Isoquinolinium Photooxidant for Arene C–H Amination

We herein report a potent photocatalytic system for arene C-H amination utilizing an isoquinolinium photooxidant. The key to the process involves <i>in situ</i> protonation of neutral isoquinoline precatalyst <b>IQ1</b>. Resulting isoquinolinium <b>IQ1•H</b><sup><b>+</b></sup> exhibits a high excited-state reduction potential (+2.33 V vs SCE), enabling single-electron-transfer oxidation of inert arenes. The optimized reaction system demonstrates a broad scope, including electronically neutral arenes and various pharmaceutical small molecules with azoles and pyridines.

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Publication Details

Journal
Organic Letters
Published
2026-03-22
DOI
https://doi.org/10.1021/acs.orglett.6c00819
Primary Topic
Synthesis and Catalytic Reactions
Type
article
Field-Weighted Citation Impact
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article

Isoquinolinium Photooxidant for Arene C–H Amination

Yuliang Liu, Taku Wakabayashi, Ye Liu, Shunsuke Chiba et al.
Organic Letters
Synthesis and Catalytic Reactions
article

Isoquinolinium Photooxidant for Arene C–H Amination

Yuliang Liu, Taku Wakabayashi, Ye Liu, Shunsuke Chiba, Itziar Guerrero
article en

Abstract

We herein report a potent photocatalytic system for arene C-H amination utilizing an isoquinolinium photooxidant. The key to the process involves <i>in situ</i> protonation of neutral isoquinoline precatalyst <b>IQ1</b>. Resulting isoquinolinium <b>IQ1•H</b><sup><b>+</b></sup> exhibits a high excited-state reduction potential (+2.33 V vs SCE), enabling single-electron-transfer oxidation of inert arenes. The optimized reaction system demonstrates a broad scope, including electronically neutral arenes and various pharmaceutical small molecules with azoles and pyridines.

Organic Letters
Nanyang Technological University (SG)
Clean water and sanitation
Openalex Percentile: Top 11%
Synthesis and Catalytic Reactions
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