potassium tert-butylate in tetrahydrofuran T=50°C; 8 h; Inert atmosphere;

titanium tetrachloride; zinc in tetrahydrofuran McMurry cyclisation; Heating;

lithium aluminium tetrahydride; diethyl ether

1: NaBH4 / methanol; CH2Cl2 / 2 h / 20 °C 2: Pd-C / triethylene glycol dimethyl ether / 24 h / Heating View Scheme

1: hydrogenchloride / methanol; water / 1 h / 20 °C 2: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 3: tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether / toluene / 15 h / 110 °C / Inert atmosphere 4: potassium tert-butylate / tetrahydrofuran / 8 h / 50 °C / Inert atmosphere View Scheme

1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether / toluene / 15 h / 110 °C / Inert atmosphere 3: potassium tert-butylate / tetrahydrofuran / 8 h / 50 °C / Inert atmosphere View Scheme

1: tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether / toluene / 15 h / 110 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran / 8 h / 50 °C / Inert atmosphere View Scheme

1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / ethylene glycol dimethyl ether; water / 5 h / 80 °C / Inert atmosphere 2: hydrogenchloride / methanol; water / 1 h / 20 °C 3: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 4: tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether / toluene / 15 h / 110 °C / Inert atmosphere 5: potassium tert-butylate / tetrahydrofuran / 8 h / 50 °C / Inert atmosphere View Scheme

1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / ethylene glycol dimethyl ether; water / 5 h / 80 °C / Inert atmosphere 2: hydrogenchloride / methanol; water / 1 h / 20 °C 3: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 4: tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether / toluene / 15 h / 110 °C / Inert atmosphere 5: potassium tert-butylate / tetrahydrofuran / 8 h / 50 °C / Inert atmosphere View Scheme

hydrogen sulfide; pre sulfided Harshaw Cr-0101 T catalyst (chromia alumina catalyst) in toluene T=500°C;