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. 2007 Nov 8;9(23):4885-8.
doi: 10.1021/ol7022505. Epub 2007 Oct 19.

Olefin Metathesis in Homogeneous Aqueous Media Catalyzed by Conventional Ruthenium Catalysts

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Free PMC article

Olefin Metathesis in Homogeneous Aqueous Media Catalyzed by Conventional Ruthenium Catalysts

Joseph B Binder et al. Org Lett. .
Free PMC article

Abstract

Olefin metathesis in aqueous solvents is sought for applications in green chemistry and with the hydrophilic substrates of chemical biology, such as proteins and polysaccharides. Most demonstrations of metathesis in water, however, utilize exotic complexes. We have examined the performance of conventional catalysts in homogeneous water/organic mixtures, finding that the second-generation Hoveyda-Grubbs catalyst has extraordinary efficiency in aqueous dimethoxyethane and aqueous acetone. High (71-95%) conversions are achieved for ring-closing and cross metathesis of a variety of substrates in these solvent systems.

Figures

Figure 1
Figure 1
Conventional ruthenium olefin metathesis catalysts.
Figure 2
Figure 2
Metathesis catalysts adapted for aqueous solvents.
Figure 3
Figure 3
RCM conversion of 0.05 M substrate 8 catalyzed by complexes 14: 1 mol % [Ru], 2:1 DME/water, 24 h, rt, under air.
Figure 4
Figure 4
Kinetics of RCM of 0.05 M substrate 8 catalyzed by complex 4 in acetone–water monitored by 1H NMR spectroscopy.

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