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Updated: Jun 7, 2025
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Trifluoromethylthiolation Carbonylation of Unactivated Alkenes via Distal Migration
Ren-Guan Miao1,2, Yuanrui Wang1, Zhi-Peng Bao1,2
1Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning 116023, China.
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.
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