Volume 42, Issue 18 pp. 2228-2234
Concise Report

Nickel/Photoredox Dual Catalytic Chan-Lam Coupling of Aryl Azides and Arylboric Acids

Xia Ge

Xia Ge

School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu, 210093 China

These authors contributed equally to this work.

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Haojie Ji

Haojie Ji

School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu, 210093 China

These authors contributed equally to this work.

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Hongjian Lu

Corresponding Author

Hongjian Lu

School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu, 210093 China

E-mail: [email protected]Search for more papers by this author
First published: 14 May 2024
Citations: 4

Comprehensive Summary

Unsymmetrical diarylamines are crucial components in many pharmaceuticals and functional materials. In this study, we introduce an efficient Chan-Lam cross-coupling method that utilizes phenylboronic acids and aryl azides as coupling agents in a redox-neutral environment, enabled by a synergistic nickel/photoredox catalytic system. This approach leverages a proton-coupled electron transfer mechanism to bypass the typical nitrene pathway associated with aryl azides, which is prone to intramolecular rearrangement, C—H amination, and reductive hydrogenation. Notably, our method exhibits broad compatibility with a variety of functional groups, including those derived from pharmaceuticals, demonstrating its versatile potential in organic synthesis and drug modification.

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