Dual Nickel-Photoredox Catalyzed Amidine-Arylation Method Mediated By In Situ Generated Triazine Cocatalyst

01 April 2025, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Herein, we report a high-yielding nickel/photoredox-catalyzed amidine arylation method that accommodates a wide range of aryl halides and amidines. The method exhibits good functional group tolerance enabling its successful application to both simple substrates and late-stage functionalization experiments. Mechanistic studies revealed the pivotal role of an in situ generated triazine co-catalyst. This information allowed us to further optimize the protocol, achieving faster reaction rates, milder conditions, and most importantly the substrate scope was expanded to sulfonamides and primary amines as well.

Keywords

amidine arylation
metallaphotoredox
flow chemistry
reaction mechanism
nickel catalysis

Supplementary materials

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Experimental data
Description
SI for experimental data for screening and optimization, reaction scope and mechanistic investigations.
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NMR spectra
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Copies of NMR (1H, 13C, and 2D where relevant) spectra of isolated compounds.
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