Direct Synthesis of α-Fluoro-α-Triazol-1-yl Ketones from Sulfoxonium Ylides: A One-Pot Approach

David Philip Day, Jorge Andrés Mora Vargas, Antonio Carlos Bender Burtoloso (Lead / Corresponding author)

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

The work reported herein showcases a new route to access α-fluoro-α-triazol-1-yl ketones from sulfoxonium ylides via α-azido-α-fluoro ketone intermediates. In a one-pot, two-step sequence, the ketosulfoxonium reactant initially undergoes insertion of F+ and N3-, followed by a subsequent CuAAC reaction with arylacetylenes to install a 1,4-triazolo moiety. The approach allows for modification to both the sulfoxonium ylide and arylacetylene reactants. Fifteen examples have been reported, with yields ranging between 22% and 75%.

Original languageEnglish
Pages (from-to)12427-12435
Number of pages9
JournalJournal of Organic Chemistry
Volume86
Issue number17
Early online date23 Aug 2021
DOIs
Publication statusPublished - 3 Sep 2021

Keywords

  • Azides
  • Hydrocarbons
  • Anions
  • Sodium
  • Ketones

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