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Synthesis of difluoroalkanes

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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.


Easily prepared 2-alkyl-1,3-dithiane derivatives were reacted with BrF3 to form the corresponding 1,1-difluoromethyl alkanes in good yield. The reaction proceeds well with primary alkyl halides. The limiting step for secondary alkyl halides is the relatively low yield of the dithiane preparation.
R. Sasson, A. Hagooly, S. Rozen, Org. Lett., 2003, 59, 3635-3641.