Sulfone as traceless activating group: Divergent synthesis of α-fluoroamides with C–F quaternary stereocenters

Jieqing Wu, Liying Fu, Renyi Diao, Longjun Nie, Chi Zhang, Yufeng Li, Chao Feng

Research output: Contribution to journalArticlepeer-review

Abstract

A novel approach to α-fluoroamides bearing a C–F quaternary stereocenter is reported herein. With sulfone installed as the activating group, an alkyl group as well as a fluorine atom was introduced successively under mild conditions. Subsequently, heterolytic fission of the C–S bond occurred smoothly under photoredox conditions to afford a tertiary radical, which then engaged in varied intramolecular cyclizations depending on substrate structure and condition applied, rendering sulfone an overall traceless activating group.

Original languageEnglish
Pages (from-to)96-100
Number of pages5
JournalGreen Synthesis and Catalysis
Volume6
Issue number1
DOIs
StatePublished - Feb 2025

Keywords

  • C–F quaternary stereocenter
  • Photoredox
  • Sulfone
  • Traceless activating group
  • α-Fluoroamide

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