Synthesis of γ,γ‐Difluoroallylic Ketones by Base‐Promoted Formal Three‐Component Carbonylative Coupling Using TosMIC as a CO Source
Abstract A base‐promoted three‐component carbonylative coupling reaction involving α‐trifluoromethyl styrenes, TosMIC, and alkyl halides is declared. TosMIC is utilized as a commercially available CO source in this strategy. A series of γ, γ‐difluoroallylic ketones were synthesized in moderate to good yields by this strategy. When allyl bromide is used as the halide, the formal 1,3‐Ts migration product is obtained. The good functional group tolerance, broad substrate scope, and simple operation demonstrate the universality and practicality of the method. The 18 O labeling experiment demonstrated that the oxygen atom in the carbonyl group originated from water.
Authors
- Dong Ma (ORCID: https://orcid.org/0000-0003-3824-234X)
- Hongtai Huang (ORCID: https://orcid.org/0009-0008-8148-0152)
- Yubo Jiang (ORCID: https://orcid.org/0009-0003-1159-8802)
- Tiebo Xiao (ORCID: https://orcid.org/0000-0003-0799-1049)
- Xiaoxiang Wu (ORCID: https://orcid.org/0000-0001-5392-3202)
Institutions
- Kunming University of Science and Technology (CN)
Publication Details
- Journal
- Asian Journal of Organic Chemistry
- Published
- 2025-03-31
- DOI
- https://doi.org/10.1002/ajoc.202500164
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00