A General and Regioselective Synthesis of 5‑Trifluoromethyl-pyrazoles

Two synthetic approaches to 4-trifluoromethylsydnones, a novel class of these mesoionic reagents, are reported. These compounds undergo regioselective alkyne cycloaddition reactions, thereby providing a general approach to 5-trifluoromethylpyrazoles. This method has been employed in a short formal s...

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Bibliographic Details
Published in:Organic letters 2012-09, Vol.14 (18), p.4858-4861
Main Authors: Foster, Robert S, Jakobi, Harald, Harrity, Joseph P. A
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Cycloaddition Reaction
Herbicides - chemical synthesis
Herbicides - chemistry
Herbicides - pharmacology
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Hydrocarbons, Halogenated - chemical synthesis
Hydrocarbons, Halogenated - chemistry
Hydrocarbons, Halogenated - pharmacology
Molecular Structure
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Pyrazoles - pharmacology
Stereoisomerism
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Summary:Two synthetic approaches to 4-trifluoromethylsydnones, a novel class of these mesoionic reagents, are reported. These compounds undergo regioselective alkyne cycloaddition reactions, thereby providing a general approach to 5-trifluoromethylpyrazoles. This method has been employed in a short formal synthesis of the herbicide fluazolate.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3021918