AI Article Synopsis
- The study introduces 4-fluorosydnones, a new type of mesoionic dipole that shows high reactivity in cycloaddition reactions with alkynes, particularly under copper catalysis or strain conditions.
- Their synthesis involves an electrophilic fluorination method using Selectfluor on σ-sydnone Pd(II) precursors.
- The reactivity of these compounds is exceptional, yielding 5-fluoro-1,4-pyrazoles quickly and selectively, with reaction rates that exceed those previously recorded for cycloalkynes, and the potential for radiolabeling with [(18)F]Selectfluor indicates their usefulness in future applications.
Article Abstract
We report the synthesis and reactivity of 4-fluorosydnones, a unique class of mesoionic dipoles displaying exquisite reactivity towards both copper-catalyzed and strain-promoted cycloaddition reactions with alkynes. Synthetic access to these new mesoionic compounds was granted by electrophilic fluorination of σ-sydnone Pd(II) precursors in the presence of Selectfluor. Their reactions with terminal and cyclic alkynes were found to proceed very rapidly and selectively, affording 5-fluoro-1,4-pyrazoles with bimolecular rate constants up to 10(4) m(-1) s(-1) , surpassing those documented in the literature with cycloalkynes. Kinetic studies were carried out to unravel the mechanism of the reaction, and the value of 4-fluorosydnones was further highlighted by successful radiolabeling with [(18) F]Selectfluor.
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