Trifluoromethylthiolation Carbonylation of Unactivated Alkenes via Distal Migration

Sulfur-containing compounds represent a significant category of organic compounds, and the introduction of sulfur groups into organic compounds can effectively enhance their biological activity and synthetic diversity. Although a variety of difunctionalization reactions of alkenes based on sulfur radicals have been documented, significant challenges remain in the carbonylative difunctionalization of unactivated alkenes by the addition of a sulfur radical. Herein, we present a trifluoromethylthiolative carbonylation reaction of unactivated alkenes, which goes through the addition of a trifluoromethylthiol radical to unactivated alkenes and then carbonylation of the newly generated carbon radical intermediate. A heterocyclic/aryl migration in the presence of carbon monoxide is crucial for the success of this methodology and finally resulted in the formation of sulfur-containing carbonylated products in good yields.

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Publication Details

Journal
Organic Letters
Published
2024-11-20
DOI
https://doi.org/10.1021/acs.orglett.4c04151
Citations
8
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
2.00

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article

Trifluoromethylthiolation Carbonylation of Unactivated Alkenes via Distal Migration

Xiao‐Feng Wu, Ren‐Guan Miao, Zhipeng Bao, Yuanrui Wang
8 citations
Organic Letters
Sulfur-Based Synthesis Techniques
2.00
article

Trifluoromethylthiolation Carbonylation of Unactivated Alkenes via Distal Migration

Xiao‐Feng Wu, Ren‐Guan Miao, Zhipeng Bao, Yuanrui Wang
article en
8 citations

Abstract

Sulfur-containing compounds represent a significant category of organic compounds, and the introduction of sulfur groups into organic compounds can effectively enhance their biological activity and synthetic diversity. Although a variety of difunctionalization reactions of alkenes based on sulfur radicals have been documented, significant challenges remain in the carbonylative difunctionalization of unactivated alkenes by the addition of a sulfur radical. Herein, we present a trifluoromethylthiolative carbonylation reaction of unactivated alkenes, which goes through the addition of a trifluoromethylthiol radical to unactivated alkenes and then carbonylation of the newly generated carbon radical intermediate. A heterocyclic/aryl migration in the presence of carbon monoxide is crucial for the success of this methodology and finally resulted in the formation of sulfur-containing carbonylated products in good yields.

Organic LettersVol. 26(47)
Dalian Institute of Chemical Physics (CN), Chinese Academy of Sciences (CN), Leibniz Institute for Catalysis (DE), Dalian National Laboratory for Clean Energy (CN)
Chinese Academy of Sciences, National Key Research and Development Program of China
Openalex Percentile: Top 14%
Sulfur-Based Synthesis Techniques
2.00
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