[(NHC)Au-I]-Catalyzed rearrangement of allylic acetates

Nicolas Marion, Ronan Gealageas, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

110 Citations (Scopus)

Abstract

{NHC)AuCl] complexes (NHC = N-heterocyclic carbene), in conjunction with a silver salt, were found to efficiently catalyze the rearrangement of allylic acetates under both conventional and microwave-assisted heating. The optimization of several reaction parameters (solvent, silver salt, and ligand) as well as a study of the reaction scope are reported. The steric hindrance of the ligand bound to gold was found crucial for the outcome of the reaction as only extremely bulky ligands permitted the isomerization.

Original languageEnglish
Pages (from-to)2653-2656
Number of pages4
JournalOrganic Letters
Volume9
Issue number14
DOIs
Publication statusPublished - 5 Jul 2007

Keywords

  • GOLD(I)-CATALYZED INTRAMOLECULAR HYDROAMINATION
  • N-HETEROCYCLIC CARBENES
  • PROPARGYLIC ESTERS
  • GOLD CATALYSIS
  • EFFICIENT FORMATION
  • ORGANIC-SYNTHESIS
  • ISOMERIZATION
  • ALKENES
  • ACCESS
  • CYCLOISOMERIZATION

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