New Desulfurizations by Nickel-Containing Complex Reducing Agents

Article abstract of DOI:10.1021/jo00312a029

Desulfurizations of saturated aliphatic or aromatic sulfoxides or sulfones are efficiently performed with nickel complex reducing agents (NiCRA's).The complete desulfurization of dithioketals can be effected in high yields with these reagents, while their half-desulfurization is efficiently achieved with 2,2'-bipyridine-modified nickel complex reducing agents (NiCRA-bpy).The desulfurization of vinyl thioethers, sulfoxides, and sulfones have been shown to be chemoselective, leaving the C-C double bond intact.The desulfurization of (E)-PhSO2(CH3)C=CHPh to cis-CH3CH=CHPh with NiCRA in the presence of quinoline is 95percent enantioselective.