1: 90 percent / ICl / CH2Cl2 / 0.5 h / Ambient temperature 2: 75 percent / RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / 1.25 h / Ambient temperature 3: 1.) ZnCl2, 2.) dichlorobis(triphenylphosphine)palladium(II), DIBALH / 1.) ether, THF, RT, 10 min, 2.) ether, THF, RT, 1.5 h View Scheme

1: 90 percent / ICl / CH2Cl2 / 0.5 h / Ambient temperature 2: 75 percent / RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / 1.25 h / Ambient temperature 3: 1.) ZnCl2, 2.) dichlorobis(triphenylphosphine)palladium(II), DIBALH / 1.) THF, RT, 10 min, 2.) THF, RT, 1.5 h 4: 69 percent / H2 / 10percent Pd/C / ethyl acetate / 1.5 h / Ambient temperature View Scheme