Access to Polysulfides through Photocatalyzed Dithiosulfonylation

Angew Chem Int Ed Engl. 2023 Jun 19;62(25):e202302199. doi: 10.1002/anie.202302199. Epub 2023 May 11.

Abstract

In this study, we outline a general method for photocatalyzed difunctionalization of alkenes, a diene, alkynes, 1,3-enynes, and [1.1.1]propellane using dithiosulfonate reagents (ArSO2 -SSR) with improved atom economy. Both "ArSO2 -" and "-SSR" on the dithiosulfonate are transferred under mild conditions with broad substrate scope, high stereoselectivity, and complete regioselectivity. Significantly, the resulting dithiosulfonylated styrene is a general and practical nucleophilic disulfuration reagent, reacting with a variety of electrophiles efficiently. Both reactions can be conducted on gram scale, rendering the approach highly valuable.

Keywords: Disulfuration; Olefins; Photocatalysis; Radicals; Synthetic Methods.

MeSH terms

  • Alkenes*
  • Alkynes
  • Catalysis
  • Indicators and Reagents
  • Polyenes*

Substances

  • polysulfide
  • Alkenes
  • Polyenes
  • Alkynes
  • Indicators and Reagents