Organic Letters 2009-11-05

Aminodifluorosulfinium tetrafluoroborate salts as stable and crystalline deoxofluorinating reagents.

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

Index: Org. Lett. 11 , 5050, (2009)

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Abstract

Aminodifluorosulfinium tetrafluoroborate salts were found to 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 easy handled crystalline salts that show enhanced thermal stability over dialkylaminosulfur trifluorides, are storage-stable, and unlike DAST and Deoxo-Fluor do not react violently with water.