Synthesis of 3,4,5-trisubstituted isoxazoles through gold-catalyzed cascade cyclization-oxidative alkynylation and cyclization-fluorination of 2-alkynone O-methyloximes

Doo Hee Song, Jae Sang Ryu

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

Gold-catalyzed tandem cyclization-oxidative alkynylation and cyclization-fluorination reactions of 2-alkynone O-methyloximes are described. The reactions proceed smoothly at room temperature in the presence of 10 mol % of (PPh3)AuNTf2, 2.5 equivalents of selectfluor, and 2 equivalents of K3PO4. 2-Alkynone O-methyloximes undergo intramolecular oxyauration/cyclization and ensuing oxidative cross-coupling and fluorination process to afford the corresponding 3,4,5-trisubstituted isoxazoles in a cascade manner.

Original languageEnglish
Pages (from-to)2635-2644
Number of pages10
JournalBulletin of the Korean Chemical Society
Volume35
Issue number9
DOIs
StatePublished - 20 Sep 2014

Keywords

  • Alkyne
  • Cross-coupling
  • Gold
  • Isoxazole
  • O-methyloxime

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