Categories: C-F Bond Formation >
Synthesis of fluoroalkanes
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Name Reactions
Recent Literature
Nucleophilic fluorination using CsF or alkali metal fluorides was completed in
short reaction time in the presence of [bmim][BF4] affording the
desired products without any byproducts. Facile nucleophilic substitutions such
as halogenations, acetoxylation, nitrilation, and alkoxylations in the presence
of ionic liquids provided the desired products in good yields.
D. W. Kim, C. E. Song, D. Y. Chi, J. Org. Chem., 2003, 68,
4281-4285.
Fluorinations of epoxides and alkyl mesylates can be effectively achieved by
reaction with Et3N • 3 HF under microwave irradiation. The
reactions were completed in a few minutes and the use of large excess of
reagents could be avoided.
T. Inagaki, T. Fukuhara, S. Hara, Synthesis,
2003, 1157-1159.
Bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor
reagent) is a new deoxofluorinating agent that is much more thermally stable
than DAST (C2H5)2NSF3. It is effective for the conversion of
alcohols to alkyl fluorides, aldehydes and ketones to the corresponding
gem-difluorides, and carboxylic acids to the trifluoromethyl derivatives with,
in some cases, superior performance compared to DAST.
G. S. Lal, G. P. Pez, R. J. Pesaresi, F. M. Prozonic, H. Cheng, J. Org.
Chem., 1999,
7048-7054.
