Abstract

An ammonium-tagged ruthenium complex, 8, was deposited on several widely available commercial solid materials such as silica gel, alumina, cotton, filter paper, iron powder or palladium on carbon. The resulting catalysts were tested in toluene or ethyl acetate, and found to afford metathesis products in high yield and with extremely low ruthenium contamination. Depending on the support used, immobilised catalyst 8 shows also additional traits, such as the possibility of being magnetically separated or the use for metathesis and subsequent reduction of the obtained double bond in one pot.

Highlights

  • Over the past decade olefin metathesis has undergone a grand development

  • A very efficient covalent immobilisation through anionic ligands was reported by Buchmeiser et al, who synthesised a series of monolith-supported catalysts which gave metathesis products with extremely low residual ruthenium [19,20,21,22,23,24]

  • We have reported on the synthesis and catalytic activity of a series of olefin metathesis catalysts bearing a quaternary ammonium group attached to the NHC ligand (Figure 2) [43,44,45,46,47]

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Summary

Introduction

Over the past decade olefin metathesis has undergone a grand development. The design of stable and active ruthenium-based metathesis catalysts has been the cardinal factor to distribute olefin metathesis in the synthesis of many important compounds [1,2,3,4]. A very efficient covalent immobilisation through anionic ligands was reported by Buchmeiser et al, who synthesised a series of monolith-supported catalysts (such as 1) which gave metathesis products with extremely low residual ruthenium [19,20,21,22,23,24]. We have reported on the synthesis and catalytic activity of a series of olefin metathesis catalysts bearing a quaternary ammonium group attached to the NHC ligand (Figure 2) [43,44,45,46,47].

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