1: tert.-butylnitrite; toluene-4-sulfonic acid / 1,2-dichloro-ethane / 6 h / 0 °C / |Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0) / toluene / 12 h / 110 °C / |Inert atmosphere View Scheme

1: tert.-butylnitrite / acetonitrile / 2 h / 80 °C 2: tert.-butylnitrite; toluene-4-sulfonic acid / 1,2-dichloro-ethane / 6 h / 0 °C / |Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / toluene / 12 h / 110 °C / |Inert atmosphere View Scheme

1: tert.-butylnitrite / acetonitrile / 2 h / 80 °C 2: tert.-butylnitrite; toluene-4-sulfonic acid / 1,2-dichloro-ethane / 6 h / 0 °C / |Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / toluene / 12 h / 110 °C / |Inert atmosphere View Scheme

1: 5 palladium on charcoal; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr 2: tert.-butylnitrite; toluene-4-sulfonic acid / 1,2-dichloro-ethane / 4 h / 0 °C / |Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / toluene / 12 h / 110 °C / |Inert atmosphere View Scheme

1: 2-(4-biphenylyl)-5-phenyl-oxazole; tert.-butylnitrite / acetonitrile / 4 h / 20 °C 2: 5 palladium on charcoal; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr 3: tert.-butylnitrite; toluene-4-sulfonic acid / 1,2-dichloro-ethane / 4 h / 0 °C / |Inert atmosphere 4: tetrakis(triphenylphosphine) palladium(0) / toluene / 12 h / 110 °C / |Inert atmosphere View Scheme