1208862-96-7Relevant academic research and scientific papers
Unravelling the olefin cross metathesis on solid support. Factors affecting the reaction outcome
Poeylaut-Palena, Andres A.,Mata, Ernesto G.
scheme or table, p. 3947 - 3956 (2010/09/17)
Olefin cross metathesis on solid support under a variety of conditions is described. A comprehensive analysis considering diverse factors governing the reaction outcome gives a series of patterns for the application of this useful methodology in organic synthesis. If the intrasite reaction is not possible, homodimerization of the soluble olefin is crucial. When the homodimer is less reactive than its monomer, reaction outcome depends on the homodimerization rate, which, in turn, depends on the precatalyst used and the reaction conditions. If the site-site interaction is a feasible process, the cross metathesis product is obtained exclusively when the newly-formed double bond is resilient to further metathetic events. Taking into account these considerations, we have demonstrated that excellent results in terms of cross metathesis coupling can be obtained under the optimized conditions, and that microwave irradiation is also an interesting alternative for the development of a practical and energy-efficient cross metathesis on solid support.
Solid-phase cross-metathesis: The effect of the non-immobilized olefin and the precatalyst on the intrasite interference
Poeylaut-Palena, Andres A.,Mata, Ernesto G.
experimental part, p. 216 - 227 (2010/08/20)
We have developed a study on the factors that influence the intrasite interactions in the cross-metathesis on solid support. When such interactions are possible, the outcome of the intrasite by-product depends on the non-immobilized olefin and the precatalyst used. The comparatively poor reactivity of first generation Grubbs precatalyst makes the easier intrasite coupling to succeed. 1.
Solid-supported cross metathesis and the role of the homodimerization of the non-immobilized olefin
Poeylaut-Palena, Andres A.,Testero, Sebastian A.,Mata, Ernesto G.
, p. 2024 - 2027 (2008/09/19)
(Chemical Equation Presented) 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.
