Nickelocene-Lithium Aluminum Hydride: A Versatile Desulfurization Reagent

Article abstract of DOI:10.1021/jo00254a009

A new homogeneous organonickel reagent prepared from nickelocene and LiAlH4 has been shown to be effective for the reduction of the carbon-sulfur bonds of thiols, thioethers, sulfoxides, and sulfones to the corresponding carbon-hydrogen bonds.Functional groups such as isolated double bonds, esters, and carbonyls as well as halides remain intact under the reaction conditions.Preliminary studies on the nature of the reagent and the mechanism for the reaction have been carried out by employing deuterium labeling experiments and spectroscopic methods.Metal hydridic species may play an important role in these reactions.The reagent can also be used to reduce the carbon-carbon double bond of conjugate enones and catalyze hydrogenation of carbon-carbon multiple bonds.A comparison of the reaction behavior of this newly developed reagent with that of Raney nickel is discussed.