Solid-Supported Cross Metathesis and the Role of the Homodimerization of the Non-immobilized Olefin

We have prepared immobilized olefins as models for the cross metathesis using different olefin partners in the presence of second generation Grubbs and Hoveyda−Grubbs precatalysts. We have demonstrated that solid-phase cross metathesis is strongly dependent on the degree of homodimerization of the n...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-03, Vol.73 (5), p.2024-2027
Main Authors: Poeylaut-Palena, Andrés A, Testero, Sebastián A, Mata, Ernesto G
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Chemical reactivity
Chemistry
Dimerization
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
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Summary:We have prepared immobilized olefins as models for the cross metathesis using different olefin partners in the presence of second generation Grubbs and Hoveyda−Grubbs precatalysts. We have demonstrated that solid-phase cross metathesis is strongly dependent on the degree of homodimerization of the non-immobilized olefin and the reactivity of such a homodimer. As in the homogeneous phase, the Hoveyda−Grubbs precatalyst was better for immobilized α,β-unsaturated carbonyl compounds.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo7025433