<i>meta</i> -NTf <sub>2</sub> substituted diaryliodonium salts: novel nitrogen-substituted aryne precursors for trapping reactions and rearrangements

We synthesized <i>meta</i>-NTf<sub>2</sub>-substituted diaryliodonium salts as novel aryne precursors, the resulting aryne intermediates underwent efficient trapping reactions with various arynophiles, enabling the difunctionalization of the benzene ring. Furthermore, we developed a trifunctionalization reaction using <i>N</i>-allylanilines, which afforded highly functionalized diarylamines with an allyl group through a cascade involving both Fries and aza-Claisen rearrangements.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc04493f
Primary Topic
Cyclization and Aryne Chemistry
Type
article
Field-Weighted Citation Impact
0.00
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article

meta -NTf 2 substituted diaryliodonium salts: novel nitrogen-substituted aryne precursors for trapping reactions and rearrangements

Li-Feng Chu, Jianwei Han, Junjie Jiang, Limin Wang
Chemical Communications
Cyclization and Aryne Chemistry
article

meta -NTf 2 substituted diaryliodonium salts: novel nitrogen-substituted aryne precursors for trapping reactions and rearrangements

Li-Feng Chu, Jianwei Han, Junjie Jiang, Limin Wang
article en

Abstract

We synthesized <i>meta</i>-NTf<sub>2</sub>-substituted diaryliodonium salts as novel aryne precursors, the resulting aryne intermediates underwent efficient trapping reactions with various arynophiles, enabling the difunctionalization of the benzene ring. Furthermore, we developed a trifunctionalization reaction using <i>N</i>-allylanilines, which afforded highly functionalized diarylamines with an allyl group through a cascade involving both Fries and aza-Claisen rearrangements.

Chemical CommunicationsVol. 61(84)
East China University of Science and Technology (CN)
Openalex Percentile: Top 81%
Cyclization and Aryne Chemistry
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