ethanol; nickel in tetrahydrofuran T=20°C; 7 h;

triphenyl phosphite; di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium in nitromethane T=50°C; 21 h;

1.1: dioxane / 20 - 50 °C 1.2: 91 percent / CuBr / dioxane / 85 °C 2.1: 90 percent Turnov. / lithium; nickel chloride; ethanol / 4,4'-di(tert-butyl)biphenyl / tetrahydrofuran / 7 h / 20 °C View Scheme

1: P(OPh)3 / [Ir(COD)Cl]2 / 4 h / 50 °C View Scheme

1: 1.) EtMgBr / 1.) ether/CH2Cl2, 35 deg C; 2.) ether/CH2Cl2, 15 h, 20 deg C 2: 82 percent / H2 / Raney Ni / ethanol / Ambient temperature View Scheme