Visible-Light-Induced Trifluoromethyl Radical Addition to Thiocarbonyl of Thioamide Derivatives
An effective trifluoromethyl radical addition to the thiocarbonyl of thioamide derivatives is described, which produces various trifluoromethylthiolated <i>N</i>-heterocycles such as 6-(trifluoromethylthio)phenanthridine, 2-(trifluoromethylthio)indole, and 2-(trifluoromethylthio)benzothiazole derivatives under visible-light irradiation. The process features advantages such as mild reaction conditions, a cheap and easily available trifluoromethyl source (CF<sub>3</sub>Br), and green energy, as well as broad substrate scope. The reaction mechanism is investigated in detail, and scale-up experiments are performed.
Authors
- Yulai Hu (ORCID: https://orcid.org/0000-0002-9630-4150)
- Ke‐Hu Wang (ORCID: https://orcid.org/0000-0001-8246-3559)
- Danfeng Huang (ORCID: https://orcid.org/0000-0002-5848-1164)
- Yuanyuan Ren
- Yuxiu Zhou
- Junjiao Wang (ORCID: https://orcid.org/0000-0003-2115-7659)
Institutions
- State Key Laboratory of Applied Organic Chemistry
- Northwest Normal University (CN)
- Lanzhou University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-02-28
- DOI
- https://doi.org/10.1021/acs.joc.5c00028
- Citations
- 3
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.37
Funders
- National Natural Science Foundation of China