Premium
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
Author(s) -
Ferré Meritxell,
Cattoën Xavier,
Wong Chi Man Michel,
Pleixats Roser
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201600632
Subject(s) - cycloisomerization , carbene , catalysis , chemistry , allylic rearrangement , enol , organic chemistry , homogeneous catalysis , solvent , polymer chemistry
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 29 Si solid‐state NMR spectroscopy, N 2 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.