potassium carbonate in methanol T=20°C; 0.166667 h; Inert atmosphere;

1.1: n-BuLi / tetrahydrofuran / 0.5 h / 0 °C 1.2: tetrahydrofuran / 4 h / 20 °C 2.1: Bu4NF / tetrahydrofuran / 8 h / 26 °C View Scheme

1: Et3N; CuI / PdCl2(PPh3)3 / tetrahydrofuran / Heating 2: K2CO3 / methanol / 2 h View Scheme

sodium amide in diethyl ether; ammonia

1: Br2 / diethyl ether 2: NaNH2 / diethyl ether; liquid ammonia View Scheme

1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 8.5 h / 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere 2.2: 0.5 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / methanol / 0.17 h / 20 °C / Inert atmosphere View Scheme

silver hexafluoroantimonate; PPh3 gold(I) chloro complex in methanol T=20°C; Inert atmosphere;