2-(dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl Au bis(trifluoromethylsulfonyl)imide; water in 1,2-dichloro-ethane T=20°C; 14 h;

1: silver(l) oxide / dimethyl sulfoxide / 12 h / 130 °C / |Sealed tube; |Inert atmosphere 2: potassium carbonate; palladium diacetate / 1-methyl-pyrrolidin-2-one / 8 h / 140 °C / |Sealed tube; |Inert atmosphere View Scheme

1.1: potassium phosphate; CuSO4‵5H2O; 1,10-phenanthroline / toluene / 48 h / Inert atmosphere; Reflux 2.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere View Scheme

1: 4-(2'-bromoethynyl)-1-fluorobenzene With n-butyllithium in tetrahydrofuran; hexane T=-78 - -30°C; deprotonation; 2: 1-bromo-2-(p-methylphenyl)acetylene With zinc dibromide; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; hexane T=0 - 25°C; Substitution;

1: 4-(2'-bromoethynyl)-1-fluorobenzene With n-butyllithium in tetrahydrofuran; hexane T=-78 - -30°C; deprotonation; 2: 1-bromo-2-(p-methylphenyl)acetylene With zinc dibromide; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; hexane T=0 - 25°C; Substitution;