New synthesis of 3-fluoropyrroles.
5-Alkoxymethyl-2-aryl-3-fluoro-1H-pyrroles and 2-aryl-3-fluoro-1H-pyrrole-5-carbaldehydes were efficiently prepared from the corresponding 2-aryl-5-(bromomethyl)-1-pyrrolines via electrophilic alpha,alpha-difluorination of the imino bond, using Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bistetrafluoroborate) and subsequent aromatization by dehydrofluorination. This methodology provides a new and easy entry toward various new 3-fluorinated pyrroles.
Surmont
Riccardo
R
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
Verniest
Guido
G
Colpaert
Filip
F
Macdonald
Gregor
G
Thuring
Jan Willem
JW
Deroose
Frederik
F
De Kimpe
Norbert
N
D000447:Aldehydes / Q000138:chemical synthesis; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*
D000447:Aldehydes; D006842:Hydrocarbons, Brominated; D006845:Hydrocarbons, Fluorinated; D011758:Pyrroles