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

Abstract

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.

Keywords

Azides / Chan-Lam reaction / Nickel / Iridium / Redox-neutral / Photochemistry

RIGHTS & PERMISSIONS

2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH