Synthesis of α-Fluorinated Areneacetates through Photoredox/Copper Dual Catalysis

Org Lett. 2022 May 6;24(17):3194-3198. doi: 10.1021/acs.orglett.2c00969. Epub 2022 Apr 25.

Abstract

The development of mild and practical conditions for the fluoroalkylation of arenes is an ongoing challenge in chemical organic synthesis. Herein, we report a metallaphotoredox method for the preparation of fluoroalkyl arenes based on the synergistic combination of Ir/Cu dual catalysis from boronic acids. The mild conditions allow broad functional group tolerance, including substrates containing aldehydes, free phenols, and N-Boc-protected amines. Mechanistic investigations support a process proceeding via photoredox/copper dual catalysis.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes
  • Amines
  • Boronic Acids*
  • Catalysis
  • Copper*

Substances

  • Aldehydes
  • Amines
  • Boronic Acids
  • Copper