Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity

J Am Chem Soc. 2020 Jan 29;142(4):1698-1703. doi: 10.1021/jacs.9b11472. Epub 2020 Jan 14.

Abstract

The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Carbon / chemistry*
  • Catalysis
  • Cyclopropanes / chemistry
  • Electrochemical Techniques / methods*
  • Ethers / chemistry*
  • Hydrogen / chemistry*
  • Photochemical Processes*
  • Proton Magnetic Resonance Spectroscopy

Substances

  • Cyclopropanes
  • Ethers
  • Carbon
  • cyclopropene
  • Hydrogen