<i>meta</i>-Substituted Diaryliodonium Salts Enabled Aryne 1,2,4′-Trifunctionalization

A novel 1,2,4'-trifunctionalization of arynes was accomplished using <i>meta</i>-substituted diaryliodonium salts through a unique [5,5]-sigmatropic shift followed by a thia-Fries rearrangement. This cascade transformation enables the sequential formation of both C-N and C-S bonds, while also achieving the synthetically challenging <i>para</i>-selective C-C bond on the non-aryne aromatic ring.

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Publication Details

Journal
Organic Letters
Published
2025-08-28
DOI
https://doi.org/10.1021/acs.orglett.5c03311
Citations
1
Primary Topic
Cyclization and Aryne Chemistry
Type
article
Field-Weighted Citation Impact
0.94

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article

meta-Substituted Diaryliodonium Salts Enabled Aryne 1,2,4′-Trifunctionalization

Li-Feng Chu, Jianwei Han, Junjie Jiang, Limin Wang
1 citations
Organic Letters
Cyclization and Aryne Chemistry
0.94
article

meta-Substituted Diaryliodonium Salts Enabled Aryne 1,2,4′-Trifunctionalization

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

Abstract

A novel 1,2,4'-trifunctionalization of arynes was accomplished using <i>meta</i>-substituted diaryliodonium salts through a unique [5,5]-sigmatropic shift followed by a thia-Fries rearrangement. This cascade transformation enables the sequential formation of both C-N and C-S bonds, while also achieving the synthetically challenging <i>para</i>-selective C-C bond on the non-aryne aromatic ring.

Organic LettersVol. 27(36)
East China University of Science and Technology (CN)
National Natural Science Foundation of China
Zero hunger
Openalex Percentile: Top 22%
Cyclization and Aryne Chemistry
0.94
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