Aminodifluorosulfinium Tetrafluoroborate Salts as Stable and Crystalline Deoxofluorinating Reagents

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...

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Bibliographic Details
Published in:Organic letters 2009-11, Vol.11 (21), p.5050-5053
Main Authors: Beaulieu, Francis, Beauregard, Louis-Philippe, Courchesne, Gabriel, Couturier, Michel, LaFlamme, François, L’Heureux, Alexandre
Format: Article
Language:English
Subjects:
Borates - chemistry
Catalysis
Combinatorial Chemistry Techniques
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Indicators and Reagents
Letter
Molecular Structure
Salts
Sulfinic Acids - chemistry
Water - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol902039q