Photoinduced Copper-Catalyzed Monofluoroalkylation of Terminal Alkynes to Propargylic Fluorides

Org Lett. 2023 Jun 23;25(24):4514-4519. doi: 10.1021/acs.orglett.3c01531. Epub 2023 Jun 8.

Abstract

A photoinduced copper-catalyzed strategy for the monofluoroalkylation of alkynes with readily available monofluoroalkyl triflates was developed. It provides a new protocol to access valuable propargyl fluoride compounds via C-C bond formation by avoiding the use of highly toxic fluorination reagents. This reaction proceeded under mild conditions to afford propargyl monofluorides in moderate to high yields. Preliminary mechanistic studies reveal that a ligand-matched alkynyl copper complex might be the key photoactive substance.

MeSH terms

  • Alkynes / chemistry
  • Catalysis
  • Copper* / chemistry
  • Fluorides* / chemistry
  • Halogenation

Substances

  • Fluorides
  • Copper
  • Alkynes