BH3-THF in methanol; ethyl acetate; acetonitrile

sodium cyanoborohydride in hexane; ethyl acetate; acetonitrile

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;

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 3.1: triethylamine; copper(l) chloride / N,N-dimethyl acetamide / 3 h / 20 - 130 °C View Scheme

1.1: bromine / ethyl acetate / 1 h / 20 °C 1.2: 2.5 h / 0 - 20 °C 2.1: N,N-dimethyl-formamide; dimethyl sulfate / N,N-dimethyl-formamide / 0.25 h / 20 °C / |Inert atmosphere 2.2: |Inert atmosphere 3.1: borane-THF / acetonitrile; methanol / 1 h / 50 °C View Scheme

1.1: bromine / ethyl acetate / 1 h / 20 °C 1.2: 2.5 h / 0 - 20 °C 2.1: N,N-dimethyl-formamide; dimethyl sulfate / N,N-dimethyl-formamide / 0.25 h / 20 °C / |Inert atmosphere 2.2: |Inert atmosphere 3.1: borane-THF / acetonitrile; methanol / 1 h / 50 °C View Scheme

in tetrahydrofuran; diethyl ether

1: tetrahydrofuran / -50 - -40 °C / |Inert atmosphere 2: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 2 h / -30 - -25 °C / |Inert atmosphere View Scheme