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Aminodifluorosulfinium Tetrafluoroborate Salts as Stable and Crystalline Deoxofluorinating Reagents

Francis Beaulieu, Louis-Philippe Beauregard, Gabriel Courchesne, Michel Couturier*, Franois LaFlamme and Alexandre L'Heureux

*OmegaChem Inc., 8800 Boul. De la Rive-Sud, Lvis, QC G6V 9H1, Canada, Email:

F. Beaulieu, L.-P. Beauregard, G. Courchesne, M. Couturier, F. LaFlamme, A. L'Heureux, Org. Lett., 2009, 11, 5050-5053.

DOI: 10.1021/ol902039q


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.

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Key Words

1,1-difluoroalkanes, fluoroalkanes, acylfluorides

ID: J54-Y2009-3310