Probing the hydrolytic reactivity of 2-difluoromethyl pyrroles.
Fiche publication
Date publication
décembre 2016
Journal
Organic & biomolecular chemistry
Auteurs
Membres identifiés du Cancéropôle Est :
Dr FIGLIOLA Carlotta
Tous les auteurs :
Melanson JA, Figliola C, Smithen DA, Kajetanowicz AK, Thompson A
Lien Pubmed
Résumé
α-Difluoromethyl pyrroles were found to be stable while N-protected with an electron-withdrawing group. Due to the propensity of pyrroles to access azafulvenium-like intermediates, the C-F bonds of an α-difluoromethyl substituent are labile under hydrolytic conditions. The presence of certain electron-withdrawing substituents about the pyrrolic ring can accelerate this process, as determined through a kinetic comparison of the deprotection and subsequent hydrolysis reactions of N-protected β-aryl α-difluoromethyl pyrroles.
Référence
Org Biomol Chem. 2016 12 20;15(1):144-152