1.
Org Biomol Chem
; 15(1): 144-152, 2016 Dec 20.
Artigo
em Inglês
| MEDLINE
| ID: mdl-27841887
RESUMO
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 ß-aryl α-difluoromethyl pyrroles.