Organocuprates Containing Dimethyl Sulfoxide Anion as a Nontransferable Ligand

Article abstract of DOI:10.1021/jo00386a001

Mixed homocuprates <(MeSOCH2CuR)Li> and <(MeSOCH2CuR)Li(LiCN)> in which the anion of dimethyl sulfoxide acts as a nontransferable ligand are readily prepared from MeSOCH2Li, alkyl- or aryllithium reagents, and Cu(I) salts.These novel cuprates are useful in the conversions of acid chlorides to ketones, conjugate additions to α,β-unsaturated ketones, S_N2' reactions with allylic or propargylic acetates and epoxides, and coupling reactions with primary iodides and tosylates.All of these reactions proceed with selective transfer of the ligand R.From the points of view of cost, availability, and lack of interference with product isolation, the Me2SO anion is an ideal nontransferable ligand.