The effect of silica-coating on catalyst recyclability in ionic magnetic nanoparticle-supported Grubbs-Hoveyda catalysts for ring-closing metathesis

Shu Wei Chen; Zhi Cheng Zhang; Ning Ning Zhai; Chong Min Zhong; Sang Gi Lee

doi:10.1016/j.tet.2014.12.024

The effect of silica-coating on catalyst recyclability in ionic magnetic nanoparticle-supported Grubbs-Hoveyda catalysts for ring-closing metathesis

Shu Wei Chen, Zhi Cheng Zhang, Ning Ning Zhai, Chong Min Zhong, Sang Gi Lee

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

The Grubbs-Hoveyda type ruthenium-carbene complexes have been covalently immobilized on both silica coated and uncoated magnetic nanoparticles utilizing an imidazolium salt linker. These MNP-supported catalysts showed comparable catalytic activity to the homogeneous imidazolium salt-tagged ruthenium catalyst in the ring-closing metathesis (RCM) of dienes, and could effectively catalyze RCM reactions in the presence of only 0.85 mol % Ru. The MNP-supported ruthenium catalysts could be easily recovered using an external magnet. The recyclability of the silica-coated MNP-supported catalysts was superior to silica uncoated MNP-supported catalysts allowing reuse 14 times, due to the increased compatibility of the silica-coated MNPs with the reaction medium.

Original language	English
Pages (from-to)	648-653
Number of pages	6
Journal	Tetrahedron
Volume	71
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2014.12.024
State	Published - 28 Jan 2015

Bibliographical note

Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.

Keywords

Immobilization
Ionic materials
Magnetic nanoparticles
Metathesis
Ruthenium

Access to Document

10.1016/j.tet.2014.12.024

Cite this

@article{dc096776ab5b4875874fab2e7db50972,

title = "The effect of silica-coating on catalyst recyclability in ionic magnetic nanoparticle-supported Grubbs-Hoveyda catalysts for ring-closing metathesis",

abstract = "The Grubbs-Hoveyda type ruthenium-carbene complexes have been covalently immobilized on both silica coated and uncoated magnetic nanoparticles utilizing an imidazolium salt linker. These MNP-supported catalysts showed comparable catalytic activity to the homogeneous imidazolium salt-tagged ruthenium catalyst in the ring-closing metathesis (RCM) of dienes, and could effectively catalyze RCM reactions in the presence of only 0.85 mol % Ru. The MNP-supported ruthenium catalysts could be easily recovered using an external magnet. The recyclability of the silica-coated MNP-supported catalysts was superior to silica uncoated MNP-supported catalysts allowing reuse 14 times, due to the increased compatibility of the silica-coated MNPs with the reaction medium.",

keywords = "Immobilization, Ionic materials, Magnetic nanoparticles, Metathesis, Ruthenium",

author = "Chen, {Shu Wei} and Zhang, {Zhi Cheng} and Zhai, {Ning Ning} and Zhong, {Chong Min} and Lee, {Sang Gi}",

year = "2015",

month = jan,

day = "28",

doi = "10.1016/j.tet.2014.12.024",

language = "English",

volume = "71",

pages = "648--653",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "4",

}

TY - JOUR

T1 - The effect of silica-coating on catalyst recyclability in ionic magnetic nanoparticle-supported Grubbs-Hoveyda catalysts for ring-closing metathesis

AU - Chen, Shu Wei

AU - Zhang, Zhi Cheng

AU - Zhai, Ning Ning

AU - Zhong, Chong Min

AU - Lee, Sang Gi

PY - 2015/1/28

Y1 - 2015/1/28

N2 - The Grubbs-Hoveyda type ruthenium-carbene complexes have been covalently immobilized on both silica coated and uncoated magnetic nanoparticles utilizing an imidazolium salt linker. These MNP-supported catalysts showed comparable catalytic activity to the homogeneous imidazolium salt-tagged ruthenium catalyst in the ring-closing metathesis (RCM) of dienes, and could effectively catalyze RCM reactions in the presence of only 0.85 mol % Ru. The MNP-supported ruthenium catalysts could be easily recovered using an external magnet. The recyclability of the silica-coated MNP-supported catalysts was superior to silica uncoated MNP-supported catalysts allowing reuse 14 times, due to the increased compatibility of the silica-coated MNPs with the reaction medium.

AB - The Grubbs-Hoveyda type ruthenium-carbene complexes have been covalently immobilized on both silica coated and uncoated magnetic nanoparticles utilizing an imidazolium salt linker. These MNP-supported catalysts showed comparable catalytic activity to the homogeneous imidazolium salt-tagged ruthenium catalyst in the ring-closing metathesis (RCM) of dienes, and could effectively catalyze RCM reactions in the presence of only 0.85 mol % Ru. The MNP-supported ruthenium catalysts could be easily recovered using an external magnet. The recyclability of the silica-coated MNP-supported catalysts was superior to silica uncoated MNP-supported catalysts allowing reuse 14 times, due to the increased compatibility of the silica-coated MNPs with the reaction medium.

KW - Immobilization

KW - Ionic materials

KW - Magnetic nanoparticles

KW - Metathesis

KW - Ruthenium

UR - http://www.scopus.com/inward/record.url?scp=84920439474&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2014.12.024

DO - 10.1016/j.tet.2014.12.024

M3 - Article

AN - SCOPUS:84920439474

SN - 0040-4020

VL - 71

SP - 648

EP - 653

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

The effect of silica-coating on catalyst recyclability in ionic magnetic nanoparticle-supported Grubbs-Hoveyda catalysts for ring-closing metathesis

Abstract

Bibliographical note

Keywords

Access to Document

Fingerprint

Cite this