sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethanol; water; toluene T=90°C; 4 h;

1: With 1-(2,6-diisopropylphenyl)-3-(2-(phenylthio)phenyl)-4,5-dihydro-imidazolium chloride; bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate in 1,4-dioxane T=100°C; 1 h; Inert atmosphere; 2: With 1-iodo-2-methylbenzene in 1,4-dioxane T=100°C; 15 h; Inert atmosphere;

1.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1.5 h / -78 - 20 °C 2.1: dimethyl sulfoxide; oxalyl dichloride; triethylamine / dichloromethane / 3 h / -78 - 20 °C 3.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 20 h / |Reflux 4.1: bis(η3-allyl-μ-chloropalladium(II)); 1-(2,6-diisopropylphenyl)-3-(2-(phenylthio)phenyl)-4,5-dihydro-imidazolium chloride; caesium carbonate / 1,4-dioxane / 1 h / 100 °C / |Inert atmosphere 4.2: 15 h / 100 °C / |Inert atmosphere View Scheme