Pp. 8-151 (144)
Reza Ranjbar-Karimi and Alireza Poorfreidoni
Fluorine atom has unique properties and has a great interest in organic
chemistry and pharmaceuticals. Insertion of fluorine atoms on pyridines induces
significant properties to the pyridine ring. The introduction of fluorine atoms on
pyridine is carried out by the fluorination of pyridine or pentachloropyridine. The
withdrawing nature of these atoms is mainly responsible for the high reactivity of
perfluoropyridines toward nucleophilic attack. Therefore, perfluoropyridines are a
significant starting material for the synthesis of other substituted pyridines, ring-fused
systems as well as macrocyclic compounds via reaction with various monodentate and
bidentate nucleophiles, whereas the nature of nucleophile, reaction condition, and
solvent have a basic role in the regiochemistry of the reactions. Furthermore, these
compounds could participate in organometallic reactions by the reaction of halogen
atom with metals and organometallic reagents. Additionally, they underwent
hydrodefluorination in photochemical reactions in the presence of catalysts.
Bidentate Nucleophile, Continuous Flow Processes, Copolymers,
Hard–Hard Interaction Principle, Hydrodefluorination, Macrocycle, Medicinal
Chemistry, Meisenheimer Intermediate, Monodentate Nucleophile, N-Methylated
Pyridinium, Nucleophilic Substitution, Organometallic Perfluoroheteroaromatics,
Pentafluoropyridine, Pentafluoropyridine Cation, Photochemical Reaction, Polyhaloheterocyls,
Radical Addition, Regioselectivity, Ring-Fused, Tetrafluoropyridine.
Department of Chemistry, Faculty of Science Vali-e-Asr University of Rafsanjan Islamic Republic of Iran.