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.
Authors
- Xiao‐Feng Wu (ORCID: https://orcid.org/0000-0001-6622-3328)
- Ren‐Guan Miao
- Zhipeng Bao (ORCID: https://orcid.org/0000-0001-8376-1195)
- Yuanrui Wang (ORCID: https://orcid.org/0000-0002-4128-0016)
Institutions
- Dalian Institute of Chemical Physics (CN)
- Chinese Academy of Sciences (CN)
- Leibniz Institute for Catalysis (DE)
- Dalian National Laboratory for Clean Energy (CN)
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
Funders
- Chinese Academy of Sciences
- National Key Research and Development Program of China