Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

Org Lett. 2021 Jan 1;23(1):190-194. doi: 10.1021/acs.orglett.0c03915. Epub 2020 Dec 23.

Abstract

This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4'-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%-97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.

Publication types

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

MeSH terms

  • Fluorides / chemical synthesis*
  • Fluorides / chemistry
  • Halogenation
  • Molecular Structure
  • Sulfur / chemistry*

Substances

  • Sulfur
  • Fluorides