A new method for synthesizing terminal olefins from esters using the Corey-Chaykovsky reagent
Related Experiment Video
Updated: Jun 24, 2025

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Hucheng Shi1, Guoren Yue1,2, Penji Yan2
1School of Chemistry and Chemical Engineering, State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, Shihezi University, Shihezi 832003, China.
Abstract:
A new method for the synthesis of terminal olefins was developed through the reaction of the Corey-Chaykovsky reagent (dimethyl-sulfonium methylide) with readily available esters. After the domino process of nucleophilic addition, elimination and rearrangement in one pot, the terminal olefins were synthesized in high yields (up to 84%) under mild conditions. The synthetic method was well tolerated by many functional groups and a new route for the synthesis of various terminal olefin derivatives is provided. In the end, a possible reaction mechanism is proposed, which is supported by DFT calculations.
More Related Videos
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Related Concept Videos
Esters to β-Ketoesters: Claisen Condensation Overview
Esters to β-Ketoesters: Claisen Condensation Mechanism
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Esters to Alcohols: Grignard Reaction
The reaction requires two equivalents of the Grignard reagent and introduces two identical alkyl groups, derived from the Grignard reagent, bonded to the hydroxyl-bearing carbon of the alcohol.
The reaction follows the typical nucleophilic acyl substitution mechanism. The Grignard...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview