1H-imidazole; iodine; triphenylphosphine in tetrahydrofuran T=20°C; 2 h;

1: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C 2: 46 percent / Ph3P; imidazole; iodine / tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: 57 percent / NaH / tetrahydrofuran / 20 °C 2.1: 96 percent / NaOCl; 2,2,6,6-tetramethylpiperidin-N-oxyl; aq. NaHCO3 / CH2Cl2 / 0 °C 3.1: N,N-diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 3.2: 31 percent / tetrahydrofuran; hexane / 16 h / 20 °C 4.1: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C 5.1: 46 percent / Ph3P; imidazole; iodine / tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: 96 percent / NaOCl; 2,2,6,6-tetramethylpiperidin-N-oxyl; aq. NaHCO3 / CH2Cl2 / 0 °C 2.1: N,N-diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 2.2: 31 percent / tetrahydrofuran; hexane / 16 h / 20 °C 3.1: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C 4.1: 46 percent / Ph3P; imidazole; iodine / tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: N,N-diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 1.2: 31 percent / tetrahydrofuran; hexane / 16 h / 20 °C 2.1: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C 3.1: 46 percent / Ph3P; imidazole; iodine / tetrahydrofuran / 2 h / 20 °C View Scheme

triethyl borane; tri-n-butyl-tin hydride in toluene T=20°C;