1: 1.) sec-butyllithium; 2.) Fe(acac)3 / 1.) THF, cyclohexane, -62 deg C, 3h; 2.) cyclohexane, THF, RT, 1h 2: 1.) s-BuLi; 2.) Fe(acac)3 / 1.) THF, cyclohexane, -62 deg C, 3h; 2.) cyclohexane, THF, RT, 1h View Scheme

iron (III) acetylacetonate; sec.-butyllithium 1.) THF, cyclohexane, -62 deg C, 3h; 2.) cyclohexane, THF, RT, 1h; Yield given. Multistep reaction. Yields of byproduct given;

sec.-butyllithium; cupric trifluoroacetate 1.) cyclohexane, -62 deg C, 3h; 2.) THF, cyclohexane, RT, 1h; Yield given. Multistep reaction. Yields of byproduct given;

1: 1.) s-BuLi / 1.) THF, cyclohexane,, -62 deg C, 4 h; 2.) THF, cyclohexane, 15 min, -62 deg C to - 44 deg C 2: 87 percent / BH3 / tetrahydrofuran / ambient temperature, 3 h, then reflux, 3 h 3: 60 percent / PBr3 / benzene / 14 h / Ambient temperature View Scheme