Synthesis and activity of soluble polymer-supported ruthenium carbene complexes: Robust, recyclable and reusable catalysts for olefin metathesis

ORGN 363

Adalie R. Motta and Qingwei Yao. Department of Chemistry and Biochemitry, Northern Illinois University, The Michael Faraday Laboratories, DeKalb, IL 60115

Soluble polymer-supported ruthenium carbene complexes 1 and 2 were synthesized and found to be highly reactive catalysts for olefin metathesis. These catalysts can be readily prepared by the ligand exchange of the Grubbs catalysts (PCy3)2Ru(=CHPh)Cl2 and (PCy3)Ru(SIMes)(=CHPh)Cl2 with a 2-isopropoxystyrene ligand attached to the commercially available poly(ethylene glycol) (PEG). The PEG-supported catalysts effectively catalyze the ring-closing metathesis of a variety of dienes leading to the formation of various carbocyclic and heterocyclic olefins. The catalysts are also reactive toward olefin cross metathesis and ring-opening cross metathesis. In each case, the catalysts can be easily separated from the reaction mixture by precipitation with diethyl ether followed by filtration. The recycled catalysts can be repeatedly reused (up to 8-12 runs) with only very slight loss of activity after each run.

Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions 8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster Sci-Mix 8:00 PM-10:00 PM, Monday, September 8, 2003 Javits Convention Center -- North Pavillion, Sci-Mix Division of Organic Chemistry The 226th ACS National Meeting, New York, NY, September 7-11, 2003