Fiche publication
Date publication
septembre 2016
Journal
Angewandte Chemie (International ed. in English)
Auteurs
Membres identifiés du Cancéropôle Est :
Dr WAGNER Alain
,
Dr KOLODYCH Sergii
,
Dr KONIEV Sasha
,
Dr ELHABIRI Mourad
Tous les auteurs :
Liu H, Audisio D, Plougastel L, Decuypere E, Buisson DA, Koniev O, Kolodych S, Wagner A, Elhabiri M, Krzyczmonik A, Forsback S, Solin O, Gouverneur V, Taran F
Lien Pubmed
Résumé
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.
Référence
Angew. Chem. Int. Ed. Engl.. 2016 Sep;55(39):12073-7
