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Updated: Jun 25, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Published on: November 9, 2019

XAT-Catalysis for Intramolecular Biaryl Synthesis.

Thomas Sephton¹, Jonathan M Large², Louise S Natrajan¹

¹School of Chemistry, University of Manchester, Manchester, M13 9PL, UK.

Angewandte Chemie (International Ed. in English)

|May 31, 2024

Summary

This summary is machine-generated.

Visible light photoredox catalysis enables efficient biaryl synthesis through radical ipso-substitution, avoiding harsh reagents. This method facilitates direct arylation of C-N bonds in anilines.

Keywords:

Aniline Biaryl Photoredox XAT

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Area of Science:

Organic Chemistry
Photocatalysis
Synthetic Methodology

Background:

Biaryl compounds are crucial in pharmaceuticals and materials science.
Traditional biaryl synthesis often relies on organometallic reagents, which can be toxic or require stoichiometric amounts.
Radical ipso-substitution presents an alternative but often requires harsh conditions or stoichiometric radical initiators.

Purpose of the Study:

To develop a novel, efficient, and milder method for biaryl synthesis using visible light photoredox catalysis.
To explore the application of radical ipso-substitution under photoredox conditions.
To enable the direct arylation of inert C-N bonds, such as those in anilines.

Main Methods:

Visible light photoredox catalysis.
Halogen-atom transfer (XAT) mechanism.
Utilizing specific amide substrates to direct ipso-substitution over ortho-addition.

Main Results:

Successful synthesis of biaryl compounds via photoredox-catalyzed ipso-substitution.
Demonstrated compatibility with various electronic properties of the migrating arene ring.
Achieved a one-pot formal arylation of aniline C-N bonds.

Conclusions:

Visible light photoredox catalysis provides a powerful and sustainable alternative for biaryl synthesis.
The developed method offers broad substrate scope and functional group tolerance.
This approach opens new avenues for C-N bond functionalization.