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.

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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
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article

Synthesis of γ,γ‐Difluoroallylic Ketones by Base‐Promoted Formal Three‐Component Carbonylative Coupling Using TosMIC as a CO Source

Dong Ma, Hongtai Huang, Yubo Jiang, Tiebo Xiao et al.
Asian Journal of Organic Chemistry
Fluorine in Organic Chemistry
article

Synthesis of γ,γ‐Difluoroallylic Ketones by Base‐Promoted Formal Three‐Component Carbonylative Coupling Using TosMIC as a CO Source

Dong Ma, Hongtai Huang, Yubo Jiang, Tiebo Xiao, Xiaoxiang Wu
article en

Abstract

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.

Asian Journal of Organic ChemistryVol. 14(6)
Kunming University of Science and Technology (CN)
Openalex Percentile: Top 95%
Fluorine in Organic Chemistry
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Synthesis of γ,γ‐Difluoroallylic Ketones by Base‐Promoted Formal Three‐Component Carbonylative Coupling Using TosMIC as a CO Source — Dong Ma, Hongtai Huang, et al. · Asian Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS