Nickel-Catalyzed Oxidative Coupling Reaction of Phenyl Benzyl Sulfoxides

A novel method to produce disulfoxides diastereoselectively from phenyl benzyl sulfoxides is reported. The Ni­(PnBu3)2Cl2]/NIXANTPHOS catalyst system successfully promotes an oxidative coupling reaction of aryl benzylic sulfoxides to disulfoxides. An intermediate aldehyde, produced from the elimination of α-hydroxy sulfoxides, is proposed to generate the key sulfenate anion, enabling the formation of the disulfoxide product. A range of disulfoxides was produced in moderate to high yields (30–83%) and diastereoselectivity (rac/meso ranging from 3:1 to >20:1).