Thiazolium-based catalysts for the etherification of benzylic alcohols under solvent-free conditions

Lucia Anna Bivona, François Quertinmont, Hazi Ahmad Beejapur, Francesco Giacalone, Mireia Buaki-Sogo, Michelangelo Gruttadauria, Carmela Aprile

Research output: Contribution to journalArticlepeer-review


Thiazolium and imidazolium hybrid materials were prepared by radical reactions between a mercaptopropyl-modified SBA-15 mesoporous silica and bis-vinylthiazolium or bis-vinylimidazolium dibromide salts. These hybrid materials were characterized by several techniques and were employed in the etherification reaction of 1-phenylethanol. Solvent-free conditions at 160C under different gas phases (oxygen, air, nitrogen and argon) were used. The thiazolium-based material displayed excellent performances. Further studies were carried out using unsupported thiazolium salts, with or without a methyl group at the C-2 position of the thiazolium moiety. These studies allowed us to propose a reaction mechanism. The supported thiazolium-based material was successfully used in the etherification reaction of two other benzylic alcohols and also in seven consecutive cycles. This work represents the first use of thiazolium-based compounds as catalysts for the etherification reaction of alcohols.

Original languageEnglish
Pages (from-to)800-810
Number of pages11
JournalAdvanced Synthesis and Catalysis
Issue number4
Publication statusPublished - 9 Mar 2015


  • catalysis
  • heterogeneous catalysis
  • organocatalysis
  • supported catalysts
  • synthetic methods


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