Olefin Metathesis in Homogeneous Aqueous Media Catalyzed by Conventional Ruthenium Catalysts

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2007 Oct 24

PMID 17949009

Citations 8

Authors

Joseph B Binder

Jacqueline J Blank

Ronald T Raines

Affiliations

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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.

Citing Articles

Aqueous olefin metathesis: recent developments and applications.

Sabatino V, Ward T Beilstein J Org Chem. 2019; 15:445-468.

PMID: 30873229 PMC: 6404410. DOI: 10.3762/bjoc.15.39.

Ammonium-tagged ruthenium-based catalysts for olefin metathesis in aqueous media under ultrasound and microwave irradiation.

Gulajski L, Tracz A, Urbaniak K, Czarnocki S, Bieniek M, Olszewski T Beilstein J Org Chem. 2019; 15:160-166.

PMID: 30745991 PMC: 6350890. DOI: 10.3762/bjoc.15.16.

Solubilization of Hydrophobic Catalysts Using Nanoparticle Hosts.

Jeong Y, Tonga G, Duncan B, Yan B, Das R, Sahub C Small. 2017; 14(7).

PMID: 29271047 PMC: 5848072. DOI: 10.1002/smll.201702198.

Olefin Metathesis Reaction in Water and in Air Improved by Supramolecular Additives.

Tomasek J, Sessler M, Groger H, Schatz J Molecules. 2015; 20(10):19130-41.

PMID: 26506329 PMC: 6332346. DOI: 10.3390/molecules201019130.

Olefin metathesis in nano-sized systems.

Astruc D, Diallo A, Gatard S, Liang L, Ornelas C, Martinez V Beilstein J Org Chem. 2011; 7:94-103.

PMID: 21286399 PMC: 3028528. DOI: 10.3762/bjoc.7.13.

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