potassium hydroxide in dimethyl sulfoxide T=25°C; 0.5 h;

1.1: Cp2ZrCl2 / hexane / 76 h / 45 °C 1.2: 92 percent / iodine / hexane / 2 h / 20 °C 2.1: 93 percent / imidazole / dimethylformamide / 5 h / 0 - 20 °C 3.1: 1,2-dibromoethane; magesium; iodine / zinc chloride / tetrahydrofuran / 2 h / 45 °C 3.2: 84 percent / (PPh3)4Pd / tetrahydrofuran / 24 h / 20 °C 4.1: 85 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C 5.1: 75 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 0.5 h / -65 - 20 °C 6.1: magnesium; iodine; 1,2-dibromoethane / HgCl2 / tetrahydrofuran / 1 h / 5 - 15 °C 6.2: 76 percent / tetrahydrofuran / 1 h / 20 °C 7.1: 82 percent / potassium hydroxide / dimethylsulfoxide / 0.5 h / 25 °C View Scheme

1.1: 93 percent / imidazole / dimethylformamide / 5 h / 0 - 20 °C 2.1: 1,2-dibromoethane; magesium; iodine / zinc chloride / tetrahydrofuran / 2 h / 45 °C 2.2: 84 percent / (PPh3)4Pd / tetrahydrofuran / 24 h / 20 °C 3.1: 85 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C 4.1: 75 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 0.5 h / -65 - 20 °C 5.1: magnesium; iodine; 1,2-dibromoethane / HgCl2 / tetrahydrofuran / 1 h / 5 - 15 °C 5.2: 76 percent / tetrahydrofuran / 1 h / 20 °C 6.1: 82 percent / potassium hydroxide / dimethylsulfoxide / 0.5 h / 25 °C View Scheme

1.1: 1,2-dibromoethane; magesium; iodine / zinc chloride / tetrahydrofuran / 2 h / 45 °C 1.2: 84 percent / (PPh3)4Pd / tetrahydrofuran / 24 h / 20 °C 2.1: 85 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C 3.1: 75 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 0.5 h / -65 - 20 °C 4.1: magnesium; iodine; 1,2-dibromoethane / HgCl2 / tetrahydrofuran / 1 h / 5 - 15 °C 4.2: 76 percent / tetrahydrofuran / 1 h / 20 °C 5.1: 82 percent / potassium hydroxide / dimethylsulfoxide / 0.5 h / 25 °C View Scheme

1.1: magnesium; iodine; 1,2-dibromoethane / HgCl2 / tetrahydrofuran / 1 h / 5 - 15 °C 1.2: 76 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 82 percent / potassium hydroxide / dimethylsulfoxide / 0.5 h / 25 °C View Scheme

1.1: 75 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 0.5 h / -65 - 20 °C 2.1: magnesium; iodine; 1,2-dibromoethane / HgCl2 / tetrahydrofuran / 1 h / 5 - 15 °C 2.2: 76 percent / tetrahydrofuran / 1 h / 20 °C 3.1: 82 percent / potassium hydroxide / dimethylsulfoxide / 0.5 h / 25 °C View Scheme

1.1: 85 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C 2.1: 75 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 0.5 h / -65 - 20 °C 3.1: magnesium; iodine; 1,2-dibromoethane / HgCl2 / tetrahydrofuran / 1 h / 5 - 15 °C 3.2: 76 percent / tetrahydrofuran / 1 h / 20 °C 4.1: 82 percent / potassium hydroxide / dimethylsulfoxide / 0.5 h / 25 °C View Scheme