Visible-Light-Driven C–H Arylation of Aminoquinones with Diaryliodonium Salts

A visible-light-driven C-H arylation of 2-amino-1,4-naphthoquinones with diaryliodonium salts has been developed using 10-phenylphenothiazine (PTH) as a photocatalyst. Mechanistic studies reveal that aminoquinone serves both as the substrate and as an electron shuttle in the electron transfer from PTH to the diaryliodonium salts. The combination of this photo-driven C-H arylation with an intramolecular SNAr cyclization provides a streamlined route to carbazolequinone scaffolds, significantly facilitating the synthesis of medicinally relevant tetracyclic architectures.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-10-14
DOI
https://doi.org/10.1021/acs.joc.6c01717
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Visible-Light-Driven C–H Arylation of Aminoquinones with Diaryliodonium Salts

Shaozhong Wang, Anam Nawaz
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Visible-Light-Driven C–H Arylation of Aminoquinones with Diaryliodonium Salts

Shaozhong Wang, Anam Nawaz
article en

Abstract

A visible-light-driven C-H arylation of 2-amino-1,4-naphthoquinones with diaryliodonium salts has been developed using 10-phenylphenothiazine (PTH) as a photocatalyst. Mechanistic studies reveal that aminoquinone serves both as the substrate and as an electron shuttle in the electron transfer from PTH to the diaryliodonium salts. The combination of this photo-driven C-H arylation with an intramolecular SNAr cyclization provides a streamlined route to carbazolequinone scaffolds, significantly facilitating the synthesis of medicinally relevant tetracyclic architectures.

The Journal of Organic Chemistry
Nanjing University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 26%
Radical Photochemical Reactions
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