bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine in tetrahydrofuran T=60°C; 2 h;

1.1: diisopropylamine; n-butyllithium; N,N'-dimethyl-N,N'-propyleneurea / tetrahydrofuran; water / 1.67 h / -78 °C / |Inert atmosphere 1.2: 1.5 h / -78 °C / |Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 2 h / 60 °C View Scheme

1: triethylamine; copper(l) chloride / N,N-dimethyl acetamide / 3 h / 20 - 130 °C 2: tetrahydrofuran / -50 - -40 °C / |Inert atmosphere 3: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 2 h / -30 - -25 °C / |Inert atmosphere View Scheme

N2; triethanolamine; dimethylammonium 2,4-dichlorophenoxyacetate; copper(l) chloride in ethyl acetate

triethylamine; copper(l) chloride in N,N-dimethyl acetamide T=20 - 130°C; 3 h;