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Synfacts 2015; 11(1): 0103
DOI: 10.1055/s-0034-1379713
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Olefin Metathesis with Ruthenium–Carbene Supported on Iron Oxide

Contributor(s):
Yasuhiro Uozumi
,
Takao Osako
Chen S.-W, Zhang Z.-C, Ma M, Zhong C.-M, * Lee S.-g. * Northwest A&F University, Yangling, P. R. of China and Ewha Womans University, Seoul, Republic of Korea
Supported Ruthenium–Carbene Catalyst on Ionic Magnetic Nanoparticles for Olefin Metathesis.

Org. Lett. 2014;
16: 4969-4971
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

carbenes - iron oxide - olefin metathesis - ruthenium

Significance

The Grubbs–Hoveyda ruthenium–carbene complex supported on ionic magnetic nanoparticles (Ru@IMNPs) was prepared by immobilization of imidazolium chloride 1 onto Fe3O4 2, anion exchange with NaPF6, and metathesis with ruthenium complex 3 (eq. 1). Ru@IMNPs catalyzed the ring-closing metathesis of dienes to give the corresponding cyclic olefins in 90–99% yield (eq. 2). The cross-metathesis of methyl acrylate with olefins using Ru@IMNPs also proceeded with high E-selectivity (eq. 3).


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Comment

In the ring-closing metathesis of N,N-diallyl tosylamide, the catalyst was recovered magnetically and reused five times without significant loss of catalytic activity (6th run: 96% conversion), although ICP-MS analysis showed significant leaching of the ruthenium species into the product (a loss of 54% of the ruthenium content of the fresh catalyst) during the initial three runs of the recycling experiment.


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