piperidine; copper(l) iodide; Pd2(PPh3)2Cl2 in N,N-dimethyl-formamide T=60°C; 10 h; Inert atmosphereGlovebox;

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 84 percent / iodine / tetrahydrofuran; hexane / -78 - 20 °C 2.1: 89 percent / NaOH / ethanol / Heating 3.1: 72 percent / piperidine; CuI / Pd(OAc)2(PPh3)2 / dimethylformamide / 5 h / 60 °C View Scheme

1: 89 percent / NaOH / ethanol / Heating 2: 72 percent / piperidine; CuI / Pd(OAc)2(PPh3)2 / dimethylformamide / 5 h / 60 °C View Scheme

1.1: NaH / tetrahydrofuran / 2 h / 20 °C 1.2: 91 percent / tetrahydrofuran / 8 h / 20 °C 2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 84 percent / iodine / tetrahydrofuran; hexane / -78 - 20 °C 3.1: 89 percent / NaOH / ethanol / Heating 4.1: 72 percent / piperidine; CuI / Pd(OAc)2(PPh3)2 / dimethylformamide / 5 h / 60 °C View Scheme

4-(N,N-dimethlyamino)pyridine; trifluoroacetyl triflate in dichloromethane T=20°C; 3 h; Title compound not separated from byproducts.;

1: palladium diacetate; anhydrous lithium acetate / 1,2-dichloro-ethane / 28 h / 80 °C / |Inert atmosphere; |Glovebox; |Schlenk technique 2: hydrogen fluoride / tetrahydrofuran; water / 1 h / 0 - 20 °C 3: N-iodo-succinimide; silver fluoride / tetrahydrofuran / 20 - 70 °C / |Inert atmosphere; |Glovebox; |Darkness 4: caesium carbonate / methanol / 3 h / 0 - 20 °C 5: Pd2(PPh3)2Cl2; copper(l) iodide; piperidine / N,N-dimethyl-formamide / 10 h / 60 °C / |Inert atmosphere; |Glovebox View Scheme

1: [bis(acetoxy)iodo]benzene; palladium diacetate; N-bromosuccinmide / 1,2-dichloro-ethane / 26 h / 50 °C / |Inert atmosphere; |Glovebox; |Schlenk technique 2: palladium diacetate; anhydrous lithium acetate / 1,2-dichloro-ethane / 28 h / 80 °C / |Inert atmosphere; |Glovebox; |Schlenk technique 3: hydrogen fluoride / tetrahydrofuran; water / 1 h / 0 - 20 °C 4: N-iodo-succinimide; silver fluoride / tetrahydrofuran / 20 - 70 °C / |Inert atmosphere; |Glovebox; |Darkness 5: caesium carbonate / methanol / 3 h / 0 - 20 °C 6: Pd2(PPh3)2Cl2; copper(l) iodide; piperidine / N,N-dimethyl-formamide / 10 h / 60 °C / |Inert atmosphere; |Glovebox View Scheme

1: potassium phosphate; dirhodium tetraacetate / 1,4-dioxane / 80 - 100 °C / |Inert atmosphere; |Glovebox; |Schlenk technique 2: [bis(acetoxy)iodo]benzene; palladium diacetate; N-bromosuccinmide / 1,2-dichloro-ethane / 26 h / 50 °C / |Inert atmosphere; |Glovebox; |Schlenk technique 3: palladium diacetate; anhydrous lithium acetate / 1,2-dichloro-ethane / 28 h / 80 °C / |Inert atmosphere; |Glovebox; |Schlenk technique 4: hydrogen fluoride / tetrahydrofuran; water / 1 h / 0 - 20 °C 5: N-iodo-succinimide; silver fluoride / tetrahydrofuran / 20 - 70 °C / |Inert atmosphere; |Glovebox; |Darkness 6: caesium carbonate / methanol / 3 h / 0 - 20 °C 7: Pd2(PPh3)2Cl2; copper(l) iodide; piperidine / N,N-dimethyl-formamide / 10 h / 60 °C / |Inert atmosphere; |Glovebox View Scheme