期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 39, 页码 12073-12077出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201606495
关键词
click chemistry; electrophilic fluorination; fluorine-18; kinetics; radiolabeling
资金
- French Research National Agency [ANR-14-CE06-0004]
- Academy of Finland [266891]
- EC [FP7-PEOPLE-2012-ITN-RADIOMI-316882]
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 s-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 radio-labeling with [F-18] Selectfluor.
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