1: With hydrogenchloride; sodium nitrite in water; acetonitrile T=0 - 5°C; Sandmeyer Reaction; 0.5 h; 2: With potassium iodide in water; acetonitrile T=20°C; Sandmeyer Reaction;

1: 78 percent / pyridine / tetrahydrofuran / 16 h / 20 °C 2: 59 percent / triphenylphosphine / bis(dibenzylideneacetone)palladium / toluene / 23 h / Heating 3: 91 percent / KOH / ethanol / 16 h / Heating View Scheme

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide / 1,4-dioxane; water / 12 h / 80 °C / Inert atmosphere 3: trifluoromethanesulfonyl azide; copper(II) sulfate; triethylamine / methanol; dichloromethane; water / 20 °C / Inert atmosphere 4: dirhodium(II) tetraoctanoate / 1,2-dichloro-ethane / 16 h / 70 °C / Inert atmosphere; Molecular sieve View Scheme

1: 1.) dicyclohexylcarbodiimide / 1) CH2Cl2, 0 deg C, 15 min; 2) CH2Cl2, 12 h 2: 26 percent / 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecanenickel(II) perchlorate / dimethylformamide / Ambient temperature; electrolysis View Scheme

1.1: tetrahydrofuran / 16 h / 20 °C / |Inert atmosphere 2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / |Inert atmosphere 2.2: 16 h / 0 - 20 °C / |Inert atmosphere View Scheme

Inert atmosphere;

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate in 1,4-dioxane; water T=80°C; Suzuki cross-coupling; 2.5 h; Inert atmosphere;

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 2.5 h / 80 °C / Inert atmosphere 2.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: dichloromethane / 20 °C / Inert atmosphere 4.1: ruthenium(III) chloride polyhydrate / isopropanol acetate / 15 h / 80 °C / Inert atmosphere 5.1: sodium tetrahydroborate / methanol; water / 20 - 100 °C / Inert atmosphere View Scheme