1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 0.17 h / 20 °C 1.2: 8 h / 50 °C 2.1: {1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}AuCl; silver trifluoromethanesulfonate / acetonitrile; water / 10 h / 80 °C / |Inert atmosphere 3.1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) / acetonitrile; water / 8 h / 28 °C / |Inert atmosphere View Scheme

water; bis-(trifluoromethylsulphonyl)amine in 1,4-dioxane T=100°C; 7 h;

1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 0.17 h / 20 °C 1.2: 8 h / 50 °C 2.1: {1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}AuCl; silver trifluoromethanesulfonate / acetonitrile; water / 10 h / 80 °C / |Inert atmosphere 3.1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) / acetonitrile; water / 12 h / 50 °C / |Inert atmosphere View Scheme

1: (i) EtMgHal, Et2O, (ii) /BRN= 102378/ 2: H2, quinoline / Lindlar catalyst / ethyl acetate 3: (i) collidine, (ii) /BRN= 956566/, acetone 4: KNH2, liq. NH3 / pentane 5: pentane / 150 °C View Scheme

1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 0.17 h / 20 °C 1.2: 8 h / 50 °C 2.1: {1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}AuCl; silver trifluoromethanesulfonate / acetonitrile; water / 10 h / 80 °C / |Inert atmosphere 3.1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) / acetonitrile; water / 10 h / 28 °C / |Inert atmosphere View Scheme

1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 0.17 h / 20 °C 1.2: 8 h / 50 °C 2.1: {1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}AuCl; silver trifluoromethanesulfonate / acetonitrile; water / 10 h / 80 °C / |Inert atmosphere 3.1: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) / acetonitrile; water / 8 h / 28 °C / |Inert atmosphere View Scheme