Related Experiment Video
Updated: Jun 8, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Improving sustainability in ene-yne cross-metathesis for transformation of unsaturated fatty esters
Virginie Le Ravalec1, Antoine Dupé, Cédric Fischmeister
1UMR CNRS Sciences Chimiques de Rennes, Université de Rennes, France.
Abstract:
Ruthenium-catalyzed ene-yne cross-metathesis is performed with stoichiometric proportions of terminal olefins and alkynes. This is made possible by the continuous addition of the alkyne to the reaction mixture. The protocol allows the ene-yne cross-metathesis reaction to be carried out with long-chain terminal olefins and in a one-pot fashion with internal olefins after shortening by ethenolysis. The efficient conversion of renewable unsaturated fatty esters from bioresources into valuable conjugated 1,3-dienes of interest for further transformations is performed using this technique under mild conditions in dimethyl carbonate; an ecofriendly solvent.
Related Concept Videos
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

