title: New synthesis of 3-fluoropyrroles.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Riccardo
authors.initials: R
authors.lastname: Surmont
authors.forename: Guido
authors.initials: G
authors.lastname: Verniest
authors.forename: Filip
authors.initials: F
authors.lastname: Colpaert
authors.forename: Gregor
authors.initials: G
authors.lastname: Macdonald
authors.forename: Jan Willem
authors.initials: JW
authors.lastname: Thuring
authors.forename: Frederik
authors.initials: F
authors.lastname: Deroose
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*
chemical_list: D000447:Aldehydes; D006842:Hydrocarbons, Brominated; D006845:Hydrocarbons, Fluorinated; D011758:Pyrroles