Categories: C-F Bond Formation >
Synthesis of benzyl fluorides
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Recent Literature
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.
A nucleophilic fluorination of triflates by weakly basic tetrabutylammonium
bifluoride provides excellent yields with minimal formation of
elimination-derived side products. Most primary and secondary hydroxyl groups
are excellent substrates, but benzylic and aldol-type secondary hydroxyl groups
give poor yields as a result of the instability of their triflates.
K.-Y. Kim, B. C. Kim, H. B. Lee, H. Shin, J. Org. Chem., 2008,
73, 8106-8108.
A desulfurizing difluorination reaction of benzyl sulfides having an
electron-withdrawing group such as an ester, a ketone, a nitrile, or an amide in
the presence of IF5 gave gem-difluoro compounds in good yield.
T. Fukuhara, S. Hara, Synlett, 2009,
198-200.
