The reaction of Grignard reagents with Bunte salts: a thiol-free synthesis of sulfides

Org Lett. 2014 Feb 21;16(4):1196-9. doi: 10.1021/ol500067f. Epub 2014 Feb 10.

Abstract

S-Alkyl, S-aryl, and S-vinyl thiosulfate sodium salts (Bunte salts) react with Grignard reagents to give sulfides in good yields. The S-alkyl Bunte salts are prepared from odorless sodium thiosulfate by an SN2 reaction with alkyl halides. A Cu-catalyzed coupling of sodium thiosulfate with aryl and vinyl halides was developed to access S-aryl and S-vinyl Bunte salts. The reaction is amenable to a broad structural array of Bunte salts and Grignard reagents. Importantly, this route to sulfides avoids the use of malodorous thiol starting materials or byproducts.

MeSH terms

  • Catalysis
  • Combinatorial Chemistry Techniques
  • Copper / chemistry
  • Indicators and Reagents
  • Molecular Structure
  • Sulfides / chemical synthesis*
  • Sulfides / chemistry

Substances

  • Indicators and Reagents
  • Sulfides
  • Copper