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Updated: Jul 25, 2025
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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
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Beyond Amide Bond Formation: TCFH as a Reagent for Esterification.
Nathaniel R Luis1, Kasey K Chung1, Matthew R Hickey2
1Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, California 91711, United States.
Organic Letters
|June 26, 2023
Summary
This study explores using N,N,N
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Ester and thioester synthesis are crucial in organic chemistry.
- Developing efficient synthetic methods is an ongoing challenge.
Purpose of the Study:
- To investigate the use of N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate (TCFH) and N-methylimidazole (NMI) for ester and thioester synthesis.
- To identify conditions for efficient synthesis with challenging substrates.
Main Methods:
- Utilized TCFH and NMI as coupling reagents.
- Investigated reactions with various alcohols and thiols, including less nucleophilic ones.
- Optimized reaction conditions to overcome challenges with different nucleophiles.
Main Results:
- TCFH/NMI effectively mediates ester and thioester formation.
- Identified specific conditions to manage reactivity differences between alcohols and thiols.
- Achieved high yields and selectivity for a broad range of substrates.
Conclusions:
- TCFH/NMI offers a versatile method for synthesizing esters and thioesters.
- The developed conditions enable efficient synthesis with diverse alcohols and thiols.
- This approach addresses limitations in current ester and thioester synthetic methodologies.
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