tetrakis(triphenylphosphine) palladium(0); potassium carbonate in ethanol; water; toluene T=80°C; Suzuki Coupling; Inert atmosphereSonicationReflux;

[RhCl(η2:η2-cycloocta-1,5-diene)]2; potassium carbonate; tris-(dimethylamino)-phosphine; caesium carbonate in toluene T=100°C; 20 h;

silver(I) acetate; sodium t-butanolate in 1,4-dioxane T=135 - 155°C;

1: triethylamine / toluene / 15 h / |Reflux; |Inert atmosphere 2: dimethylsulfide borane complex / dichloromethane / 2 h / 0 °C / |Inert atmosphere 3: toluene / 1 h / 20 °C / |Schlenk technique; |Inert atmosphere 4: toluene; o-di-fluorobenzene / 16 h / 140 °C / |Inert atmosphere 5: potassium hydrogen difluoride / toluene; methanol; water / 2 h / 0 - 20 °C / |Schlenk technique; |Sealed tube; |Cooling; |Inert atmosphere 6: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water; ethanol / 80 °C / |Inert atmosphere; |Sonication; |Reflux View Scheme

1: dimethylsulfide borane complex / dichloromethane / 2 h / 0 °C / |Inert atmosphere 2: toluene / 1 h / 20 °C / |Schlenk technique; |Inert atmosphere 3: toluene; o-di-fluorobenzene / 16 h / 140 °C / |Inert atmosphere 4: potassium hydrogen difluoride / toluene; methanol; water / 2 h / 0 - 20 °C / |Schlenk technique; |Sealed tube; |Cooling; |Inert atmosphere 5: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water; ethanol / 80 °C / |Inert atmosphere; |Sonication; |Reflux View Scheme

methylamine T=180°C; sealed tube;

1: 90 percent / 24 h / Ambient temperature 2: 8 percent / aq. methylamine / 180 °C / sealed tube View Scheme