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Updated: May 29, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Regio- and stereoselective multisubstituted enol ester synthesis.
Noriko Okamoto1, Yoshihisa Miwa, Hideki Minami
1Faculty of Pharmaceutical Sciences, Hiroshima International University, 5-1-1 Hirokoshingai, Kure, Hiroshima 737-0112, Japan.
Researchers achieved regioselective and stereoselective cohalogenation of alkynes using N-bromosuccinimide and N-iodosuccinimide. The stereoselectivity of the resulting alkenes varied with alkyne substituents, enabling efficient synthesis of enol esters.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Alkyne functionalization is crucial for synthesizing complex organic molecules.
- Controlling regio- and stereoselectivity in alkyne reactions remains a significant challenge.
Purpose of the Study:
- To develop a method for regioselective and stereoselective cohalogenation of alkynes.
- To investigate the influence of alkyne substituents on the stereoselectivity of the reaction.
- To establish a one-pot procedure for synthesizing multisubstituted enol esters via cohalogenation and cross-coupling.
Main Methods:
- Co-halogenation of various alkynes using N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS).
- Analysis of the stereochemical outcome of the cohalogenation reaction based on alkyne substituents.
- Sequential palladium-catalyzed cross-coupling of the resulting vinyl halides with organoboron reagents in a one-pot process.
Main Results:
- Regio- and stereoselective cohalogenation of alkynes with NBS and NIS was successfully achieved.
- The stereoselectivity of the alkene products was found to be dependent on the electronic and steric properties of the alkyne substituents.
- A one-pot protocol combining cohalogenation and Suzuki-Miyaura cross-coupling provided efficient access to diverse multisubstituted enol esters.
Conclusions:
- The developed cohalogenation method offers a versatile route to functionalized alkenes with controlled stereochemistry.
- The one-pot strategy streamlines the synthesis of complex enol esters, reducing reaction steps and improving efficiency.
- This approach expands the synthetic toolbox for constructing valuable organic intermediates and products.
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