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Electrochemical Benzylic C(sp³)-H Direct Amidation.

Anthony Choi¹, Oliver H Goodrich², Alexander P Atkins¹

¹School of Chemistry, University of Bristol, Bristol BS8 1TS, U.K.

Organic Letters

|January 16, 2024

Summary

Researchers developed a novel electrochemical method for direct benzylic C-H amidation, enabling flexible synthesis of secondary amides from readily available starting materials.

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Published on: December 16, 2019

Area of Science:

Organic Chemistry
Electrochemistry
Synthetic Methodology

Background:

Amide bonds are crucial functional groups in many molecules.
Traditional amide bond formation methods are robust but can lack synthetic flexibility.
Alternative strategies for amide bond synthesis are needed to enhance control.

Purpose of the Study:

To develop a new electrochemical method for C-N bond formation.
To achieve direct benzylic C(sp3)-H amidation.
To enable the synthesis of secondary amides with improved flexibility.

Main Methods:

Electrochemical oxidation of benzylic C-H bonds.
Coupling of secondary benzylic substrates with primary benzamides.
Utilizing flow chemistry for scalable synthesis.

Main Results:

Successful formation of non-amide C-N bonds via direct amidation.
Synthesis of diverse secondary amides demonstrated.
Multigram scale-up achieved using flow electrochemistry.

Conclusions:

The developed electrochemical method offers a novel route to secondary amides.
Direct benzylic C-H amidation provides synthetic advantages.
Flow chemistry enables efficient and scalable production.