Synthesis of α‐Fluoroketones from Carboxylic Acids via Decarboxylation of Fluorinated Malonates
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Author (Corporation)
Publication date
29.01.2025
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Type
01A - Journal article
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Helvetica Chimica Acta
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Volume
108
Issue / Number
3
Pages / Duration
e202400187
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Wiley
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Abstract
α-Fluoroketones are versatile intermediates for the synthesis of fluorinated heterocycles and other fluorine-containing building blocks. We have recently disclosed a novel route to such an α-fluoroketone using the corresponding benzoic acid as a starting material. The reaction sequence started with the CDI-activation of the carboxylic acid and reaction with diethyl malonate, fluorination of the resulting acyl malonate with Selectfluor, and finally a double-decarboxylation to provide the desired α-fluoroketone in 73 % yield over three telescoped steps. We were interested in the generality of this approach to access α-fluoroketones from readily available carboxylic acids. In this article, we disclose the crucial modifications of the reaction conditions that were needed to make them broadly applicable to a diverse array of carboxylic acids. Under the optimized conditions, a wide range of α-fluoroketones were isolated in good to excellent yields and in high purity.
Keywords
Decarboxylation, Fluorination, Malonate, Selectfluor, α-Fluoroketone
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ISBN
ISSN
0018-019X
1522-2675
1522-2675
Language
English
Created during FHNW affiliation
Yes
Strategic action fields FHNW
Publication status
Published
Review
peer-reviewed
Open access category
Closed
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Citation
Davenport, R., Cibiras, R., & Schäfer, G. (2025). Synthesis of α‐Fluoroketones from Carboxylic Acids via Decarboxylation of Fluorinated Malonates. Helvetica Chimica Acta, 108(3), e202400187. https://doi.org/10.1002/hlca.202400187