We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Ultrafast Click Chemistry with Fluorosydnones.
- Authors
Liu, Hui; Audisio, Davide; Plougastel, Lucie; Decuypere, Elodie; Buisson, David ‐ Alexandre; Koniev, Oleksandr; Kolodych, Sergii; Wagner, Alain; Elhabiri, Mourad; Krzyczmonik, Anna; Forsback, Sarita; Solin, Olof; Gouverneur, Véronique; Taran, Frédéric
- 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 PdII 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 104 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 [18F]Selectfluor.
- Subjects
ALKYNE synthesis; RADIOLABELING; FLUORINATION kinetics; COPPER analysis; RING formation (Chemistry)
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 39, p12252
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201606495