title: Mild fluorination of chloropyridines with in situ generated anhydrous tetrabutylammonium fluoride.
abstract: This paper describes the fluorination of nitrogen heterocycles using anhydrous NBu4F. Quinoline derivatives as well as a number of 3- and 5-substituted pyridines undergo high-yielding fluorination at room temperature using this reagent. These results with anhydrous NBu4F compare favorably to traditional halex fluorinations using alkali metal fluorides, which generally require temperatures of ≥100 °C.
authors.affiliation: Department of Chemistry, University of Michigan , 930 N. University Avenue, Ann Arbor, Michigan 48109, United States.
authors.forename: Laura J
authors.initials: LJ
authors.lastname: Allen
authors.forename: Joseck M
authors.initials: JM
authors.lastname: Muhuhi
authors.forename: Douglas C
authors.initials: DC
authors.lastname: Bland
authors.forename: Rachel
authors.initials: R
authors.lastname: Merzel
authors.forename: Melanie S
authors.initials: MS
authors.lastname: Sanford
mesh_terms: D005459:Fluorides / Q000737:chemistry*; D054879:Halogenation; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D008672:Metals, Alkali / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D008672:Metals, Alkali; D011725:Pyridines; D000644:Quaternary Ammonium Compounds; C009405:tetrabutylammonium; D005459:Fluorides