Electrochemical Sulfoxidation of Thiols and Alkyl Halides

J Org Chem. 2022 May 20;87(10):6942-6950. doi: 10.1021/acs.joc.2c00412. Epub 2022 May 5.

Abstract

Sulfoxides are actively engaged as versatile synthetic building blocks, chiral ligands, bioactive molecules, and function materials. However, their oxidative syntheses from thioethers are inevitably impeded by overoxidation, excess oxidants, and the tedious preparation of thioethers. To address these shortcomings, we report herein a highly selective electrochemical sulfoxidation reaction featuring the use of simple starting materials, i.e., thiols and alkyl halides, in a single operation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ligands
  • Oxidation-Reduction
  • Sulfhydryl Compounds* / chemistry
  • Sulfides / chemistry
  • Sulfoxides* / chemistry

Substances

  • Ligands
  • Sulfhydryl Compounds
  • Sulfides
  • Sulfoxides