Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers

Davide Bello, David O'Hagan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)
1 Downloads (Pure)

Abstract

A new method for the preparation of alpha-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynyl sulfides with 3HF center dot Et3N, a process that requires Lewis acid activation using BF3 center dot Et2O and TiF4. The method gives access to a range of α-fluorovinyl thioethers, some in high stereoselectivity with the Z-isomer predominating over the E-isomer. The α-fluorovinyl thioether motif has prospects as a steric and electronic mimetic of thioester enols and enolates, important intermediates in enzymatic C-C bond forming reactions. The method opens access to appropriate analogues for investigations in this direction.

Original languageEnglish
Pages (from-to)1902-1909
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Volume11
DOIs
Publication statusPublished - 14 Oct 2015

Keywords

  • Alkynyl sulfides
  • Alpha-fluorovinyl thioethers
  • Hydrofluorination
  • Lewis acids
  • Organofluorine
  • Efficient catalyst
  • Vinyl sulfides
  • Thiols
  • Substrate
  • Mimetics
  • Flouride

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