palladium diacetate; caesium carbonate; triphenylphosphine in 1-methyl-pyrrolidin-2-one T=90°C; 1 h; Inert atmosphere;

aluminum oxide; alkali metal fluoride in N,N-dimethyl-formamide T=153°C; 4 h;

[bis(acetoxy)iodo]benzene in acetonitrile T=20°C; 2 h; Inert atmosphere;

triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide in N,N-dimethyl-formamide 1.) r.t., 1 h, 2.) 60 deg C, 16 h;

[2,2']bipyridinyl; palladium (II) trifluoroacetate; water; trifluoroacetic acid in tetrahydrofuran T=80°C; 36 h; Inert atmosphereSchlenk technique;

1: 2-chlorophenol With dichloro bis(acetonitrile) palladium(II); C31H36O2*BF4(1-)*H(1+); lithium tert-butylate in toluene T=20°C; Sonogashira Cross-Coupling; 0.5 h; Inert atmosphere; 2: 3-chlorophenylacetylene in toluene 0.75 h; Inert atmosphereReflux; 3: in methanol; toluene 3 h; Inert atmosphereReflux;

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine / tetrahydrofuran / 0.67 h / 0 °C / |Inert atmosphere 2: tetrabutylammomium bromide; dihydrogen peroxide; sodium hydroxide / dichloromethane; water / 0 °C 3: silver trifluoromethanesulfonate; {1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}AuCl / chloroform / 0.08 h / 20 °C 4: hydrogenchloride / chloroform; water / 0.17 h / 20 °C View Scheme

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine / tetrahydrofuran / 0.67 h / 0 °C / |Inert atmosphere 2: tetrabutylammomium bromide; dihydrogen peroxide; sodium hydroxide / dichloromethane; water / 0 °C 3: silver trifluoromethanesulfonate; {1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}AuCl / chloroform / 0.08 h / 20 °C 4: hydrogenchloride / chloroform; water / 0.17 h / 20 °C View Scheme

1: sodium hydride / N,N-dimethyl-formamide / 20 °C / |Inert atmosphere; |Cooling with ice 2: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 50 °C / |Inert atmosphere 3: hydrogenchloride / methanol; water / |Reflux; |Inert atmosphere 4: potassium carbonate / water / 2 h / 110 °C / |Microwave irradiation; |Inert atmosphere; |Green chemistry View Scheme

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 50 °C / |Inert atmosphere 2: hydrogenchloride / methanol; water / |Reflux; |Inert atmosphere 3: potassium carbonate / water / 2 h / 110 °C / |Microwave irradiation; |Inert atmosphere; |Green chemistry View Scheme