Functionalized Diaryliodonium Salts with <i>N</i> ‐Reactive Amides: Versatile Reactivity for Constructing Benzo‐Fused Nitrogen Heterocycles

Diaryliodonium(III) salts with N ‐reactive amides are proposed as new attractive synthetic tools for the construction of benzo‐fused nitrogen heterocycles. In this study, we have developed an efficient preparation method for ortho ‐functionalized diaryliodonium salts bearing N ‐phthalimide ( N ‐NPhth) groups. Unlike strategies requiring ortho ‐leaving groups, these salts demonstrated their application in both transition metal‐free and transition metal‐catalyzed sequential coupling reactions, leading to the construction of five‐ and seven‐membered heterocyclic compounds.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2026-04-21
DOI
https://doi.org/10.1002/adsc.70399
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
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Functionalized Diaryliodonium Salts with N ‐Reactive Amides: Versatile Reactivity for Constructing Benzo‐Fused Nitrogen Heterocycles

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Functionalized Diaryliodonium Salts with N ‐Reactive Amides: Versatile Reactivity for Constructing Benzo‐Fused Nitrogen Heterocycles

Naoki Miyamoto, Kotaro Kikushima, Yasuyuki Kita, Toshifumi Dohi, Arisu Kasai
article en

Abstract

Diaryliodonium(III) salts with N ‐reactive amides are proposed as new attractive synthetic tools for the construction of benzo‐fused nitrogen heterocycles. In this study, we have developed an efficient preparation method for ortho ‐functionalized diaryliodonium salts bearing N ‐phthalimide ( N ‐NPhth) groups. Unlike strategies requiring ortho ‐leaving groups, these salts demonstrated their application in both transition metal‐free and transition metal‐catalyzed sequential coupling reactions, leading to the construction of five‐ and seven‐membered heterocyclic compounds.

Advanced Synthesis & CatalysisVol. 368(9)
Ritsumeikan University (JP)
Openalex Percentile: Top 11%
Catalytic Cross-Coupling Reactions
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