copper(l) iodide 1.) THF, -30 deg C, 15 min, 2.) THF, -30 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

Yield given;

caesium carbonate in N,N-dimethyl-formamide T=110°C; 4 h;

1: 1.) CuI / 1.) THF, -30 deg C, 15 min, 2.) THF, -30 deg C, 1 h 2: 1.) potassium tert-butoxide / 1.) THF, 45 deg C, 45 min; other reagents: NaH, NaOH/tetrabutylammonium bromide, NaOH/tetrabutylammonium fluoride, 2.) THF, 21 deg C, 1 h 3: 1.) ozone, Sudan red, 2.) NaBH4, NaOH / 1.) CH2Cl2, ethanol, 2.) CH2Cl2, ethanol, 25 deg C, 12-16 h 4: 88 percent / triethylamine / CH2Cl2 / 0 - 5 °C / 1-2 h View Scheme