Sol–Gel Immobilized N-Heterocyclic Carbene Gold Complex as a Recyclable Catalyst for the Rearrangement of Allylic Esters and the Cycloisomerization of γ-Alkynoic Acids

Meritxell Ferré, Xavier Cattoën, Michel Wong Chi Man, Roser Pleixats

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11 Citations (Scopus)

Abstract

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim The synthesis of a bis-silylated (NHC)AuCl (NHC=N-heterocyclic carbene) complex and the formation of a hybrid silica material by the sol–gel process by cogelification with tetraethylorthosilicate under fluoride catalysis are described. This material was characterized by using 29Si solid-state NMR spectroscopy, N2 sorption measurements, electron microscopy, and elemental analysis. It was tested as a reusable catalyst in the rearrangement of allylic esters in conjunction with a silver salt under microwave conditions and it displayed a much better performance than a homogeneous analogue. This catalyst is active and recyclable in the cycloisomerization of γ-alkynoic acids to five-membered enol-lactones at room temperature in two reaction media, a toluene/water biphasic system and a deep eutectic solvent.
Original languageEnglish
Pages (from-to)2824-2831
JournalChemCatChem
Volume8
Issue number17
DOIs
Publication statusPublished - 7 Sep 2016

Keywords

  • carbene ligands
  • gold
  • immobilization
  • sol–gel processes
  • supported catalysts

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