An Intramolecular Minisci Reaction in Aqueous Media Using Langlois’ Reagent

A trifluoromethylpyridylation of unactivated alkenes in aqueous solution under open air is reported. This process allows the incorporation of trifluoromethyl and the construction of pyridines annulated to saturated cycles via an intramolecular Minisci reaction using Langlois' reagent (CF<sub>3</sub>SO<sub>2</sub>Na) as a trifluoromethyl source. Extrusion of air from the reaction is not required. A broad functional group tolerance is observed. A series of five-, six-, and seven-membered cycles are obtained, exhibiting great potential application in the preparation of diversified pyridines.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-02-10
DOI
https://doi.org/10.1021/acs.joc.4c01652
Citations
1
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.79

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article

An Intramolecular Minisci Reaction in Aqueous Media Using Langlois’ Reagent

Wengui Wang, Shoufeng Wang, Jing Li
1 citations
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
0.79
article

An Intramolecular Minisci Reaction in Aqueous Media Using Langlois’ Reagent

Wengui Wang, Shoufeng Wang, Jing Li
article en
1 citations

Abstract

A trifluoromethylpyridylation of unactivated alkenes in aqueous solution under open air is reported. This process allows the incorporation of trifluoromethyl and the construction of pyridines annulated to saturated cycles via an intramolecular Minisci reaction using Langlois' reagent (CF<sub>3</sub>SO<sub>2</sub>Na) as a trifluoromethyl source. Extrusion of air from the reaction is not required. A broad functional group tolerance is observed. A series of five-, six-, and seven-membered cycles are obtained, exhibiting great potential application in the preparation of diversified pyridines.

The Journal of Organic ChemistryVol. 90(7)
University of Jinan (CN)
National Natural Science Foundation of China, University of Jinan
Clean water and sanitation
Openalex Percentile: Top 31%
Fluorine in Organic Chemistry
0.79
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