1.1: triphenylphosphine; 1H-imidazole; iodine / dichloromethane / 2 h / |Darkness; |Inert atmosphere 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.67 h / |Darkness; |Inert atmosphere 2.2: 45 °C / |Inert atmosphere 3.1: potassium carbonate / methanol / 35 h / |Darkness; |Inert atmosphere 4.1: Mn(dpm)3; tert.-butylhydroperoxide; phenyl silane / isopropyl alcohol; hexane / |Inert atmosphere View Scheme

1.1: caesium carbonate / N,N-dimethyl-formamide / 0.67 h / |Darkness; |Inert atmosphere 1.2: 45 °C / |Inert atmosphere 2.1: potassium carbonate / methanol / 35 h / |Darkness; |Inert atmosphere 3.1: Mn(dpm)3; tert.-butylhydroperoxide; phenyl silane / isopropyl alcohol; hexane / |Inert atmosphere View Scheme

1: potassium carbonate / methanol / 35 h / |Darkness; |Inert atmosphere 2: Mn(dpm)3; tert.-butylhydroperoxide; phenyl silane / isopropyl alcohol; hexane / |Inert atmosphere View Scheme

iodine

nitric acid

N-chloro-succinimide in water; acetonitrile T=20°C; 1 h;

indium; ammonium chloride in ethanol Reduction; 2 h; Heating;

1.1: n-BuLi / hexane; tetrahydrofuran / -40 - 20 °C 1.2: 75 percent / hexane; tetrahydrofuran / 2 h / 20 °C 2.1: n-BuLi; diisopropylamine / hexane; tetrahydrofuran / 1.17 h / -78 - -40 °C 2.2: trimethyl borate / hexane; tetrahydrofuran / -40 - 20 °C 2.3: 83 percent / sodium sulfate / diethyl ether / 0.5 h / 20 °C 3.1: tetrakis(triphenylphosphine)palladium(0) / 1,2-dimethoxy-ethane / 0.17 h / 20 °C 3.2: 79 percent / aq. NaHCO3 / 1,2-dimethoxy-ethane / 4 h / Heating 4.1: POCl3 / 1 h / 20 °C 4.2: 92 percent / 12 h / 70 °C 5.1: 92 percent / AlCl3; LiAlH4 / diethyl ether / 2 h / 20 °C 6.1: 92 percent / aq. H2O2; acetic acod / CH2Cl2 / 3 h / 30 °C View Scheme

water; 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) in acetonitrile 1 h; Reflux;

water; 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) in acetonitrile T=20°C; 0.333333 h;