In recent years, the organocatalytic electrophilic fluorination reactions have
been extensively explored for the synthesis of organofluorine compounds. The
systematic introduction of fluorine atom often improves a number of properties of
fluorinated molecules including metabolic stability and various pharmacological
properties and thus frequently employed to design fluorinated drugs. The
enantioselective electrophilic fluorination via organocatalysis has emerged as the most
powerful approach for the synthesis of organofluorine compounds as the
organocatalytic approaches have several advantages in terms of economical and
environmental benefit. In this chapter, the most important developments of
organocatalytic enantioselective electrophilic fluorination are highlighted using new
types of electrophilic fluorinating reagents (NFSI, F-TEDA-BF4, F-CA-BF4) in the
presence of readily available different types of organocatalysts such as different amine
based catalysts, phase-transfer catalysts, Brønsted acid and H-bonding catalysts, which
are stable, easy to handle, more efficient and selective. Some recent advances with
fascinating examples, mechanism of electrophilic fluorination, mode of activation of
catalysts, catalytic cycles, controlling product selectivity and synthesis of chiral
fluorine containing drugs have been described.
Keywords: Amine catalysts, Asymmetric fluorination, Biologically active
compounds, Catalysis, Electrophilic fluorination, Fluorinating reagents, Green
chemistry, Hydrogen bonding catalyst, N-fluorobenzenesulfonimide (NFSI),
Organocatalyst, Organofluorine compounds, Pharmaceuticals, Phase-transfer
catalysis, Selectfluor (F-TEDA-BF4), Quaternary ammonium salts.
