diethylamino-sulfur trifluoride in dichloromethane T=20°C; 19 h; Reflux;

silver nitrate; 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) in water; acetone T=55°C; 1 h; Inert atmosphereSchlenk technique;

potassium fluoride in 1-methyl-pyrrolidin-2-one T=200°C; 48 h; Inert atmosphere;

potassium fluoride; copper(l) iodide in N,N-dimethyl acetamide T=120°C; 24 h; Inert atmosphereGloveboxDarkness;

1: copper(l) iodide; potassium fluoride / dimethyl sulfoxide / 15 h / 60 °C / Inert atmosphere 2: water; potassium carbonate / methanol / 2 h / 25 °C / Inert atmosphere 3: potassium fluoride / 1-methyl-pyrrolidin-2-one / 48 h / 200 °C / Inert atmosphere View Scheme

1: lithium hexamethyldisilazane / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 2: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) / acetonitrile / 0.25 h / 20 °C / |Inert atmosphere 3: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate); silver nitrate / water; acetone / 1 h / 55 °C / |Inert atmosphere; |Schlenk technique View Scheme

potassium acetate; palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene] in 1,4-dioxane T=100°C; 18 h;

AlCl3, aluminium chloride in hexane T=20°C; Friedel Crafts alkylation; 10 h;