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Updated: Aug 12, 2025

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

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Published on: October 30, 2018

Development of copper-catalyzed deaminative esterification using high-throughput experimentation.

Yuning Shen¹, Babak Mahjour¹, Tim Cernak²

¹Department of Medicinal Chemistry, University of Michigan, Ann Arbor, MI, 48109, USA.

Communications Chemistry

|January 25, 2023

Summary

This summary is machine-generated.

This study introduces a novel copper-catalyzed deaminative esterification using aryl amines, significantly expanding chemical space for drug discovery and materials science by repurposing readily available building blocks.

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Area of Science:

Organic Chemistry
Catalysis
Chemical Synthesis

Background:

Amine and carboxylic acid building blocks are cost-effective and diverse, offering opportunities to expand chemical space.
Existing esterification methods, like Fischer esterification, have limitations in substrate scope and feedstock utilization.

Purpose of the Study:

To develop a novel copper-catalyzed deaminative esterification reaction.
To complement existing amide coupling reactions and expand accessible chemical space.
To enable efficient repurposing of aryl amines for ester synthesis.

Main Methods:

Copper-catalyzed C-N bond activation of aryl amines via diazonium salt intermediates.
High-throughput experimentation in microliter reaction droplets for reaction optimization.
Chemoinformatic analysis of commercial building blocks to assess chemical space expansion.

Main Results:

The deaminative esterification reaction demonstrated robust performance across hundreds of substrate pairs.
This method nearly doubles the available esterification chemical space compared to classic Fischer esterification.
The reaction is suitable for late-stage diversification of complex molecules.

Conclusions:

The developed copper-catalyzed deaminative esterification provides a powerful new tool for organic synthesis.
This method significantly enhances the utility of aryl amines as ester precursors.
The approach effectively expands chemical space and facilitates building block repurposing.