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

ChemInform ◽  
2006 ◽  
Vol 37 (29) ◽  
Author(s):  
Grant S. Forman ◽  
Robert P. Tooze
Keyword(s):  
Carbene Complexes ◽  
2Nd Generation ◽  
Cross Metathesis ◽  
Acrylate Esters

Ruthenium–Carbene Complexes in the Synthesis of Polybutadiene and Its Cross-Metathesis with Polynorbornene

2019 ◽  
Vol 61 (1) ◽  
pp. 65-75 ◽  
Author(s):  
A. A. Morontsev ◽  
M. L. Gringolts ◽  
M. P. Filatova ◽  
A. S. Peregudov ◽  
T. R. Akmalov ◽  
...  
Keyword(s):  
Carbene Complexes ◽  
Cross Metathesis

Cross-Metathesis of Vinylsilanes with Allyl Alkyl Ethers Catalyzed by Ruthenium−Carbene Complexes

2002 ◽  
Vol 21 (5) ◽  
pp. 840-845 ◽  
Author(s):  
Małgorzata Kujawa-Welten ◽  
Cezary Pietraszuk ◽  
Bogdan Marciniec
Keyword(s):  
Carbene Complexes ◽  
Cross Metathesis ◽  
Alkyl Ethers

Cross-Metathesis/Intramolecular (Hetero-)Michael Addition: A Convenient Sequence for the Generation of Carbo- and Heterocycles

Synthesis ◽  
2017 ◽  
Vol 49 (13) ◽  
pp. 2787-2802 ◽  
Author(s):  
María Sánchez-Roselló ◽  
Carlos del Pozo ◽  
Javier Miró
Keyword(s):  
Michael Addition ◽  
Olefin Metathesis ◽  
High Stability ◽  
Functional Group ◽  
Domino Reactions ◽  
Simple Manner ◽  
Great Ability ◽  
Carbene Complexes ◽  
Cross Metathesis ◽  
Metathesis Reactions

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

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

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.

scholarly journals 1H NMR Analysis of the Metathesis Reaction between 1-Hexene and (E)-Anethole Using Grubbs 2nd Generation Catalyst: Effect of Reaction Conditions on (E)-1-(4-Methoxyphenyl)-1-hexene Formation and Decomposition

Catalysts ◽  
2021 ◽  
Vol 11 (12) ◽  
pp. 1483
Author(s):  
Marthinus Rudi Swart ◽  
Charlene Marais ◽  
Elizabeth Erasmus
Keyword(s):  
1H Nmr ◽  
Maximum Concentration ◽  
Metathesis Reaction ◽  
Reaction Conditions ◽  
2Nd Generation ◽  
Cross Metathesis ◽  
First Order Kinetics ◽  
Different Temperatures ◽  
The Cross ◽  
Catalyst Effect

The metathesis of 1-hexene and (E)-anethole in the presence of Grubbs 2nd generation catalyst was monitored by in situ 1H NMR spectroscopy at different temperatures (15 °C, 25 °C, and 45 °C) and anethole mol fractions (XAnethole ≈ 0.17, 0.29, 0.5, 0.71, 0.83). Time traces confirmed the instantaneous formation of (E)-1-(4-methoxyphenyl)-1-hexene, the cross-metathesis product. A maximum concentration of (E)-1-(4-methoxyphenyl)-1-hexene is reached fairly fast (the time depending on the reaction conditions), and this is followed by a decrease in the concentration of (E)-1-(4-methoxyphenyl)-1-hexene due to secondary metathesis. The maximum concentration of (E)-1-(4-methoxyphenyl)-1-hexene was more dependent on the XAnethole than the temperature. The highest TOF (3.46 min−1) was obtained for the reaction where XAnethole was 0.16 at 45 °C. The highest concentration of the cross-metathesis product was however achieved after 6 min with an anethole mol fraction of 0.84 at 25 °C. A preliminary kinetic study indicated that the secondary metathesis reaction followed first order kinetics.

scholarly journals Practical highly enantioselective synthesis of (R)- and (S)-(E)-4-hydroxynon-2-enal.

2009 ◽  
Vol 56 (1) ◽  
Author(s):  
Marek Komisarski ◽  
Zuzanna Kaczmarska ◽  
Jarosław T Kuśmierek
Keyword(s):  
Optical Purity ◽  
Enantioselective Synthesis ◽  
The Other ◽  
Metathesis Reaction ◽  
2Nd Generation ◽  
Cross Metathesis ◽  
Cell Components ◽  
One Step ◽  
The Individual ◽  
Cell Cycle Signaling

Oxidative stress enhances lipid peroxidation (LPO) implicated in cancer promotion and progression. (E)-4-Hydroxynon-2-enal 1 (trans-4-hydroxy-2-nonenal, HNE) is one of the most abundant products of LPO. Reactions of HNE with DNA and proteins are responsible for its mutagenic and toxic effects. On the other hand, HNE is regarded as a key molecule in stress mediated cell cycle signaling. LPO generates racemic HNE (rac-1); however, it is expected that the individual enantiomers will behave differently in their interactions with cell components. The study of HNE stereochemistry in its chemical and biochemical interactions is hindered by the lack of expedient methods for preparation of pure enantiomers. This study presents one step synthesis of HNE in a cross-metathesis reaction between the commercially available oct-1-en-3-ol and acrolein in the presence of 2nd generation Grubbs catalyst. The use in the metathesis reaction of enantiomers of oct-1-en-3-ol obtained via Candida antarctica lipase resolution of the racemate allowed us to prepare of 4-(R)- and 4-(S)-enantiomers of HNE (R-1 and S-1, respectively) with excellent optical purity (97.5 and 98.4% ee, respectively) and good chemical yields (70%).

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