Improved Cross-Metathesis of Acrylate Esters Catalyzed by 2nd Generation Ruthenium Carbene Complexes.

The high stability and functional group compatibility of ruthenium carbene complexes confer them a great ability to catalyze domino processes. For this reason, the combination of metathesis reactions with additional transformations in a domino fashion has been exploited extensively, with the result of expanding the utility of ruthenium carbene complexes beyond that of just olefin metathesis. Among those domino processes, it is worth mentioning the sequence of cross-metathesis/intramolecular Michael addition, which allows for the generation of a wide variety of carbo- and heterocycles in a very simple manner, taking advantage of the benefits of domino reactions. Carbon-, oxygen- and nitrogen-centered nucleophiles are good partners in this protocol, the versatility of which has been illustrated with the synthesis of several biologically important compounds.1 Introduction2 Cross Metathesis/Intramolecular Aza-Michael Addition Sequences3 Cross Metathesis/Intramolecular Oxa-Michael Addition Sequences4 Cross Metathesis/Intramolecular Michael Addition Sequences5 Conclusions and Outlook

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ChemInform Abstract: Cross-Metathesis of Vinylsilanes with Styrene Catalyzed by Ruthenium-Carbene Complexes.

ChemInform ◽

10.1002/chin.200021065 ◽

2010 ◽

Vol 31 (21) ◽

pp. no-no

Author(s):

Cezary Pietraszuk ◽

Bogdan Marciniec ◽

Helmut Fischer

Keyword(s):

Carbene Complexes ◽

Cross Metathesis

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Cross-Metathesis of Vinylsilanes with Styrene Catalyzed by Ruthenium−Carbene Complexes

Organometallics ◽

10.1021/om9909901 ◽

2000 ◽

Vol 19 (5) ◽

pp. 913-917 ◽

Cited By ~ 55

Author(s):

Cezary Pietraszuk ◽

Bogdan Marciniec ◽

Helmut Fischer

Keyword(s):

Carbene Complexes ◽

Cross Metathesis

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PLANT OIL VALORIZATION BY CROSS-METATHESIS REACTIONS: SYNTHESIS OF FINE CHEMICALS FROM METHYL OLEATE

Latin American Applied Research - An international journal ◽

10.52292/j.laar.2020.477 ◽

2020 ◽

Vol 50 (2) ◽

pp. 139-144

Author(s):

Andres Trasarti ◽

Eduardo Gonzalez ◽

Pablo Nieres ◽

Carlos Apesteguia

Keyword(s):

Liquid Phase ◽

Methyl Oleate ◽

Catalyst Deactivation ◽

Side Reaction ◽

Batch Reactors ◽

Reactant Ratio ◽

Fine Chemicals ◽

Plant Oil ◽

2Nd Generation ◽

Cross Metathesis

This work studies the production of high-value compounds by the cross-metathesis of methyl oleate (MO) with ethylene, cinnamonitrile and cinnamaldehyde using the 2nd generation Hoveyda-Grubbs complex (HG) as catalyst, either dissolved in toluene or supported on silica. Reactions were carried out in batch reactors between 313 and 343 K. The yield to cross-metathesis products (YC-M) for the MO cross-metathesis with cinnamonitrile and cinnamaldehyde increased with the initial molar reactant ratio (RCN/MO, RCA/MO), reaching YC-M values of 82% and 95%, respectively, at R = 7. No catalyst deactivation took place during the 400-min catalytic runs. The liquid-phase cross-metathesis of MO with ethylene (ethenolysis) was performed over HG(10%)/SiO2 catalysts, producing 1-decene and methyl 9-decenoate, a valuable intermediate for the synthesis of pheromones. At RC2/MO = 2.5, the selectivity to ethenolysis products was 77% at 82% MO conversion. The MO self-metathesis was the only side reaction observed in all the catalytic tests.

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