Intermolecular metathesis of a Z-olefin with A3009 (cat.), 0.5 mol%, D2O, 1.1 h

Metathesis Catalyst Usable in Water Media (AquaMet)

AquaMet (A3009) is a Hoveyda-type ruthenium metathesis catalyst that is stable to air and moisture. Thanks to an internal quaternary ammonium group, it can be applied to metathesis reactions in water media, with D2O as the solvent in the examples shown in the brochure. Two example reactions are presented: intermolecular metathesis of a Z-olefin using 0.5 mol% catalyst in D2O for 1.1 h, and ring closing metathesis of a quaternary ammonium substrate using 2.5 mol% catalyst in D2O for 2.5 h.¹) In a TCI practical example, AquaMet catalyzes the formation of a cyclopentene ring from diethyl diallylmalonate in dichloromethane at room temperature for 6 h, giving diethyl cyclopent-3-ene-1,1-dicarboxylate in 98% yield after purification by silica-gel column chromatography.

Intermolecular metathesis of a Z-olefin with A3009 (cat.), 0.5 mol%, D2O, 1.1 h
Source: TCI brochure RR082
Ring closing metathesis with A3009 (cat.), 2.5 mol%, D2O, 2.5 h
Source: TCI brochure RR082

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References

  1. K. Skowerski, G. Szczepaniak, C. Wierzbicka, Ł. Gułajski, M. Bieniek, K. Grela, Catal. Sci. Technol. 2012, 2424. doi:https://doi.org/10.1039/C2CY20320K

Download TCI brochure Metathesis Catalyst Usable in Water Media AquaMet (PDF)

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