1: 2-dimethylamino-2'-dicyclohexylphosphino-binaphthyl; potassium phosphate; phenol / Pd2(dba)3 / toluene / 15 h / 50 °C 2: 164 mg / titanium trichloride; ammonium acetate / ethanol; H2O / 0.25 h / 20 °C View Scheme

in dimethyl sulfoxide T=80°C; 6.16667 h;

1: With iron; acetic acid in ethanol T=20°C; 2.08333 h; Heating / reflux; 2: With sodium hydroxide in diethyl ether; water

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

in tetrahydrofuran T=-40°C; 1.5 h;

vinyl-magnesium bromide in tetrahydrofuran; ethylene glycol dimethyl ether T=-78°C; 4 h; Inert atmosphere;

T=120°C; 2 h;

1: thien-3-yl bromide With copper(l) iodide T=160°C; 1 h; 2: 2-nitro-4-fluoro-bromobenzene T=200°C; 0.833333 h; 3: With copper T=200 - 210°C; 15 h;

1: H2 / Raney Ni 2: 95 percent / 16 h / Heating 3: 79 percent / diphenyl ether / 1 h / Heating 4: 92 percent / AcONa; H2 / Pd/C / acetic acid / 10 h / 20 °C / 1810.02 Torr 5: 58 percent / POCl3 / 0.83 h / 90 °C View Scheme

copper