1: With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'- binaphthyl in toluene T=100°C; 0.05 h; Inert atmosphere; 2: With sodium t-butanolate in toluene T=0 - 70°C;

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 2 h / 50 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride; water / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme

1: Cu 2: (reduction) View Scheme

1: phenol With caesium carbonate in acetonitrile T=20°C; 0.166667 h; 2: 2-bromo-4-fluoro-1-nitrobenzene in acetonitrile T=50°C; 65 h;

1.1: 57 percent / tetrahydrofuran / -40 °C 2.1: 48 percent / BuLi / tetrahydrofuran; hexane / -75 °C 3.1: 93 percent / BuLi / hexane; tetrahydrofuran / 25 °C 4.1: 2,2,6,6-tetramethylpiperidine; N,N,N',N'-pentamethyldiethylenetriamine; BuLi / tetrahydrofuran; hexane / 6 h / -75 °C 4.2: 62 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane / -75 - 25 °C 5.1: 94 percent / tetrabutylammonium fluoride hydrate / tetrahydrofuran / 25 °C View Scheme

1: tetrahydrofuran / 1 h / -50 °C 2: palladium diacetate; tris-(o-tolyl)phosphine; triethylamine / acetonitrile / |Inert atmosphere; |Reflux; |Large scale 3: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C / |Inert atmosphere View Scheme

Pd0(tris(tert-butyl)phosphine)2; bis(dibenzylideneacetone)-palladium(0) in toluene T=20°C; Stille coupling; 36 h;

tetrabutylammomium bromide; sodium hydroxide in dichloromethane T=20°C; 16 h;