Nickel-Mediated Elimination of Hydrogen Halide from Primary and Secondonary Alkyl Bromides and Iodides. Synthetic Aspects

Article abstract of DOI:10.1021/jo00274a010

Treatment of alkyl bromides or iodides with a low-valent nickel complex generated in situ and 1,8-diazabicyclo<5.4.0>undec-7-ene in THF under argon leads on oxidative workup to alkenes.Primary halides give predominantly or exclusively the terminal alkene whereas acyclic secondary halides give a mixture.The thermodynamically most stable alkene is isolated from the cyclic congeners, 3α-, and 3β-bromocholestane, and from cholesteryl bromide.