lt;1,4-bis-(diphenylphosphine)butanegt;palladium(II)

iron tribromide in tetrahydrofuran; tert-butyl methyl ether T=20°C; 1.16667 h; Inert atmosphereSchlenk technique;

1: 3-chloro-6-chloropyridine With caesium carbonate; 1,3-bis(2,4,6-trimethylphenyl)imidazolinium chloride; palladium diacetate in 1,4-dioxane T=80°C; 0.666667 h; 2: carbon monoxide; 3,4,5-trimethoxyphenylboronic acid in 1,4-dioxane T=100°C; Suzuki cross-coupling; P=37503 Torr; 23 h;

hexamethyl-distannane; tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane 18 h; Heating;

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; water Suzuki cross-coupling; Heating;

1: acetophenone With potassium tert-butylate in tetrahydrofuran T=20°C; 0.75 h; 2: (Z)-N-(2-chloro-3-(dimethylamino)allylidene)-N-methylmethanaminium hexafluorophosphate(V) With 1,4-diaza-bicyclo[2.2.2]octane T=45°C; 3 h; 3: With ammonium acetate 6 h; Heating; Further stages.;

1.1: nBuLi / tetrahydrofuran / -78 °C 1.2: B(OiPr)3 / tetrahydrofuran / -78 - 20 °C 1.3: 36 percent / NaOH / tetrahydrofuran; H2O 2.1: 55 percent / Na2CO3 / Pd(PPh3)4 / H2O; 1,2-dimethoxy-ethane / Heating View Scheme

iron(III) sulfide; dipotassium peroxodisulfate; trifluoroacetic acid in dichloromethane; water T=20°C; 40 h; Overall yield = 64.2percent; regioselective reaction;

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

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