1: 38.1 percent / TiCl4 / CH2Cl2 / 5 h / 0 °C 2: 81.1 percent / AlH2Cl / diethyl ether / 24 h / Heating 3: 80 percent / Nafion-H, toluene / 24 h / Heating View Scheme

hydrogen; sodium t-butanolate; 1,3-bis(2,6-di-(i-propyl)phenyl)-4,5-dihydroimidazolium tetrafluoroborate; [Ni0(1,5-cyclooctadiene)2] in m-xylene T=100°C; P=750.075 Torr; 16 h; Inert atmosphere;

1: 38.1 percent / TiCl4 / CH2Cl2 / 5 h / 0 °C 2: 81.1 percent / AlH2Cl / diethyl ether / 24 h / Heating 3: 25 percent / AlCl3, NeNO2, toluene / 12 h / Ambient temperature View Scheme