Categories: C-F Bond Formation >
Synthesis of acyl fluorides
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.
Aminodifluorosulfinium tetrafluoroborate salts act as efficient
deoxofluorinating reagents when promoted by an exogenous fluoride source and, in
most cases, exhibited greater selectivity by providing less elimination
byproduct as compared to DAST and Deoxo-Fluor. Aminodifluorosulfinium
tetrafluoroborates are storage-stable, and unlike DAST and Deoxo-Fluor do not
react violently with water.
F. Beaulieu, L.-P. Beauregard, G. Courchesne, M. Couturier, F. LaFlamme, A.
L'Heureux, Org. Lett., 2009,
11, 5050-5053.
Deoxo-Fluor is a versatile and
mild reagent for acyl fluoride generation and subsequent one-flask amide
coupling. The conversion of acids to amides and Weinreb amides and the use
of Deoxo-Fluor as peptide-coupling reagent have been explored. Products were isolated
after facile purification in good yields.
J. M. White, A. R. Tunoori, B. J. Turunen, G. I.
Georg, J. Org. Chem., 2004, 69, 2573-2576.
