sodium tetrahydroborate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; N,N,N',N,-tetramethylethylenediamine in tetrahydrofuran T=20°C; 6 h; Inert atmosphere; regioselective reaction;

1: N,N,N',N,-tetramethylethylenediamine; sodium tetrahydroborate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / tetrahydrofuran / 6 h / 20 °C / |Inert atmosphere 2: N-bromosuccinmide / tetrahydrofuran / 4 h / -78 °C / |Inert atmosphere 3: palladium diacetate; triphenylphosphine; N,N,N',N,-tetramethylethylenediamine; sodium tetrahydroborate / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere View Scheme

copper(I) bromide dimethylsulfide complex in acetonitrile T=70°C; 16 h; Schlenk techniqueInert atmosphere;

1: palladium diacetate; triphenylphosphine; N,N,N',N,-tetramethylethylenediamine; sodium tetrahydroborate / tetrahydrofuran / 3 h / 20 °C / |Inert atmosphere 2: N,N,N',N,-tetramethylethylenediamine; sodium tetrahydroborate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / tetrahydrofuran / 6 h / 20 °C / |Inert atmosphere View Scheme

1: N-bromosuccinmide / tetrahydrofuran / 5 h / -78 °C / |Inert atmosphere; |Reflux 2: N,N,N',N,-tetramethylethylenediamine; sodium tetrahydroborate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / tetrahydrofuran / 6 h / 20 °C / |Inert atmosphere View Scheme

1.1: sodium hydride / tetrahydrofuran / |Inert atmosphere 1.2: 0.5 h / 0 - 20 °C / |Inert atmosphere 2.1: N-bromosuccinmide / tetrahydrofuran / 5 h / -78 °C / |Inert atmosphere; |Reflux 3.1: N,N,N',N,-tetramethylethylenediamine; sodium tetrahydroborate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / tetrahydrofuran / 6 h / 20 °C / |Inert atmosphere View Scheme

trifluoroacetic acid in dichloromethane Ambient temperature;

trifluoroacetic acid in dichloromethane 3 h; Ambient temperature; Further byproducts given;