Catalysis Letters

, Volume 144, Issue 3, pp 373–379 | Cite as

Biotinylated Metathesis Catalysts: Synthesis and Performance in Ring Closing Metathesis

  • Anna Kajetanowicz
  • Anamitra Chatterjee
  • Raphael Reuter
  • Thomas R. Ward
Article

Abstract

Nine biotinylated Grubbs–Hoveyda and Grubbs-type metathesis catalysts were synthesized and evaluated in ring closing metathesis reactions of N-tosyl diallylamine and 5-hydroxy-2-vinylphenyl acrylate. Their catalytic activity in organic- and aqueous solvents was compared with the second generation Grubbs–Hoveyda catalyst. The position of the biotin-moiety on the N-heterocyclic carbene was found to critically influence the catalytic activity of the corresponding ruthenium-based catalysts.

Graphical Abstract

Keywords

Fluorescence assay Aqueous catalysis Ring closing metathesis Coumarin Hoveyda–Grubbs 

Supplementary material

10562_2013_1179_MOESM1_ESM.docx (998 kb)
Supplementary material 1 (DOCX 1000 kb)

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Anna Kajetanowicz
    • 1
  • Anamitra Chatterjee
    • 1
  • Raphael Reuter
    • 1
  • Thomas R. Ward
    • 1
  1. 1.Department of ChemistryUniversity of BaselBaselSwitzerland

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