Copper-Mediated Direct Trifluoromethylation of Trichloromethyl Alkanes
CF<sub>3</sub>CCl<sub>2</sub>-containing compounds are of significant synthetic value but are typically synthesized from environmentally harmful hydrochlorofluorocarbons (CFCs). Herein, we report the use of a well-defined Cu(I) complex, [(bpy)Cu(CF<sub>3</sub>)], as an efficient trifluoromethylating reagent for the direct trifluoromethylation of trichloroalkanes under mild conditions, affording CF<sub>3</sub>CCl<sub>2</sub>-containing products with excellent chemoselectivity. This protocol also enabled the gram-scale synthesis of cyhalothric acid ester, which is a key intermediate in the production of pyrethroid pesticides.
Authors
- Matthew Hughes
- Zhuang Hou (ORCID: https://orcid.org/0000-0002-4933-4226)
- Zehai Lu (ORCID: https://orcid.org/0000-0001-6114-9456)
- Yongrui Luo (ORCID: https://orcid.org/0000-0001-9137-2595)
- Linhua Wang (ORCID: https://orcid.org/0000-0002-0956-0472)
- Stephen Smith
- Qilong Shen (ORCID: https://orcid.org/0000-0001-5622-153X)
- Ziming Wu (ORCID: https://orcid.org/0000-0001-7155-6653)
Institutions
- Shenyang Pharmaceutical University (CN)
- Chinese Academy of Sciences (CN)
- Syngenta (United States) (US)
- Manufacturing Technology Centre (United Kingdom) (GB)
- Shanghai Institute of Organic Chemistry (CN)
- Syngenta (Switzerland) (CH)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-06
- DOI
- https://doi.org/10.1021/acs.orglett.5c00697
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Chinese Academy of Sciences
- Syngenta International