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
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).
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.
