tetrabutyl ammonium fluoride in tetrahydrofuran T=25°C; 0.0833333 h;

1.1: 89 percent / BuLi / hexane; tetrahydrofuran / 0.25 h / 25 °C 2.1: sec-butyllithium; N,N,N',N'-pentamethyldiethylenetriamine / pentane; tetrahydrofuran / 6 h / -75 °C 2.2: 84 percent / 1,2-dibromo-1,1,2,2-tetrafluoroethane / pentane; tetrahydrofuran 3.1: 89 percent / tetrabutylammonium fluoride hydrate / tetrahydrofuran / 0.08 h / 25 °C View Scheme

1.1: sec-butyllithium; N,N,N',N'-pentamethyldiethylenetriamine / pentane; tetrahydrofuran / 6 h / -75 °C 1.2: 84 percent / 1,2-dibromo-1,1,2,2-tetrafluoroethane / pentane; tetrahydrofuran 2.1: 89 percent / tetrabutylammonium fluoride hydrate / tetrahydrofuran / 0.08 h / 25 °C View Scheme

1.1: 52 percent / tetrahydrofuran / 1.5 h / -40 °C 2.1: 56 percent / BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 3.1: 89 percent / BuLi / hexane; tetrahydrofuran / 0.25 h / 25 °C 4.1: sec-butyllithium; N,N,N',N'-pentamethyldiethylenetriamine / pentane; tetrahydrofuran / 6 h / -75 °C 4.2: 84 percent / 1,2-dibromo-1,1,2,2-tetrafluoroethane / pentane; tetrahydrofuran 5.1: 89 percent / tetrabutylammonium fluoride hydrate / tetrahydrofuran / 0.08 h / 25 °C View Scheme

1.1: 72 percent / nitric acid; sulfuric acid; water / 0.25 h / 0 °C 2.1: 52 percent / tetrahydrofuran / 1.5 h / -40 °C 3.1: 56 percent / BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 4.1: 89 percent / BuLi / hexane; tetrahydrofuran / 0.25 h / 25 °C 5.1: sec-butyllithium; N,N,N',N'-pentamethyldiethylenetriamine / pentane; tetrahydrofuran / 6 h / -75 °C 5.2: 84 percent / 1,2-dibromo-1,1,2,2-tetrafluoroethane / pentane; tetrahydrofuran 6.1: 89 percent / tetrabutylammonium fluoride hydrate / tetrahydrofuran / 0.08 h / 25 °C View Scheme

1.1: 56 percent / BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 2.1: 89 percent / BuLi / hexane; tetrahydrofuran / 0.25 h / 25 °C 3.1: sec-butyllithium; N,N,N',N'-pentamethyldiethylenetriamine / pentane; tetrahydrofuran / 6 h / -75 °C 3.2: 84 percent / 1,2-dibromo-1,1,2,2-tetrafluoroethane / pentane; tetrahydrofuran 4.1: 89 percent / tetrabutylammonium fluoride hydrate / tetrahydrofuran / 0.08 h / 25 °C View Scheme

copper(l) iodide in ethyl acetate T=140°C; 5 h;

potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct in N,N-dimethyl-formamide T=100°C; Inert atmosphere;