Visible-light-induced radical trifluoromethylation/cyclization of alkynes: synthesis of CF <sub>3</sub> -containing dioxodibenzothiazepines

A simple and metal-free photoinduced radical trifluoromethylation/cyclization reaction of alkynes with readily preparable and air-stable trifluoromethyl thianthrenium triflate (TT-CF<sub>3</sub><sup>+</sup>OTf<sup>-</sup>) as the trifluoromethyl source has been developed. This transformation can be carried out without using metal catalysts and strong oxidants, providing an avenue to construct a series of potential pharmaceutically valuable trifluoromethylated dioxodibenzothiazepines under mild conditions. This protocol offers a green strategy for the synthesis of useful CF<sub>3</sub>-containing seven-membered N-heterocycles.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob01520k
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Visible-light-induced radical trifluoromethylation/cyclization of alkynes: synthesis of CF 3 -containing dioxodibenzothiazepines

Yangjie Wu, Yusheng Wu, Dapeng Zou, Yang Geng et al.
Organic & Biomolecular Chemistry
Fluorine in Organic Chemistry
article

Visible-light-induced radical trifluoromethylation/cyclization of alkynes: synthesis of CF 3 -containing dioxodibenzothiazepines

Yangjie Wu, Yusheng Wu, Dapeng Zou, Yang Geng, Xiaoyu Chen, Wu Zhiyong, Pan Liu
article en

Abstract

A simple and metal-free photoinduced radical trifluoromethylation/cyclization reaction of alkynes with readily preparable and air-stable trifluoromethyl thianthrenium triflate (TT-CF<sub>3</sub><sup>+</sup>OTf<sup>-</sup>) as the trifluoromethyl source has been developed. This transformation can be carried out without using metal catalysts and strong oxidants, providing an avenue to construct a series of potential pharmaceutically valuable trifluoromethylated dioxodibenzothiazepines under mild conditions. This protocol offers a green strategy for the synthesis of useful CF<sub>3</sub>-containing seven-membered N-heterocycles.

Organic & Biomolecular ChemistryVol. 23(46)
Zhengzhou University (CN), Tyvak (United States) (US), Zhengzhou Railway Vocational & Technical College (CN), Henan Agricultural University (CN)
Openalex Percentile: Top 74%
Fluorine in Organic Chemistry
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