silver carbonate in tetrahydrofuran; hexane T=40°C; 25 h;

1: potassium carbonate; iodine / H2O / 13 h / 20 - 50 °C 2: 920 mg / silver(I) carbonate / hexane; tetrahydrofuran / 25 h / 40 °C View Scheme

1: 73 percent / KOH / 2-methyl-propan-2-ol / 10 h / Heating 2: potassium carbonate; iodine / H2O / 13 h / 20 - 50 °C 3: 920 mg / silver(I) carbonate / hexane; tetrahydrofuran / 25 h / 40 °C View Scheme

tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide T=80°C; 8 h;

1.1: 82 percent / tetrakis(triphenylphosphine)palladium(0) / dimethylformamide / 8 h / 80 °C 2.1: diisobutyl aluminum hydride / toluene / 12 h / 20 °C 2.2: 43 percent / sodium borohydride / methanol / 12 h / 20 °C 3.1: 66 percent / POCl3 / dimethylformamide / 0.67 h / 100 °C View Scheme