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Selective monofluorination of diols using DFMBA.
Atsushi Yoneda1, Tsuyoshi Fukuhara, Shoji Hara
1Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan.
Chemical Communications (Cambridge, England)
|July 13, 2005
Summary
Selective monofluorination of diols was achieved using DFMBA, enabling the synthesis of optically-active fluorohydrin derivatives. This new method offers a valuable tool for creating complex fluorinated organic compounds.
Area of Science:
- Organic Chemistry
- Fluorine Chemistry
Background:
- Selective functionalization of diols is crucial in organic synthesis.
- Fluorinated compounds possess unique properties valuable in pharmaceuticals and materials science.
Purpose of the Study:
- To develop a selective method for monofluorination of 1,2- and 1,3-diols.
- To explore the synthesis of optically-active fluorohydrin derivatives.
Main Methods:
- Reaction of 1,2- and 1,3-diols with DFMBA (N-fluorobenzenesulfonimide).
Main Results:
- Selective monofluorination of various 1,2- and 1,3-diols was successfully achieved.
- The developed method is effective for synthesizing optically-active fluorohydrin derivatives.
Conclusions:
- DFMBA is an efficient reagent for selective monofluorination of diols.
- This method provides a viable route to optically-active fluorohydrins, important synthetic intermediates.